Vacation Condo Rentals By Owner In Chicago, IL

$638.31

Cozy Downtown MICH AVE #7 | gym+rooftop

Chicago, Illinois, United States

Feel at Home and Unwind when you come to Chicago.brbrGuests love staying with us because:br-Central Location on Grant Park (no car needed!)br-FAST WIFIbr-En-suite Laundrybr-Did we mention the Lake & Park are outside our front door br-Comfy Queen bedsbr-1 closed & 1 loft style bedroombr-Shared Rooftop Deck stunning viewsbr-Gymbr-3 blocks from Red `L` subwaybr-Close to Grant Park, The Bean, Soldier Field, MuseumsbrbrIf you`re interested in booking, see our FAQs below.brbrA manicured park. Waves crashing along the Lake Michigan. brbrWhen you`re here, you`re given a bird’s eye view of Chicago’s Front Yard, or more commonly known as Grant Park. brbrDrop your bags in your private space, complete with cozy beds, sky-high ceilings, and expansive windows allowing sunlight to pour in. brbrMake your way to the fitness center for a quick workout and then grab a breath of fresh air on the rooftop. brbrTime to hit the pavement. Saunter the art-filled halls at the Art Institute of Chicago. Wander past the 19th-century mansions on Prairie Avenue. Then fill your belly at The Dearborn (we recommend the mouth-watering fish and chips). Trade your sneakers for your go-to night-out pair. Let your ears guide you to the bustling bars. Try a new cocktail. Or order a pint and join the locals as they cheer on the Cubs. br brWorking, relaxing, living. Our spaces have all the other essentials you need for your stay. br- Contact-free check-in - Super-fast WiFibr- Fresh towels and bathroom essentials - Pre-cleaning before your arrivalbr- Plenty of space to workbr- HDMI cord for streamingbr- Fitness centerbr- Rooftopbr- En-suite laundrybr- Fully equipped kitchenbrbrYou access the property on Michigan Avenue. You are given a PIN or virtual key to access the front door.brbrOnce you get inside the building, you walk all the way back to the service elevator because it is the only elevator that takes you to the 12th floor Penthouse floor.brbrOnce to the floor, you walk to your apartment. Once in the apartment, you will find a modern space with two bedrooms, two bathrooms, a modern kitchen, and a living room equipped with TV.brbrYou have private, full access to the unit, the shared rooftop, and the shared gymbrbrWe`re here to help!brbrThe South Loop is such a dynamic mix of attractions and histories that the neighborhood tends to be seen as many different things to many different people. Consider the assorted areas that comprise the South Loop:brbrMuch of its eastern edge is encompassed by the Museum Campus, an impressive collection of cultural treasures that includes the Field Museum, Adler Planetarium and Shedd Aquarium. This campus sits on scenic lakefront parklands that are an extension of Grant Park. With 319 acres of green space and recreational fields, Grant Park is known as `Chicago`s front yard` to locals and also plays host to major city events such as Taste of Chicago, Chicago Blues Festival and Lollapalooza.brbrJutting out further into Lake Michigan is Northerly Island, a peninsula sought out by nature lovers, while along the southern edge the sports fans know Soldier Field as the stadium for the beloved Chicago Bears football team. Meeting attendees are most familiar with McCormick Place, the largest convention center in the country, which is also in the immediate area.brbrAnd yet there are even more facets to the South Loop. History buffs point out the Motor Row District along South Michigan Avenue and nearby Prairie Avenue District, the `Millionaire`s Row` that was lined with mansions belonging to Chicago`s most wealthy elite during the end of the 19th century.brbrIn the adjacent Printer`s Row neighborhood, urban loft condos now fill the commercial spaces in what was formerly the center of the Midwest`s publishing industry. Connections to this past are still seen within the venerable, independent book store and annual summer lit fest here. But business professionals and students have brought new life and redevelopment (though the vibe remains mellow), filling the restaurants, music clubs, smaller theaters and museums that have all established themselves in the community.brbrWe are very central and in close walking distance to the subway stops at Roosevelt and Harrison. We recommend NOT renting a car, and walking, ubering, and using public transit for your stay.brbr*There is a flight of stairs to access the elevatorbrbr❎No Local Guests (City or Suburbs)br Quiet hours: 10pm to 8ambr Minimum age of 24 to bookbrbr Last-Minute Bookings PolicybrTo ensure a smooth check-in, all same-day reservations will REQUIRE HOST APPROVAL. Please message us first so we can confirm and ensure everything is set for your arrival. This helps us make sure the space is properly prepared and ready for your stay.brbrThe base price for this home is for 4 guests only. There will be an extra guest fee of $10 per guest per night if your group exceeds to 4 people. br brSmall Pet Fee (Under 20lbs, No shedding) - $150brLarge Pet Fee (Over 20lbs) - $200 plus a $200 