Cook Area Rentals
From $102 per night (USD)VRBO
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 $102 per night (USD)VRBO
From $154 per night (USD)Expedia
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 $154 per night (USD)Expedia
From $118 per night (USD)VRBO
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 $118 per night (USD)VRBO
From $1175 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 $1175 per night (USD)VRBO
From $786 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 $786 per night (USD)VRBO
From $199 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 $199 per night (USD)VRBO
From $369 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 $369 per night (USD)VRBO
From $273 per night (USD)Expedia
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 ...
From $273 per night (USD)Expedia
From $138 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 $138 per night (USD)VRBO
From $223 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 to ...
From $223 per night (USD)Expedia
From $217 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 $217 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
From $439 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 $439 per night (USD)VRBO
From $316 per night (USD)VRBO
#1804 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $316 per night (USD)VRBO
From $311 per night (USD)VRBO
#1404 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $311 per night (USD)VRBO
From $321 per night (USD)VRBO
#1604 - Kasa Magnificent Mile Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chic ...
From $321 per night (USD)VRBO
From $119 per night (USD)VRBO
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 si ...
From $119 per night (USD)VRBO
From $563 per night (USD)Expedia
Spacious Family Glenwood Estates Home w/ Hot Tub!
- Bedrooms:
- 2
- 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 $563 per night (USD)Expedia
From $123 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 $123 per night (USD)VRBO
From $401 per night (USD)Expedia
LakeHouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 16
Entertain in style, practice yoga, or enjoy a glass of wine on this huge private space. Ideal for Corporate Short or Lon ...
From $401 per night (USD)Expedia
From $281 per night (USD)VRBO
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 $281 per night (USD)VRBO
From $345 per night (USD)Expedia
❤️ 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 $345 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 $175 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 $175 per night (USD)Expedia
From $287 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 $287 per night (USD)VRBO
From $1130 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 $1130 per night (USD)Expedia
From $799 per night (USD)VRBO
Coach House with Heated Garage and Private Rooftop Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This charming 1884 coach house sits on Lincoln Park’s most prestigious block. A 7-minute walk to the Red Line, you're ju ...
From $799 per night (USD)VRBO
From $136 per night (USD)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 ...
From $136 per night (USD)Expedia
From $982 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 $982 per night (USD)VRBO
From $149 per night (USD)VRBO
Don't miss out on this one! No cleaning fee.\nIdeal for McCormick Cntr and U of C
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Beautiful, comfortable, PRIVATE garden unit of a 3 floor home located in the historic Bronzeville neighborhood of Chicag ...
From $149 per night (USD)VRBO
From $488 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 $488 per night (USD)VRBO
From $485 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 $485 per night (USD)VRBO
From $503 per night (USD)VRBO
Fabulous 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 $503 per night (USD)VRBO
From $341 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 a sweeping Terrace and resort-like amenities are just steps ...
From $341 per night (USD)Expedia
From $531 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 Terrace view. Resort-like amenit ...
From $531 per night (USD)VRBO
From $468 per night (USD)Expedia
Luxury Modern home minutes from Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Newly rehabbed single family home with parking in Chicago's popular Pilsen neighborhood. Close to transportation, 18th s ...
From $468 per night (USD)Expedia
From $215 per night (USD)VRBO
Tasteful Logan Square 2BR w/ Gym, Roof Deck, 1 block to L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this beautiful two bedroom Blueground apartment. You’ll love comin ...
From $215 per night (USD)VRBO
From $720 per night (USD)Expedia
Gorgeous NEW 5 BDR/ 4BA in Logan Square w/Parking!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
In desirable LOGAN SQUARE - 10 minutes from Downtown Chicago, steps away from the new Restaurant Row on Diversey Avenue! ...
From $720 per night (USD)Expedia
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Smart Loop 1BR w/ Pool, Gym, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Chicago Loop furnished one bedroom apa ...
