Home Vacation Home Rentals By Owner In Chicago, IL

Showing 20 Of 354 Vacation Rentals
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Exceptional(19)

$1395.95

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Private Vacation Home

Luxurious, custom built single family home near Wrigley

Chicago, Illinois, United States

Welcome to one of the best home rentals in Chicago! Built in 2015, this 5 bedroom, 6 bathroom also boasts has an office, rec room/playroom and gym. Walkable to both Wrigleyville and Southport corridor, featuring a fully equipped kitchen, 2 fireplaces, 2 washer/dryers, wine fridge and radiant floors in basement and master bath. Outside has a spacious front yard, top floor roof deck, and an entertainers dream backyard including built in grill. Great for a weekend rental or longer stay.
Bed 5

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Bath 5

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Sleep 10

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$106.58

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Private Vacation Home

Detached, private, spacious, free garage, fast wifi, 5min to metra in Ravenswood

Chicago, Illinois, United States

Fully renovated in July 2025, this charming detached coach house from 1897 blends historic character with modern comfort. Set on a spacious 8,000+ sq ft lot, the property is shared with a classic Chicago two-flat, surrounded by a beautiful garden offering a rare sense of privacy and tranquility in the city.brbrThe home features a private entrance, direct access to garage parking, and is flooded with natural light through new European tilt-and-turn windows. Inside, enjoy a massive bedroom large enough to comfortably fit two queen beds and a dedicated workspace perfect for families, remote workers, or longer stays.brbrEverything is brand new:br- A stylish kitchen with stainless steel appliancesbr- A fully updated bathroombr- In-unit laundrybr- central ACbr- tank water heaterbr- New flooring throughoutbrbrLocated in the heart of Ravenswood, this home is just a 5-minute walk to the Metra (12min fast ride to Loop), close to the CTA Brown Line, and walking distance to Andersonville, Lincoln Square, and local hospitals. Enjoy the quiet charm of tree-lined streets with the convenience of being steps from restaurants, shops, bars, and cultural attractions like the iconic Green Mill and Wrigley Field.brbrComfortably sleeps up to 4 guests, ideal for:br- Travel professionalsbr- Expats settling into Chicagobr- Families renovating their primary homebrbrThis is a truly unique space that offers both comfort and character in one of Chicagos most beloved neighborhoods.
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Bath 1

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Sleep 4

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Exceptional(2)

$475.0

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Private Vacation Home

Modern Townhome in the Heart of Hyde Park

Chicago, Illinois, United States

Located in in the center of Hyde Park, this modern IM Pei townhome is a perfect place for your next stay in Chicago. Only 1 mile from University of Chicago campus and lake Michigan and 1 block from fantastic restaurants on 53rd street.brbrOur family friendly home has recently been renovated with an open concept first level and a private patio with grill, table, and chimenea off the kitchen. brbrThe second level has three bedrooms. Primary bedroom has a queen bed, and the second bedroom has 2 twin beds. The third bedroom is a small room kids with a twin bed.brbrThe lower level has a family room with large tv and guest room with a full-size murphy bed. There is a bathroom with shower in the lower level as well. We also have a washer and dryer on this level that guests are free to use. brbrSince this is our family home, please note there will be personal items such as toys, food, clothing, pictures, etc. However, we will leave plenty of space for hanging clothes in the bedrooms and an empty fridge and cabinet for your food. brbrAlso, please note we only have a tv in the primary bedroom and secondary bedroom, not in the main living space. We do however have high-speed internet and lots of board games you are welcome to use.brbrLicense numberbrR23000098049
Bed 4

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Bath 2

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Sleep 7

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Exceptional(48)

$1275.37

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Private Vacation Home

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Chicago, Illinois, United States

Come Enjoy Chicago's best rental property. We really have it all and we are in a perfect location, you won't have more fun anywhere in the city! Our building offers a stately layout with all the modern upgrades. brbrWe have a 2 huge living rooms with a flat screen TVs and comfy brand new couches. Either of the two formal dining rooms are perfect for large gatherings, the expandable dining tables can seat up to 12 comfortably for large dinner parties. The brand new large chefs kitchens are perfect for cooking up that big dinner, or for hanging out at the breakfast bar. 3 Bedrooms, a work desk (hopefully you don't need to use it) and a renovated bathroom round out the first level. The downstairs is where the real fun can be found. We have a huge, wide open rec room with an 8ft Pool table, a card table, a sitting area and a bar with 6 stools with a fridge. You'll never want to leave!! There are 3 bedrooms and 2 bathrooms on this level too. The top floor offers 4 bedrooms, 2 brand new bathrooms, another dining room, another kitchen, amazing views and a balcony. The outside features an expansive private patio with a table for 6 and a grill. You can sit and watch as the city life goes by while you relax and enjoy a cocktail. All this, and we are in the best location in Chicago, 1 block to Wrigley field, 3 blocks to the Redline 'El' train, 2 blocks to the Southport Neighborhood and 3 blocks to all of Lakeview / Boystown / Halsted. With over 100 restaurants and 80 bars within half a mile, you will need to come back year after year to see just that. Come check out all of the festivals, shows at Metro, Cubs games all summer, Pride Weekend, and the general fun that is this vibrant part of the city.
Bed 10

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Bath 5

Bath

Sleep 26

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Exceptional(1)

$2282.72

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Private Vacation Home

Vacation home just 2 minutes drive to Wrigley Field

Chicago, Illinois, United States

This brand new Greystone is in the heart of North Center Lakeview, Chicago. Walking distance to Wrigley, Andersonville, Boystown, Southport Corridor, etc. Home has gourmet kitchen with 2 islands, family room with floor to ceiling windows and fireplace, living room, dining room, rec room, 4 bedrooms with an integrated office. Outdoor patio space, playground set and rooftop deck with tables. brbrHome is attached to an in-law suite also available which features a family room, kitchen, office, laundry, full bath and 2 bedrooms with queen size beds available for additional charge.
Bed 4