refundable security deposit and subject to host approval. brIf the pet sheds, we will require an additional $150 refundable Security deposit.brUnauthorized Pets - $250 plus any damages or additional cleaning costs incurredbrbrUnauthorized Late Check Out -Up to the cost of any impacted nights subsequent to originally scheduled check-out brSmoking in Room/Common Area - $500.00 minimum charge and eviction from Rental Unit brExcessive Cleaning - Up to $125.00 per hour of additional cleaning needed brDamaged or Missing Items - Varies depending on cost of itembrMissing Keys - $50.00 minimum chargebrMissing Fob - $150.00 minimum chargebrbrNoise Complaints: potential warning issued or, if necessary, eviction with no refund and a charge of up to $1,000.00 brParty in Unit or Common Area - Up to $2,000.00 plus any damages to the unit brForgotten Personal Belongings - $75.00 minimum chargebrIf items are left behind and guest wants it mailed back, guest will be charged a $50 trip fee along with the shipping costbr brNo Unauthorized Late Check Out without notice from Host.brIf our cleaners agree to early check-in / check out they charge us: br-Early check-Ins at 2pm $100 br-Late Check-Outs at noon $100 br brAll guest names and ages must be registered before you are allowed to check in. br brThere is a NOISE MONITORING system within the home to track decibel noise level. Please respect our neighbors and do not get too loud outside quiet hours :)brbrbrQ: Is the neighborhood safe brA: Very much so. 24 hours a day.brbrQ: What about PARKING brA: We don’t recommend driving because we are so centrally located. You may find a lot or garage nearby for $18-30 / night. There are multiple garages or valet services within 2 blocks. brbrQ: Do I need to bring towels, a hair dryer, or linens brA: Nope! we provide all these things. We also provide you and your guests with a starter pack of toilet papersbrbrQ: When can I check in or check out brA: Check in is 4pm and check out is 10am. Early check ins can be difficult if there are guests who checked out same day. We ask for an early check-in, or a late-check out fee, if you request either.brbrQ: Is the Gym and Rooftop shared brA: Yes, it is shared so please be respectful of other tenants and guests using the space.brbrQ: Luggage Drop-Off / Storage brA: If you do not have flights that coincide with our check-in and checkout times, you may store your bags with Radical Storage near our property. It allows you to store your bags for your optimal time :)brbrQ: Can I come and go as I please brA: Yes. And we wouldn`t trust any listing with which this isn`t the case.brbrQ: Is the place professionally cleaned between guests brA: Yes, and we take pride in providing a clean home for guests.brbrQ: What`s my total booking price brA: We honestly have no idea. With fees included, it only shows the guest how much they pay. This figure should be present after you enter your dates. Note that, pricing varies on a daily basis, and it actually uses some crazy algorithm to adjust it automatically, so I don`t actually control this.brbrQ: Are the beds comfortable brA: Very. Some guests say they`re the best they`ve ever slept on!brbrNo Agency Relationship. Nothing herein contained shall be deemed to authorize or empower either party to act as agent for the other party to this Agreement, or to conduct business in the name, or for the account, of the other party to this Agreement.brbrGuest VerificationbrAs part of our vetting process, we may ask guests to confirm a few details — such as their names, ages, where they’re traveling from, or their travel plans — before accepting a booking. In some cases, we may also request a valid government-issued ID for verification purposes. This helps us ensure that all stays are safe, transparent, and in line with our house policies.brbrUnresponsive GuestbrIn some cases, if a guest does not respond within a reasonable period, we reserve the right to cancel the reservation. brFor same-day bookings, this timeframe is up to 2 hours or less. For all other bookings, this timeframe is up to 8 hours. This ensures that we can provide the best experience and availability for all our guests.brbrOnline Check-In & Rental Agreement RequiredbrBefore receiving check-in instructions, all primary guests must complete our online check-in form and review/sign our rental agreement. This helps verify guest details and ensures a smooth, secure arrival.brbrEXTRA GUEST CHARGEbrThe base price covers 4 guests. For more than 4 guests, there is an extra guest fee of $10 per guest for the full number of nights.brExample: 1 extra guest for a 5-night stay = $10 × 5 nights = $50.brbrRefundable Security Deposit: A $300 refundable security deposit is required and will be `held` or `authorized` (not `charged`) by Chicago Hospitality Club on your card. Any property damage or extra charges may be deducted from the deposit. VRBO collects platform payments/charges separately, while Chicago Hospitality Club handles the deposit, so seeing both on your statement is normal. The deposit is automatically released 3-7 days after checkout.brbrKeys & AirTags:brFor

