Vacation Rentals By Owner In Chicago, IL

$211.0

Lux West Loop Studio w/ Pool, Gym, nr. Restaurant Row, by Blueground

Chicago, Illinois, United States

Feel at home wherever you choose to live with Blueground. You’ll love this pretty West Loop furnished one bedroom apartment with its modern decor, fully equipped kitchen, and comfortable living room with great views. Ideally located, you’re close to all the best that Chicago has to offer! (ID #CHI275)brbrDesigned with you in mindbrbrGorgeous furniture, fully equipped kitchen, smart TV, and a premium wireless speaker are just a few of the amenities you’ll find inside this one bedroom apartment. Ideally located in Chicago, you’ll find a lot to love outside as well. When you’re ready to relax, you’ll be happy to discover every Blueground bedroom comes with superior quality mattresses, fully stocked linens, and cozy towels. We handle everything so you can simply show up and start living. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryerbr - Elevatorbr - Swimming poolbr - Washing machinebr - Loungebr - Parkingbr - Pets allowedbr - Rooftop BBQbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrLocated in West Loop, this furnished rental invites you to explore the edges of downtown Chicago. From endless dining and bar options to art galleries and stylish shops, West Loop has emerged with so much to offer daily. During weekends, residents savor trips to the Chicago French Market and the vibrant strip of Randolph Street. The latter is known as “Restaurant Row” and is lined with some of the city’s best eateries. Fulton Market, one of the hippest and fastest-growing neighborhoods, is ideal for dinner and drinks. Union Station is only a 5 to 10 minute walk away.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brParking is offered based on availability and is subject to a fee.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - This apartment is located near a railway, so expect to hear moderate noise when trains passbr - This is a guarded building equipped with a doorman/concierge at all times

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$232.0

/ Nightly

Apartment

Bright Loop 1BR w/ Gym, Pool, nr. Financial District, by Blueground

Chicago, Illinois, United States

Show up and start living from day one in Chicago with this cheery one bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped The Loop home with stunning views over the city. (ID #CHI211)brbrDesigned with you in mindbrbrAs with any Blueground apartment, you’ll find a thoughtfully designed space complete with beautiful furniture and a fully equipped kitchen in this one bedroom property. And, thanks to our superior quality mattresses, fully stocked linens, and towels, you can relax knowing you’ll always feel comfortably at home. When you’re ready for some fun, you can take in the Chicago vibes or bring the entertainment to you with the premium wireless speaker or smart TV. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryerbr - Elevatorbr - Swimming poolbr - Washing machinebr - Loungebr - Pets allowedbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is situated in the most dynamic and convenient place to live in Chicago, The Loop. With its endless shopping, fine dining, stunning park, river and lake views, and entertainment opportunities, everything is possible at a moment’s notice. The area is a cultural getaway for professionals and students, who can combine work with pleasure. Discover landmark buildings like the Willis Tower and The Art Institute of Chicago. Millenium Park, near Lake Michigan, is always worth a visit. The Loop is within reach of accessible transportation, offering non-stop public transit, buses, and taxis. Union Station is approximately a 10 minute train ride.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - This apartment is located near a railway, so expect to hear moderate noise when trains passbr - This is a guarded building equipped with a doorman/concierge at all times

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2

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$336.0

/ Nightly

Apartment

Ideal Loop 1BR w/ Roof deck & Gym, near Michigan Avenue, by Blueground

Chicago, Illinois, United States

Feel at home wherever you choose to live with Blueground. You’ll love this beautiful The Loop furnished one bedroom apartment with its modern decor, fully equipped kitchen, and comfortable living room with great views. Ideally located, you’re close to all the best that Chicago has to offer! (ID #CHI193)brbrDesigned with you in mindbrbrAs with any Blueground apartment, you’ll find a thoughtfully designed space complete with beautiful furniture and a fully equipped kitchen in this one bedroom property. And, thanks to our superior quality mattresses, fully stocked linens, and towels, you can relax knowing you’ll always feel comfortably at home. When you’re ready for some fun, you can take in the Chicago vibes or bring the entertainment to you with the premium wireless speaker or smart TV. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr Queen Bed, 63in/160cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - Doormanbr - Dryerbr - Elevatorbr - Washing machinebr - Loungebr - Pets allowedbr - Rooftop BBQbrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is situated in the most dynamic and convenient place to live in Chicago, The Loop. With its endless shopping, fine dining, stunning park, river and lake views, and entertainment opportunities, everything is possible at a moment’s notice. The area is a cultural getaway for professionals and students, who can combine work with pleasure. Discover landmark buildings like the Willis Tower and The Art Institute of Chicago. Millenium Park, near Lake Michigan, is always worth a visit. The Loop is within reach of accessible transportation, offering non-stop public transit, buses, and taxis. Union Station is approximately a 10 minute train ride.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPets are welcome, though weight limits and breed restrictions apply and may incur fees.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - This apartment is located near a railway, so expect to hear moderate noise when trains passbr - This apartment is located in an older building, there may be a few quirks

