Cook Area Rentals
From $259 per night (USD)VRBO
Top floor of Historic Oak Park Home /2 Car Garage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Fran ...
From $259 per night (USD)VRBO
From $227 per night (USD)Expedia
Stylish Luxe King bed w/Free Parkng near DT Oak Pk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous 2bed/2bath packs a powerful punch, and more amenities than you'll know what to do with. -1 Private Parkin ...
From $227 per night (USD)Expedia
From $283 per night (USD)VRBO
Chicago's Hidden Treasure \"Evanston, IL\" Urban Luxury with comfort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Unive ...
From $283 per night (USD)VRBO
From $283 per night (USD)Expedia
Half a mile from everything in the heart of Evanston, Illinois
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...
From $283 per night (USD)Expedia
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Nice 3 bedroom fully loaded
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 1
Nice place on a very quite block, The house has plenty space Clean and sterilize. It has all Amenities to make it a very ...
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From $330 per night (USD)Expedia
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: This beautiful, newly remodeled, spacious, 3 bed 2 bath ranch style home is set back on a large lot. Located cl ...
From $330 per night (USD)Expedia
From $133 per night (USD)VRBO
\"The Estates\" 2 PRIVATE BEDROOMS in our Home, Hot Tub/Bathrooms & More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
PRIVATE ROOMS IN OUR HOME AS WE LIVE IN THE PROPERTY. NOT ENTIRE HOUSE!!! The “Estates” is an affordable place with ...
From $133 per night (USD)VRBO
From $1235 per night (USD)Expedia
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Located inside one of the iconic Wrigley Rooftops, and just a few steps away from Wrigley Field, this apartment offers a ...
From $1235 per night (USD)Expedia
From $283 per night (USD)VRBO
Chicago's Hidden Treasure, \"EVANSTON, IL\"
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Northwestern Alumni, Parents, Corporate Travelers, and Evanston Adventure Seekers!! This property is all about coming t ...
From $283 per night (USD)VRBO
From $963 per night (USD)Expedia
Nice cozy home to experience on your vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Nice 3 bedroom 2 bathroom with laundry room. Nice walkthrough garage. The house is amazing with hardwood floors and kitc ...
From $963 per night (USD)Expedia
From $204 per night (USD)VRBO
Updated Forest Park 3 BR Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming and recently updated 3BR bungalow in a friendly neighborhood is perfect for families, business travelers, ...
From $204 per night (USD)VRBO
From $1235 per night (USD)Expedia
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up and ...
From $1235 per night (USD)Expedia
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“The Estates Suite” PRIVATE BEDROOM in our Home and use of the Hottub.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
PRIVATE ROOM IN OUR HOME AS WE LIVE IN THE PROPERTY. NOT ENTIRE HOUSE!!! The “Estates Suite” is an affordable place wi ...
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From $1235 per night (USD)Expedia
Wrigley Field Grand Slam Suite 4 Bedrooms, 2 Bathrooms
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to the Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up ...
From $1235 per night (USD)Expedia
From $339 per night (USD)VRBO
✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...
From $339 per night (USD)VRBO
From $171 per night (USD)Expedia
Angie & Mike's Nest!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated three bedroom & 1 bath apartment with stainless steel appliances. The space The apartment is in the se ...
From $171 per night (USD)Expedia
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Bright and Spacious 2BR 2BA Apt., FREE PARKING, Walk to Train
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Queen Anne home built in 1876 is located in the heart of Oak Park, just a few minutes walk to Frank Lloyd Wright ho ...
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From $290 per night (USD)Expedia
Lovely 2 Bedroom Condo With Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
lovely 2 bedroom condo with air conditioning wireless internet clothes and washing machine great place for business peo ...
From $290 per night (USD)Expedia
From $140 per night (USD)VRBO
Cozy modern unit w/ easy access to downtown Chi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a newly remodeled two bedroom lower unit in the historic Oak Park suburb of Chicago. This unit is within walking d ...
From $140 per night (USD)VRBO
From $893 per night (USD)VRBO
Elegantly decorated spacious 4 bedroom, 5 bathroom home in historic Oak Park
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
This home is meticulously decorated with amazing opulent lighting, stain glass pocket doors, and a great floor plan. Th ...