2

Bed

2

Bath

5

Sleeps

$318.43

/ Nightly

Condo

Luxury, spacious first floor brownstone in east Lincoln Park

Chicago, Illinois, United States

Enjoy the best of Chicago’s neighborhoods, parks and lakefront from the comfort of this 2400 square foot home with two separate large living spaces. Outside is the historic facade and a quiet tree-lined street in the upscale Lincoln Park neighborhood. Inside is the luxury and convenience of a modern home with beautiful hardwood floors, a gas fireplace, whole house audio controlled by Sonos, and a fully-stocked chef’s kitchen.brbrIf you’d rather not cook, you are located in the perfect place to explore the many restaurants and bars the neighborhood and the city has to offer. The location provides easy access to transportation around the city by train, bus or ride share services. While the hustle and bustle of city life can be found just around the corner, our street is quiet and tree lined, perfect for a good night’s sleep. The park is just a block away and beyond that the lakefront provides ample opportunity for exercise and recreation with it’s walking and bike paths and beaches. brbrThe home encompasses the first floor and lower garden level of the building. The unit has it’s own entrance from the charming front porch with a vestibule. The family room and dining room face the street where you can read a book or watch the 55” flat screen TV as you enjoy the fire and watch the world go by out the large front window decorated with period stained glass. Also on the main floor are the primary bedroom with king bed, extra large walk-in master closet and primary bath which features a large shower and a soaking tub, along with dual sinks. There is a 1/2 bath in the hallway of the main floor, and finally, the gourmet kitchen with large island, gas range, dishwasher, microwave and large refrigerator. Off the kitchen, enjoy the comfort and quiet of the covered back deck with its large sectional couch and gas grill.brbrThe lower level of the unit features a large second family room with a pool table, 82” smart TV and two couches that fold out to the most comfortable pull-out beds you’ve ever experienced, one a king and the other a queen. Down the hall, there are two bedrooms, one with a king bed and the other with a queen. These bedrooms are serviced by another full bathroom. Finally, there is a proper laundry room with extra large washer and dryer and plenty of room to hang dry clothes.brbrA secured parking space is located directly behind the unit. Entry to parking area from the street is accessed through an electronic gate. In 2025/26, a 2nd spot is available four spaces down for $275/mo.brbrThe home is owner-occupied part of the year so it is fully stocked with linens, towels, beach towels, hair dryers, iron and ironing board, cookware and basic tools. In season, there are four bikes for your use. We have great neighbors and they are our friends so we ask that anyone using our home respect that relationship with thoughtful behavior.brbrHome is not ADA accessible. brbrCheck in/out policy to be tailored to guest needs. Come and enjoy this home in the heart of Lincoln Park.

Bed

Bath

Sleeps

$541.73

/ Nightly

Condo

Wrigley Field MVP Suite 1 Bedroom Apartment

Chicago, Illinois, United States

Recently built from the ground up and featured on the Travel Channel, you will love our beautifully furnished one-bedroom apartment just steps from Wrigley Field. Situated as close to the entrance to the park as you can get within one of the iconic Wrigley Rooftops. You will be able to immerse yourself in the surrounding Wrigleyville festivities while relaxing comfortably in your fully furnished, private apartment. br Our one-bedroom MVP Suite will accommodate 4 guests comfortably with a king size bed in the bedroom and a sleeper-sofa in the living room. Beds are equipped with luxurious down bedding and high thread-count bed linens as well as top-rated memory foam mattresses. br The MVP Suite also boasts a fully equipped gourmet kitchen, fireplace, dining area, and washer and dryer in-unit. With the combination of the beautiful amenities in our brand new MVP Suite and the exciting surroundings of Wrigleyville, you will be sure to enjoy yourself in this unique location. Don't forget to bring your baseball glove for those fly balls!brbrbrbrCity of Chicago License # 2446867

