Chicago Rentals
- From $90 per night (USD)
VRBO
Beautiful South Loop 1BR w\/ Gym & Lounge, 1 block to L, 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 $90 per night (USD)VRBO
- From $132 per night (USD)
VRBO
Sleek West Loop 1BR w\/ Gym & Pool in heart of Greektown, 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 $132 per night (USD)VRBO
- From $208 per night (USD)
VRBO
Luxe West Loop 1BR w\/ Pool, Coworking & Gym, 1 block to L, 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 $118 per night (USD)
VRBO
Premium South Loop 1BR w\/ Gym & Lounge, 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 cozy South Loop furnished one bedroom apartme ...
From $118 per night (USD)VRBO
- From $427 per night (USD)
VRBO
MICH AVE Downtown, Grant Park, Museums 2bd\/2ba #23
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly renovated Michigan Ave, Grant Park, Museum Campus 2bed/2bath home! Guests LOVE staying with us bec ...
From $427 per night (USD)VRBO
- From $453 per night (USD)
VRBO
MICH AVE Downtown, Grant Park, Museums 2bd #4
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our Grant Park, Museum Campus 2bed/2bath home! Guests LOVE staying with us because: -Central location close ...
From $453 per night (USD)VRBO
- From $435 per night (USD)
VRBO
Downtown MICH AVE #20, Grant Park, Museums 2bd\/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our newly renovated Michigan Avenue, Grant Park, Museum Campus 2bed/2bath home! Guests love staying with us ...
From $435 per night (USD)VRBO
- From $441 per night (USD)
VRBO
MICH AVE #5 Downtown, Grant Park, Museums 2bd\/2ba
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our MIchigan Avenue, Grant Park, Museum Campus 2bed/2bath home! If you're interested in booking, see our FAQ ...
From $441 per night (USD)VRBO
- From $213 per night (USD)
VRBO
Bright River North 1BR w\/ Gym, Rooftop, walk to Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright River North furnished one bedroom apar ...
From $213 per night (USD)VRBO
- From $144 per night (USD)
VRBO
Expansive Lincoln Park 2BR, walk to L + Clark Street dining, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this pretty Lincoln Park furnished two bedroom apa ...
From $144 per night (USD)VRBO
- From $172 per night (USD)
VRBO
2BR in Andersonville-Walk to train, beach, shops and restaurants!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Two bedroom apartment right in Historic Uptown / Andersonville. One block from CTA redline and one block from Clark Stre ...
From $172 per night (USD)VRBO
- From $457 per night (USD)
VRBO
Spacious River North 3BR w\/ Gym, Rooftop, walk to L & Park, by Blueground (ID #CHI323)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated River North furnished three bed ...
From $457 per night (USD)VRBO
- Click For Pricing
VRBO
Smart West Loop 1BR, walk to Dining, Market, steps from L, 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 ...
Click For PricingVRBO
- From $225 per night (USD)
VRBO
Spacious Gold Coast 1BR, w\/ W\/D, Gym nr Magnificent Mile by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this lovely Gold Coast furnished one bedroom apart ...
From $225 per night (USD)VRBO
- Click For Pricing
VRBO
Convenient Loop 1BR w\/ Gym + Theatre Room near Grant Park by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy The Loop furnished one bedroom apartment ...
Click For PricingVRBO
- From $324 per night (USD)
VRBO
Kasa | Relaxing 1 BD + Near Local Eateries | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $324 per night (USD)VRBO
- From $434 per night (USD)
VRBO
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $434 per night (USD)VRBO
- From $327 per night (USD)
VRBO
Kasa | Traditional 1 BD + Fast Wifi | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $327 per night (USD)VRBO
- From $347 per night (USD)
VRBO
Kasa | Classic 2 BD + Near Grant Park | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $347 per night (USD)VRBO
- From $381 per night (USD)
VRBO
Kasa | Welcoming 2 BD + Game Room Access | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $381 per night (USD)VRBO
- From $331 per night (USD)
VRBO
Kasa | Inviting 1 BD + Game Room Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $331 per night (USD)VRBO
- From $388 per night (USD)
VRBO
Kasa | Family Friendly 2 BD + Fast Wifi | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $388 per night (USD)VRBO
- From $314 per night (USD)
VRBO
Kasa | Comfy 1 BD + Game Room Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $314 per night (USD)VRBO
- From $317 per night (USD)
VRBO
Kasa | Welcoming 1 BD + Fast Wifi | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $317 per night (USD)VRBO
- From $1003 per night (USD)
VRBO
Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom \/ Unit 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Modern, large, & art filled downtown townhouse in Chicago's happening RiverWest neighborhood. 3000+ sq ft 4-bedroom 3. ...