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Bath 3

Bath

Sleep 10

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$613.87

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Private Vacation Home

4BR Retreat with Spa Tub + Private Backyard, Near University of Chicago and Lake

Chicago, Illinois, United States

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfortbrbrUnwind in the spa-style bath tub, relax in the private backyard oasis, comfortably accommodating your group for morning coffees.brbrSteps from Metra station with a direct train to Downtown, 4mins away from the presidential Obama center in Jackson pack, griffin museum of science & industry and lake.brbr The Spacebrbr4 spacious bedrooms with comfortable sleeping arrangementsbrbr2 beautiful bathrooms, including a luxurious spa-style bathroom with a freestanding soaking tubbrbrFully decorated interior with modern finishes throughoutbrbrBright, open living areas with a library and a space for relaxation.brbrFully equipped kitchen for home-cooked mealsbrbrbrbr Outdoor Backyard RetreatbrbrEnjoy your private backyard oasis, perfect for morning coffee, evening relaxation, or outdoor dining, a rare city feature.brbrbrbr Prime LocationbrbrMinutes from the University of ChicagobrbrSteps from the Stony Island Metra train — direct access to Downtown ChicagobrbrClose to Lake Michigan, beaches, and lakefront trailsbrbrEasy access to Hyde Park dining, Griffin museum, promontory point and vintage coffee shops .brbrbrbr⭐ Perfect ForbrbrVisiting professors, medical professionals, and UChicago affiliatesbrbrFamilies and groups seeking space and comfortbrbrGuests wanting a quiet neighborhood with a quick downtown commutebrbrExperience the best of South Shore with the comfort of a fully renovated home, a spa-like bathroom, and unmatched transit convenience. We look forward to hosting you!brbrbrbr Guest AccessbrbrGuests will have exclusive access to the entire main unit of the home, including all living spaces, bedrooms, bathrooms, kitchen, and the private backyard.brbrThe lower basement unit is locked for storage and not accessible to guests. It is completely separate from the main living space and does not affect your privacy or comfort during your stay.brbrYou will enjoy a private, comfortable stay with no shared interior spaces.brbrbrbrbr Other Things to NotebrbrNo parties or events are permitted at any time.brbrOnly registered guests listed on the reservation are allowed on the property.brbrLong-term stays (30+ days) may require a background check and completion of a local lease agreement, in accordance with local regulations.brbrFor safety and to help ensure a peaceful stay for all guests and neighbors, security cameras monitor the exterior of the property only.brbrNoise monitoring devices (no cameras, no recording of conversations) are in place to help maintain quiet hours and neighborhood respect.brbrThese measures are in place to provide a safe, comfortable, and enjoyable experience for everyone.
Bed 4