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2

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$78.0

/ Nightly

Apartment

Blueground | The Loop, AC, w/d, nr Willis Tower

Chicago, Illinois, United States

Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped The Loop home with stunning views over the city. (ID #CHI1232)brbrDesigned with you in mindbrbrThoughtfully designed with bespoke finishes, modern furnishings, and a fully equipped kitchen, you’ll enjoy that “I’m home” feeling with this Blueground apartment. Whether you’re lounging in your sophisticated living room streaming the latest and greatest entertainment on the smart TV or premium wireless speaker, or getting some well-earned rest on the superior quality mattress with fully stocked linens, you’ll fall in love with everything this The Loop apartment has to offer. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - Dryerbr - Washing machinebrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is situated in the most dynamic and convenient place to live in Chicago, The Loop. With its endless shopping, fine dining, stunning park, river and lake views, and entertainment opportunities, everything is possible at a moment’s notice. The area is a cultural getaway for professionals and students, who can combine work with pleasure. Discover landmark buildings like the Willis Tower and The Art Institute of Chicago. Millenium Park, near Lake Michigan, is always worth a visit. The Loop is within reach of accessible transportation, offering non-stop public transit, buses, and taxis. Union Station is approximately a 10 minute train ride.brbrOther things to notebrbrThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brPlease keep in mind that this is a walk up building.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.brbr Also notebr - This apartment's central location means it can be noisy at timesbr - This apartment is located near a railway, so expect to hear moderate noise when trains passbr - This apartment is located on a busy street

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$120.0

/ Nightly

Apartment

Blueground | The Loop, pool & gym, nr Willis

Chicago, Illinois, United States

Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming home to this thoughtfully furnished, beautifully designed, and fully equipped The Loop home with stunning high floor views over the city. (ID #CHI1178)brbrDesigned with you in mindbrbrAs with any Blueground apartment, you’ll find a thoughtfully designed space complete with beautiful furniture and a fully equipped kitchen in this one bedroom property. And, thanks to our superior quality mattresses, fully stocked linens, and towels, you can relax knowing you’ll always feel comfortably at home. When you’re ready for some fun, you can take in the Chicago vibes or bring the entertainment to you with the premium wireless speaker or smart TV. This apartment also offers in-apartment laundry.brbrSleeping arrangementsbrbr King Bed, 70.8in/180cmbrbrAmenitiesbrbrBuilding amenities unique to this one bedroom apartment include an on-site:brbr - BBQ Areabr - Doormanbr - Dryerbr - Elevatorbr - Game roombr - Swimming poolbr - Washing machinebr - Loungebr - Media roombrbrArrival and ongoing supportbrbrThe entire apartment is yours to enjoy!brbrThroughout your stay, you’ll have access to our Client Experience team through the Blueground App. You can schedule additional cleanings, submit maintenance requests, and view our neighborhood recommendations with just a few taps.brbrWe’ll share all details upon confirmation of your stay.brbrIdeally LocatedbrbrThis furnished rental is situated in the most dynamic and convenient place to live in Chicago, The Loop. With its endless shopping, fine dining, stunning park, river and lake views, and entertainment opportunities, everything is possible at a moment’s notice. The area is a cultural getaway for professionals and students, who can combine work with pleasure. Discover landmark buildings like the Willis Tower and The Art Institute of Chicago. Millenium Park, near Lake Michigan, is always worth a visit. The Loop is within reach of accessible transportation, offering non-stop public transit, buses, and taxis. Union Station is approximately a 10 minute train ride.brbrOther things to notebrbrBuilding amenities may have an extra cost.brThis Blueground apartment has flexible lease options, allowing you to book it for one month, a year, or more.brWe take great pride in ensuring every photo displayed is shot in our own units with our actual furnishings. That said, we regularly refresh our decor and furniture arrangement, which may differ from what’s pictured.brbrA security deposit of $500 is required at booking, which will be returned within 2-4 weeks after the check-out, minus any deductible damages.

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$905.07

/ Nightly

Private Vacation Home

Last-Minute Chicago home with Rooftop Views +Private HOT TUB -Garage-Sleeps 12

Chicago, Illinois, United States

Hurry - only a few weekends left this season! Experience Chicago in style from our Villa, your private 3-story luxury retreat near the Bean.brbr! Free Private Garagebr! Hot Tubbr! 360° Roof Deck with Skyline + Willis Tower ViewsbrbrPerfect for family trips, romantic escapes, or friend getaways!br+Private keyless entrybr+Luxury KING, 2 QUEEN beds + cozy fireplacebr+Full kitchen + balconybr+ 3 Smart TVs (Netflix, Disney+, Prime)br+ Super-fast WiFibrbrBook now for your unforgettable Chicago stay!brbrKey Features:brbr- King Suite: Fireplace, Smart TV, and a spa-like steam shower.br-Queen Suite: Private access to a stunning roof deck.br- Fully stocked kitchen with a balcony.br- Coffee Bar: Equipped with a Keurig & French press.br-65 Smart TV: Netflix, Disney+, and Prime streaming.br- Super-fast WiFi for work or play.br-Private car garage for added convenience.br-Roof deck: Incredible views of the Willis Tower.br- Pet-friendly with a fenced-in backyard for your furry friends.brbrbrThis “cool, fun house” is thoughtfully designed for relaxation and entertainment. Whether you’re exploring Chicago, attending an event, or enjoying cozy nights in, this home has everything you need. From high-end amenities to breathtaking views, it promises to wow you, your family, and your friends.brbrP.S Please let us know at least 24 hours in advance if you’d like to use the hot tub. This allows us to ensure the water is clean, warm, and ready for your enjoyment. Hot tub Service Fee $75.00 brUnwind in style with our SaluSpa Hollywood AirJet Hot Tub, complete with ambient color-changing LED lights- perfect for 4 to 6 guestsbrbrbrIMPORTANT : br1) Limit Use to 5 Guests – For safety and comfort, no more than 5 people in the hot tub at a time.br2) Keep It Clean – Please NO soap, oils, bubbles, food, glassware, or smoking in or near the tub.br3) Children Under 12 – Must be supervised by an adult at all times.br4) Protect the Cover – Do not sit or stand on it. Always resecure the cover when finished.br5)Power Down After Use – Turn off jets and lights to help conserve energy.br6)Respect the Space – Excessive mess or damage may result in a $200+ cleaning or repair fee.brbrbrThank you for helping us maintain a safe and enjoyable experience for all guests! brbrbrLocation Highlights:brbr5 minutes to Fulton Market's best restaurantsbr5 minutes to United Center Arena (games & concerts)br7 minutes to Grant Park & Michigan Avenuebr10 minutes to Lake Michiganbr 7 minutes to the Medical District

