Cook Area Rentals
- From $332 per night (USD)
VRBO
Kasa | Urban 1BD\/1BA, Walk to Mag Mile | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $332 per night (USD)VRBO
- From $339 per night (USD)
VRBO
Kasa | Spacious River North Apartment | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $339 per night (USD)VRBO
- From $672 per night (USD)
VRBO
Designer 3BR Luxury Penthouse in Heart of Fulton Market | Featured In Architectu
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Spectacular 2,500 square foot brick-and-timber penthouse with 15 foot ceilings located in the heart of the vibr ...
From $672 per night (USD)VRBO
- From $535 per night (USD)
Expedia
McCormick Place 2b\/2b family unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • ...
From $535 per night (USD)Expedia
- From $1477 per night (USD)
VRBO
Spectacular Fulton Market Penthouse, Sleeps 24 in Style | Featured In Architectu
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 24
Summary: 2 side-by-side designer penthouse apartments comprising 5,000 square feet (the entire top floor) of a brick-and ...
From $1477 per night (USD)VRBO
- From $757 per night (USD)
VRBO
Chic Penthouse Corner 3BR Loft In Fulton Market | Featured In Architectural Dige
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Stunning 2,500 square foot brick-and-timber luxury penthouse with 15 foot ceilings located in the heart of the ...
From $757 per night (USD)VRBO
- From $250 per night (USD)
VRBO
2\/2 Apt in the City | Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Summary: LOCATION! LOCATION! LOCATION! DOWNTOWN CHICAGO! The perfect crash pad (*NO PARTIES*) to explore the heart o ...
From $250 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Charming Fully Furnished 2BD\/1 BA Home in Homewood, IL
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly remodeled 2BD/1BA home on a quiet street. Minutes from the metra station to take you to downtown Chicago and minut ...
From $189 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Chicago Family Apartment - Kids & Pets Welcome!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Explore the Windy City with this stylish 2-bedroom, 2-bath apartment! In walking distance, you'll find a variety of loca ...
From $275 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Spacious 4 bedroom ranch home. Near Chicago
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Single level ranch home. Very quiet and spacious! Extra large master bedroom with Walkin closet. Free Wifi. Smart TV wi ...
From $270 per night (USD)VRBO
- From $280 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 $280 per night (USD)VRBO
- From $238 per night (USD)
VRBO
Delightful Home
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 4
Looking for a suburban getaway that blends family friendly surroundings with an easy drive to the windy city? Then this ...
From $238 per night (USD)VRBO
- From $135 per night (USD)
VRBO
NEW! Serene Garden-Level Apt: 30 Miles to Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the suburbs for a relaxing getaway in Steger while staying at this tastefully appointed 1-bed, 1- Loft sleepin ...
From $135 per night (USD)VRBO
- From $700 per night (USD)
Expedia
Million Dollar Views! Luxury Downtown Skyhouse!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning, Floor to Ceiling Panoramic Skyline Views from this Spacious 3-Bedroom, 2.5 Bath Apartment in the Sky! Located ...
From $700 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Suite 1 on Southport 4 Queen Beds!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $256 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Chic, Cozy home, by Blue Line Train Stop + Free parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in this chic and artfully designed condo. This sun-kissed 1-bedroom apartment in Irving Park is located in the cit ...
From $125 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Perfect weekend getaway 2BR 2BA Apartment near Wrigley Field
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your getaway location in the heart of the Roscoe Village neighborhood of Chicago! A short walk to Wrigley Fie ...
From $300 per night (USD)VRBO
- From $350 per night (USD)
VRBO
Fully furnished long term rental home Western Springs
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
One of a kind find in historic Western Springs! Come and experience this rarely available, FULLY furnished 3 bedroom/2 b ...
From $350 per night (USD)VRBO
- From $115 per night (USD)
VRBO
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 mi ...
From $115 per night (USD)VRBO
- From $331 per night (USD)
VRBO
Kasa | Near Loyola, Red Line, & Local Cuisine | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $331 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Kasa | River North, Walk to Red Line | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $261 per night (USD)VRBO
- From $391 per night (USD)
VRBO
Kasa | River North 2BD\/2BA Perfect for Families | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $391 per night (USD)VRBO
- From $376 per night (USD)
VRBO
Kasa | Family Friendly River North 2BD + Kitchen, W\/D | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $376 per night (USD)VRBO
- From $149 per night (USD)
Expedia
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 $149 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Large, sunny 3 bedroom apartment two blocks from down town Oak Park.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our beautifully decorated second floor apartment has it all. Sunny, spacious and clean. Three large bedrooms with newly ...
From $196 per night (USD)VRBO
- From $256 per night (USD)
Expedia
Spacious 2 bedroom& 2 bath Hot Bronzeville Condo Beauty
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The entire group will enjoy great access to this centrally located Condominium masterpiece. Loaded with great amenities, ...
