Chicago Rentals
From $433 per night (USD)VRBO
EAST LAKEVIEW DESIGNER CONDO 2 BED/2 BATH, SLEEPS 6!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
In the heart of Lakeview, still close to downtown, museums and McCormick Place. A quick stroll to Lake Michigan and the ...
From $433 per night (USD)VRBO
From $349 per night (USD)VRBO
Urban Luxury Home In Downtown Chicago!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Enjoy a stay at a world travelers' custom designed home! **PLEASE READ DESCRIPTION BELOW AND CONTACT US BEFORE REQUESTI ...
From $349 per night (USD)VRBO
From $595 per night (USD)VRBO
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 18
Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for ...
From $595 per night (USD)VRBO
From $237 per night (USD)Expedia
Downtown Guild #4 | Mag Mile, Gold Coast, The Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
𝐅𝐞𝐞𝐥 𝐚𝐭 𝐇𝐨𝐦𝐞, 𝐔𝐧𝐰𝐢𝐧𝐝, 𝐚𝐧𝐝 𝐄𝐧𝐣𝐨𝐲 𝐭𝐡𝐞 𝐚𝐦𝐞𝐧𝐢𝐭𝐢𝐞𝐬 𝐲𝐨𝐮 𝐝𝐞𝐬𝐞𝐫𝐯𝐞 𝐰𝐡𝐞𝐧 𝐲𝐨𝐮 ...
From $237 per night (USD)Expedia
From $330 per night (USD)VRBO
Downtown Urban Oasis! Near Transit, Sites, Nightlife -- Huge Deck + Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy a stay at a world travelers' Windy City home! **PLEASE READ FULL DESCRIPTION BELOW AND CONTACT US BEFORE REQUESTI ...
From $330 per night (USD)VRBO
From $483 per night (USD)VRBO
Magic Factory Loft 2West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Spacious Bright & Spotlessly Clean in the Heart of Everything Chicago - Chef Kitchen 3 bedrooms, 2 full baths Sleeps 8 g ...
From $483 per night (USD)VRBO
From $87 per night (USD)VRBO
Modern Coach House 2BR/1BA/Den in Hyde Park/ Kenwood, walk to U of C & Lakefront
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Kenwood Coach House| Rear Coach House Fully Furnished! Near U of C Hospital Hospital Staff/ Clinical Rotations REQUIRE ...
From $87 per night (USD)VRBO
From $103 per night (USD)Expedia
Mod Loop 1BR, w/ Gym, Pool nr the Millenium Park by Blueground
- 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 $103 per night (USD)Expedia
From $99 per night (USD)VRBO
Ideal River North 1BR w/pool, gym, nr. L & Magnificent Mile
- 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 $99 per night (USD)VRBO
From $237 per night (USD)Expedia
Hip Loop 1BR w/ Gym, Pool, W/D, nr. Financial District, 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 $237 per night (USD)Expedia
From $99 per night (USD)VRBO
Cozy West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, 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 $99 per night (USD)VRBO
From $138 per night (USD)Expedia
Hip River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Rush & Division furnished one bedroom ap ...
From $138 per night (USD)Expedia
From $163 per night (USD)VRBO
Bright Loop 1BR w/ Gym, Roofdeck, 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 $163 per night (USD)VRBO
From $488 per night (USD)Expedia
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Walk to almost everything Chicago has to offer- Downtown, Mag Mile, North Ave beach, zoo, and Lincoln park, restaurants, ...
From $488 per night (USD)Expedia
From $631 per night (USD)VRBO
Stone Mansion Sleeps 10-20 Free Parking Near Lake, Red Line and Wrigley
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Lots of room for you to stretch out and enjoy the great location in East Lakeview. Nearby to public transportation incl ...
From $631 per night (USD)VRBO
From $772 per night (USD)VRBO
Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Our unique Lincoln Park Rowhouse is located in the heart of Lincoln Park and is perfect for your next group gathering in ...
From $772 per night (USD)VRBO
From $181 per night (USD)VRBO
Amazing Streeterville 1BR w/ Gym, Pool, walk to Navy Pier, 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 $181 per night (USD)VRBO
From $233 per night (USD)Expedia
Beautiful Streeterville 1BR w/ Deck & Pool, walk to Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Streeterville furnished one bedroom apa ...