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$318.68

/ Nightly

Apartment

Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!

Chicago, Illinois, United States

Welcome to Vintage City Chic: The Artist's Haven, where timeless elegance meets artistic inspiration in a meticulously restored 1920's building. Ideal for group trips, university visits, or weekend getaways, indulge in sophisticated living with exquisite furnishings and vintage flair. Book your unforgettable experience today.brbrbrbrbrAnimal PolicybrWe welcome one animal per reservation with a one-time nonrefundable fee of $185.00. Please note that animals are not permitted on beds, sofas, or any furniture. An additional cleaning fee starting at $185.00 will apply if there is evidence of an animal on furniture or if more than one animal is brought during the stay. This policy helps ensure the highest standard of cleanliness and comfort for all guests.brbrThank you for your understanding!

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$250.95

/ Nightly

Apartment

Cozy North Side Chicago Studio APT for Exploring

Chicago, Illinois, United States

Enjoy a fun and peaceful stay in Chicago's famous and vibrant North Side neighborhood. Our place is conveniently located near multiple restaurants, grocery stores, laundromats, local stores, and, most importantly, public transportation outside the door. We offer contemporary fixtures and fittings, high-speed wifi, TV, and many other amenities that make this the perfect vacation!

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$540.02

/ Nightly

Condo

Classic Lincoln Park 2 bedroom condo- parking included

Chicago, Illinois, United States

Stay in the heart of Lincoln Park, just steps from top attractions like Pequod's Pizza. Enjoy nearby Mariano's grocery, restaurants, shops, a movie theater, and easy public transit access. Inside the condo, a clean and cozy space featuring comfortable queen beds, a desk for remote work, and a fully equipped kitchen for meals in. Plus one car gated parking for your car. Perfect for both business and leisure to enjoy Chicago!brbrI will be responding to your questions by email/ text.brbrLincoln Park is the best place to kick off your exploration of Chicago. Enjoy!brbrThe condo is yours to enjoy. I will be available by phone or text if you need anything.brbrThis vintage unit has been decorated with a mid century modern flair. I am an Airbnb superhost. Book with confidence. You will love the comfortable and stylish space.brbrwalk, bike, car, bus, ELbrbrOne car outdoor secure parking is included with self check in and free Wi-fi. brWell behaved pets are invited and pet fee of $250 will be paid direct post booking. brCity of Chicago registration # R22000089549