Click For PricingVRBO
From $130 per night (USD)Expedia
Gorgeous Loop 1BR w/ Gym, Pool, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Chicago Loop with views over the city. It’ll be easy to ...
From $130 per night (USD)Expedia
From $162 per night (USD)VRBO
Mod West Loop 1BR w/ Pool, Gym, nr. Fulton Market & L, 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 si ...
From $162 per night (USD)VRBO
From $114 per night (USD)Expedia
Roomy Lakeview 1BR w/ W/D, Gym, near Lakefront Trail, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $114 per night (USD)Expedia
From $147 per night (USD)VRBO
Generous River North 1BR w/ Gym, Rooftop walk to L and Parks, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this charming one bedroom Blueground apartment. You’ll love coming ...
From $147 per night (USD)VRBO
From $261 per night (USD)Expedia
Generous River North 3BR w/ Gym, Rooftop, walk to L & Park, by Blueground (ID #CHI324)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the best of Chicago, with this three bedroom apartment in River North with balcony views over the city. It’ll b ...
From $261 per night (USD)Expedia
From $167 per night (USD)VRBO
Rad West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, 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 si ...
From $167 per night (USD)VRBO
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Hip Loop 1BR w/ Gym, Pool, W/D, nr. Financial District, by Blueground
- 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 ...
Click For PricingExpedia
From $140 per night (USD)VRBO
Smart Loop 1BR w/ Gym, Pool, near Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...
From $140 per night (USD)VRBO
From $454 per night (USD)Expedia
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful, modern and newly furnished 4br/2 bath condo at a desirable location for business conventions and vacation tra ...
From $454 per night (USD)Expedia
From $270 per night (USD)VRBO
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Beautiful, newly renovated condo located in the heart of Chicago Chinatown with 2 bedroom, 1 bath, a spacious living roo ...
From $270 per night (USD)VRBO
From $458 per night (USD)Expedia
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
Newly remodeled apartment with 4 bedrooms, 4 bathrooms, a spacious & modern living area, FREE private parking and plenty ...
From $458 per night (USD)Expedia
From $447 per night (USD)VRBO
4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 11
Beautiful, modern and newly furnished 4 br/1.5 bath condo at a desirable location for both business conventions and vaca ...
From $447 per night (USD)VRBO
From $260 per night (USD)Expedia
Cozy Family 3BR Oasis: Park, Private Yard, & BBQ!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Charming Oasis! Step into this delightful 3-BR, 1-BA retreat in a friendly neighborhood with views of a ...
From $260 per night (USD)Expedia
From $322 per night (USD)VRBO
Cozy, Comfortable and Convenient apartment. Close to everything!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully designed space. Very relaxing layout with all the amenities of home. Minutes from Oak Park Arts district. A ...
From $322 per night (USD)VRBO
From $277 per night (USD)VRBO
Spacious 2-BR Condo + Free On-Site Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $277 per night (USD)VRBO
From $149 per night (USD)VRBO
Hip River North 1BR w/ Gym + Pool + W/D near Mag Mile by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in River North with views over the city. It’ll be easy to ...
From $149 per night (USD)VRBO
From $1808 per night (USD)Expedia
Downtown Sleep 20 | Mag Mile 6bd/6ba
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 16
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐚𝐭 𝐨𝐮𝐫 𝐪𝐮 ...
From $1808 per night (USD)Expedia
From $365 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 $365 per night (USD)VRBO
From $290 per night (USD)VRBO
Best Lincoln Square Location - Spacious 2 bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Charming apartment in an updated 1800s beautiful brick building. Located in the heart of Chicago's Lincoln Square neighb ...
From $290 per night (USD)VRBO
From $204 per night (USD)VRBO
Amazing Lakeview 1BR w/ Rooftop Pool, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Lake View East furnished one bedroom a ...
From $204 per night (USD)VRBO
From $166 per night (USD)Expedia
Stunning Lakeview 1BR w/ Rooftop Pool, near Wrigley Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Lake View East furnished one be ...