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Bath 2

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Sleep 10

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$644.29

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Private Vacation Home

Windy City Getaway | 3BR 2BA Chicago Townhouse by RedAwning

Chicago, Illinois, United States

Experience Chicago up close and personal when you stay at this 3-bedroom,brbr2.5-bathroom vacation rental. Boasting stylish contemporary decor, a gorgeousbrbrkitchen, and an unbeatable location just steps away from the Metra Line, thisbrbr3-story townhome is the perfect place to kick off your upcoming trip to thebrbrWindy City. Catch a game at one of the nearby stadiums, check out the manybrbrsurrounding tourist destinations, or grab a slice of Chicago's famous deep-brbrdish pizzas when you stay at this getaway.brbrbrbrbrbrbrbrEscape to the vibrant city of Chicago and experience the perfect blend ofbrbrurban living and cozy comfort at our charming townhouse. Nestled in a primebrbrlocation near the Metra line, this inviting unit awaits to make your stay inbrbrthe Windy City truly memorable.brbrbrbrbrbrbrbrAs you step inside, you'll be greeted by a contemporary and tastefullybrbrdecorated interior, designed with your utmost comfort in mind. The townhousebrbrfeatures three bedrooms, providing ample space for families or groups ofbrbrfriends seeking a delightful getaway. Rest assured, a good night's sleep isbrbrguaranteed on the plush beds, ensuring you wake up refreshed and ready tobrbrexplore all that Chicago has to offer.brbrbrbrbrbrbrbrStart your day with a cup of freshly brewed coffee in the fully equippedbrbrkitchen, boasting state-of-the-art appliances and everything you need tobrbrprepare delicious meals. The open-plan layout seamlessly connects the kitchenbrbrto the spacious living area, making it the perfect spot to unwind after a daybrbrof sightseeing or business meetings. Sink into the comfortable sofas and catchbrbrup on your favorite shows on the large flat-screen TV, or simply enjoy thebrbrcompany of your travel companions.brbrbrbrbrbrbrbrOne of the highlights of this townhouse is the delightful balcony and patiobrbrcombo. Step outside and feel the refreshing breeze as you bask in the sunlightbrbron the balcony or enjoy a casual outdoor meal on the patio. It's an idealbrbrsetting to sip on a glass of wine and watch the world go by.brbrbrbrbrbrbrbrChicago's rich culture and diverse attractions are just a stone's throw away.brbrHop on the nearby Metra line to easily access the city's iconic landmarks andbrbrrenowned neighborhoods. Discover the world-class art at the Art Institute ofbrbrChicago, take in the stunning skyline views from Willis Tower, and embrace thebrbrlively atmosphere of Millennium Park. The townhouse's strategic locationbrbrensures that you won't miss out on any of the city's gems.brbrbrbrbrbrbrbrAfter a day of exploration, return to the townhouse to unwind and recharge forbrbranother exciting day ahead. Freshen up in the clean and modern bathrooms,brbrcomplete with all the amenities you might need during your stay.brbrbrbrbrbrbrbrIf you're looking to experience Chicago like a local, venture into thebrbrneighborhood surrounding the townhouse. The area is teeming with trendy cafes,brbrchic boutiques, and delicious eateries serving up a variety of cuisines.brbrEmbrace the unique charm of the local community and get a taste of what makesbrbrChicago so special.brbrbrbrbrbrbrbrWith its unbeatable location, stylish interior, and thoughtful amenities, ourbrbrChicago townhouse is the perfect home base for your urban adventure. Book nowbrbrand embark on an unforgettable journey in the heart of one of America's mostbrbrexciting cities. We can't wait to host you and ensure your stay in Chicago isbrbrfilled with wonderful memories.brbrbrbrbrbrbrbr**★☆ NEARBY ATTRACTIONS, LANDMARK & RESTAURANTS☆★** brbr☀Shedd Aquarium- 31 min drive brbr☀Buckingham Fountain- 21 min drive brbr☀The Art Institute of Chicago- 21 min drive brbr☀Navy Pier- 25 min drive brbr☀Lincoln Park Zoo- 18 min drive brbr☀Kilbourn Park- 10 min drive brbr☀LaBagh Woods- 10 min drive brbr☀Millenium Park- 19 min drive brbr☀Riverwalk- 21 min drive brbr☀North Park Village Nature Center- 13 min drive brbr☀Garfield Park Conservatory- 19 min drive brbr☀Chicago Cultural Center - 18 min drive brbr☀Breakfast House & Coffee Bar- 9 min drive brbr☀Eris Brewery- 12 min drive brbr☀Peru Criollo- 6 min drive brbr☀Smoque BBQ- 4 min drive brbr☀Thai Aree House- 6 min drive brbr☀ Portillo's Hotdogs- 9 min drivebrbrbrbrbrbrbrbr**★☆ KEY FEATURES ☆★** brbr☀Balcony brbr☀Patio brbr☀Near public transportation brbr☀Close to tourist destinationsbrbrbrbrbrbrbrbr**★☆ BEDROOM ARRANGEMENT☆★** brbrBR1: 1 Queen Bed brbrBR2: 1 Queen Bed brbrBR3: Full Daybed with twin trundle brbr1st Floor Couch Sofa Bed (Full)brbrbrbrbrbrbrbr**★☆ LIVING ROOM ☆★** brbrEnjoy a warm and inviting living room, boasting both coziness and ample space.brbrUnwind on a comfortable couch, perfect for snuggling up with your loved onesbrbrduring a movie night. For added entertainment, there is an abundance of boardbrbrgames to keep everyone engaged. The room receives abundant natural light,brbrcreating a seamless and pleasant flow that fosters a strong sense ofbrbrtogetherness, ideal for bonding with friends and family.brbrbrbrbrbrbrbr**★☆ KITCHEN & DINING ☆★** brbrThe gorgeous kitchen provides an excellent space to prepare a complete meal tobrbrcater to the entire group.brbrbrbrbrbrbrbr**★☆ PARKING ☆★** brbr☀ 2 Parking spots in the garage brbr☀ Free Street parkingbrbrbrbrbrbrbrbr**★☆ HOUSE RULES ☆★** brbr☀ No smoking brbr☀ There is a $500 fee for smoking in the premises brbr☀ Pets are not allowed brbr☀ No events, parties, or large gatherings brbr☀ Must be at least 25 years old to book brbr☀ Please report any damages that occur during the stay brbr☀ Guests may request an early check-in (up to 3 hours before 4pm) or a latebrbrcheck-out (up to 2 hours after 10am), so long as there is not a reservationbrbrbooked at our property for the day of your request. Please message us a day inbrbradvance to confirm availability and receive the applicable fee quote.brbrbrbr☀Extra Guests: If more guests than permitted are found at the property, webrbrreserve the right to deny entry based on policies. Extra guests will bebrbrtreated as trespassers. An additional fee of $50/night per extra guest maybrbrapply, or we might request that you vacate the property. brbr☀If uncertain about guest numbers or daytime visitors, please reach out. Webrbraim to prevent any misunderstandings.brbrbrbrbrbrbrbr**★☆ Book Now & Let Us Take Care of You! ☆★ **brbrbrbrFree garage parking for two standard size vehicles. Large extended crew cabbrbrtrucks and 8+ passenger vans can be parked on Kostner Street, which offersbrbrfree non-residential parking.brbrbrbr
Bed 3

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Bath 2

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Sleep 9

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Exceptional(11)