From $893 per night (USD)VRBO
From $251 per night (USD)VRBO
Relaxing Oak Park Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This charming Oak Park Bungalow offers a quiet relaxing environment to unwind after a busy day of site seeing in Chicag ...
From $251 per night (USD)VRBO
From $354 per night (USD)Expedia
5 Star Upscale Entire Family Neighborhood Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This home is located on the River Side/ N. River Side part of Berwyn and Oak Park in a delightful quiet family neighbor ...
From $354 per night (USD)Expedia
From $68 per night (USD)VRBO
“The Executive” PRIVATE BEDROOM and Bathroom in our Home with use of the Hot tub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
PRIVATE ROOM IN OUR HOME AS WE LIVE IN THE PROPERTY. NOT ENTIRE HOUSE!!! The “Estates Executive” is an affordable place ...
From $68 per night (USD)VRBO
From $250 per night (USD)VRBO
Pet-Friendly Family Apartment - Near NU Campus!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Explore the Windy City with this stylish 2-bedroom, 2-bath apartment! In walking distance, you'll find a variety of loca ...
From $250 per night (USD)VRBO
From $252 per night (USD)VRBO
Family Apartment w/ Deck + Yard Near Northwestern
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the joys of Evanston from this completely redone 2-bed, 2-bath vacation rental located just over 2 miles from ...
From $252 per night (USD)VRBO
From $147 per night (USD)Expedia
1BR Apartment - Walk to Shops - Downtown OAK PARK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 m ...
From $147 per night (USD)Expedia
From $183 per night (USD)VRBO
Free Parking, Balcony near Universities, NAPA, Ravinia and train to Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this calm and stylish apartment. All new and fresh ! Sunny corner with 1bedrooms 1 bath. Moder ...
From $183 per night (USD)VRBO
From $279 per night (USD)Expedia
Elegant|Brand New Remodeled|1BR|Next to Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...
From $279 per night (USD)Expedia
From $159 per night (USD)VRBO
Urban Farmhouse near O’Hare Airport
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The house is over 100 years old. Has many modern amenities including central air in the summer and radiant heat in the ...
From $159 per night (USD)VRBO
From $324 per night (USD)Expedia
Lincoln Park Light Filled Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows, & the c ...
From $324 per night (USD)Expedia
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A5 Luxurious Garden Unit Near Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Looking for a romantic getaway? Check out this intimate private unit crafted for two! Everything you see, touch & feel i ...
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From $189 per night (USD)Expedia
Large, modern 2 bedroom in the heart of Forest Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet and spacious lofted 2 bedroom unit steps from the heart of downtown Forest Park's Madison St. There you will find ...
From $189 per night (USD)Expedia
From $391 per night (USD)VRBO
\"Bliss of Evanston\" 180°view, 2BDR +2Bath UrbanLux
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping terrace view, resort-like ameniti ...
From $391 per night (USD)VRBO
From $285 per night (USD)Expedia
\"Joy of Evanston\" 1BDR, KING EXEC Suite, pool+Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Eco-Friendly, modern, sleek, condo with modern finishes and resort-like amenities are just steps from Northwestern Unive ...
From $285 per night (USD)Expedia
From $449 per night (USD)VRBO
\"Unity of Evanston\" 3 BDR+2BA ModernLuxe High Rise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Modern-Luxe experience at the Unity of Evanston Condo. Elegant finishes and a sweeping view. Resort-like amenities with ...
From $449 per night (USD)VRBO
From $357 per night (USD)VRBO
Classic Oak Park Home, 11 Mi to Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
- Walk to Shopping & Dining - In-Unit Laundry Experience the best of Chicago from this 4-bedroom, 1.5-bathroom home in ...
From $357 per night (USD)VRBO
From $238 per night (USD)VRBO
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Be sure to check out the VIDEO tour push the arrow on the third photo. Happy to accommodate same day reservations pl ...