From $1003 per night (USD)VRBO
- From $115 per night (USD)
VRBO
Splendid Streeterville 1BR w\/ Gym, Pool, near Navy Pier, 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 $306 per night (USD)
VRBO
Kasa | Inviting 1 BD + Pet Friendly | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $306 per night (USD)VRBO
- From $307 per night (USD)
VRBO
Kasa | Classic 1 BD + Gym Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $307 per night (USD)VRBO
- From $324 per night (USD)
VRBO
Kasa | Modern 1 BD + Gym Access | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $324 per night (USD)VRBO
- From $373 per night (USD)
VRBO
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $373 per night (USD)VRBO
- From $366 per night (USD)
VRBO
Kasa | Family Friendly 2 BD + Pet Friendly | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $366 per night (USD)VRBO
- From $186 per night (USD)
VRBO
Roomy South Loop 1BR w\/ Pool, Lounge, walk to CTA Trains, 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 $186 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Sonder Greektown | One-Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Tradition meets modern amenities at Greektown. In the heart of this historic neighborhood, your stylish space includes a ...
From $368 per night (USD)VRBO
- From $111 per night (USD)
VRBO
Airy South Loop 1BR w\/ Lounge, Pool & Gym near Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop. with balcony views over the city. It’ll be ...
From $111 per night (USD)VRBO
- Click For Pricing
VRBO
Bright South Loop 1BR w\/ Pool, Gym, walk to Museum Campus, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in South Loop. with views over the city. It’ll be easy to ...
Click For PricingVRBO
- From $1563 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 $1563 per night (USD)VRBO
- From $85 per night (USD)
VRBO
Roomy Lakeview 1BR w\/ Courtyard & W\/D, 2 blocks to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Lakeview furnished one-bedroom apartment ...
From $85 per night (USD)VRBO
- From $324 per night (USD)
VRBO
Newly Renovated 4BR/2BA Condo in Historic Greystone Bldg in Hyde Park w/parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Beautiful, newly renovated 1900sq ft 4BR/2BA condo in a historic greystone building with in-unit washer/dryer and a gene ...
From $324 per night (USD)VRBO
- From $261 per night (USD)
VRBO
Roomy Ravenswood 2BR w\/ Rooftop, BBQ, next to Brown line, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Ravenswood furnished two bedroom apartme ...
From $261 per night (USD)VRBO
- From $252 per night (USD)
VRBO
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, open ...
From $252 per night (USD)VRBO
- From $585 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 $585 per night (USD)VRBO
- Click For Pricing
VRBO
Sleek Loop 1BR w\/ Gym, W\/D & Pool, near Millennium Park, 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
- Click For Pricing
VRBO
Roomy Loop 1BR w\/ Gym, W\/D & Pool, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one-bedroom Blueground apartment. You’ll love coming h ...
Click For PricingVRBO
- From $370 per night (USD)
VRBO
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 $370 per night (USD)VRBO
- From $100 per night (USD)
VRBO
Lovely River North 1BR w\/ Gym, Pool, near L stop & Beach, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated River North furnished one bedro ...
From $100 per night (USD)VRBO
- From $161 per night (USD)
VRBO
Darling 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 River North. with views over the city. It’ll be easy to ...
From $161 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Ultra Modern Wicker Park Pad w\/ HUGE Outdoor Space
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Our Townhouse sits in an incredible location. 1 minute away from 90/94 expressway, on a quiet cul-de-sac in Wicker Park. ...
From $179 per night (USD)VRBO
- From $128 per night (USD)
VRBO
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 South Loop furnished one bedroom apar ...
From $128 per night (USD)VRBO
- From $258 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 $258 per night (USD)VRBO
- From $224 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 $224 per night (USD)VRBO
- Click For Pricing
VRBO
Chic Lakeview 2BR w\/ W\/D & Pool, 3 blocks to Lakefront, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Lakeview. with views over the city. It’ll be easy to si ...