1

Bed

1

Bath

4

Sleeps

$312.28

/ Nightly

Condo

2-bedroom condo in perfect Chicago with WiFi, AC. Start your getaway

Chicago, Illinois, United States

Escape to a marvelous 2-bedroom condo in Chicago. This serene retreat features a king bed and a twin bed, perfect for a tranquil night's sleep. With a cozy bathtub/shower, guests can unwind after a day of exploring the city. Enjoy all that Chicago has to offer when you stay at our place.

Bed

Bath

Sleeps

$822.45

/ Nightly

Condo

Spacious 4-bedroom condo in wonderful Chicago with WiFi, AC

Chicago, Illinois, United States

Chicago is waiting for you at this 4-bedroom condo. Step into this enchanting space with 3 queen beds and 1 king bed, perfect for a soothing getaway. Enjoy the delightful living room with a cozy sofa bed for extra comfort. With WiFi, a washing machine, AC, and more, your stay will be stress-free. We'll be available to answer any questions while you stay at our place.

4

Bed

2

Bath

9

Sleeps

$486.5

/ Nightly

Condo

NEW! Fully Updated Jr. 1 Bed, Steps from Lincoln Park by AllSet Turnover

Chicago, Illinois, United States

My bright and stylish Jr. 1-bed, 1-bath condo is located in a prime LincolnbrbrPark location. Thoughtful touches can be felt throughout with an openbrbrliving/bedroom area, queen size bed (additional queen sofa bed), full kitchenbrbrand modern bath—perfect for solo travelers or couples. You’ll be steps frombrbrLincoln Park, the lakefront, shops, dining, and public transit. Enjoy easybrbrcity living in one of Chicago’s most walkable neighborhoods. Book now andbrbrstart planning your next Windy City adventure! brbrGeneral Policies: brbr brbrGuest Age Policy – Guests aged 18-24 may book on an exception basis. Pleasebrbrinclude your age, reason for booking, and who will be staying with you in yourbrbrinquiry. brbr brbrLocal Guest Policy – Local guests are permitted to book on an exception basisbrbronly. Parties, gatherings, and group events are strictly prohibited.brbrUnauthorized gatherings or events will result in termination of reservationbrbrwithout refund. brbr brbrPrimary Guest Responsibility – The booking guest must stay for the fullbrbrduration and is responsible for all guests. If booking on behalf of someonebrbrelse, please contact us to discuss exceptions. brbr brbrParking – Street parking may be available but is not guaranteed. Read allbrbrposted signs to avoid tickets or towing. To secure a spot, use parking appsbrbrlike SpotHero or ParkWhiz. brbr brbrCity Noise – Some ambient noise is part of city living. brbrTAX ID: R25000128452brbrbrbr

1

Bed

1

Bath

4

Sleeps

Select Dates for Price

Condo

Club 1919 – Chic Urban Retreat w/ Private Patio in the Heart of Chicago

Chicago, Illinois, United States

Discover comfort, style, and unbeatable access to everything Chicago has to offer from this design-forward 1-bedroom, 1.5-bath condo with indoor garage parking in the vibrant South Loop. The spacious unit features a cozy queen bed in sound proofed bedroom, modern furnishings, and all the essentials — including central heat and AC, in unit washer/dryer, and fast Wi-Fi and cable.brbrWhat truly sets this place apart A rare 400 sq. ft. private patio — perfect for morning coffee, evening wine, entertaining a few friends or colleagues or just lounging after a day of exploring the city. You're just steps from the CTA Red & Green Lines, restaurants, museums, and the lakefront.brbrNeed recs We’re happy to share our favorite local spots during your stay.

1

Bed

1

Bath

2

Sleeps

$252.19

/ Nightly

Condo

Great condo in a great location!!

Chicago, Illinois, United States

2 bedroom 2 bathroom. Gated parking in the back. Washer and dryer in the unit. Fully furnished.. a/c and heat that guest control. WiFi and flat screen TVs also provided. Secure building. I love the safe environment. Restaurant and hospital is in walking distance. Lake front is a 7 minute drive away. Down town Chicago is a 10 minute drive also..