$1793.89

/ Nightly
Private Vacation Home

Family Friendly, Lovely 6 Bd Retreat w/ Game Room, Back Deck & Bar

Chicago, Illinois, United States

Welcome to Your Ultimate Chicago Getaway!brbrProperty Type: Spacious 3200 sq ft House with Back Deck and Covered Garage brBedrooms: 6 | Bathrooms: 3 | Accommodates: 16 guests comfortably (Note: Max 12 adults, 4 children under 18, per city of Chicago guidelines).brbr ️ Discover Your Dream Stay:brbrWalk into a haven of comfort with two luxurious king beds, three cozy queen beds, and a Super Mario themed bunk room that's perfect for kids and adults alike. The highlight A speakeasy-style basement that boasts a full bar, a game room filled with fun, and a retro popcorn machine for movie nights. Not to mention the large back deck, where you can savor outdoor grilling, unwind on the couch, and gather around the picnic table. Our home is designed for your relaxation and entertainment.brbr Exceptional Features:brbrImagine evenings on the large back deck, grilling up a feast under the lights, and lounging around the fire table with your loved ones. Need to work remotely No problem! We offer multiple dedicated workspaces. You'll also enjoy the luxury of top-quality mattresses, pillows and linens for a restful night's sleep. Plus, each bed comes with a choice of memory foam pillows or luxury down pillows, so there's an option for everyone.brbr Convenient Amenities:brbrStay connected with high-speed WiFi, and keep comfortable year-round with air conditioning/heating systems. Laundry is a breeze with a washer and dryer, and our fully stocked kitchen is designed after my own mother's kitchen, filled with enough place settings and cookware for the entire group. Park your car in our free covered garage, or use the free street parking out front.brbr Luxurious Touches:brbrSip cocktails around the outdoor fire table, mix your drinks at the basement's built-in bar, and challenge your friends to a game of pool, foosball, or shuffleboard. Revel in the modern and spacious decor that adds to the ambiance of your stay. The house is not just well-appointed; it's thoughtfully decorated with beautiful art adorning the walls and lush, green plants strategically placed throughout.brbr Explore the Neighborhood:brbrWe're nestled on a quiet, tree-lined street just minutes away from Chicago's vibrant scene. Easy access to major highways and public transportation means you can explore the city effortlessly. Conveniently located near the airport and downtown, our property is the perfect base for exploring Chicago's best attractions.brbr House Rules:brbrPlease note our house rules: no pets, no smoking, and no parties. We want to ensure a peaceful and pleasant stay for all our guests.brbr Check-In/Out:brbrCheck-in is at 4 PM, and check-out is at 10 AM, allowing our dedicated cleaning team ample time to prepare for the next guests. Enjoy the convenience of self-check-in and check-out with our smart WiFi locks.brbr⏳ Minimum Stay:brbrOur minimum stay requirement varies by season, typically ranging from 2 to 3 nights.brbr Why Choose Us brbrWhat sets us apart Spacious bedrooms for rejuvenating nights, multiple common areas with top-notch amenities, and the personal touch that makes your stay truly memorable.brbr Cleanliness and Safety: brbrWe take cleanliness and safety seriously. Our professional cleaning team follows COVID-19 protocols to ensure your well-being.brbr Host Availability:brbrWhile I'm available remotely, our local staff is ready to assist in case of emergencies.brbr Your Expectations:brbrWe want you to have a fantastic time, and we kindly ask that you leave the place in good condition, respecting our cleaners' hard work.brbr Additional Information:brbrConveniently located near the airport and downtown, our property is the perfect base for exploring Chicago's best attractions.brbr Ready to experience the best of Chicago Book your stay today and enjoy the comfort, convenience, and entertainment our home offers!br
Bed 6

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Bath 3

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Sleep 16

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Exceptional(1)

$493.96

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Private Vacation Home

Comfy Chinatown Townhome and 2 garage spots!

Chicago, Illinois, United States

Forget your worries in this spacious and serene space. This 2,200 sqft, 3 bed / 2.5 bath Townhome located in Chinatown is the perfect escape for families and groups looking for a comfortable, quiet retreat, amid vibrant surroundings. Easy access to every major highway. Free 2 car garage spots for those driving!brbr1 mile from McCormick and Wintrustbr3.5 miles to Rush / Stroger ~10minbr4.1 miles to Northwestern ~16minbr6.1 miles to U of C Hospital Hyde Park ~17minsbrbrThe spacebr*STAIRS: This unit has 5 short flights of stairs in the townhome. From garage entrance, 1 flight down to game room and one flight up to living area, around 5 steps each. From living area, 1 flight to kitchen, around 5 steps. From Kitchen to bedrooms, 2 flights around 10 steps.brbr*Please note, this Property does not allow smoking, prolonged drinking and partying! If you’re a disrespectful, loud or rowdy group, THIS SPACE IS NOT FOR YOU. The property has outdoor cameras and noise decibel detection devices that are monitored at all times.*brbr*Please note, this townhome is in a residential area. This listing is for one unit! There may be interaction with other guests outside with shared courtyard and parking areas. We ask everyone to be kind and courteous while staying at our property. Please respect the quiet hours starting at 10pm*brbr▶We follow Airbnb's COVID-19 Cleaning Protocolsbrbr▶Comcast Business WiFibrbr▶Our home is uniquely situated in a cozy part of a booming and animated town. The interior is very simple, clean, and cozy.brbr▶Fully equipped kitchen is stocked with all the tools you need to stay in and cook a great meal. Comfortable furniture to lounge and relax and a smart TV setup.brbr▶Sleeping arrangements:brbrBedroom 1: Queen bedbrBedroom 2: Queen bedbrBedroom 3: Queen bedbr2 foldable twin memory foam floor mattressesbrbr▶Our beds have crisp linens and the bathrooms are stocked with fresh towels. We also provide essentials like a hair dryer, clothes iron, etc. and you have full access to the in-unit washer and dryer.brbr▶2 car garage parking with free street parking for large vehicles or extra vehicles. Garage fits up to 2 standard SUVs at most. There is free street parking if needed.brbrPets allowed. $200 feebrbrOn the bottom floor there is a game room with foosball table, darts and TV. Please enjoy but respect and treat properly.brbrWe love our space and we hope you do too!
Bed 3

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Bath 2

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Sleep 8

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$393.88

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Private Vacation Home

Spacious 5-bedroom bungalow in delightful Chicago with AC, WiFi

Chicago, Illinois, United States

Make yourself at home in this 5-bedroom Chicago retreat. This adorable bungalow features 2 queen beds, 2 twin beds, and 1 full bed, perfect for families or groups of friends. With amenities like a washing machine, AC, WiFi, and heating, guests can relax and unwind in this soothing space. Three bathrooms ensure everyone has their own space to freshen up. Enjoy your time in Chicago at our fantastic bungalow.
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Bath 2