2

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2

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4

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$80.73

/ Nightly

Apartment

Industrial Loft 2BR + DRUM KIT + Exposed Brick + 2 Private Decks & Lush Backyard

Chicago, Illinois, United States

Welcome to your bright and spacious Chicago loft retreat. This thoughtfully designed 2-bedroom, 1-bath apartment blends industrial character with warm, comfortable living — perfect for mid-term stays, remote work, relocations, traveling professionals, or extended city visits & a FULL DRUM KIT perfectly tuned for your enjoyment! Super RARE! brbrThe space features exposed brick walls, vaulted ceilings, rich hardwood floors, and oversized windows that fill the home with natural sunlight throughout the day. The open, airy layout creates a true loft-style atmosphere while still feeling cozy and functional.brbrEnjoy:br* Chill vibes br* Two GIANT comfortable bedroomsbr* One full bathroom with soaking tub br* Vaulted ceilings and industrial loft detailsbr* Beautiful exposed brick throughoutbr* Hardwood flooringbr* Tons of natural lightbr* Two private exterior decks with outdoor furniturebr* Open living and dining areasbr* Relaxed, stylish atmosphere ideal for extended staysbrbrWhether you’re in Chicago for work, a transition between homes, creative projects, or simply looking for a comfortable longer stay, this space offers a peaceful and inspiring place to settle in.brbrLocated on a residential street just 3 miles from the Medical District, 4 miles from Magnificent Mile/Downtown, easy access to the I-290 highway, downtown & other entertainment areas.brbrCTA (public transportation): Grand Bus, Augusta Bus, Homan Bus Chicago bus. Buses transfer to train lines.brbr• ✦ Fully equipped kitchen for home-cooked mealsbr• ✦ 2.4GHz WiFi—guest network connection for emails, and light workbr• ✦ Access to a lush backyard, great for morning coffee or evening unwindingbr• ✦ Free street parking 1/2 block away around the corner on Augusta ave br• ✦ On-site vending machine for fun late-night munchiesbr• ✦ Free laundry available br• ✦ Bluetooth Soundbar for wireless music & movies! brbrReasonable LOUD levels at night is not a problem. brbrNestled in a vibrant, residential neighborhood just steps from the nature filled Humboldt Park—one of the city’s largest green spaces, great for hiking or biking, & easy walking distance to a huge swimming pool! Just a small bike ride away from bars, coffee shops and restaurants. Whether you’re here to create, relax, or explore, this garden-level getaway is the perfect place to land.brbrHumboldt Park is a vibrant and historic neighborhood on Chicago’s West Side, known for its deep Puerto Rican roots, beautiful green spaces, and artistic spirit. Notably, L. Frank Baum wrote The Wonderful Wizard of Oz while living just steps from Humboldt Park, adding a touch of literary magic to its rich legacy. Today, the neighborhood is celebrated for its iconic Paseo Boricua, colorful murals, historic greystone architecture, and strong community pride that honors its past while embracing creative growth.brbrYou can rent a Divvy Bike in walking distance and ride the 606 trail or take one bus directly to Navy Pier, Magnificent Mile, Oak Street Beach, or River North.brbrBook your stay and experience the authentic side of Chicago! RECOMMENDATIONS [nearby]: Arcadia Foremost Liquor Store- Best alcohol & beer selection brSpinning J: Coffee shop + Breakfast $$brCalifornia Clipper: Cocktails + Live Music $$brRootstock Wine Bar: Date Spot + Upscale American cuisine $$$brSegnatore: Italian cuisine + Bar $$$brSuncatcher Brewing: Brewery $$brLucy’s: Burgers + Milkshakes $$brAztec Dave’s: Tacos + Margaritas $$brThe Hi-Lo: Cocktails $$brBoulevard Sports Bar: BBQ + UFC fights $$brOffset BBQ: BBQ, Bar + Live Blues $$brBulerias Tapas Bar: Spanish cuisine $$$brEsmeralda’s Lounge: Cocktails + Live House Music $$brBarbaro Taqueria: Modern Mexican cuisine + Bar $$brRichmond’s Sports Bar: Sports + Pool Table $brJibarito y Mas- Famous Puerto Rican sandwich invented here in Humboldt Park. Has fried plantains instead of bread. Gluten free brThe Continental: 4am Bar / 5am Saturdays $$brKimball Arts Center: Coffee shop $$brGaoku: Japanese cuisine + Bar $$$brRosa’s Lounge: Live Blues + Bar $$brLou Malnati’s: Deep Dish Pizza [Doordash Favorite] $$brZoku: Sushi + Thai cuisine [Doordash Favorite] $$brSeoul Taco: Korean Bulgogi Tacos [Doordash Favorite] $$brCermak Fresh Market: Grocery store brArcadia Foremost: Craft Beer + Liquor storebrIvy Hall Logan Square: Dispensary brHumboldt Park: Nature Urban HikebrMonster Ramen- chef owned best Ramen soup brLATE NIGHT FOOD: [Dine-in or Carry-out]brBeetle Bar & Grill: American 4pm-1am $$brCleo’s Bar: American $$ brRosati’s Pizza: Slice 12am-3am $$brDublin's Bar & Grill: American/Seafood 11am-4am (5am Saturdays) $$brGriddle 24: Breakfast 24 hours $$brEl Ranchito: Tacos + Margaritas 24 hours $brTRANSPORTATION:brBus Stops: $2.50 per ride (have exact change). “Unlimited Ride Passes” for 1, 3, 7, 30 day passes available on “Ventra” app. TIP: Google & Apple Maps has an option to route directions using public transportation.br65 Grand Bus (Grand & Homan stop) to Navy Pier. br66 Chicago Bus (Chicago & Homan stop) to Magnificent Mile, River North, Ukrainian Village neighborhoods, transfer to Red Line trains.br82 Kimball-Homan Bus (Homan & Augusta Stop) to Logan Square & Avondale neighborhoods. br70 Division Bus (Division & Homan stop) to Wicker Park, Old Town & Gold Coast Neighborhoods.brbrDivvy Bikes: download Divvy app, walk to August ave & Central Park ave, activate and ride.brLyft app: taxi service + you can rent electric scootersbrLOCAL TIPS:brWater Taxi: hop on in Chinatown or at the Michigan ave stop. The boat serves beer & has a restroom. Buy a one way ticket ($15), you can stay on and not get off until you get back to where you began OR feel free to hop on and off to explore with roundtrip tickets. It is the cheapest boat ride in Chicago.brChinatown: Neighborhood with great food, gifts and Chicago memorabilia at affordable rates. Routing to “Chinatown Square Zodiacs” will land you right in the middle as there is two sections of this neighborhood.br606 Trail: transformed from an abandoned railway into an elevated urban hiking walking/jogging/cycling trail stretching 2.7 miles. Unlike the Lakefront trail, this path feels authentically local rather than tourist-oriented. The pathway connects Wicker Park, Bucktown, Humboldt Park, and Logan Square, offering both a scenic route filled with art installations and a practical way to explore these vibrant districts.brChicago is known for the the home of House music and a high tempo form of Jazz. Jazz, Blues & house music clubs are everywhere. Just ask more info about the live music & dance scene. brChicago is known for segregated neighborhoods and fusion food from all over the world. Try any local restaurants and you’ll love it!