2

Bed

2

Bath

4

Sleeps

$121.29

/ Nightly

Condo

Beautiful, furnished condo with great view in luxurious River North high rise

Chicago, Illinois, United States

Super host (on another platform) and now looking forward to hosting here on VRBO! This is the perfect home base for your trip to Chicago. This beautifully furnished condo is steps from Michigan Avenue shops and the best boutiques and restaurants. Includes 24/7 doorman, access to newly renovated bbq deck, pool and sun deck, gym, movie theatre, laundry room, business center and large party room. brbrYou'll enjoy peace & quiet on a high floor with an amazing south-facing view.brbrParking space is available (at a fee). Dedicated covered parking space must be reserved at time of booking.brbrThis is a one bedroom, furnished unit which includes bedding, towels and all the kitchen basics for cooking. The main room has a couch, television and table, and the bedroom has a very comfy bed as well as a small sitting area. In the bedroom closet you will also find a blow-up bed and extra bedding should you need it for more than two guests.brbrThink of this as a home away from home. Any of the condo building's amenities are available forbryour use.brbrNote:brThis condo may only be rented for stays of 32 nights or longer due to city of chicago regulations. Also, all guests will be provided with the condo building rules, and must sign a lease rider and lease (lease refers to VRBO agreement 100%) which is required by the condo association.

1

Bed

1

Bath

3

Sleeps

$128.64

/ Nightly

Condo

Historic Gold Coast Condo - Half Block From Beach & Major Attractions

Chicago, Illinois, United States

Charming one bedroom, historic Gold Coast Greystone on a *quiet* residential street awaits your arrival. Enjoy an evening glass of wine overlooking late 1800s mansions from the balcony, or wind down with a stroll through Chicago’s most exclusive and historic neighborhood. Just steps from the Lake, Oak Street Beach, The Mag Mile, museums, leading city attractions, dining, nightlife, world-class shopping, grocery stores, cafés, and running paths— this flat sits in arguably THE best location to enjoy the city. Live like a local near all the action. brbrFully appointed kitchen, high speed Wi-Fi, and in-building laundry facilities ensure guests all the comforts of home and reliable connectivity for remote work. AC in the summer, toasty radiant heat in the winter, and cool lake breezes from the open balcony door at your discretion..brbrGuest access: Private balcony. Laundry room is within a common area on the first floor (coin operated). Free parking available on the street in front of the condo using complimentary guest permit passes provided with this booking for the duration of your stay.

Bed

Bath

Sleeps

$900.45

/ Nightly

Condo

Gather Together & WFH in Piece of Chicago History

Chicago, Illinois, United States

‘The Wellington’ was created for those looking to gather in a piece of Chicago history. This thoughtfully refurbished 1920s factory is the hidden gem of Lakeview & Roscoe Village - secluded from the hustle, yet a quick walk to world class restaurants, bars & Wrigley Field. Large enough to host families & friends uniting together, yet configured for travelers looking to work from ‘home’ in the heart of The Second City.brbr→ 2,400ft² / 222m²br→ Entire first floor with private accessbr→ Free parkingbr→ Quiet & safe family neighborhoodbrbrThe front half of the space is designed as a fully open floor plan including an expansive kitchen island, exposed brick living room with smart TV and dining table for 10.brbrTwo of the bedrooms are off the main hallway across from one full and one half bathroom. The first bedroom (aka. the green room) has a full-size bunk bed large enough to sleep four. The work station is set up with Zoom in mind - backgrounds are important!brbrThe second bedroom (aka. the blue room) sleeps two with a queen-size bed featuring old school architectural drawings against a modern abstract painted backdrop.brbrThe primary suite is secluded in the back of the unit with a small step up into a private bathroom and spacious bedroom (aka. the black & white room) with his & her closets.brbr+ Wireless internet is always available.br+ Artisanal coffee will be waiting for you from a local roaster along with a variety of gourmet teas.br+ Kitchen has a french press, tea kettle, toaster, cookware, utensils, glasses, cutlery, sharp knives, cutting boards, baking sheets and all the basic tools like wine openers, cheese graters, vegetable peelers, pizza cutters, etc.br+ Bathrooms are stocked with all the amenities of home including shampoo, conditioner, body wash, hair dryer, paper towels, toilet paper, tissue, sponges, hand soap and dish soap.br+ TV with streaming options.br+ Luggage racks and hangers.br+ Foldable crib is available in the primary suite closet.brbrGuest accessbrDuring your stay, the whole unit is yours and only yours. You will have a code for key-less access to come and go as you please.brbrWasher and dryer are available in the basement. If you need access, don't hesitate to ask!brbrOther things to notebrWe do have a commuter train (Metra) that goes by, on average, every hour - it's 10 seconds and minimal noise indoors.brbrPlease remember that you're staying in a house, not a hotel. Please treat the space with respect - it was designed for our family and we hope you treat it that way.brbrIf any problems arise, we will do our best to take action ASAP.brbrEarly check-ins and late check-outs are difficult to accommodate, however please let us know if you need to drop off bags early or keep them late.