From $233 per night (USD)Expedia
From $207 per night (USD)VRBO
Trendy 2BR Apartment in Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Whatever brings you to town, our bright and airy two-bedroom apartment unit is complete with everything you need to feel ...
From $207 per night (USD)VRBO
From $1234 per night (USD)Expedia
Entire house 1 city block from Wrigley Field.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
We are very excited to prepare this amazing 2 story (with basement) home for your future stays. We are located in the he ...
From $1234 per night (USD)Expedia
From $127 per night (USD)VRBO
Bright and Cozy 1BR Apartment in Logan Square!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our 1-bedroom/1 bath apartment is perfect for getaway to Chicago. We're located in the trendy Logan Square neighborhood. ...
From $127 per night (USD)VRBO
From $842 per night (USD)Expedia
Large 4BR/3BA • Safe Old Town Location • Walk Everywhere
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
🛏 Sleeping Arrangements, Plenty of room for everyone to have their own space! Bedroom 1: King bed Bedroom 2: Queen bed ...
From $842 per night (USD)Expedia
From $92 per night (USD)VRBO
Luxe West Loop Studio 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. It’ll be easy to simply show up and start li ...
From $92 per night (USD)VRBO
From $315 per night (USD)VRBO
❤️ Spacious and Airy Apartment With Parking On Site!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $315 per night (USD)VRBO
From $99 per night (USD)VRBO
Gorgeous 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 sophisticated West Loop furnished one bedroom ...
From $99 per night (USD)VRBO
From $173 per night (USD)Expedia
Spacious Loop 1BR w/ Pool, Gym, nr. the L & Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming Chicago Loop furnished one bedroom a ...
From $173 per night (USD)Expedia
From $467 per night (USD)VRBO
Woodlawn Oasis...10 Minutes to Dining & Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Cour ...
From $467 per night (USD)VRBO
From $193 per night (USD)Expedia
The Avondale Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a private three bedroom house you will be reserving in the Avondale neighborhood. Plenty of available free stree ...
From $193 per night (USD)Expedia
From $200 per night (USD)VRBO
Stunning Logan Square 2BR w/ Roof Deck & Gym, 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 balcony views over the city. It’ll be ...
From $200 per night (USD)VRBO
From $380 per night (USD)Expedia
NEW LUXURY PENTHOUSE CONDO
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...
From $380 per night (USD)Expedia
From $1109 per night (USD)VRBO
THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 28
Walk to everything Chicago has to offer- Downtown and Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars ...
From $1109 per night (USD)VRBO
From $388 per night (USD)VRBO
Stunning Corner 2BR in the Loop | City & Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city an ...
From $388 per night (USD)VRBO
From $522 per night (USD)VRBO
Spectacular Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $522 per night (USD)VRBO
From $2796 per night (USD)Expedia
The Orleans - Entire Building - With Rooftop Deck!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: This property can be rented out and you would have access to the entire building which consists of 4 individual ...
From $2796 per night (USD)Expedia
From $214 per night (USD)VRBO
LOCATION!! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury condo in a FANTASTIC location! Remodeled upscale condo located on the brink of River North/Gold Coast/Streetervil ...
From $214 per night (USD)VRBO
From $192 per night (USD)Expedia
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Av ...
From $192 per night (USD)Expedia
From $210 per night (USD)VRBO
Airy West Loop 1BR w/ Pool, Pet Spa, near Restaurant Row, by Blueground
- 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 $210 per night (USD)VRBO
From $133 per night (USD)Expedia
Modern Logan Square 1BR w/ Roof Deck & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this roomy Logan Square furnished one bedroom apar ...
From $133 per night (USD)Expedia
From $676 per night (USD)VRBO
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 22
Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost eve ...
From $676 per night (USD)VRBO
From $167 per night (USD)Expedia
Cozy Loop 1BR w/ Pool, Gym, nr. Merchandise Mart & L, by Blueground
- 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 $167 per night (USD)Expedia
From $159 per night (USD)VRBO
Retro Apartment in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full o ...
From $159 per night (USD)VRBO
From $297 per night (USD)Expedia
Modern Wrigley Oasis with Parking!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully designed in the heart of Wrigley. Steps away from Wrigley Field, bars, restaurants and shops! This modern oa ...