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Sleep 8

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$414.04

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Private Vacation Home

Spacious 3BR Duplex for Groups-Near Airport & Downtown-Cozy & Quiet

Chicago, Illinois, United States

Welcome to Chicago — Your Perfect Weekend EscapebrRated 10/10 by past guests! They loved the fully stocked kitchen, cozy bedrooms, and quiet neighborhood. Perfect for weekend getaways, families, or business trips.brEnjoy a comfortable, private stay in this 3BR / 2BA first-floor duplex. Located in the safe Jefferson Park neighborhood, you’re just 15 minutes from O’Hare, close to major highways, and a short walk to the Jefferson Park Transit Center for easy city access. Whether you’re here for a quick recharge or a busy weekend, this home is designed for easy arrival, great sleep, and stress-free comfort.brThe Space:brYou’ll have exclusive access to a private first-floor apartment plus garden level in a two-unit home. Shared areas include the backyard and laundry room, while your living space remains fully private. What Guests Love:br“House was clean and as described. Quiet neighborhood, parking was always available… Host is responsive and helpful.” – Dec 1, 2025brProfessionally cleaned & sanitized before every staybrHigh-speed Wi-Fi for work or streamingbrSmart TV with streaming optionsbrFully stocked kitchen for easy meals or quick breakfastsbrCoffee maker, kettle, toaster, microwave & waffle makerbrHotel-quality essentials: shampoo, conditioner, body wash & morebrCookware, bakeware, sharp knives & full utensil setbrHair dryer, iron & ironing boardbrLuggage racks & plenty of hangersbr“Everything was nice and comfortable, clean and convenient. I will stay here again on our next trip.” – Sep 16, 2025brJust bring your bags — everything else is ready.brPerfect for Weekend TravelersbrEasy self check-inbrQuiet, residential setting for restful nightsbrComfortable beds and thoughtful touches throughoutbrIdeal for 2–4 night staysbr“OMG! Fantastic place to stay, truly loved the home. Easy to go in and out and host very kind and friendly. When I come back, I will choose this home again!” – Sep 13, 2025. House Rules (Summary)brThis home is best suited for quiet, respectful guests:brNo parties, events, or unregistered guestsbrQuiet hours: 10 PM – 8 AMbrNo smoking inside (designated outdoor areas provided)brNo pets unless pre-approvedbrRegistered guests onlybrPlease remove shoes on carpeted areasbrFull house rules provided upon booking.brImportant NotesbrGovernment ID and security deposit may be required for certain bookingsbrLocal bookings allowed by exception onlybrPlease report any issues during your stay so we can assist immediately. We look forward to hosting you and providing a comfortable, relaxing stay in Chicago!
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(23)

$197.5

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Private Vacation Home

Home Sweet Home

Chicago, Illinois, United States

Newly finished basement with 2 bedrooms and everything is brand new. Very good location near O'Hare airport which is 20 minutes away. Rosemont Convention Center and Fashion Outlet with many brand stores and restaurants is 10 minutes away. Close to the HIP MALL with Starbucks, Target, and many small food places (0.5 miles away). 3 miles to public transport - Blue Line. 20 min To Downtown Chicago. No parties allowed. No smoking. No same city booking.
Bed 2

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Bath 1

Bath

Sleep 4

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Exceptional(15)

$353.4

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Private Vacation Home

Enjoy Chicago/suburbs 2BR townhouse fully equipped

Chicago, Illinois, United States

Be in Chicago and just minutes away from the suburbs. Minutes from Oak Park (Hemingway’s hometown). Close to downtown Oak Park, Elmwood Park, Forest Park, River Grove where you can enjoy great restaurant. Walk to Metra station to catch the train to downtown Chicago.
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Bath 1

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Sleep 6

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$303.04

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Private Vacation Home

Beautiful newly renovated townhome, very quite, safe, centralized location.

Chicago, Illinois, United States

You will experience, high end appliances, glass staircase, wood floors throughout, secluded private backyard, T.V’s and Wi-Fi throughout premises and three levels of brand new living space. Upper levels house three bedrooms which include the Primary bed and bathrooms, Jack and Jill bathroom with two adjacent bedrooms. Mainfloor features an open floor plan of living, dinning and cooking space with half bathroom. The lower level has beautiful tiled fiooring, washer and dryer, and huge bedroom with a live-in host that will accommodate your grocery and navigational needs. This home is armed with high-end security cameras and alarm features. There are fire extinguishers on the upper and lower levels. brThere is tons of free street parking to accommodate multiple cars.brThe area is centrally located between, Jackson Park Golf Course, take a nice walk on the University of Chicago’s campus, Lake Shore Drive with public beaches. This community neighbors the infamous Hyde Park area which holds a host of restaurants, shopping, hair and nail salons, and movie theater. brYou can enter our Downtown area directly on Lake Shore Drive with 15 minutes as you enjoy the scenic view of Lake Michigan and our museums campuses, which is one of my favorite features of this properties location.brYou will enjoy the quite, peaceful neighborhood along with the beautifully renovated home.
Bed 4

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Bath 4

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Sleep 8

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Exceptional(36)