From $256 per night (USD)Expedia
- From $541 per night (USD)
VRBO
LUXURIOUS LINCOLN PARK Home w\/ Rooftop (+parking)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Escape into this Lincoln Park Masterpiece! Guests love this home because: - Surrounded by top-notch restaurants/retai ...
From $541 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Smart Home in Logan Square by the 606 Trail
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This property is a smart home with 3 bedrooms and 2 1/2 bathrooms, with a garage for a small to medium size SUV, which c ...
From $450 per night (USD)VRBO
- From $271 per night (USD)
VRBO
Charming Sauk Village Ranch Home w\/ Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Looking for a suburban getaway that blends family-friendly surroundings with an easy drive to the Windy City? Then this ...
From $271 per night (USD)VRBO
- From $199 per night (USD)
VRBO
Modern Apartment in Berwyn
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax in this calm, stylish space. Located 5 miles away from Midway Airport, 20min to Down Town. 3 BD, 1BA ...
From $199 per night (USD)VRBO
- From $197 per night (USD)
VRBO
The New SHOW STOPPER Brand new spacious beauty ready to enhance your stay !
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This newly renovated, spacious, sophisticated condo features high ceilings, open kitchen, balcony, and laundry room. ...
From $197 per night (USD)VRBO
- From $163 per night (USD)
Expedia
Luxury Home Away From Your Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a newly rehab house remodeled a year ago this house is your home away from home!! Upstairs Downstairs All Bedroo ...
From $163 per night (USD)Expedia
- From $129 per night (USD)
VRBO
Charming 1 Bedroom entire Apartment - 1 Mile from Wrigley
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Wonderful and spacious 1 bedroom apartment in the Northside of Chicago. Strong WiFi for your business and viewing. Right ...
From $129 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple dir ...
From $368 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Urban Farmhouse near O’Hare Airport
- Bedrooms:
- 2
- 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 $125 per night (USD)VRBO
- From $288 per night (USD)
Expedia
Charming|Comfortable|1BR|Lincoln Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $288 per night (USD)Expedia
- From $83 per night (USD)
VRBO
Modern|Aesthetic|2BR|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 $83 per night (USD)VRBO
- From $227 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 $227 per night (USD)Expedia
- From $262 per night (USD)
VRBO
Trendy|Comfortable|1BR|Lincoln Square
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $262 per night (USD)VRBO
- From $320 per night (USD)
VRBO
Kasa | Explore Museums and Shopping | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $320 per night (USD)VRBO
- From $461 per night (USD)
VRBO
Kasa | Sunny, Spacious Family 2BD\/2BA | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $461 per night (USD)VRBO
- From $519 per night (USD)
VRBO
Kasa | Perfect for Traveling Families | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $519 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Kasa | Spacious 1BD\/1BA Nearby Shopping | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $329 per night (USD)VRBO
- From $90 per night (USD)
Expedia
Clean Cozy Comfortable
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Clean Cozy Comfortable 2 bedrooms apartment 2nd floor with all the amenities of home. Close to nearby local shopping an ...
From $90 per night (USD)Expedia
- From $718 per night (USD)
VRBO
❤️🔥MAGNIFICENT NEW Home w\/8 Beds & Free Parking❤️🔥
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Summary: Our home is a brand-new construction single family residence. Construction was complete in the summer of 2021. ...
From $718 per night (USD)VRBO
- From $224 per night (USD)
VRBO
❤️ Stylish and Cozy 2BR in Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Chicago! Our large 2-bedroom/1 bathroom apartment unit is perfect for getaway to Chicago. Stretch out on ...
From $224 per night (USD)VRBO
- From $165 per night (USD)
VRBO
3BR Spacious Home Away From Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Windy City and home of amazing restaurants, great sports teams, and of course the lake! Whether you are t ...
From $165 per night (USD)VRBO
- From $342 per night (USD)
VRBO
4\/2 Home + Foosball Table | Near Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to this four bedroom, two bathroom apartment located in the neighborhood of Lakeview. The location is f ...
From $342 per night (USD)VRBO
- From $152 per night (USD)
VRBO
Roomy Lincoln Park 2BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lincoln Park. with views over the city. It’ll be easy t ...
From $152 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Sleek Lincoln Park 1BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Lincoln Park furnished one bedroom ...
From $160 per night (USD)Expedia
- From $89 per night (USD)
VRBO
Ideal Lincoln Park 1BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cheery Lincoln Park furnished one bedroom apa ...
From $89 per night (USD)VRBO
- From $155 per night (USD)
Expedia
A Peaceful 2BR Lincoln Park Coach House - FREE PARKING
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Elegantly decorated and cozy 2-bedroom apartment. Both bedrooms have queen beds. Some Highlights: ✔Free parking in the ...