From $238 per night (USD)VRBO
From $259 per night (USD)Expedia
Beautiful & Cozy 2bd/1b Near O’Hare & Metra (MD-W)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to the peaceful Galewood/Elmwood Park area of Chicago. We are in the boarder line of Chicago/Suburbs. Our Home i ...
From $259 per night (USD)Expedia
From $250 per night (USD)VRBO
Charming, light-filled 5br Wilmette home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 6
Light and art filled 5br, 2ba, 2fp, garage, huge fenced backyard. Beautifully designed and landscaped. Kitchen boasts ne ...
From $250 per night (USD)VRBO
From $329 per night (USD)Expedia
Contemporary 2BR Flat Right Next to Wrigley Field & Transit ❤️ Cubs!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience city life; Located in Wrigley! Feel like a local! We're experienced! we've hosted more than 1000 reservati ...
From $329 per night (USD)Expedia
From $245 per night (USD)VRBO
Monthly Specials! Cozy Home away from Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
In the HOMETOWN OF OUR POPE LEO, a cozy home away from home. 7 minutes to the city of Chicago, 22 minutes to Downtown. ...
From $245 per night (USD)VRBO
From $401 per night (USD)Expedia
*Comfortable & Spacious Home Close to Downtown*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
We are Airbnb Superhosts and have been on the platform since 2016. This is a Comfortable & Spacious beautifully furnish ...
From $401 per night (USD)Expedia
From $1082 per night (USD)VRBO
Everything You Need For The Perfect Vacation! 2 Modern Units, Pets are Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $1082 per night (USD)VRBO
From $227 per night (USD)VRBO
Best Value, Quality Stay! Pet-Friendly Property, Close to Water Tower Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $227 per night (USD)VRBO
From $554 per night (USD)VRBO
Spacious Good-Value Accommodation! Pet-Friendly Property, Near Willis Tower!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $554 per night (USD)VRBO
From $561 per night (USD)VRBO
A Place You'll Surely Enjoy! Near Chicago History Museum, Pet-Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $561 per night (USD)VRBO
From $326 per night (USD)VRBO
Affordability Meets Comfort! Close to Water Tower Chicago, Pets Are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $326 per night (USD)VRBO
From $256 per night (USD)VRBO
Always a Great Idea To Unwind! Pet-Friendly Property, Near Marina City!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $256 per night (USD)VRBO
From $229 per night (USD)VRBO
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Guests will find a sophisticated urban retreat designed for both business and leisure travelers at this property. The el ...
From $229 per night (USD)VRBO
From $212 per night (USD)VRBO
Comfortable Stay, Convenient Location! With Complimentary Airport Shuttle!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $212 per night (USD)VRBO
From $592 per night (USD)VRBO
Your Home Away From Home! 4 Affordable Units, Pets are Allowed!
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 16
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $592 per night (USD)VRBO
From $190 per night (USD)VRBO
Best Value, Quality Stay! Pets are Allowed, With Onsite Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $190 per night (USD)VRBO
From $158 per night (USD)VRBO
Always a Great Idea To Unwind! With Onsite Parking, Pets Allowed!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $158 per night (USD)VRBO
From $196 per night (USD)VRBO
Indulge in Home Like Comfort! Pet-Friendly, w/ Airport Shuttle Service!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $196 per night (USD)VRBO
From $443 per night (USD)VRBO
Ideal Mix of Comfort and Value! 3 Relaxing Units, Pets are Welcome!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $443 per night (USD)VRBO
From $162 per night (USD)VRBO
Make Your Trip More Enjoyable! Pet-friendly Property, w/ Airport Shuttle Service
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $162 per night (USD)VRBO
From $299 per night (USD)VRBO
Comfort and Relaxation! 2 Comfortable Units, Near Chicago O'Hare Int'l Airport
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $299 per night (USD)VRBO
From $170 per night (USD)VRBO
Better Choice for your Vacation! Near Chicago O'Hare International Airport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $170 per night (USD)VRBO
From $149 per night (USD)VRBO
Spacious Good-Value Accommodation! Pet-Friendly Property with Onsite Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $149 per night (USD)VRBO
From $331 per night (USD)Expedia
Great location-King beds-Kids playroom
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Close to Woodfield Mall. Private office, high speed internet. Spacious, King Beds. Outdoor Oasis, Kids playroom, Indoor ...