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$1010.48

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Apartment

Two-Story Penthouse, City Views, Pool, Gym

Chicago, Illinois, United States

Summary:brbrThe Penthouses at Grand Plaza PH#BbrbrExperience Chicago from the top in this stunning 2-story penthouse at Grand Plaza. This luxury home offers unmatched panoramic views of the city and Lake Michigan. Featuring 2 bedrooms, 3 baths, and resort-style amenities, it comfortably accommodates up to 6 guests. Enjoy a true penthouse lifestyle with a fireplace, private balconies, and a fully equipped kitchen, all in the heart of the city. License #2210737brbrbrbrThe Space:brbrYour stay unfolds across a magnificent two-story duplex apartment where floor-to-ceiling windows frame the spectacular city skyline and Lake Michigan. The expansive living room, complete with a gorgeous gas fireplace, is the perfect place to relax after a day of exploring.brbrbrbr -Living Area: Expansive living room with a gas fireplace and dramatic city views.brbr -Kitchen: Fully equipped kitchen with stainless steel appliances.brbr -Dining: Formal dining area for enjoying meals.brbr -Outdoor Space: Multiple private balconies to take in the fresh air and stunning vistas.brbr -Primary Bedroom: Plush King bed with a private en-suite full bathroom, including a relaxing bathtub.brbr -Second Bedroom: Comfortable Queen bed.brbr -Bathrooms: Three full bathrooms, with one conveniently located off the kitchen.brbrbrbrKey In-Unit Amenities:brbr -Fast Wi-Fi & Smart TVbrbr -Dedicated workspacebrbr -In-unit washer and dryer with detergent providedbrbrAmple clothing storagebrbrbrbrGuest Access:brbrGuests will have private access to the entire two-story penthouse apartment. brbrbrbrAdditionally, you will enjoy full access to the Grand Plaza's resort-style amenities, including:brbr -Outdoor pool and sundeckbrbr -Outdoor kitchen and dining area for grillingbrbr -State-of-the-art fitness centerbrbr -Indoor basketball courtbrbr -Outdoor running trackbrbr -Game room with a pool tablebrbr -Business center with workstationsbrbrbrbrThe building also features a 24-hour door staff for your convenience and security, and an in-building Jewel/Osco grocery store.brbr-Discounted Indoor parking garage at $46/daybrbr-On-call maintenancebrbrbrbrThe Neighborhood:brbrThe Magnificent Mile is Chicago’s premier commercial district. The vibrant, bustling area is home to upscale shops, luxe fashion outlets, cool restaurants and posh hotels. Landmarks include the historic Chicago Water Tower, the neo-Gothic Tribune Tower, the terracotta Wrigley Building skyscraper and the 100-story John Hancock Center, which has a rooftop observation deck with fine dining and panoramic city viewsbrbrbrbrGetting Around:brbr-Walk Score: 100 – steps from dining, shopping, and nightlifebrbr-50 feet to the Red Linebrbr-Near Magnificent Mile, Millennium Park, Riverwalkbrbr-Surrounded by top restaurants, coffee shops, and boutiquesbrbr-CTA Bus Stops Nearby – Multiple lines within 1 block for access to neighborhoods like West Loop, Lincoln Park, and Hyde Parkbrbr-Uber, Lyft & Taxis – Abundant and easily accessible at all hoursbrbr-Divvy Bike Station – 1 block eastbrbrbrbrOther Things to Note:brbrLicense #: 2210737brbr Check-in is anytime after 4:00 PM.brbr Check-out is by 10:00 AM.brbr Children are welcome. A pack-n-play is available upon request.brbrFor security purposes, a government-issued photo ID and a complete guest list are required prior to check-in.brbrbrbrInteraction with Guests:brbrWe are here to ensure you have a wonderful stay. While we respect your privacy, we are available to answer any questions or provide assistance via the messaging platform throughout your visit.

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$344.04

/ Nightly

Hotel

Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly

Chicago, Illinois, United States

Experience the Windy City's elegance & charm from our central, downtown locationbrbrThis listing is for a room within a hotel.brbr✦ Your room is 220 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ You may keep your luggage at the front desk if you arrive early.brbr✦ Fitness center is available.brbr✦ Paid valet parking – 1 space(s), available for $77 per day.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $27.26 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $75 per stay up to 7 days and $150 for longer staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Laundry dryer is not available in the unit.brbr✦ Microwave, tea kettle, and coffee maker are only available upon request.brbr✦ Complimentary Bicyclesbrbr✦ The required refundable security deposit is charged per night on a valid credit card.

1

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1

Bath

2

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$178.23

/ Nightly

Private Vacation Home

Charming 4-bedroom house with AC and WiFi in fabulous Chicago

Chicago, Illinois, United States

Discover this fantastic 4-bedroom gem in Chicago. This superb house comes equipped with all the essentials for a comfortable stay, including WiFi, AC, heating, and a hair dryer. Experience what Chicago has to offer with a stay at our house.