3

Bed

2

Bath

12

Sleeps

$187.56

/ Nightly

Condo

Stunning 3 BR in prime Chicago location

Chicago, Illinois, United States

Enjoy the ultimate Chicago experience with a comfortable stay at this large, luxurious, sun-filled stylish 3BR condo. Unbeatable central location in an upscale Lincoln Park neighborhood puts all the very best of Chicago within easy reach. brbrSurrounded by spectacular restaurants, bars, theaters and world-class architecture. 1200 acres of Lincoln Park, a world class Zoo, Wrigley Field, Navy Pier, Art Institute, River North and Downtown attractions are only a 5-10 minute ride or a quick train away.brbrBig living room & separate dining room. In-unit laundry & New Kitchen. Tall ceilings & beautiful Hardwood floors! And the location rocks! Close to the trains & Close to all the hot spots in Lincoln Park! Free street parking or option to reserve a dedicated covered garage spot.

Bed

Bath

Sleeps

$393.31

/ Nightly

Condo

Spacious 3BDR Luxury Penthouse 10 min from Downtown Chicago

Chicago, Illinois, United States

Stylish 3BD/2BA penthouse with high ceilings, oversized windows, stainless steel appliances, quartz countertops, in-unit laundry, and parking. Located in Bronzeville, just 10 mins to downtown, 8 mins to the University of Chicago, 18 mins to Soldier Field, and 25 mins to Midway Airport. Perfect for families or groups seeking comfort, convenience, and a premium city stay.

Bed

Bath

Sleeps

$1278.32

/ Nightly

Condo

Wrigley Field Home Run 4 Bedroom, 2 Bathroom

Chicago, Illinois, United States

Welcome to Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up and featured on the Travel Channel, you will love our beautifully appointed four-bedroom apartment just steps from Wrigley Field. Situated as close to the entrance to the park as you can get within one of the iconic Wrigley Rooftops, you will be able to immerse yourself in the surrounding wrigleyville festivities while relaxing comfortably in your fully furnished, private apartment. br Our four-bedroom Home Run Suite will accommodate 9 guests comfortably with queen size beds in three of the bedrooms and a queen and twin size bed in in the fourth bedroom. All beds come with luxurious down bedding and high thread-count bed linens as well as top-rated memory foam mattresses. br The suite also boasts a fully equipped gourmet kitchen, gas fireplace, dining area, and washer and dryer in-unit. With the combination of the beautiful amenities in our brand new Home Run Suite and the exciting surroundings of Wrigleyville, you will be sure to enjoy yourself in this unique location. Don't forget to bring your baseball glove for those fly balls!

4

Bed

2

Bath

9

Sleeps

$557.81

/ Nightly

Condo

Condo in Hyde park 2 min UofC 6mi downtown

Chicago, Illinois, United States

Your cozy getaway awaits in Chicago at this brilliant condo. With 4 bedrooms including 2 queen beds and 2 full beds, this terrific space is perfect for families or groups of friends. Enjoy the convenience of amenities like a washing machine, WiFi, heating, AC. With 2 bathrooms to accommodate guests, this tremendous condo provides a comfortable and spacious stay. We hope you enjoy what our place and Chicago has to offer.

