Cook Area Rentals
From $231 per night (USD)VRBO
Very clean, cozy IRVING PARK & ELSTON FREE STREET PARKING
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
2ND FLOOR UNIT in a 3 story building condo features 1 king bd, 2 bd is semi private with a curtains to enclosed the roo ...
From $231 per night (USD)VRBO
From $222 per night (USD)Expedia
Bright 2BR Apt w/ Private Entrance & Laundry by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This central location can't be beat! Situated on the border of Lakeview and Wrigleyville and only 1 mile from historic ...
From $222 per night (USD)Expedia
From $1708 per night (USD)VRBO
West Loop Group Retreat: 2 Penthouses, Balconies
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Summary: Imagine your entire group enjoying a seamless Chicago experience at 'The Adler', our exclusive collection of tw ...
From $1708 per night (USD)VRBO
From $384 per night (USD)Expedia
4 bedrooms, 6 beds, 2 full baths, and open basement loft
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
4 bedrooms, 6 beds, 2 full baths, and open basement loft. Your family of 10+ persons will be close to everything when yo ...
From $384 per night (USD)Expedia
From $585 per night (USD)VRBO
2BR Designer Loft: Modern Luxe in City Center
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury apartment is meticulously designed ...
From $585 per night (USD)VRBO
From $2668 per night (USD)VRBO
Vacation home just 2 minutes drive to Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This brand new Greystone is in the heart of North Center Lakeview, Chicago. Walking distance to Wrigley, Andersonville, ...
From $2668 per night (USD)VRBO
From $566 per night (USD)VRBO
New, Sleek 2BR - Perfect Blend of Comfort & Style in Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Welcome to your chic, new retreat in downtown Chicago! This brand new luxury apartment is meticulously designed ...
From $566 per night (USD)VRBO
From $132 per night (USD)Expedia
A Chic 8th Floor Studio Inside Vintage Style Building With Spectacular Lake View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Here’s to your perfect getaway on the South Shore of Lake Michigan in Chicago which is located only minutes from the hea ...
From $132 per night (USD)Expedia
From $131 per night (USD)VRBO
Outstanding W Loop 1BR w/ Gym, Pool, Rooftop, Spa & W/D, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Fulton Market District with views over the city. It’ll ...
From $131 per night (USD)VRBO
From $398 per night (USD)Expedia
Cozy house in the city
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 9
Experience Burbank like a local in this enchanting 3-bedroom house. Step inside and be greeted by an adorable living spa ...
From $398 per night (USD)Expedia
From $98 per night (USD)VRBO
Amazing W Loop 1BR w/ Spa, W/D, Gym, Biz Center & A/C, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Fulton Market District furnishe ...
From $98 per night (USD)VRBO
From $201 per night (USD)Expedia
Peloton available in the APT, WiFi, access to very fun restaurants and bars
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to this fantastic apartment in Chicago. This cozy space offers one bathrooms equipped with a shower, bathtub, an ...
From $201 per night (USD)Expedia
From $127 per night (USD)VRBO
Chicago Furnished 2-bedroom apartment with free WiFi & heated bathroom floors!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 1
The property is a two-unit building with a basement. The second floor is rented to a long-term tenant. Your unit is on t ...
From $127 per night (USD)VRBO
From $438 per night (USD)Expedia
Spacious 4-bedroom house in fabulous Chicago Back Yard Pond, and Theatre
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Chicago is waiting for you at this 4-bedroom house. With 2 queen beds, 1 bunk bed, and 1 twin bed, this lovely property ...
From $438 per night (USD)Expedia
From $1968 per night (USD)VRBO
Spacious 7-bedroom house in marvelous Chicago with AC, WiFi
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 12
Your home away from home in Chicago with 7 charming bedrooms, each featuring a cozy queen bed. This awesome house comes ...
From $1968 per night (USD)VRBO
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4-bedroom house in fantastic La Grange with WiFi, fitness room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This La Grange house is perfect for a holiday stay! The space is open concept for an ideal sharing space. There is a fir ...