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$676.92

/ Nightly

Apartment

4 Bedroom, Sleeps 20 people!

Chicago, Illinois, United States

Summary:brbrExperience Chicago and Pilsen as being in the heart of 18th st. Some of the best food, music and nightlife Chicago has to offer right outside your front door!brbrbrbrThe Space:brbr4 bedroom, 4 bathroom home that can sleep 20 people!brbrbrbrBedroom #1 - King Bed (sleeps 2)brbrBedroom #2 - 2 Queen Beds (sleeps 4)brbrBedroom #3 - 2 bunk beds with full mattresses (sleeps 8)brbrBedroom #4 - 2 bunk beds with full mattresses (sleeps 8)brbrbrbrThese are if everyone doubles up in a bed. 11 separate beds, great for groups. Please no parties or smoking in the unit. We do have neighbors!!!brbrbrbr$250 lockout fee if needed to call a locksmith to let in. If keys at property and lost this charge will apply. If no keys, this will not be applicable unless tampering was made with our digital door lock systembrbrbrbrGuest Access:brbrThe entire unitbrbrbrbrThe Neighborhood:brbrNear the vibrant 18th street! Nightlife, restaurants, the best bars and food are right down the street!brbrbrbrGetting Around:brbrUber is plentiful in the city. Can rent a car as well. There is free street parking nearbybrbrbrbrOther Things to Note:brbr$250 lockout fee if needed to call a locksmith to let in/lost keys if they are given out. $500 fine for smoking inside the home or throwing an event or party. These are strictly prohibited.brbrbrbrInteraction with Guests:brbrOur concierge team is available from 10am–8pm Sunday-Thursday and 10am–12am Friday and Saturday. Messages received outside of these hours will be addressed promptly the following day. We curate a refined, hands-off experience so you can immerse yourself in comfort and relaxation — with attentive support whenever needed.brbrbrbrSunday - Thursday: 10am - 8pmbrbrFriday & Saturday: 10am -12am

4

Bed

4

Bath

20

Sleeps

$723.52

/ Nightly

Private Vacation Home

Steps to Lake & Beach! Multi-Level Oakland Haven

Chicago, Illinois, United States

3 Mi to McCormick Place & Museum Campus | 4 Mi to Downtown | Fire Pit + BBQ | Basketball CourtbrbrExperience the perfect blend of city energy and lakeside relaxation at this expansive Chicago vacation rental! Start your morning with a stroll to Oakwood Beach, then cheer on the Bears at Soldier Field or dive into history at the Field Museum. As evening rolls in, retreat to one of the decks to sip cocktails and catch up with the whole crew. Your Windy City getaway is ready for you!brbr-- THE PROPERTY --brbrR24000117504brbrOUTDOOR LIVINGbr- Furnished upper & lower decksbr- Half-court basketball courtbr- Grill, fire pitbrbrINDOOR LIVINGbr- Open-concept layoutbr- 5 Smart TVsbr- 8-person dining area, high-top seatingbr- Office w/ dedicated workspacebr- Washer/dryerbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Cooking & baking basics, dishware/flatwarebr- 2 mini refrigerators, 3 microwavesbr- 2 drip coffee makers (coffee provided)brbrACCESSIBILITYbr- Multi-level home, 10 steps to enterbr- All bedrooms on 2nd floor & 3rd floorbrbrPARKINGbr- Driveway (5 vehicles)brbr-- THE LOCATION --brbr- Nestled in Oakland neighborhood on Chicago's South Sidebr- Walk to Oakwood Beach, Burnham Park & Lake Michiganbr- 2 miles to The University of Chicago & Hyde Parkbr- 3 miles to Soldier Fieldbr- 4 miles to McCormick Place, Field Museum & Shedd Aquariumbr- 5 miles to Millennium Park & Chicago Riverwalkbr- 11 miles to Wrigley Fieldbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr**No Smoking / No Vaping / No Pets**br- Smoking or vaping outdoors must be away from doors and windowsbr- Dispose of cigarette waste properly and not in the yard or on the pavementbrbr**Quiet, Professional Environment - Primarily on 1st Floor**brbr- Quiet hours: **8:00 PM – 8:00 AM**br- Excessive noise and loud sounds are prohibited.br- No parties, events, or gatheringsbr- No unregistered visitors unless pre-approvedbr- Avoid slamming doors or disruptive movementbr- Headphones required for gamingbr- Television and music volumes to be maintained below 50% of max volumebr- Phone and video calls must be kept at low volumebr- No speakerphone use on first floorbrbr**Kitchen & Food Etiquette**brbr- If you cook, you must cleanbr- Return the kitchen to its original conditionbr- Wipe down counters, stovetops, and sinks after use using soap and water or provided vinegar and water spray bottlesbr- Do not leave dishes in the sinkbr- Please rinse dishes before loading into dishwasherbr- Only adults 21 years or older are allowed to use the range and stovebr- The cooktop and oven exhaust fan must be used — on high — during most cookingbr- Always double or triple check that you have turned off all burners and the oven when finished using thembrbr**Laundry Etiquette**brbr- Clean the lint trap before and after each usebr- Do not overfill with and use only liquid detergent; follow machine directionsbrbr**Trash & Recycling**brbr- Garbage must be taken out daily if full and if raw meats are disposed ofbr- Please utilize the refuse containers located at the rear of the premisesbr- Recycle in the blue container out backbr- Do not litter indoors or outdoorsbrbr**Bathroom Expectations**brbr- Maintain decorum in the half bathroom; keep it clean and presentablebr- Keep bathroom surfaces tidy; remove hair from drainsbr- Do not flush paper towels or sanitary napkinsbrbr**Garbage Disposal Rules**brbr- The garbage disposal is **not** a grinderbr- **Do not dispose of eggshells or food debris** in the garbage disposalbr- Do not use garbage disposal for eggshells, and vegetable and meat skinsbr- The garbage disposal is meant for exceedingly small food itemsbr- Do not pour grease and liquids that coagulatebrbr**Respect for Spaces**brbr- Respect spaces at all timesbr- Clean up after yourself in all common areasbr- Clean up outdoor areas after usebrbr**Energy & Home Systems**brbr- Turn lights off in common and private areas when not in usebr- The thermostat automatically adjusts to help save energy.br- Each suite includes supplemental heating and cooling appliancesbr- Do not tamper with thermostats, smoke detectors, or security devicesbrbr**Shoes & Cleanliness**brbr- Remove outdoor shoes in the foyer, and immediately after entering from the veranda and/or backdoorbr- Outdoor shoes are not permitted to walk around indoorsbrbr**Maintenance & Safety**brbr- Report any damages immediately to your Guest Contactbr- Report any mechanical, electrical, or appliance issuesbr- Be mindful of water and energy usagebr- Treat furnishings, appliances, and fixtures with carebr- Report all lapses in cleaning by the cleaning staffbr- Report all cleaning recommendationsbr- Please report any damages that occur to both the Guest Contact and EvolvebrbrADDITIONAL INFORMATIONbr- This multi-level home requires 10 steps to enter and interior stairs to access all bedrooms