$1214.63

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Private Vacation Home

Bucktown Home - Rooftop Deck, Game Rm, & Garage

Chicago, Illinois, United States

Summary:brbrWelcome to our home in Chicago! brbrbrbr- Sleeps up to 14 with 4 bedrooms and 3.5 bathrooms brbr- Spacious living area with designer couches and a 65-inch smart TV brbr- Vibrant basement with arcade games and another 65-inch smart TV brbr- Two outdoor rooftop patios with BBQ grill and games brbr- Free parking for up to 4 cars brbrbrbrBook your stay with TheDreamRentals today!brbrbrbrThe Space:brbrWelcome to our brand-new construction single-family residence, completed in the summer of 2021. Be among the first to experience the beauty and comfort of our home, designed to accommodate up to 15 guests with 7 individual beds. Spanning 4 floors, this spacious property features 4 bedrooms and 3.5 bathrooms, making it perfect for large groups or families. Nestled in a vibrant neighborhood of Chicago, our home is ideally located between Logan Square and Bucktown. brbrbrbrComfortable Accommodation:brbr- Sleeps up to 14 guestsbrbr- 4 bedrooms with comfortable bedsbrbr- 3.5 bathrooms for conveniencebrbr- Ear plugs and white noise monitors provided in each bedroom to help with noise from the trainbrbrbrbrInterior Feeling:brbr- Gorgeous kitchen with modern appliancesbrbr- Spacious dining area for shared mealsbrbr- Living room featuring designer couchesbrbr- 65-inch smart TV for movie nights or gamingbrbr- Vibrant basement with a Mortal Kombat arcade machine and foosball tablebrbr- Additional 65-inch smart TV for Netflix and chillbrbrbrbrOutdoor Bliss:brbr- Two outdoor rooftop patios for warm-weather enjoymentbrbr- Rooftop patio on the fourth floor with beautiful viewsbrbr- Second-floor patio above the garage, perfect for gatheringsbrbr- BBQ grill and patio furniture available during warmer monthsbrbr- Turf and games for added funbrbrbrbrDelightful Dining:brbr- Fully equipped kitchen for cooking and entertainingbrbr- Ample dining space for enjoying meals togetherbrbrbrbrProfessional Cleaning:brbr- Thoroughly cleaned and sanitized before each staybrbr- High standards of cleanliness maintained throughout the propertybrbrbrbrParking:brbr- 2-car garage available for guest usebrbr- Additional private space behind the garage for 2 more carsbrbr- Park up to 4 cars for FREE in ChicagobrbrbrbrBook with us today and enjoy exclusive discounts with our trusted local vendors! Elevate your stay with special rates on limo services, private yacht charters, helicopter rides, kayak rentals, outdoor sauna experiences, private chefs, and so much more. Let us help you create an unforgettable experience from start to finish!brbrbrbrGuest Access:brbrOur space also includes parking in a 2-car garage and there is private space behind the garage that can fit 2 more cars. Park up to 4 cars for FREE in Chicago.brbrbrbrGuests will access the home via self-check in and a lockbox.brbrbrbrThe Neighborhood:brbrThe property is situated in a very cool and one of the most HIP neighborhoods of Chicago. It is right in the middle of Logan Square and Bucktown. There are plenty of fine dining options and bars.brbrbrbrThe best Ramen is located right around the corner called Wasabi. brbrbrbrTwo great taco places called L'Patron and Taqueria Chingón are a few blocks away. brbrbrbrEasy Does it: Outdoor wine bar that is great for summer time winebrbrbrbrEmporium Arcade Bar: Enjoy a game of pool or ping pong while enjoying your favorite beerbrbrbrbrConcord Music Hall: One of Chicago's most popular music venues is right around the cornerbrbrbrbrGetting Around:brbrAlso, the Blue Line train goes right behind the home. You can hop on 1-block away on Western and Milwaukee to ride right into the city or to O'hare airportbrbrbrbrOther Things to Note:brbrOne thing to note, the blue-line L train runs right behind the home. The train passes every 30-minutes roughly.brbrbrbrCheck-In and Check-Out: Check-in time is 4:00 PM, and check-out time is 11:00 AM. If you require early check-in or late check-out, please let us know in advance, and we'll do our best to accommodate your request.brbrbrbrNo Smoking: For the comfort of all guests, smoking is strictly prohibited within the house. Please smoke outside.brbrbrbrPet Policy: We adore pets, but unfortunately, the property is not pet-friendly. We appreciate your understanding in adhering to this policy.brbrbrbrQuiet Enjoyment: Respect for fellow residents and neighbors is paramount. Please keep noise levels at a considerate level, especially during quiet hours, to maintain a peaceful environment.brbrbrbrMaximum Occupancy: The maximum number of guests allowed in the house is as indicated in your booking details. Hosting additional overnight guests without prior approval is not permitted.brbrbrbrMonitoring: We have camera's outside of the home for your safety. It will be recording during the reservations. Tampering with these will result in a fine.brbrbrbrSecurity: To abide by all legal requirements and building security rules, you will be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, and pass through our verification portal. Security deposit of $500 will be required before check in.brbrbrbrChicago Registration Number: R22000077481brbrShared Housing Unit Operation License Number: 2823378brbrbrbrInteraction with Guests:brbrYour comfort and enjoyment are of the utmost importance to us. Here's what you can expect in terms of interaction:brbrbrbrPrivacy Respected: While we're available to assist you throughout your stay, we respect your privacy and understand that you're here to relax and unwind. Enjoy the penthouse as if it were your own private haven.brbrbrbrSupport at Your Fingertips: Should you have any questions, need recommendations, or encounter any issues during your stay, feel free to reach out to us. We're just a message or call away and are dedicated to ensuring your comfort.brbrbrbrEmergency Assistance: In case of any emergencies or urgent matters, you'll find contact information for our responsive team in the provided house manual.brbrbrbrFeedback Welcomed: We value your feedback and would love to hear about your experience. If there's anything we can do to enhance your stay or if you have suggestions for improvement, please don't hesitate to share.brbrbrbrOur goal is to strike the perfect balance between being available to meet your needs and respecting your desire for a tranquil and enjoyable stay.
Bed 4

Bed

Bath 3

Bath

Sleep 17

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Exceptional(60)