Click For PricingVRBO
- From $120 per night (USD)
VRBO
Trendy Loop 1BR w\/ Gym, W\/D & Pool, 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 stylish The Loop furnished one-bedroom apartm ...
From $120 per night (USD)VRBO
- From $111 per night (USD)
VRBO
Sleek 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 spacious one bedroom Blueground apartment. You’ll love coming ...
From $111 per night (USD)VRBO
- From $172 per night (USD)
VRBO
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 River North. with views over the city. It’ll be easy to ...
From $172 per night (USD)VRBO
- From $108 per night (USD)
VRBO
Dreamy Loop 1BR w\/ Gym, W\/D & Pool, near Millennium Park, 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 $108 per night (USD)VRBO
- Click For Pricing
VRBO
Dreamy Loop 1BR w\/ Gym, W\/D & Pool, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one-bedroom The Loop apartment with views over the city. It’ll be easy to simpl ...
Click For PricingVRBO
- From $174 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 Lakeview furnished one bedroom ...
From $174 per night (USD)VRBO
- From $297 per night (USD)
VRBO
Modern 4 Bedroom Greystone | White Sox
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Three story Greystone which still has the original charm with it's 2 story entrance is nestled within a very hi ...
From $297 per night (USD)VRBO
- From $407 per night (USD)
VRBO
Kasa | Spacious 2BD 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 $407 per night (USD)VRBO
- From $354 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 $354 per night (USD)VRBO
- From $240 per night (USD)
VRBO
One half 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 $240 per night (USD)VRBO
- From $478 per night (USD)
VRBO
2BD\/2BA Near Wrigley, Lincoln Square. Family Friendly Boutique Hotel
- 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 $478 per night (USD)VRBO
- From $125 per night (USD)
VRBO
Cozy Portage Park Furnished Apt, Free Parking, Dogs, Kids, Quiet & 420 Compliant
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Full use of second story private apartment. Renovated, registered historic Chicago multi-apartment bungalow located in t ...
From $125 per night (USD)VRBO
- From $172 per night (USD)
VRBO
iKlektik House Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Fully furnished one bedroom in Ukrainian Village/West Town. Voted best top ten neighborhood in the United States. Close ...
From $172 per night (USD)VRBO
- From $138 per night (USD)
VRBO
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 $138 per night (USD)VRBO
- From $179 per night (USD)
VRBO
Rad 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 sophisticated one bedroom Blueground apartment. You’ll love c ...
From $179 per night (USD)VRBO
- From $3829 per night (USD)
VRBO
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Chicago’s Gold Coast Luxury Single Family Home. The location is so perfect it cannot be beat! IG: ChicagoLuxuryVRBO. Ho ...
From $3829 per night (USD)VRBO
- From $167 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 $167 per night (USD)VRBO
- From $175 per night (USD)
VRBO
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 $175 per night (USD)VRBO
- From $120 per night (USD)
VRBO
Walking distance to Lake Michigan, shops and restaurants.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Sky View Condo at Residence on the Avenue is a spacious 1800 sq. ft condo . This is one of our 3 rentals. The Sky Vi ...
From $120 per night (USD)VRBO
- From $160 per night (USD)
VRBO
Chic Loop 1BR w\/ Gym, W\/D & Pool, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one-bedroom The Loop apartment. It’ll be easy to simply show up and start living ...
From $160 per night (USD)VRBO
- From $683 per night (USD)
VRBO
Spectacular Corner 3BR Loft In Fulton Market | Featured In Architectural Digest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Stunning 2,500 square foot brick-and-timber luxury loft with 15 foot ceilings located in the heart of the vibra ...
From $683 per night (USD)VRBO
- From $523 per night (USD)
VRBO
Beautiful Corner 2 Bedroom in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This corner apartment is in a perfect location with panoramic city views in multiple directions. With over 1,20 ...
From $523 per night (USD)VRBO
- From $289 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 $289 per night (USD)VRBO
- From $146 per night (USD)
VRBO
Ideal West Loop 1BR w/ Gym, Pool & Lounge, 2 blocks from L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this beautiful West Loop furnished one-bedroom apa ...
From $146 per night (USD)VRBO
- From $545 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 $545 per night (USD)VRBO
- Click For Pricing
VRBO
Bucktown Bungalow *Prime Location* Private Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spend your summer vacation lounging on the roof deck at our lovely Bucktown home! Perfect location to explore all that C ...