5

Bed

5

Bath

7

Sleeps

$601.51

/ Nightly

Apartment

1 Free Parking, Sleeps 10

Chicago, Illinois, United States

Summary:brbrStunning 3-bedroom modern garden unit apartment with 1 Gated Parking Space, Pool Table (Also a dining table), Private Patio with 1 king bed and 4 full beds, perfect for groups & families up to 10.brbrContact us for a rental car before your trip! We can deliver the car to the airport, to the property or your desired location, completely up to you! brbrbrbrYou are a 7-minute Uber away from restaurants in downtown, Millennium Park, and 15 mins to Navy Pier!brbrbrbrThe Space:brbrStunning 1,500 sqft apartment with 3 bedroomsbrbrbrbrThis is the perfect place for tourists to immerse themselves in the central vibe of Chicago, and enjoy all the activities that Wicker Park has to offer.brbrbrbrThis beautiful luxury home offers high-end amenities through and through!brbrbrbrHome Layout:brbr- Living room with sofa and 65 TVbrbr- Kitchen with dining table and Pool Tablebrbr- Bedroom #1: One King bed w/attached bathroom #1. Private access to Patio and 55 Smart TVbrbr- Bathroom #1: Full bathroom w/ shower and bathtub.brbr- Bedroom #2: Two Full beds w/ detached bathroom #2brbr- Bedroom #3: Two Full beds w/ detached bathroom #2brbr- Bathroom #2: Full bathroom w/ Shower and bathtubbrbrbrbr[Others]brbr- 1 Gated Parking space in the buildingbrbrbrbrHome Highlights:brbr- Stylish interior design and beautiful furniture in a luxury home with high-end finishes.brbr- Hotel-grade bedding for a comfortable sleepbrbr- Fully-stocked kitchen with Keurig coffee maker and coffee pods, pots, pans, bowls, plates, glasses and utensilsbrbr- 65 Smart TV with all streaming channels in living roombrbr- High-speed WIFI for all your working-from-home needs!brbr- In-unit Washer/Dryerbrbr- Smart home ready with electronic lock.brbrbrbrYou are only:brbr12 mins from Downtown Chicagobrbr22 mins from O'Hare International Airportbrbr15 mins to Navy Pierbrbr15 mins from Millennium Parkbrbr16 mins to the Field Museumbrbr14 mins to The Art Institute of ChicagobrbrbrbrOther Things to Note:brbrPlease review the information below before you book. We want our guests to have the right expectations and upfront information when they book so you can have a smooth and happy experience every time.brbrbrbr- This is a large garden unit in an apartment building with other long-term residents. brbrbrbr- Please ensure quiet hours after 10 PM so other unit residents can sleep.brbrbrbr- There are 8 steps down leading into the apartment.brbrbrbr- The 1 parking space is gated and you will have to enter a code to enter the apartment building's parking lot.brbrbrbrImportant: We are committed to protecting our properties and keeping up-to-date with short-term rental regulations, which is why you will be asked to complete our independent verification.brbrbrbrPlease note: Before your booking begins, you will need to verify your details with us to complete your booking. You will be contacted via email and/or text to complete the verification. You will also be given the choice between paying a refundable deposit or buying a non-refundable damage waiver. We suggest you buy the damage waiver as this protects you in case you cause accidental damage during a booking.