4

Bed

2

Bath

13

Sleeps

$1262.36

/ Nightly

Condo

Gorgeous 3BR River North Condo - Free Parking

Chicago, Illinois, United States

Experience luxury in this stunning downtown Chicago condo, nestled in River North. Ideal for families & business travelers, this 2-story retreat features a gourmet kitchen, elegant dining area, and a cozy basement theatre.brbrRelax in stylish bedrooms or indulge in the basement spa-like amenities. With complimentary parking and easy access to vibrant dining/nightlife, this exceptional property promises an unforgettable Windy City experience.brbrFor reference, Hotel Godfrey is less than 400ft away.

3

Bed

2

Bath

8

Sleeps

$143.47

/ Nightly

Condo

Fully Furnished Gold Coast Luxury Condo with Sunset View Ideal for 30+ Day Stays

Chicago, Illinois, United States

Luxury High-Rise Condo in Chicago’s Gold Coast, Perfect for Long-Term StaysbrbrExperience upscale city living in this fully furnished high-floor condo on the border of Chicago’s Gold Coast and River North. Ideal for extended stays (30 days or more), this spacious one-bedroom unit features a custom kitchen with granite countertops, stainless steel appliances, and a breakfast bar. Relax in the marble bathroom with a double vanity and jacuzzi tub, and take in stunning west-facing sunset views through floor-to-ceiling windows.brbrProperty Highlightsbr• In-unit washer and dryerbr• High-speed WiFi and dedicated workspacebr• Spa-style bathroom with jacuzzi tubbr• Custom kitchen with full-size appliancesbr• Piano, pool table, and access to a movie theaterbr• Fire pit, outdoor dining area, and BBQ grillbr• Indoor fireplace and ceiling fanbr• Smart TV and multiple entertainment optionsbr• Fully stocked kitchen with dishwasherbr• Pet-friendly with assistance animals always allowedbrbrBuilding Amenitiesbr• Outdoor pool and hot tubbr• 24-hour doormanbr• Fitness center and gymbr• Business center and theater roombr• Elevator accessbr• Paid parking available on premisesbrbrIdeal ForbrTraveling professionals, nurses, medical students, and corporate guests. Minutes from Northwestern Memorial Hospital, Lurie Children’s, Rush University Medical Center, and more.brbrNeighborhood OverviewbrSteps from Michigan Avenue, you will have access to luxury shopping, Oak Street Beach, top-rated dining, Whole Foods, Trader Joe’s, and public transit. One of Chicago’s most walkable neighborhoods, offering a perfect mix of classic charm and modern convenience.

Bed

Bath

Sleeps

$667.13

/ Nightly

Condo

Spacious 3/2 Duplex In Wicker Park Area

Chicago, Illinois, United States

I promise you'll feel right at home in this lovely 3 bed/2.5 bath duplex down. It's perfect for a family, parents get to stay upstairs, kids downstairs with their own rec room w/Smart TV, OR groups visiting this wonderful city. It's a bright open floor plan with living room, dining room, kitchen, master bed/bath, and powder room on main floor all with hardwood floors. The lower level features a huge family room with wet bar, game table, 2 bedrooms (2 twins/1 Queen) a full bath and murphy bed for a little extra sleeping room when needed. There's a gas burning fireplace on main level and on the lower level. Open eat-in kitchen with premium appliances, granite countertops and breakfast bar. The master bedroom features a king size bed, en suite bath with separate shower w body sprays jacuzzi tub. In unit washer/dryer. It also has 2 private outdoor spaces, deck off master, and garden terrace off family room. Secured free parking and plenty of street parking. Location, location, location! It's 2 blocks to the Blue Line/Division stop and only steps to the 56 bus at Milwaukee Ave. Walk to Division St shops, restaurants and bars. 1 mile to popular Fulton Market restaurants , 2 miles to loop, Millenium Park, and Michigan Ave, 3 miles to Wrigley Field.