From $166 per night (USD)Expedia
From $135 per night (USD)VRBO
Charming Logan Square 2BR w/ Gym, Roof Deck, 1 block to L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Logan Square with views over the city. It’ll be easy to ...
From $135 per night (USD)VRBO
From $623 per night (USD)VRBO
Adorable single family home in Logan Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
I bought this house in Spring of 2016 and have been remodeling and updating it. There are 2 bedrooms upstairs with a ful ...
From $623 per night (USD)VRBO
From $311 per night (USD)VRBO
Lakeview/LincolnPark 2BR/1BA Updated Vintage Apartment in walkable neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and club ...
From $311 per night (USD)VRBO
From $642 per night (USD)Expedia
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Wrigleyville condo is located 1/2 block from Wrigley Field and Clark Street. Also close to Southport corridor and Brown ...
From $642 per night (USD)Expedia
From $228 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 $228 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 $1250 per night (USD)VRBO
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 20
Luxurious Upscale Duplex Penthouse Property - Sleeps up to 14 people with over 5600 sq ft in this Duplex Penthouse! Rec ...
From $1250 per night (USD)VRBO
From $465 per night (USD)VRBO
Single Family Home! Sleeps 8 Lincoln Park/Lakeview
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
House located in Lakeview / Lincoln Park - close to other popular Chicago neighborhoods. New furniture throughout house. ...
From $465 per night (USD)VRBO
From $227 per night (USD)VRBO
North Center - Modern, Safe, Family-Friendly, Solar-Powered Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nicely renovated, modern kitchen and bath, comfortable beds, and solar-powered. Great location in a safe neighborhood, J ...
From $227 per night (USD)VRBO
From $214 per night (USD)Expedia
Luxe Near North 2BR w/ Roof & Gym, close to Red Line, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Goose Island furnished two bedroom ap ...
From $214 per night (USD)Expedia
From $753 per night (USD)VRBO
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
This is THE place to stay for all things Chicago. Everything you need is here: * Fabulous well stocked chef's kitch ...
From $753 per night (USD)VRBO
From $95 per night (USD)VRBO
Cozy & Spacious Guest Suite in Beautiful, Quiet Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 950 sq. ft. guest suite in a quiet, upscale neighborhood is less than a mile from Bartlett Hills Golf Club, a mile ...
From $95 per night (USD)VRBO
From $214 per night (USD)VRBO
Cozy 2BR haus inn Pilsen with patio and fire pit 🔥
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Forget your worries in this spacious and serene space. You have many options steps away including a byob pizza parlor, t ...
From $214 per night (USD)VRBO
From $172 per night (USD)Expedia
Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Licensed by the City of Chicago: Studio 1: 2209375 Immaculately clean, quiet studio, housed in a brick coach house off ...
From $172 per night (USD)Expedia
From $311 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 $311 per night (USD)VRBO
From $383 per night (USD)Expedia
3 #3A - 3 Bedroom Condo w Parking - Chinatown, McCormick Place, Wintrust Arena
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
New condo in the heart of Chicago Chinatown with 3 bedrooms, 2 baths, a spacious living area and FREE private parking. T ...
From $383 per night (USD)Expedia
From $311 per night (USD)VRBO
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 $311 per night (USD)VRBO
From $300 per night (USD)Expedia
3 BD condo near to downtown, Gold Coast and Michigan Avenue.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Situated on quiet side street across from 19c. church, steps from popular bars, restaurants, and public transportation. ...
From $300 per night (USD)Expedia
From $957 per night (USD)VRBO
Luxéry Stay \"Hollywood\" Downtown/McCormick/WinTrust Area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Looking for a beautiful oasis in the midst of the city? Look no further, as this beautiful 3 bedroom gives you ...
From $957 per night (USD)VRBO
From $1251 per night (USD)Expedia
DTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Feel at Home, Unwind, and Enjoy the amenities you deserve with two 2-Story Downtown Penthouses with Million $ Views. Gu ...