From $155 per night (USD)Expedia
- From $136 per night (USD)
VRBO
Serene Garden-Level Apt: 30 Miles to Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to the suburbs for a relaxing getaway in Steger while staying at this tastefully appointed 1-bed, 1-bath basement ...
From $136 per night (USD)VRBO
- From $1044 per night (USD)
VRBO
\"Holy Cow\"! 4bed 4bath Duplex Penthouse w\/ 3,000 sqft Private Roof-Deck!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
"Wow" Step outside & be face-to-face with the iconic Wrigley Field, home of the Chicago Cubs!! Best Space in Wrigley! ...
From $1044 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Bucktown Blue Bungalow-Perfect Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to Bucktown! You will love exploring the city of Chicago and this is the perfect location to do so. Take a walk, ...
From $175 per night (USD)VRBO
- From $771 per night (USD)
VRBO
Wrigley Field\/Lakeview -Entire Home- Large Groups!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 20
"Welcome to your exclusive 2-story haven flooded with natural light! Dual TV areas with brand new 70" and 55" TVs create ...
From $771 per night (USD)VRBO
- From $232 per night (USD)
VRBO
Stay in \"The Glen\" Business District! Free Breakfast, Pool. | Staybridge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled in "The Glen" business district, our suite is perfect for both business and leisure travelers. It has many ameni ...
From $232 per night (USD)VRBO
- From $348 per night (USD)
VRBO
Contemporary Suite in \"The Glen\" Business District | 24 Hour Fitness Center + Indoor Pool + Kitchen
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a stay in "The Glen" business district, courtesy of our contemporary suite! It has many amenities you're sure to l ...
From $348 per night (USD)VRBO
- From $146 per night (USD)
VRBO
Real Comfort in a 2BR APT close to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the vibrant city of Chicago! Experience the perfect home away from home in our stylish and fully furnished 2- ...
From $146 per night (USD)VRBO
- From $204 per night (USD)
Expedia
Your 1BR Homey Haven in Vibrant Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the allure of urban living at its finest with a warm invitation to our exquisitely renovated one-bedroom apartm ...
From $204 per night (USD)Expedia
- Click For Pricing
VRBO
Luxe West Loop Studio w\/ Gym, Pool, Coworking, walk to UIC, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this sophisticated one bedroom Blueground apartment. You’ll love c ...
Click For PricingVRBO
- From $276 per night (USD)
VRBO
Hotel Quality Meets Local Living 4A
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Best in the City" - Chicago Magazine. Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just ...
From $276 per night (USD)VRBO
- From $251 per night (USD)
VRBO
Hotel Quality meets Local Living 3C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Best in the City" - Chicago Magazine. Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just ...
From $251 per night (USD)VRBO
- From $264 per night (USD)
VRBO
Hotel Quality Meets Local Living Deluxe Studio 3A
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Best in the City" - Chicago Magazine. Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just ...
From $264 per night (USD)VRBO
- From $85 per night (USD)
VRBO
Serene Evanston 1BR w\/ Dishwasher, walk to Northwestern, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Evanston furnished one bedroom apar ...
From $85 per night (USD)VRBO
- From $172 per night (USD)
Expedia
Sunny Lincoln Park 2BR w\/ Lounge, Roof & Gym, near DePaul, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lincoln Park. with views over the city. It’ll be easy t ...
From $172 per night (USD)Expedia
- Click For Pricing
VRBO
Amazing Uptown 1BR w\/ Roof & W\/D, 1 block to Red Line, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Uptown. with views over the city. It’ll be easy to simp ...
Click For PricingVRBO
- Click For Pricing
Expedia
Bright Uptown 1BR w\/ W\/D & Roof, near Aragon Ballroom, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful Uptown furnished one bedroom apartm ...
Click For PricingExpedia
- From $149 per night (USD)
VRBO
Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kick back and relax in this cozy, calm and stylish 1 bedroom, 1 bath unit with a spacious kitchen, a dedicated work spac ...
From $149 per night (USD)VRBO
- From $228 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 $228 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Stunning 1,200 square foot top-floor corner penthouse with oversize windows, an open layout, and dramatic city ...
From $360 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Kasa | River North 1BD, Nearby Museums | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $329 per night (USD)VRBO
- From $340 per night (USD)
VRBO
Kasa | Prime Location-Access to Hotspots | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $340 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Kasa | River North, Stylish 1BD | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
From $329 per night (USD)VRBO
- From $242 per night (USD)
VRBO
The quality of the hotel meets the local life 3B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just 8 minutes from downtown, in the heart o ...
From $242 per night (USD)VRBO
- From $249 per night (USD)
VRBO
Hotel Quality meets Local Living 4B
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Best in the City" - Chicago Magazine. Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just ...
From $249 per night (USD)VRBO
- From $127 per night (USD)
VRBO
Elegant Loop 1BR w\/ Gym, Roof Deck, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated The Loop furnished one bedroom ...