Click For PricingVRBO
- From $149 per night (USD)
VRBO
Ideal Streeterville 1BR w/ Gym, Pool, 1 block to Navy Pier, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this pretty one-bedroom Blueground apartment. You’ll love coming h ...
From $149 per night (USD)VRBO
- From $104 per night (USD)
VRBO
Classic Gold Coast 2BR w\/ Gym, Roof Deck, near Water Tower, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two bedroom apartment in Gold Coast. with views over the city. It’ll be easy to ...
From $104 per night (USD)VRBO
- From $842 per night (USD)
VRBO
Stunning Designer Loft in Fulton Market, Sleeps 24 | Featured In Architectural D
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 24
Summary: 2 beautiful side-by-side apartments comprising 5,000 square feet (the entire 2nd floor) of a brick-and-timber l ...
From $842 per night (USD)VRBO
- Click For Pricing
VRBO
Chic South Loop 1BR w/ Lounge, Pool & Gym near Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright South Loop furnished one-bedroom apart ...
Click For PricingVRBO
- From $259 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 $259 per night (USD)VRBO
- From $362 per night (USD)
VRBO
Wrigleyville Inn, Beautiful Modern 1 Bedroom, Steps from Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently built from the ground up and featured on the Travel Channel, you will love our beautifully furnished one-bedroo ...
From $362 per night (USD)VRBO
- Click For Pricing
VRBO
Chic South Loop 2BR w\/ Pool, Workspace, near Grant Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this comfortable South Loop furnished two bedroom ...
Click For PricingVRBO
- From $548 per night (USD)
VRBO
Sonder Jewelers Row | Two-Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Jewelers Row is the architectural gem of the Chicago Loop. Designed by Adler and Sullivan, the innovative style adds a m ...
From $548 per night (USD)VRBO
- From $421 per night (USD)
VRBO
Sonder Jewelers Row | Superior One-Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Jewelers Row is the architectural gem of the Chicago Loop. Designed by Adler and Sullivan, the innovative style adds a m ...
From $421 per night (USD)VRBO
- From $549 per night (USD)
VRBO
Sonder Jewelers Row | Superior Two-Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Jewelers Row is the architectural gem of the Chicago Loop. Designed by Adler and Sullivan, the innovative style adds a m ...
From $549 per night (USD)VRBO
- From $793 per night (USD)
VRBO
Sonder The Plymouth | Spacious Three-Bedroom Apartment
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $793 per night (USD)VRBO
- From $960 per night (USD)
VRBO
Sonder The Plymouth | Four-Bedroom Apartment
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $960 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Sonder The Plymouth | Two-Bedroom Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $565 per night (USD)VRBO
- From $738 per night (USD)
VRBO
Sonder The Plymouth | Superior Three-Bedroom Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $738 per night (USD)VRBO
- From $570 per night (USD)
VRBO
Sonder South Wabash | Superior One-Bedroom Apartment w\/ Balcony City View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kit ...
From $570 per night (USD)VRBO
- From $744 per night (USD)
VRBO
Sonder The Plymouth | Three-Bedroom Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
With its ornate exterior and art-deco sign, The Plymouth is a South Loop staple. Step through the glass doors and into t ...
From $744 per night (USD)VRBO
- From $361 per night (USD)
VRBO
Kasa | Modern 1B\/1BA with Fast WiFi + Full Kitchen | 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 $361 per night (USD)VRBO
- From $407 per night (USD)
VRBO
Kasa | Family 2BD\/2BA with In-Unit W\/D + Full Kitchen | 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 $407 per night (USD)VRBO
- From $401 per night (USD)
VRBO
Kasa | Urban 2BD Near Magnificent Mile | 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 $401 per night (USD)VRBO
- From $352 per night (USD)
VRBO
Kasa | Fast WiFi, 1BD\/1BA with Full Kitchen | 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 $352 per night (USD)VRBO
- From $432 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 $432 per night (USD)VRBO
- From $895 per night (USD)
VRBO
MAG MILE MEGA ENTIRE FLOOR 4BD\/4BA+Parking&Rooftop
- 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 $895 per night (USD)VRBO
- From $778 per night (USD)
VRBO
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 $778 per night (USD)VRBO