3

Bed

2

Bath

10

Sleeps

$543.42

/ Nightly

Apartment

Spacious 5-bedroom/2-bathroom apartment in marvelous Chicago with AC, Wi-Fi

Chicago, Illinois, United States

Drive Times (with light traffic)br25 Min — Downtown Chicagobr15 Min — Hyde Parkbr40 Min — Indiana Dunes National Parkbr30 Min — Midway Airportbr42 Min — O’Hare Airportbr18 Min ---- Guaranteed Rate Fieldbr20 Min ---- McCormick Place, China Town, Grant Parkbr35 Min ---- Wrigley Field StadiumbrbrWelcome to your perfect getaway in Avalon Park, Chicago! This spacious 5-bedroom home comfortably accommodates up to 10 guests. You'll find three cozy queen bedrooms, one king bedroom, and a full bedroom with a roller bed for extra sleeping space. The home features two bathrooms—one on the main floor with a Jacuzzi and the second on the upper level with a bathtub and stand-up shower.brbrEnjoy a fully equipped kitchen with a latte machine, Keurig, and all the essentials to create a delicious meal. The dining and living room areas are perfect for family time, with recliner sectionals and a smart TV for entertainment. Two bedrooms also include smart TVs for added convenience.brbrLocated on a quiet residential street, you'll have access to a two-car driveway. For families, we provide a pack and play, as well as board games for a fun time together. Work remotely in comfort with a dedicated desk area and fast Wi-Fi throughout the home.brbrWe’re happy to offer a complimentary bottle of wine upon your arrival, along with coffee, tea, and coffee pods. Fresh linens, extra pillows, and towels are provided for your comfort throughout your stay.brbrWhether you're visiting for leisure or business, this home offers everything you need for a relaxing and enjoyable stay!brbrbrGuest accessbrSpacious 5-Bedroom Home in Chicago – Perfect for Your Stay!brbrWhat You Need to Know Before Booking:br• Private & Secure: This listing is for the main home only. The basement is a separate unit occupied by tenants who do not have access to your space, and guests do not have access to theirs.br• No Backyard Access: The backyard is used by the basement residents’ dogs, who are unleashed during bathroom breaks. For safety reasons, please do not enter the backyard unless it’s an emergency.br• Smoking Policy: Smoking is permitted only on the front porch with the front door completely closed to keep the home fresh and comfortable for all guests.brbrI’m Kimberly, your host, and I’m here to ensure you have a smooth and enjoyable stay. If you have any questions about the home or your booking, don’t hesitate to reach out—I’d be happy to assist!brbrWe look forward to hosting you in Chicago!brbrOther things to notebrThermostat is typically set between 68-72 degrees on Heat mode during the winter months, please contact us if you’d like us to adjust this prior to your arrival or during your stay.

5

Bed

2

Bath

10

Sleeps

$1343.13

/ Nightly

Bed & Breakfast

Five bedroom - 3 bath - Sleeps 12

Chicago, Illinois, United States

This full apartment has four bedrooms on the third floor with 2 shared bathrooms and a fifth bedroom on the second floor with a private bathroom. Two rooms have a full size bed, the rest have a queen sized bed and on the third floor there is a pull out sofa. So can sleep 10-12 people. This is smack dab in the middle of boystown, so some rooms can be loud. There is no parking on site, we offer parking permits for the surrounding area.

Bed

Bath

Sleeps

$489.54

/ Nightly

Condo

Chic Chinatown Apt w parking!

Chicago, Illinois, United States

Charming 1,000 square foot condo located in Chinatown, part of the South Loop/McCormick neighborhood. This 3 bedroom / 1.5 bath home is perfect for families and groups looking for a comfortable escape amid vibrant surroundings. Being in the central area of the city we have easy access to every major highway: 90/94, 290, 55, & Lake Shore Drivebrbr1 mile from McCormick and Wintrustbrbr3.5 miles to Rush / Stroger ~10minbr4.1 miles to Northwestern ~16minbr6.1 miles to U of C Hospital Hyde Park ~17minsbrbr*STAIRS: This unit has 3 flights of stairs from main entrance (around 30 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 apartment is in a residential building. This listing is for one unit! There may be interaction with other guests outside with shared driveway 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 bedbrbr▶Our beds have crisp linens and the bathrooms are stocked with fresh towels and bath products. We also provide essentials like a hair dryer, clothes iron, etc. and you have full access to the in-unit washer and dryer.brbr▶1 designated outdoor parking space with free street parking for extra vehicles. NOTE: the space is small and can fit a medium size SUV or smaller. If you have a 4x4 truck or larger please park on the street.brbrPets allowed. $200 feebrbrWe love our space and we hope you do too!

3

Bed

1

Bath

6

Sleeps

$170.2

/ Nightly

Apartment

Charming 3-bedroom apartment in the Old Norwood Park neighborhood of Chicago

Chicago, Illinois, United States

Discover this captivating 3-bedroom apartment nestled within a historic building in the heart of Old Norwood Park. This beautifully updated home boasts a stunning blend of classic charm and modern convenience.brbrInside, you'll find:brA completely renovated kitchen featuring butcher block countertops, top-of-the-line appliances, and ample cabinet space for culinary inspiration.brAn updated bathroom, three bedrooms offering comfortable retreats for relaxation and rest.brbrOriginal architectural details add character and warmth, such as original stained glass windows, bookshelves, and fireplace mantel (non-functioning fireplace.brbrExperience the vibrant Old Norwood Park lifestyle:brbrWalkability at its finest: Enjoy easy access to a plethora of local amenities, including charming cafes, trendy restaurants, and lively bars.brbrEmbrace the outdoors: Spend leisurely afternoons in nearby parks, perfect for picnics, dog walks, and enjoying the fresh air.brbrImmerse yourself in history: Explore the rich heritage of the neighborhood, with its beautiful architecture and fascinating local history.brbrAccessiblity:brEnjoy excellent public transportation access with nearby CTA buses, PACE buses, the CTA Blue Line, and Metra trains. Easily explore the city and suburbs with convenient connections.brbrO'Hare International Airport is just a 10-minute drive away, making travel a breeze.br

3

Bed

1

Bath

5

Sleeps

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