From $297 per night (USD)Expedia
From $1486 per night (USD)VRBO
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME! ABSOLUTELY NO PARTIES!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
PRISTINE PREMIER LUXURY 3-STORY GREYSTONE HOME!!! ABSOLUTELY NO PARTIES OR LARGE GATHERINGS! We reserve the right t ask ...
From $1486 per night (USD)VRBO
From $168 per night (USD)VRBO
Fun / Bright / Cubs Apt | Near Wrigley!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: A short 10 minute walk from Wrigley Field (0.8 miles) , and everything the popular Wrigleyville has to offer. ...
From $168 per night (USD)VRBO
From $208 per night (USD)VRBO
Sleek West Loop 1BR w/ Gym, Pool, near Fulton Market, 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 $208 per night (USD)VRBO
From $96 per night (USD)Expedia
Premium Logan Square 1BR w/ Roof Deck & Gym, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable Logan Square furnished one bedroo ...
From $96 per night (USD)Expedia
From $297 per night (USD)VRBO
A home away from home! <No events allowed>
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
vacation rental cleaning protocol Major surfaces are sanitized and disinfected. Major surfaces include countertops, ...
From $297 per night (USD)VRBO
From $296 per night (USD)VRBO
Upgraded,Spacious 3 Bedroom Apartment.
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Bright and beautiful top floor 1200 sq. ft, 3 bedrooms apartment located in Jefferson Park,9 minutes from O hare Interna ...
From $296 per night (USD)VRBO
From $304 per night (USD)VRBO
NEW LUXURY CONDO WITH PATIO DECK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
OVERVIEW: This is a high end first floor condo that comfortably sleeps 5 persons. Luxury bathrooms. Fully equipped chef’ ...
From $304 per night (USD)VRBO
From $567 per night (USD)VRBO
Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! This home is perfec ...
From $567 per night (USD)VRBO
Click For PricingVRBO
Hip West Loop 2BR w/ Gym, Pool, near Fulton Market, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
Click For PricingVRBO
From $140 per night (USD)Expedia
Mod West Loop 2BR w/ Gym, Pool, W/D, nr. Fulton Market, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in West Loop with balcony views over the city. It’ll be ea ...
From $140 per night (USD)Expedia
From $167 per night (USD)VRBO
Mod River North 2BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Rush & Division with high floor views over the city. It ...
From $167 per night (USD)VRBO
From $105 per night (USD)Expedia
Hip River North 1BR w/ Pool + Roof Deck near Mag Mile, 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 $105 per night (USD)Expedia
From $114 per night (USD)VRBO
Open River North 1BR w/ Gym, W/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Rush & Division with high floor views over the city. It ...
From $114 per night (USD)VRBO
From $169 per night (USD)Expedia
Roomy River North 2BR w/ Gym, Deck & Pool, walk to Mag Mile, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Rush & Division furnished two bedroom ...
From $169 per night (USD)Expedia
Click For PricingVRBO
Smart West Loop 1BR w/ Pool, Gym, nr. Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated West Loop furnished one bedroom ...
Click For PricingVRBO
From $211 per night (USD)Expedia
Ideal Gold Coast 2BR, w/ Gym, Lounge, W/D, nr Oak Street by Blueground
- 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 $211 per night (USD)Expedia
From $836 per night (USD)VRBO
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to an amazing, 3-story art filled modern single family home in Chicago's vibrant RiverWest neighborhood. 3500 s ...
From $836 per night (USD)VRBO
From $457 per night (USD)VRBO
Gorgeous Home Near Wrigley Field
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern design of a historic Chicago row house in one of the "cities best" neighborhoods. This home was totally redesigne ...
From $457 per night (USD)VRBO
From $675 per night (USD)VRBO
3 Bedroom/ 2 Bathroom Luxury Suite in Vibrant Andersonville
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Live like a local in one of Chicago’s best neighborhoods! Located in a family-owned boutique building in the vibrant and ...
From $675 per night (USD)VRBO
From $344 per night (USD)Expedia
BEAUTIFUL 4/20 FRIENDLY 2 BR 2 BA DUPLEX -TWO FLOORS - IN SIZZLING SOUTH SHORE!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We invite you to our beautiful home, minutes from Downtown, Hyde Park, Golfing, Fishing, and the Beach! Floor 1 feature ...