Bed

Bath

Sleeps

$435.98

/ Nightly

Condo

The Bucktown House - Suite #4 - Heart of Wicker/Bucktown, 10 minutes to downtown

Chicago, Illinois, United States

CITY OF CHICAGO VACATION RENTAL LICENSE #2246788brbrWe have been operating as a professionally managed vacation rental since 2009. Please check out our many great reviews. We have many reviews on the other major vacation rental website. Please inquire and we can send some over. Our other properties are located a few blocks away on a quiet tree-lined street. In total our units can accommodate 23 guests, so please inquire about availability for larger groups. You can also check out our profile to view the other listings. brbrLocated on the lively Damen Avenue where you'll have world-class culture at your fingertips. Our thoughtfully designed interiors will accommodate couples, solo adventurers, business travelers, families (with kids), and big groups.brbrThe SpacebrbrOpen the door of this unassuming second floor walkup, and you’ll find a truly singular place to live while you explore the hip Bucktown/Wicker Park neighborhood. The custom furniture and décor were hand picked by interior designer Jean Alan, all with your comfort in mind. We’ll provide luxe amenities for your stay in this 3 bedroom, 2 bath stunner, a spacious haven for your family or friends.brbrIf you love to entertain, you’ll be thrilled by the formal dining room and gourmet kitchen. If you need a relaxing respite from the city, you’ll adore the sun room off the kitchen. This unit is full of thoughtfully designed features:brbrLiving room features a custom sofa bed that can pull out and sleep two.brSmart TV with streaming services, Xfinity TV Cable Channels, and Xfinity Gigabit Internet Service.brBeautifully tiled bathrooms with (MALIN+GOETZ) toiletries, plush towels, and bathrobes.brGourmet kitchen with custom maple cabinets, granite countertops, a gas range, dishwasher, microwave, frost free refrigerator, and a filtered water system.brEnclosed porch/sun room with breakfast nook.brFormal dining room with a marble table that seats six.brQueen-sized bed with a custom upholstered headboard, reading lamps, and flat screen TV in the master bedroom.brTwo twin-sized beds with reading lamps in the guest bedroom.brIn the front bedroom, there’s a trundle bed (twin size bed with a pull-out twin underneath).brHeat and central air conditioning with individual climate control.brLaundry facilities in unit with complimentary detergent.brStreet parking is ample and free.brbrGuest AccessbrbrThe building is secured with keyless punch code entry system. The apartment is on the second floor, up the stairs.brbrThe NeighborhoodbrbrBucktown is not just a peaceful residential enclave, it’s also full of incredible arts, dining and activities. The Bucktown House is within walking distance of Holstein Park and The 606 Bloomingdale Trail, a walking/biking trail surrounded by installation art and creative urban landscaping.brbrStroll down Damen Avenue for a shopping experience second only to Michigan Avenue, or for a diverse selection of international cuisine. In the evening you can take in a show at the Gallery Cabaret, the Trap Door Theater, or Gorilla Tango Theater - all within easy walking distance of home.brbrThe surrounding neighborhood has no shortage of dining options, from single-barrel bourbon and pork belly tacos on the outside patio at Big Star to nine-course menus at Schwa, an upscale BYOB. Or if it's nightlife you're after, try Bangers & Lace for a hunting lodge vibe or work your way through the Chop Shop's cocktail program.brbrAnd if you tire of the local scene, just take the blue line and in 20 minutes you’ll be near Navy Pier. Bucktown is a locus of Chicago’s beauty, entertainment, and culture - book now to stay in the heart of it all.brbr**No pets are allowed, especially cats. This includes support cats, service cats and pet cats. The owner has a severe cat allergy and any cat dander in the apartment would cause a major health threat.

Bed

Bath

Sleeps

$346.79

/ Nightly

Condo

The Chic Urban Oasis Near the Lake!

Chicago, Illinois, United States

Welcome to our Urban Oasis located in Chicago's Historic Southshore! Only a 15 min drive to Downtown & a 5 min walk to the lake! 5 min walk to the Metra Southshore Train Station. We are walking distance from a Golf Course. While you may encounter the rich tapestry of city life, including diverse residents, we want to assure you that the area is safe and welcoming. It's the perfect spot for those looking to immerse themselves in the true Chicago experience while enjoying the comforts of home.

4

Bed

1

Bath

6

Sleeps

Vacation Condo Rentals By Owner In Chicago, IL

$638.31

$318.43

$541.73

$312.28

$822.45

$486.5

$252.19

$121.29

$128.64

$900.45

$187.56

$393.31

$1278.32

$557.81

$1262.36

$143.47

$667.13

$435.98

$346.79

Rent a place that suits your needs

Most popular vacation rentals in Chicago

$2319.21

$2427.16

$2731.80

$2999.50

$3259.71

$3780.16

$320.07

$317.86

$318.18

$318.68

Most Popular Cities in Illinois