$949.8

/ Nightly
Private Vacation Home

Only Urban Beach House in Chicago

Chicago, Illinois, United States

Chicago’s ONLY Urban Beach House combines the best of beach life and urban life! Perfect for couples, students, faculty, families, and vacationers who want to experience the beach house lifestyle while enjoying all of the amenities, conveniences and excitement of an urban location.brbrVirtual tour link: https://www.smartfloorplan.com/p/t/shell5.php id=v450743brbr1131 W. Morse Ave. is uniquely located just steps from Lake Michigan, Loyola Park and the sandy shores of Loyola, Leone and Albion Beaches. Enjoy convenient access to the CTA Sheridan Bus, the CTA Morse Ave. “El” train station and the Metra train station at Morse Ave. Bicycle enthusiasts can rent a Divvy bicycle within a short distance of the property and explore Chicago’s premiere Lakefront path and bicycle routes. brbrLoyola, DePaul and Northwestern Universities will find this property conveniently located to their campuses. Loyola is in walking distance and DePaul and Northwestern are a short CTA stop away. The house is surrounded by dozens of restaurants and bars, retail and a movie theater all within steps of the house. The City of Evanston, the home of Northwestern University, is a short commute and is considered the Northshore’s capital for restaurants, shopping, and nightlife.brbrLoyola Park offers wide open sandy beaches perfect for exploring. The park is a haven for the sports enthusiast with four tennis courts, basketball courts, three baseball diamonds, sports fields, volleyball courts on the sand and land, a field house, a playground, a fitness circuit course, a nearly 2/3-mile walking trail along the beaches of Lake Michigan, and more. brbrPROPERTY OVERVIEW: br1131 W Morse is loaded with features, including: brbr• a large bedroom with 1 King sized bed that converts to 2 Twins (sleeps 2)br• a 2nd bedroom with 1 King sized bed that converts to 2 Twins (sleeps 2)br• a 3rd bedroom with 1 Queen sized bed (sleeps 1-2)br• a 4th bedroom with 1 Twin sized bed (sleeps 1)br• a lower level Family Room with a couch convertible to a Full bed (sleeps 1-2)br• The house sleeps 8-9 peoplebr• Bedrooms can also be officesbr• 3 full bathrooms with newly rehabbed oversized showers br• a newer chefs kitchen with granite countertops and stainless steel appliances, plenty br of cookware and appliancesbr• a large living room with decorative fireplacebr• a family room with bar and French doors leading to a deckbr• an office/game roombr• a fitness room with workout equipment, weights, ball and yoga matsbr• WIFIbr• two tv’s and cable (Netflix, Amazon Video, etc.)br• washer/dryer with laundry supplies, ironing board and ironbr• front porch and 2 rear decksbr• complete patio furniture setbr• an outdoor fire pit and new 6-burner gas grill for cookingbr• large rear yard with yard gamesbr• direct access to the park and beachbr• 2 indoor garage parking spaces for an additional fee (Free street parking or two br garage spaces for $15/night per space)br• air conditioningbr• 100% smoke freebr• 100% pet freebrbrbrBedroom DescriptionsbrCommodore Room: King bed can be converted to two Twin XL bedsbrbrLake Room: Twin XL beds can be converted to a King bed.brbrBoat Room: Boat themed room with Queen bed. (sleeps 1-2)brbrRogers Room: Rogers Park, Chicago themed room with Twin bed and balconybrbrCabin Room: couch convertible to a Full bed (sleeps 1-2)
Bed 4

Bed

Bath 3

Bath

Sleep 10

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Exceptional(19)

$1090.48

/ Nightly
Private Vacation Home

Luxury SOHO Styled Two-Level Townhouse - Old Town

Chicago, Illinois, United States

Summary:brbrNEWLY CONSTRUCTED TOWNHOUSE IN THE HEART OF OLD TOWN!brbrbrbrThis private luxury townhouse (duplex) is perfectly located in vibrant Old Town-surrounded by nightlife, restaurants, cultural attractions, and is only a 5 min walk to the beach, steps from Lincoln Park, and next to Second City. This 2,800 square foot townhouse features 13 foot ceilings, open floorplan, private patio, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between.brbrbrbrThe Space:brbrLocated on bottom two floors of a two unit townhouse just steps from Old Town's famous Wells street, your luxurious townhouse was designed to look and feel like a SOHO loft apartment, sleeping up to 14 people and is perfectly situated for large groups, families, events, and curated dinners. Everything flows around the spacious and open living room and chef's kitchen, featuring high-end cooking appliances and designer level finishes, which creates a unique environment for entertaining and gathering with your group.brbrbrbrYour spacious living/dining room combo is decorated in modern contemporary art and features a large sofa, accent chairs, dining table for 10+ people, and smart TV (Netflix, Hulu, Prime, etc. compatible).brbrbrbrAttached to the dining room, the chef's kitchen includes designer cabinetry and is outfitted with top of the line Gaggenau gas-powered ranges, oven, microwave, and fridge with oversized island, plenty of cabinetry, plates, cups, and cutlery and Nespresso coffee maker, amongst others.brbrbrbrThis one of a kind townhouse comfortably sleeps 14 people and has 3 bedrooms and 3 full bathrooms, with the downstairs area converted into another large sleeping area. The main bedroom with a king bed, full bath, outfitted with a steam and waterfall shower. Two additional bedrooms feature queen beds. Converted basement area has two full over full bunk beds and open seating area. Lastly, we also have a queen size air mattress for additional sleep use. brbrbrbrSleeping arrangements/room layout:brbrMain bedroom (bedroom 1): King Bed, bathroom with steam and showerbrbrBedroom 2: Queen bedbrbrBedroom 3: Queen bedbrbrConverted Sleeping Area: Two bunk beds (full over full)brbrAdditional Queen Air MattressbrbrbrbrWe provide one parking permit per day of your stay for the permitted street parking directly in front of the building. Lastly, there is a paid parking garage and paid street parking as well.brbrbrbrOur units are made up fresh before each guest and their group arrives. Our professional cleaning service that we use on all of our properties do a thorough job of cleaning all areas, focusing on high touch point areas. Each bed is stripped and all sheets, pillow covers, and duvet covers are washed thoroughly after each stay.brbrbrbrTo abide by all legal requirements and building security rules, you may be asked to provide a copy of your official government-issued photo ID, confirm your contact information, provide a valid credit card with a name that matches your ID, pass through our verification portal and, in some instances, complete a criminal background check.brbrbrbrImportant note: The information is collected for screening and verification only and is not stored or used for any other purposes.brbrbrbrPlease be advised that all guests will be asked to sign a rental usage agreement that governs the terms of the stay. By completing the reservation you agree to the following:brbrbrbr-You agree to be bound by our rental terms and conditions.brbr-You acknowledge that you will be required to provide a copy of a valid government-issued ID and matching credit card prior to check-in.brbr-You acknowledge that you may be required to undergo a background check if mandated by the property management company or the building, as stated in accordance with your rental agreement and the condition of the booking.brbr-You understand that your check-in instructions might be withheld until you have successfully completed our verification portal.brbrbrbrGuest Access:brbrYou will have full access to all rooms and spaces inside the unit, except for one utility closet. Temporary access codes will be shared 24 hours before rental commencement by email.brbrbrbrInteraction with Guests:brbrWe pride ourselves on making our guest's stay as enjoyable as possible. We live in Chicago and are available should anything come up.
Bed 3