From $344 per night (USD)Expedia
From $617 per night (USD)VRBO
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 20
Imagine a stone castle, medieval style; except this one has an 85" HDTV, Wifi, 16' long granite bar with full kitchen an ...
From $617 per night (USD)VRBO
From $315 per night (USD)Expedia
Trendy West Town Flat - 2 bed / 1.5 bath with parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Find your wanderlust in this perfectly located West Town condo. Situated between Chicago’s West Loop and Wicker Park ne ...
From $315 per night (USD)Expedia
From $569 per night (USD)VRBO
The Greenleaf House—Whole House
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 12
The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gat ...
From $569 per night (USD)VRBO
From $446 per night (USD)VRBO
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: [NOTE: The main rooftop is currently closed for seasonal repairs and is slated to reopen in Spring 2026. The 2n ...
From $446 per night (USD)VRBO
From $371 per night (USD)VRBO
Spacious 4 Bedroom (5 queen beds) 2 Bath in the kenwood neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
*Please inquire before requesting to book* 4 bedroom 2 bath apartment. In the Historic up and coming kenwood neighbor ...
From $371 per night (USD)VRBO
From $397 per night (USD)VRBO
Beautiful Luxury Loft in Fulton Market, Sleeps 12 | Featured In Architectural Di
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Summary: Newly renovated designer 2,500 square foot brick-and-timber loft with 15 foot ceilings located in the heart of ...
From $397 per night (USD)VRBO
From $376 per night (USD)VRBO
Luxury, spacious first floor brownstone in east Lincoln Park
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the best of Chicago’s neighborhoods, parks and lakefront from the comfort of this 2400 square foot home with two s ...
From $376 per night (USD)VRBO
From $326 per night (USD)VRBO
Modern 4 Bedroom Apt Next to Park&Pool | Lakeview
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Ready to stay in MODERN Chicago? Our NEWLY FINISHED 2-level masterpiece has IMPECCABLE DESIGN, 4 bedrooms, IN-U ...
From $326 per night (USD)VRBO
From $755 per night (USD)VRBO
MAG MILE MEGA Entire Floor 4BD 4BA +Rooftop&Gym
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome! You've found a hidden gem in the Gold Coast / Streeterville neighborhood: Guests love our home because: - You ...
From $755 per night (USD)VRBO
From $639 per night (USD)Expedia
GROUP LUX in Old Town 4bd/3ba (+Rooftop/Parking)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertai ...
From $639 per night (USD)Expedia
From $233 per night (USD)VRBO
Best Location! Luxury 51st FL Amazing Views of Lake & City, Hotel-like Amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
51st Floor! Best Value in Chicago! Luxe condo in a FANTASTIC location! Perfect for vacation, short-term housing or cor ...
From $233 per night (USD)VRBO
From $96 per night (USD)Expedia
Fantastic River North 1BR w/ Gym, Rooftop, 1 block to L, 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 $96 per night (USD)Expedia
From $1941 per night (USD)VRBO
Luxurious Four-Level Home with Personal Touches Everywhere
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 17
Cook in a dream kitchen with top-of-the-line appliances at this sprawling and luxurious home located on a quiet, one-way ...
From $1941 per night (USD)VRBO
From $148 per night (USD)Expedia
Modern South Loop 1BR w/ Pool + Gym, walk to Soldier Field, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish Central Station furnished one bedroom ...
From $148 per night (USD)Expedia
From $273 per night (USD)VRBO
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
1700 sqft penthouse in the historic west end of the West Loop. Nestled on a quiet street, minutes away from incredible r ...
From $273 per night (USD)VRBO
From $432 per night (USD)Expedia
Soft Suede and Warm Bricks at a Stylish Rogers Park Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...
From $432 per night (USD)Expedia
From $531 per night (USD)VRBO
Lincoln Park Charm Near Everything + On site Parking Spot Included
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come stay at this gorgeous, clean, renovated, top-floor apartment in beautiful Lincoln Park. The unit is located on a qu ...