Click For PricingExpedia
From $572 per night (USD)VRBO
NEW! Charming 3bd Bungalow in Vibrant Andersonville by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our vintage Andersonville bungalow! Built in the 1920s, our home exudes character with original floors, wind ...
From $572 per night (USD)VRBO
From $491 per night (USD)Expedia
Historic Manor House Private Guest Suite Evanston
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the Guest Suite of this exquisitely restored Historic Landmark Manor House, one block to Lake Michigan's beaches ...
From $491 per night (USD)Expedia
From $586 per night (USD)VRBO
Concert Stay! New 4BR Apt by Salt Shed
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Simplify your Chicago trip with our brand-new 4-bedroom, 3-bathroom apartment in the heart of Lincoln Park. Per ...
From $586 per night (USD)VRBO
From $606 per night (USD)Expedia
4BR Lincoln Park Getaway: Steps to Red Line
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Dive into the dynamic Chicago lifestyle at ‘The Flux’, our 4-bedroom, 3-bathroom getaway. This modern space off ...
From $606 per night (USD)Expedia
From $604 per night (USD)VRBO
4BR Group Retreat near Lincoln Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Make your group trip to Chicago easy and enjoyable at 'The Glow,' a 4-bedroom, 3-bathroom apartment near Lincol ...
From $604 per night (USD)VRBO
From $602 per night (USD)Expedia
Family-Friendly 4BR in Lincoln Park, Safe Area
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Find your peaceful haven in 'The Aura,' a 4-bedroom, 3-bathroom apartment near Lincoln Park. The Space: Enjoy ...
From $602 per night (USD)Expedia
From $594 per night (USD)VRBO
The Nova: 4BR Family Friendly near Lincoln Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Make your Chicago family trip unforgettable at 'The Nova,' a convenient 4-bedroom, 3-bathroom apartment near Li ...
From $594 per night (USD)VRBO
From $2274 per night (USD)Expedia
Luxury Downtown PH: Bean & Lake Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Chicago's Exclusive Orion Penthouse! Wake to breathtaking Bean & Park views from your 21st-floor, 3000ft² haven ...
From $2274 per night (USD)Expedia
From $247 per night (USD)VRBO
Chic 2-bedroom apartment with WiFi and AC in marvelous Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Kick back and relax in this calm, stylish top Unit space. You will love everything from the decor to the cozyness of thi ...
From $247 per night (USD)VRBO
From $89 per night (USD)Expedia
Blueground | South Loop 1bd apartment
- 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 ...
From $89 per night (USD)Expedia
From $189 per night (USD)VRBO
Award-winning, charming, 1-bedroom apartment with AC, WiFi in Pleasant Oak Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in comfort in this 1-bedroom 2nd floor apartment located in Historic village of Oak Park. Impeccably restored, the ...
From $189 per night (USD)VRBO
From $277 per night (USD)Expedia
Spacious 3-bedroom corporate condo in wonderful North Kenwood in Hyde Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Your Chicago adventure begins at this 3-bedroom corporate apartment. With 3 queen beds, 1 king bed, and 1 full bed, this ...
From $277 per night (USD)Expedia
From $233 per night (USD)VRBO
Jumbo 3bd In Hot Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Bring the whole family to this great place with lots of room for fun Comfortable 1100 sqft 3 BR 1 BA located in the beau ...
From $233 per night (USD)VRBO
From $424 per night (USD)Expedia
Chicago West Town Row House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Located in Chicago’s West Town neighborhood, you, your family and friends will be close to everything when you stay at t ...
From $424 per night (USD)Expedia
From $374 per night (USD)VRBO
Spacious 4-bedroom bungalow in family friendly Lincolnwood with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of Lincolnwood in this freshly remodeled 4-bedroom Bungalow. Nestled on a quiet street, minutes fro ...