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Bath 3

Bath

Sleep 14

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Exceptional(1)

$505.59

/ Nightly
Private Vacation Home

Large Space With Garage

Chicago, Illinois, United States

Our spacious property is perfect for large families, group getaways, or business stays. With 10beds, 4 bedrooms and 2 bathrooms.brbr ️ Comfortable & Flexible Sleeping ArrangementsbrbrOur home offers a total of 10 beds, 1 sofa bed, 1 toddler bed, and 1 twin luxury air mattress, thoughtfully arranged to accommodate a variety of group sizes and needs:br • 1 King-size bedbr • 2 Queen-size bedsbr • 2 Full-size bedsbr • 1 Full-size bunk bed (perfect for kids or teens)br • 1 Twin-size bamboo bedbr • 2 Twin-size collapsible beds (convert into comfortable luxury chairs)br • 1 Twin-size luxury air mattressbr • 1 Toddler bedbr • 1 Sofa bedbrbrAdditionally, we feature a luxury reclining massage chair that’s so comfortable, guests often enjoy resting or even sleeping in it.brbr Entertainment & ComfortbrbrAs previous guest suggested, we have put television in every bedroom and bought more couch. Enjoy movie nights or your favorite shows on our 75-inch luxury TVs located in every bedroom and the living room. Perfect for relaxing after a long day.brbr ️ Fully Equipped Gourmet KitchenbrbrCook and entertain with ease in our fully equipped kitchen, featuring high-end appliances, a coffee maker, and a luxury toaster. We have everything you need to prepare meals for your group.brbr Parking & Conveniencebr • Enclosed garage for guest usebr • Multiple free parking spaces in front of the garage and throughout the propertybrbr⚠️ Important Guest PolicybrbrTo ensure a comfortable experience for everyone, please provide an accurate guest count at the time of booking.brbrMisrepresentation of the number of guests may result in restricted access to certain spaces or termination of your stay without refund. We appreciate your honesty and cooperation in helping us maintain a quality experience for all guests.brbrWhether you’re gathering with family or traveling with friends, this spacious and well maintained home offers comfort, luxury, and flexibility for an unforgettable stay.brbrSave yourself the $80 per night parking fee downtown by taking advantage of our free complimentary parking offer. brbrBig family Group getaway We’ve got more sleeping space than you’ll know what to do with. Try finding this much space and this kind of deal anywhere else. We’ll wait.brbrIf there's anything specific you're hoping for, don't hesitate to share it with me. I'm here to work together and find a way to make it happen if it's within reach! brbrbrbr*** It's important to understand that we will terminate your stay with no refunds if you misrepresent the number of guests brbr** This home is an ideal choice for families, traveling professionals, large groups seeking cost-effective accommodations, as well as couples looking for a cozy retreat. Instead of booking separate hotel rooms, which can be more expensive and separate everyone, this option keeps everyone together, fostering a more enjoyable and memorable trip.brbrID verification may be required in certain situations.brbrSecure your date now to prevent others from booking it. NOTE : we constantly look for ways to upgrade our space and add any new thing we feel might make guest stay more enjoyable, sometimes you might notice some changes/upgrade that we have yet to picture and upload.
Bed 4

Bed

Bath 2

Bath

Sleep 16

Sleeps
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$390.86

/ Nightly
Private Vacation Home

Clean, Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

Chicago, Illinois, United States

A gorgeous, spacious and relaxing 2 bedroom, 1 bathroom in Logan Square - one of Chicago's hottest neighborhoods.brbrWhile staying at this urban oasis you'll be centrally located to the city's best restaurants, sporting events, concerts and more. We provide high-end amenities for your stay including organic mattresses and high-end sheets.
Bed 3

Bed

Bath 1

Bath

Sleep 6

Sleeps
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$706.66

/ Nightly
Private Vacation Home

Envitae Hotel, 4BR Modern Sleek Apartment

Chicago, Illinois, United States

pA short distance from a water park, cycling, and more, this pet-friendly vacation home lets you experience it all. Armitage Avenue is an easy 14-minute walk away, so you can leave your car at the property, which offers onsite parking, or jump in your vehicle to make short work of the 3-minute drive to Lake Michigan. Check out other neighborhoods and see more of Chicago by hopping on a metro at North-Clybourn Station, just 5 minutes away by foot. /ppOnce you get back to this 1202-sq-ft vacation home, you can enjoy your surroundings with the firepit, fitness center and BBQ grill. As for the great indoors, you can come inside and enjoy the free WiFi and TV. /ppA living room, a dining area, air conditioning, and an office are featured at this 4-bedroom, 3-bathroom rental. Bathroom amenities include a hair dryer, towels, and toilet paper. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an electric kettle, and a microwave. And you won't have to pack extra clothes, because you'll have a washer and dryer, too. /p
Bed 4

Bed

Bath 3

Bath

Sleep 10

Sleeps

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Sleep 22

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$2427.16

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Bed 11

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Private Historical Mansion,Luxury Home in Chicago’s Gold Coast, Event-Capable.

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Bed 5

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Bath 5

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Sleep 14

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$3780.16

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$320.07

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Bed 1

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Bath 1

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Sleep 2

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$317.86

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Bed 2

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Sleep 6

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Bath 1

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Sleep 2

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$318.68

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Bed 2

Bed

Bath 1

Bath

Sleep 6

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