From $531 per night (USD)VRBO
From $455 per night (USD)Expedia
1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Beautiful and newly furnished condo in the heart of Chicago Chinatown area with 4 bedrooms, 2 baths, two separate living ...
From $455 per night (USD)Expedia
From $313 per night (USD)VRBO
Walking distance to restaurants, shops and Lake Michigan,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Residence on the Avenue. A Spacious 1700 sq.ft. condo in a stunning blonde brick/limestone 1928 building on a tree lined ...
From $313 per night (USD)VRBO
From $170 per night (USD)Expedia
Smart River North 1BR w/ Gym, Pool, near L stop & Beach, 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 $170 per night (USD)Expedia
From $88 per night (USD)VRBO
Elegant Lakeview 1BR w/ Gym, Pool, 1 block to Lincoln Park, 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 $88 per night (USD)VRBO
From $4175 per night (USD)Expedia
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Chicago’s Gold Coast Luxury Single Family Home. The location is so perfect it cannot be beat! IG: ChicagoLuxuryVRBO. We ...
From $4175 per night (USD)Expedia
From $263 per night (USD)VRBO
Great Location-Beautiful Friendly Andersonville Neighborhood
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
City of Chicago Vacation LICENSE NO.: 2209341 This Vintage Early 1900’s 2-Flat 2nd floor apartment is in the beautiful t ...
From $263 per night (USD)VRBO
From $255 per night (USD)Expedia
Walking distance to restaurants, shops and Lake Michigan,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Residence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. We are a ...
From $255 per night (USD)Expedia
From $595 per night (USD)VRBO
The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We are happy to announce our 2nd Wrigleyville location. The Wrigleyville VIP sits just behind the Hotel Zachary, on the ...
From $595 per night (USD)VRBO
From $302 per night (USD)Expedia
One block from Lincoln Park and the zoo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Our place is a newly renovated.! You'll love the kitchen, the fireplace, the outdoor deck and it's coziness. Perfect for ...
From $302 per night (USD)Expedia
From $385 per night (USD)VRBO
Family Friendly 2BD/2BA Near Wrigley, Lincoln Square
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Live like a local in one of Chicago’s best neighborhoods at a top rated property! Located in a family-owned boutique bui ...
From $385 per night (USD)VRBO
From $159 per night (USD)Expedia
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
What guests like most? Super clean. Super comfortable. Super Host. Full use of second story fully furnished private apa ...
From $159 per night (USD)Expedia
From $181 per night (USD)VRBO
iKlektik House Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Fully furnished one bedroom in Ukrainian Village/West Town. Voted best top ten neighborhood in the United States. Close ...
From $181 per night (USD)VRBO
From $156 per night (USD)Expedia
Charming River North 1BR w/ Gym, Pool, near L stop & Beach, by Blueground
- 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 $156 per night (USD)Expedia
From $171 per night (USD)VRBO
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)VRBO
From $284 per night (USD)Expedia
✨|Beautiful|Comfy|1br|✨LincolnSq.|Near Wrigley| ✨
- 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 $284 per night (USD)Expedia
From $350 per night (USD)VRBO
✨Rustic Studio Apartment Heart of 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 $350 per night (USD)VRBO
From $347 per night (USD)Expedia
Inviting Stylish Home with Covered Patio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The residence features a subtle boho-chic inspired aesthetic, rustic wood furnishings, a breakfast bar, an open-plan mai ...
From $347 per night (USD)Expedia
From $318 per night (USD)VRBO
⭐|Stylish|Comfy|Lincoln Sq.| 2BR |✨|Near Wrigley|⭐
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the vibrant neighborhood of Lincoln Square, just a few min from an array of amazing restaurants, breweries/ba ...
From $318 per night (USD)VRBO
From $325 per night (USD)Expedia
🌟Homey|Snuggly|Modern|1BR Lakeview - Near Wrigley🌟
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Lakeview is home to Wrigleyville, Wrigley field home of the Chicago Cubs and Belmont theatre district which has over 30 ...
From $325 per night (USD)Expedia
From $422 per night (USD)VRBO
Soft Palate & Warm Bricks At A Rogers Park Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...
From $422 per night (USD)VRBO
From $777 per night (USD)Expedia
Historic luxury townhouse on Chicago's Gold Coast
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after loca ...
From $777 per night (USD)Expedia