From $374 per night (USD)VRBO
From $224 per night (USD)Expedia
Charming Home in Portage Park
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This cozy four-bedroom, two-bathroom home is ideally located near O’Hare Airport and downtown Chicago, offering convenie ...
From $224 per night (USD)Expedia
From $451 per night (USD)VRBO
New! Spacious Home 6BD/3BTH - Sleeps 16! in Hoffman Estates!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 16
Stay at our newly styled 6 bedroom / 4BTH home in Hoffman Estates where your entire group can retreat, whether it be a ...
From $451 per night (USD)VRBO
From $239 per night (USD)VRBO
Tree Top View 3-bedrm Oak Park comfortable, quiet, convenient
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Oak Park from this Tree Top View next to Rehm Park, playground pool and conservatory in a fabulou ...
From $239 per night (USD)VRBO
From $407 per night (USD)VRBO
Charming 4-bedroom house with WiFi, AC in superb Chicago Chatham
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this charming house in Chicago, centrally located and perfect for small groups or families. This marvelous p ...
From $407 per night (USD)VRBO
From $117 per night (USD)Expedia
Comfortable 2-bedroom apartment in phenomenal Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your home away from home! Comfortable apartment with an open layout, modern kitchen, and stainless steel appl ...
From $117 per night (USD)Expedia
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Charming 2-bedroom condo with AC and WiFi in lakefront downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Unwind in Chicago at this charming condo. With 2 bedrooms featuring 2 queen beds, 2 bathrooms with a shower with body so ...
Click For PricingVRBO
Click For PricingExpedia
Charming 3-bedroom apartment in the Old Norwood Park neighborhood of Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Discover this captivating 3-bedroom apartment nestled within a historic building in the heart of Old Norwood Park. This ...
Click For PricingExpedia
From $96 per night (USD)VRBO
Beautiful 2 Bedroom located in a Unique Private Park. Near Beaches Near Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Make yourself at home in this brilliant 2-bedroom Chicago retreat. With 2 full beds, a cozy living space, and a bathroom ...
From $96 per night (USD)VRBO
From $156 per night (USD)Expedia
Modern Deluxe Studio Suite in lovely Oak Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located studio. In charming Oak Park, with a tourist friendly and trendy d ...
From $156 per night (USD)Expedia
From $314 per night (USD)VRBO
Schaumburg Sanctuary - New!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
This memorable house is the perfect home base for your trip to Schaumburg. With 3 bedrooms, this gorgeous property offer ...
From $314 per night (USD)VRBO
From $113 per night (USD)VRBO
Finished Basement in Historic Oak Park with 2 cats
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Kick back and relax in this fully finished basement with one lockable bedroom with full bed and another sleeping and gat ...
From $113 per night (USD)VRBO
From $145 per night (USD)VRBO
Blueground | River North, pool & w/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $145 per night (USD)VRBO
From $109 per night (USD)Expedia
Blueground | The Loop, pool & w/d, nr park
- 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 ...
From $109 per night (USD)Expedia
From $1409 per night (USD)VRBO
Luxury Designer Combo | Private Patio | Gold Coast
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 20
Summary: TWO BRAND NEW APARTMENTs IN THE HEART OF GOLD COAST! Enjoy your own luxury units in Chicago's Gold Coast-the c ...
From $1409 per night (USD)VRBO
From $126 per night (USD)Expedia
Blueground | River North, pool & w/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in River North with balcony views over the city. It’ll be ...
From $126 per night (USD)Expedia
From $227 per night (USD)VRBO
Blueground | The Loop, pool & w/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $227 per night (USD)VRBO
From $153 per night (USD)Expedia
Blueground | River North, pool & AC, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming River North furnished one bedroom ap ...
From $153 per night (USD)Expedia
From $250 per night (USD)VRBO
Blueground | Streeterville, pool & gym, nr pier
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this beautiful one bedroom Blueground apartment. You’ll love comin ...