From $331 per night (USD)Expedia
From $370 per night (USD)VRBO
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Experience the charm of Old Town in our spacious 3-bedroom coach house! This comfortable oasis offers a fully equipped ...
From $370 per night (USD)VRBO
From $439 per night (USD)Expedia
5-minute walk to the largest old school arcade in America! Family friendly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Bring the whole family to this great place with lots of room for fun. We are located 10 miles from Downtown Chicago. Ple ...
From $439 per night (USD)Expedia
From $181 per night (USD)VRBO
Cozy 3-bedroom vacation home just 17 minutes from Lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to our cozy 3-bedroom vacation home in Calumet Park, just a short 17-minute drive from the stunning shores of Lak ...
From $181 per night (USD)VRBO
From $146 per night (USD)Expedia
Chicago style apt/Near Hosp/ORD/MDW/DT
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your family will be close to everything at this centrally-located place. Stay includes: *Free Street Parking *Free Wifi ...
From $146 per night (USD)Expedia
From $319 per night (USD)VRBO
Cozy retreat in a prime location
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a clean and comfortable stay with a luxurious king bed and a private backyard. Located in a peaceful neighborhood, ...
From $319 per night (USD)VRBO
From $304 per night (USD)Expedia
Modern 4BR Retreat Near MDW | LCP Collection
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Enjoy a fresh stay in this newly remodeled 4BR, 2BA home in Burbank, IL, perfect for families and groups. With ...
From $304 per night (USD)Expedia
From $215 per night (USD)VRBO
420 zen environment surrounded by boho chic decor~Luv Happii House.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Charming, vintage style canna friendly bed & breakfast. Perfect for a weekend getaway, business trip, work from home alt ...
From $215 per night (USD)VRBO
From $387 per night (USD)Expedia
Newly Revamped Home - For privacy lovers
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Big family? Group getaway? We’ve got more sleeping space than you’ll know what to do with. Try finding this much space a ...
From $387 per night (USD)Expedia
From $140 per night (USD)VRBO
Lakeview Lux - Apt #2
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $140 per night (USD)VRBO
From $153 per night (USD)Expedia
Lakeview Lux - Apt #1
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...
From $153 per night (USD)Expedia
From $252 per night (USD)VRBO
2-Bed 2-Bath Apt | close to UC w/ Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minute ...
From $252 per night (USD)VRBO
From $1446 per night (USD)Expedia
The Grand Kimball Lodge, Logan Square, Sleeps 20
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 20
Summary: Welcome to The Grand Kimball Lodge — a one-of-a-kind experience that’s been featured in Architectural Digest's ...
From $1446 per night (USD)Expedia
From $91 per night (USD)VRBO
3 bedrooms In the Windy City
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Anything you need, we have it! Anything you need, we have it! Anything you need, we have it! Anything you need, we have ...
From $91 per night (USD)VRBO
From $113 per night (USD)Expedia
Charming Coach House in Chicago's Hot Wicker Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wicker Park is known as Chicago's trendy enclave. Chicagoans and tourists alike are drawn to this hot spot neighborhood. ...
From $113 per night (USD)Expedia
From $486 per night (USD)VRBO
St.Bens, Jacuzzi, EV Parking! 4 beds, Walk to Wrigley Field & Brown Line!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Looking for a spacious, stylish, and fully-equipped home in the heart of Chicago? Book your stay now and make this beau ...
From $486 per night (USD)VRBO
From $351 per night (USD)VRBO
Luxury Chicago 2 Story Condo: 10 Mins to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Experience luxury in our 2 bedroom (3 bed) duplex down, spread over 2 levels, our home offers over 1800+ sq ft of room. ...
From $351 per night (USD)VRBO
From $283 per night (USD)VRBO
Newly Designed 3bd In Heart of Ukrainian Village by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the charm of Ukrainian Village in my beautifully designed home just steps from award winning restaurants, cafe ...