From $1251 per night (USD)Expedia
From $222 per night (USD)VRBO
50th Floor Mag Mile Studio VIEW, Pool, Gym, Balcony
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
"Step into the vibrant heart of River North, where your window frames forever views and the sky blushes with the best s ...
From $222 per night (USD)VRBO
From $202 per night (USD)Expedia
Classic Lakeview 2BR w/ Deck, Pool & Gym, nr Lincoln Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this pretty two bedroom Blueground apartment. You’ll love coming h ...
From $202 per night (USD)Expedia
From $360 per night (USD)VRBO
The Logan Square Guest House - Classic Vintage Comfort With Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
You will be transported when you stay with us in this hip and charming space in Chicago's most vibrant neighborhood! Enj ...
From $360 per night (USD)VRBO
From $538 per night (USD)Expedia
DTown Penthouse 2bd +Parking, Gym, Pvt Patio, Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $538 per night (USD)Expedia
From $570 per night (USD)VRBO
Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional ser ...
From $570 per night (USD)VRBO
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Luxe Ranch & Spa House Retreat! Pets Welcome
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
We now have the newly renovated Hot Tub Room off the rear yard with additional indoor tiled bench style seating. The ho ...
Click For PricingExpedia
From $285 per night (USD)VRBO
Sleepy Sanctuary
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A spacious, modern and comfortable 2 bedroom, 1 bathroom flat situated in the quiet and relaxing Evanston neighborhood, ...
From $285 per night (USD)VRBO
From $250 per night (USD)Expedia
Trendy Streeterville Studio w/ Pool & Gym, nr Navy Pier, 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 ...
From $250 per night (USD)Expedia
From $352 per night (USD)VRBO
Lovely 3-bedroom apartment in Bronzeville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our spacious 3-bedroom, 2-bathroom apartment on the 3rd floor of a multi-unit walk-up. Enjoy the convenience ...
From $352 per night (USD)VRBO
From $224 per night (USD)Expedia
Ahh-mazing Home, rooftop deck, near lake front. Easy commute to Navy Pier/Loop.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 4
Book your Holiday-Get-away! This luxury space is elegantly adorned with central air, ample room for living, entertaining ...
From $224 per night (USD)Expedia
From $80 per night (USD)VRBO
Sleek Edgewater 1BR w/ Gym, Deck & Lounge, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Edgewater Beach furnished one bedroo ...
From $80 per night (USD)VRBO
From $139 per night (USD)Expedia
lovely and cozy vintage two bedroom, 🐾friendly apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Comfy and cozy, second floor apartment located in an incredibly beautiful & safe neighborhood on chicago’s northwest sid ...
From $139 per night (USD)Expedia
From $115 per night (USD)VRBO
Modern Gold Coast 1BR w/ Doorman & Gym, 2 blocks to L, by Blueground
- 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 $115 per night (USD)VRBO
From $178 per night (USD)VRBO
Ukrainian Village Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the heart of Ukrainian village and just a few short minutes from downtown, your family will be close to every ...
From $178 per night (USD)VRBO
From $231 per night (USD)VRBO
Monthly Specials! Cozy Home away from Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Cozy home away from home. 7 minutes to the city of Chicago, 22 minutes to Downtown. Comfortable is what I feel when I'm ...
From $231 per night (USD)VRBO
From $401 per night (USD)VRBO
STYLISH-LOCAL-COMFY-SAFE 5 night min.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located in Chicago to all of Chicago. Located in Chicago’s Andersonville & Edgewater area. Down the stre ...
From $401 per night (USD)VRBO
From $428 per night (USD)VRBO
*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 $428 per night (USD)VRBO
Click For PricingExpedia
Chic West Loop 2BR w/ Theater & Gym, nr Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this stylish two bedroom Blueground apartment. You’ll love coming ...
Click For PricingExpedia
From $1134 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 $1134 per night (USD)VRBO
From $286 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 $286 per night (USD)VRBO