From $250 per night (USD)VRBO
From $220 per night (USD)Expedia
Charming Oak Park Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our cozy 2-bedroom apartment. This inviting space offers comfort and convenience and is perfect for families, ...
From $220 per night (USD)Expedia
From $271 per night (USD)VRBO
Private Home Awaits
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Escape to this brilliant 4-bedroom Homewood house, where guests can unwind in a tranquil setting. With amenities like a ...
From $271 per night (USD)VRBO
From $176 per night (USD)Expedia
Blueground | River North, pool & w/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this stylish one bedroom Blueground apartment. You’ll love coming ...
From $176 per night (USD)Expedia
From $120 per night (USD)VRBO
Blueground | River North, pool & w/d, nr Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in River North with balcony views over the city. It’ll be ...
From $120 per night (USD)VRBO
From $170 per night (USD)VRBO
Spacious 2-bedroom apartment in Forest Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this cozy comfort of home for you at this beautiful newly remodeled 2-bedroom apartment. The space features 2 bran ...
From $170 per night (USD)VRBO
From $363 per night (USD)VRBO
Dazzling Des Plaines-Single Level Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This charming 3-bedroom, 1.5-bath ranch in Des Plaines offers comfort and convenience. The fully stocked kitchen is perf ...
From $363 per night (USD)VRBO
From $323 per night (USD)Expedia
Spacious 4-bedroom house in awesome Chicago with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Chicago is waiting for you at this 4-bedroom house. With 1 king bed, 1 full bed, and 1 child bed, this lovely property o ...
From $323 per night (USD)Expedia
From $202 per night (USD)VRBO
Blueground | Hyde Park, AC, w/d, nr museum
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in East Hyde Park with views over the city. It’ll be easy ...
From $202 per night (USD)VRBO
From $93 per night (USD)Expedia
Blueground | The Loop, pool & gym, nr Willis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with high floor views over the city. It’ll ...
From $93 per night (USD)Expedia
From $167 per night (USD)VRBO
Blueground | The Loop, pool & gym, nr Willis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Chicago Loop furnished one bedroom apart ...
From $167 per night (USD)VRBO
From $196 per night (USD)VRBO
Charming 3-bedroom house with AC and WiFi in phenomenal Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Make yourself at home in this 3-bedroom Chicago retreat. This house boasts 1 queen bed and 2 full beds, perfect for a gr ...
From $196 per night (USD)VRBO
From $208 per night (USD)VRBO
Welcome to Lux! 2BR in Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Enjoy a stylish experience at this centrally-located place. This 1,100 square foot apartment offers comfortable and comp ...
From $208 per night (USD)VRBO
Click For PricingExpedia
3 Mi to Credit Union 1 Amphitheatre: Suburban Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Proximity to Golf Courses | Day Trips to Chicago | 2 Smart TVs | Free WiFi Nestled in Country Club Hills, with easy acc ...
Click For PricingExpedia
From $588 per night (USD)VRBO
NEW! Charming Belmont Heights Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Discover your home away from home in this newly renovated 4-bedroom, 2-bathroom single-family gem in the serene Belmont ...
From $588 per night (USD)VRBO
From $129 per night (USD)Expedia
Chic 1-bedroom apartment in amazing Chicago location with Gigabit-WiFi & AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Make yourself at home in this welcoming 1-bedroom Chicago retreat. This apartment features a cozy living room with a sof ...
From $129 per night (USD)Expedia
From $345 per night (USD)VRBO
Spacious 4-bedroom house in fabulous Bridgeview with fitness room, WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover this phenomenal 4-bedroom gem in Bridgeview. With 1 king bed, 2 full beds, and 1 queen bed, this house offers a ...
From $345 per night (USD)VRBO
From $254 per night (USD)VRBO
Modern & Spacious Stay in Historic Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to this spacious 3-bedroom, 2-bathroom apartment in the heart of Bronzeville! Perfect for families, fri ...
From $254 per night (USD)VRBO
From $112 per night (USD)VRBO
Blueground | Lakeshore East, pool & w/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in New Eastside with balcony views over the city. It’ll be ...