From $283 per night (USD)VRBO
From $368 per night (USD)Expedia
Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR/2BA Apartment in Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
"Your Chicago Adventure Begins Here: Modern 3BR/2BA Haven, Just 10 Minutes from Downtown! Get ready to experience the b ...
From $368 per night (USD)Expedia
From $163 per night (USD)VRBO
Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
5 bed 2 full bathroom with 2,600 of living space. Property is located on a quiet street with long term ownership. Restau ...
From $163 per night (USD)VRBO
From $291 per night (USD)Expedia
Full suburban home 30 mins from downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Bring the whole family to this great place with lots of room for fun. Full house in quiet suburb with free garage access ...
From $291 per night (USD)Expedia
From $161 per night (USD)VRBO
iKlektik House // Robin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bright, Sunny and Stylish one bedroom, full kitchen, balcony over looking the backyard in West Town. Close to Wicker Par ...
From $161 per night (USD)VRBO
From $149 per night (USD)VRBO
Maximum Comfort! w/ Complimentary Airport Shuttle Service, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $149 per night (USD)VRBO
From $162 per night (USD)VRBO
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our generously sized rooms and suites are packed with thoughtful extras like comfortable bedding, ergonomic workstations ...
From $162 per night (USD)VRBO
From $190 per night (USD)VRBO
Best Pick! Spacious and Pet-friendly Unit, Free Airport Shuttle Service!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $190 per night (USD)VRBO
From $158 per night (USD)VRBO
Hassle-free Stay w/ Complimentary Airport Shuttle, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $158 per night (USD)VRBO
From $298 per night (USD)Expedia
Stylish Streeterville 2BR w/ Lounge & Pool, nr Riverwalk, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...
From $298 per night (USD)Expedia
From $127 per night (USD)VRBO
Great South Loop 1BR w/ Games & Pool, nr Park & Train, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop. It’ll be easy to simply show up and start l ...
From $127 per night (USD)VRBO
From $196 per night (USD)Expedia
Upscale Streeterville Jr 1BR w/ Gym, nr Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...
From $196 per night (USD)Expedia
From $145 per night (USD)VRBO
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our generously sized rooms and suites are packed with thoughtful extras like comfortable bedding, ergonomic workstations ...
From $145 per night (USD)VRBO
From $197 per night (USD)VRBO
Best Value, Quality Stay! Pets Allowed, Complimentary Airport Shuttle!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $197 per night (USD)VRBO
From $149 per night (USD)VRBO
Convenience & Comfort! w/ Airport Shuttle Service, Pet-friendly Property!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $149 per night (USD)VRBO
From $212 per night (USD)VRBO
Maximum Comfort! With Airport Shuttle Service, Pets are Welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...
From $212 per night (USD)VRBO
From $165 per night (USD)VRBO
Your Home Away From Home! Pet-friendly Property, Full Kitchen, Free Shuttle!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...
From $165 per night (USD)VRBO
From $332 per night (USD)VRBO
TWO Comfortable 1BR Suites With Kitchens, Short Drive to Kohl Children's Museum!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...
From $332 per night (USD)VRBO
From $138 per night (USD)VRBO
Spacious Unit with Full Kitchen, Free Airport Shuttle! Near Ruby Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...
From $138 per night (USD)VRBO
From $497 per night (USD)VRBO
THREE Convenient 1BR Suites with Kitchens, Pets Are Welcome, Airport Shuttle!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...
From $497 per night (USD)VRBO
From $662 per night (USD)VRBO
FOUR Large 1BR Suites with Full Kitchen, Free Shuttle Chicago O'Hare Airport!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...
From $662 per night (USD)VRBO
From $1032 per night (USD)VRBO
-Lovely 5BD/3BR/3Parking on premises/Sleeps 14 guests/Andersonville
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...
From $1032 per night (USD)VRBO
From $107 per night (USD)VRBO
Upscale River North 1BR w/ Coffee Shop & Gym, nr Lake, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near North with views over the city. It’ll be easy to s ...
From $107 per night (USD)VRBO
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13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Laptop-Friendly Workspace | 10 Mi to Airport Make yourself at home at this 3-bedroom, 2-bath vacation rental in Maywood ...
Click For PricingExpedia