From $127 per night (USD)VRBO
- From $202 per night (USD)
Expedia
Luxe West Loop 1BR w\/ Gym, Pool, Coworking, walk to UIC, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop. with views over the city. It’ll be easy to s ...
From $202 per night (USD)Expedia
- From $524 per night (USD)
VRBO
Spacious Family Glenwood Estates Home w\/ Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Find your new favorite spot in the suburbs of Chicago when you stay at this 4-bedroom, 2.5-bathroom vacation rental! Thi ...
From $524 per night (USD)VRBO
- From $568 per night (USD)
Expedia
McCormick Place 2b\/2b corner unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $568 per night (USD)Expedia
- From $98 per night (USD)
VRBO
Comfort\/Clean! Free Parking 15 min ORD\/Downtown2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A friendly welcome to all Business travelers & Tourists! Great 1 bed-apartment /kitchen/dining area/living room (queen ...
From $98 per night (USD)VRBO
- From $318 per night (USD)
Expedia
LakeHouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
Large Parties (3 large beds + 4 Queen Airbeds for additional sleep arrangements). Entertain in style, practice yoga, or ...
From $318 per night (USD)Expedia
- From $249 per night (USD)
VRBO
Hotel Quality meets Local Living 4C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Best in the City" - Chicago Magazine. Ruby Room Inn & Spa is one of Chicago's most unique overnight destinations. Just ...
From $249 per night (USD)VRBO
- From $273 per night (USD)
Expedia
New&Modern Apartment only 4 miles away from Midway Airport.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located 4 miles away from Midway Airport in Chicago, SeatGeek Stadium 4 miles away, 20min to Down Town, and 15min to Amp ...
From $273 per night (USD)Expedia
- From $340 per night (USD)
VRBO
❤️ Modern 2BR Apt Right next to Wrigley Field & Transit
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Experience city life; Located in Wrigley! Feel like a local! ✔️Right Next to Wrigley Field (1 block away); Home of Chi ...
From $340 per night (USD)VRBO
- From $171 per night (USD)
Expedia
Airy South Loop 2BR w\/ Roof, Gym & Lounge, 1 block to L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in South Loop. with high floor views over the city. It’ll ...
From $171 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $160 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 $160 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Large apt , close to trader Joe , cta , beach NU
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Large apt , central air one story walk up , large gourmet kitchen , two full bath , three bedrooms , mater bedroom has p ...
From $399 per night (USD)VRBO
- From $232 per night (USD)
VRBO
Executively Appointed Condo, w\/resort amenities, IND GAR, Pool, Gym+ Biz Lounge
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Terrace and resort-like amenities are just steps ...
From $232 per night (USD)VRBO
- From $150 per night (USD)
VRBO
Modern West Loop 2BR w\/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this roomy two bedroom Blueground apartment. You’ll love coming ho ...
From $150 per night (USD)VRBO
- From $749 per night (USD)
Expedia
River North 3BR\/2BA: HUGE, Parking, Center Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Experience an urban oasis unlike any other: - Complimentary parking for one vehicle in our attached lot - Spacious, re ...
From $749 per night (USD)Expedia
- From $355 per night (USD)
VRBO
Coach House w\/ Heated Garage & Pvt. Rooftop Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This historic coach house from 1884 rests on the most prestigious block in Chicago. Located in the quiet Lincoln Park ne ...
From $355 per night (USD)VRBO
- Click For Pricing
Expedia
Luxe Logan Square 2BR w\/ Gym, Roof Deck, 1 block to L, by Blueground (ID #CHI371)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Logan Square furnished two bedr ...
Click For PricingExpedia
- From $819 per night (USD)
VRBO
Stylish 4 Bedroom \/ 4 bath in the Loop | Sleeps 12 | Roof Deck
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: 2 stylish corner apartments in a perfect location with fabulous city views in multiple directions. This bright ...
From $819 per night (USD)VRBO
- From $348 per night (USD)
Expedia
\"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 $348 per night (USD)Expedia
- From $455 per night (USD)
VRBO
Stylish Corner 2 Bedroom in the Heart of Chicago | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This stylish corner apartment is in a perfect location with fabulous city views in multiple directions. It's a ...
From $455 per night (USD)VRBO
- From $417 per night (USD)
VRBO
Luxury Corner 2 Bedroom in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This stylish corner apartment is in a perfect location with fabulous city views in multiple directions. It's a ...
From $417 per night (USD)VRBO
- From $270 per night (USD)
VRBO
\"Joy of Evanston\" 1BDR, KING EXEC Suite, pool+Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Terrace and resort-like amenities are just steps ...
From $270 per night (USD)VRBO
- From $484 per night (USD)
Expedia
\"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 Terrace view. Resort-like amenit ...
From $484 per night (USD)Expedia