From $112 per night (USD)VRBO
From $202 per night (USD)Expedia
Blueground | Lakeshore East, pool & w/d, nr park
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this charming two bedroom Blueground apartment. You’ll love coming ...
From $202 per night (USD)Expedia
From $422 per night (USD)VRBO
Modern 2-bedroom townhome in Chicago with private patio
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
Welcome to the safe and peaceful Chicago neighborhood Bucktown! This property lives like a single family home and consis ...
From $422 per night (USD)VRBO
From $195 per night (USD)VRBO
Modern Airport Oasis -Minutes from O'Hare Airport and Downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space: Relax in simplicity at this peaceful, centrally located spot. Just 15 minutes from O'Hare airport, 20 ...
From $195 per night (USD)VRBO
From $212 per night (USD)VRBO
Modern & Cozy house in Chicago suburb
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Kick back and relax in this calm, stylish space. Luxurious serene house with 3 spacious bedrooms with high-end memory fo ...
From $212 per night (USD)VRBO
From $252 per night (USD)VRBO
Spacious 3-bedroom apartment in cool Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Make yourself at home in this 4-bedroom Chicago retreat. This marvelous apartment features 4 queen beds, a cozy living s ...
From $252 per night (USD)VRBO
From $492 per night (USD)VRBO
LUXE Vintage Green Loft - 10min to Downtown, Movie Rm, Student & Family-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to a Luxury Vintage Getaway with a 24/7 dedicated team ensuring a comfortable and unforgettable stay. ✔ Central ...
From $492 per night (USD)VRBO
From $289 per night (USD)Expedia
Charming 3-bedroom townhome in Pleasant Des Plaines with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your Des Plaines adventure begins at this welcoming 3-bedroom townhome. With 1 king bed and 2 queen beds, guests will fi ...
From $289 per night (USD)Expedia
From $401 per night (USD)VRBO
Spacious Freshly Renovated 4Br/2Ba house with AC and WiFi Near O'Hare Airport
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This enjoyable house in Elk Grove Village offers 4 bedrooms with a variety of bed sizes to accommodate all guests. With ...
From $401 per night (USD)VRBO
From $167 per night (USD)Expedia
Spacious 4-bedroom house in cool Chicago with AC, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Beautiful 4 bedroom lots of closets / 2 bath home Central A/C * Huge 'Chef' Kitchen with stove, microwave, fridge, dish ...
From $167 per night (USD)Expedia
From $616 per night (USD)VRBO
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Stay in a historic home in Old Town, within walking distance of Downtown, the Magnificent Mile, restaurants, bars, bouti ...
From $616 per night (USD)VRBO
From $94 per night (USD)Expedia
< 2 Mi to UChicago: Apt Near Bus Stops!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Laptop-Friendly Desk | 3 Smart TVs | 7 Mi to The Loop Nestled in the Washington Park neighborhood, this Chicago vacati ...
From $94 per night (USD)Expedia
From $172 per night (USD)VRBO
Just Updated! Charming 3-bedroom 25 Minutes from Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Burbank, this charming house offers 3 bedrooms with a king, queen, and twin bed. Just a short drive from Chi ...
From $172 per night (USD)VRBO
From $279 per night (USD)Expedia
Andersonville Charming 3 Bedroom/2 Bath House with Family Room plus Yard & Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Andersonville - voted the 2nd best neighborhood in the world in 2021 by Time Out - this fully FURNISHED sing ...
From $279 per night (USD)Expedia
From $290 per night (USD)VRBO
Comfy 2-bedroom apartment with AC, WiFi in Oak Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Oak Park, this delightful apartment is a brilliant choice for guests seeking a cozy retreat. With 2 bedrooms ...
From $290 per night (USD)VRBO
From $220 per night (USD)Expedia
Spacious 3-bedroom apartment with AC,WiFi in charming Bartlett,free washer/dryer
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Relax with the whole family at this peaceful place to stay. This 1,100-square-foot basement guest suite apartment offers ...
From $220 per night (USD)Expedia
From $238 per night (USD)VRBO
Blueground | Lakeshore East, pool & w/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in New Eastside with balcony views over the city. It’ll be ...
From $238 per night (USD)VRBO
From $131 per night (USD)Expedia
Blueground | Lakeshore East, pool & w/d, nr park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one bedroom Blueground apartment. You’ll love coming ...
From $131 per night (USD)Expedia
From $324 per night (USD)VRBO
Modern Ukrainian Village Oasis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your stylish retreat in Chicago’s vibrant Ukrainian Village! This newly renovated, modern condo offers two sp ...
From $324 per night (USD)VRBO
From $277 per night (USD)Expedia
River North High Rise w/Amazing Views and Parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
31+ day rental ONLY. Fully furnished and all utilities included. Amazing views of the city from this oasis perched in th ...
From $277 per night (USD)Expedia
From $138 per night (USD)VRBO
Blueground | West Loop, pool & gym, nr Willis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable West Loop Gate furnished one bedr ...
From $138 per night (USD)VRBO
From $141 per night (USD)Expedia
Blueground | River North, rooftop & gym, nr Mart
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish River North furnished one bedroom apa ...
From $141 per night (USD)Expedia
From $208 per night (USD)VRBO
Remote Worker Special: 2-bedroom townhome in Jackson Park Highlands neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Your new home away from home! This beautiful townhouse offers a cozy retreat with a queen bed and a full bed. Enjoy the ...
From $208 per night (USD)VRBO
From $352 per night (USD)VRBO
Spacious 4-bedroom apartment in fabulous Chicago with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
This Chicago apartment boasts 4 inviting bedrooms with queen beds. The bathroom comes equipped with a bathtub and a hair ...
From $352 per night (USD)VRBO
From $137 per night (USD)VRBO
Blueground | West Loop, gym & bbq, nr Willis Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in West Loop. It’ll be easy to simply show up and start li ...
From $137 per night (USD)VRBO
From $263 per night (USD)Expedia
Chic 2-bedroom apartment with WiFi, AC in lovely Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Stay comfortably in Chicago at this 2-bedroom apartment. This charming property features 1 king bed and 1 queen bed, per ...
From $263 per night (USD)Expedia
From $480 per night (USD)VRBO
Luxury Meets Comfort: River North Rentals with Chic Style & Prime Chicago Access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $480 per night (USD)VRBO
From $370 per night (USD)VRBO
Stay Chic in Chicago: River North Suites w/ Luxe Amenities & Prime Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $370 per night (USD)VRBO
From $519 per night (USD)VRBO
Luxury Suites in Chicago's West Loop – Steps from Dining, Shopping & Attractions
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $519 per night (USD)VRBO
From $844 per night (USD)VRBO
Luxury Suites in Chicago's West Loop – Modern Comfort Meets Vibrant City Life
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $844 per night (USD)VRBO
From $370 per night (USD)VRBO
Experience the Suite Life in Chicago’s Iconic Old Town – Spacious Stays Await
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $370 per night (USD)VRBO
From $1565 per night (USD)VRBO
Luxury West Loop Stay: Modern Suites w/ Balcony, Resort Amenities & City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled in Chicago's vibrant West Loop, Level Fulton Market brings an unparalleled hospitality experience with modern st ...
From $1565 per night (USD)VRBO
From $486 per night (USD)VRBO
Live the Suite Life: Historic Old Town Chicago Stays with Modern Luxury & Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
With its historic architecture and tree-lined streets, Chicago’s Old Town is one of the city’s most iconic neighborhoods ...
From $486 per night (USD)VRBO
From $414 per night (USD)VRBO
Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
In a city known for its neighborhoods, River North stands out. You’ll find chic galleries, buzz-worthy restaurants and v ...
From $414 per night (USD)VRBO