North Branch of the Chicago River Rentals
- From $348 per night (USD)
VRBO
Kasa | Work Remotely with Fast Wifi | 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 $348 per night (USD)VRBO
- From $335 per night (USD)
VRBO
Kasa | Walk to Gold Coast | 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 $335 per night (USD)VRBO
- From $389 per night (USD)
VRBO
Kasa | Spacious 2BD\/2BA Walk to Gold Coast | 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 $389 per night (USD)VRBO
- From $399 per night (USD)
VRBO
Kasa | Family Friendly 2BD Walk to 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 $399 per night (USD)VRBO
- From $317 per night (USD)
VRBO
Kasa | Contactless 1BD\/1BA Nearby Nightlife | 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 $317 per night (USD)VRBO
- Click For Pricing
VRBO
Kasa | Get Some Air on Your Balcony | 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 ...
Click For PricingVRBO
- From $290 per night (USD)
VRBO
Kasa | Sunny Space, Full Kitchen + Fast Wi-Fi | 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 $290 per night (USD)VRBO
- From $392 per night (USD)
VRBO
Kasa | Family Friendly 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 $392 per night (USD)VRBO
- From $173 per night (USD)
VRBO
Kasa | Downtown 1BD\/1BA, Walk to Nightlife | 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 $173 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Lovely 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 $116 per night (USD)Expedia
- Click For Pricing
VRBO
Modern Near North 1BR w\/ Gym & Lounge, near shopping, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy Near North Side furnished one-bedroom ap ...
Click For PricingVRBO
- From $245 per night (USD)
Expedia
Trendy West Town Flat - 2 bed \/ 1.5 bath with parking
- Bedrooms:
- 2
- 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 $245 per night (USD)Expedia
- From $467 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 $467 per night (USD)VRBO
- From $518 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 $518 per night (USD)VRBO
- From $857 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 $857 per night (USD)VRBO
- From $510 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 $510 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 $572 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 $572 per night (USD)VRBO
- From $424 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 $424 per night (USD)VRBO
- From $553 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 $553 per night (USD)VRBO
- From $710 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 $710 per night (USD)VRBO
- From $1027 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 $1027 per night (USD)VRBO
- From $591 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 $591 per night (USD)VRBO
- From $772 per night (USD)
VRBO
Sonder The Plymouth | Superior Three-Bedroom Apartment
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Avec son extérieur orné et son enseigne art déco, The Plymouth est un incontournable de South Loop. Franchissez les port ...
From $772 per night (USD)VRBO
- From $951 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 $951 per night (USD)VRBO
- From $191 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 $191 per night (USD)VRBO
- From $186 per night (USD)
VRBO
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 $186 per night (USD)VRBO
- From $689 per night (USD)
VRBO
Sonder Greektown | Three-Bedroom Apartment
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Tradition meets modern amenities at Greektown. In the heart of this historic neighborhood, your stylish space includes a ...
From $689 per night (USD)VRBO
- From $391 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 $391 per night (USD)VRBO
- From $329 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 $329 per night (USD)VRBO
- From $389 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 $389 per night (USD)VRBO
- From $386 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 $386 per night (USD)VRBO
- From $359 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 $359 per night (USD)VRBO
- From $462 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 $462 per night (USD)VRBO
- From $924 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 $924 per night (USD)VRBO
- From $1592 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 $1592 per night (USD)VRBO
- From $287 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 $287 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 $96 per night (USD)
Expedia
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 $96 per night (USD)Expedia
- From $95 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 $95 per night (USD)VRBO
- From $183 per night (USD)
Expedia
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 $183 per night (USD)Expedia
- From $377 per night (USD)
VRBO
Kasa | Fast WiFi, Full Kitchen and Lovely City Views | 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 $377 per night (USD)VRBO
- 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 $117 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 $117 per night (USD)VRBO
- From $177 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 River North. with views over the city. It’ll be easy to ...
From $177 per night (USD)Expedia
- 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 $393 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 $393 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 $4050 per night (USD)
Expedia
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 $4050 per night (USD)Expedia
- From $150 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 $150 per night (USD)VRBO
- From $109 per night (USD)
Expedia
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 $109 per night (USD)Expedia
- From $1105 per night (USD)
VRBO
Prime location Historic Chicago Townhouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago Located on one of the desirab ...
From $1105 per night (USD)VRBO
- From $652 per night (USD)
Expedia
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Lincoln Park is one of the most coveted areas to live or stay in Chicago. DePaul University is less than a block away. L ...
From $652 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Modern Lincoln Park Hideaway 1 Bd\/1Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to a recently renovated sanctuary in the sought-after neighborhood of West Lincoln Park. Indulge in the abundance ...
From $191 per night (USD)VRBO
- From $717 per night (USD)
Expedia
53\/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Embark on an extraordinary journey with Penthouse#3 – not just a rental, but a breathtaking haven in the heart of Chicag ...
From $717 per night (USD)Expedia
- Click For Pricing
VRBO
Airy 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 apartment in The Loop. with views over the city. It’ll be easy to si ...
Click For PricingVRBO
- From $562 per night (USD)
Expedia
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 24
Temporarily live in the best neighborhood in Chicago in an amazing Furnished Custom Single Family Home brought to you by ...
From $562 per night (USD)Expedia
- From $733 per night (USD)
VRBO
51\/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Indulge in the extraordinary at Penthouse#4 – not just a rental, but a magnificent haven soaring above Chicago. Picture ...
From $733 per night (USD)VRBO
- From $401 per night (USD)
Expedia
52th Floor Penthouse - Fireplace, VIEWS, grocery store in building.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with floor to ceiling window in ...
From $401 per night (USD)Expedia
- From $350 per night (USD)
VRBO
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Penthouse unit is a magnificent unique rental in Chicago. Towering above the city, with floor to ceiling window in ...
From $350 per night (USD)VRBO
- From $265 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 $265 per night (USD)Expedia
- From $270 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 $270 per night (USD)VRBO
- From $284 per night (USD)
Expedia
⭐|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 $284 per night (USD)Expedia
- From $235 per night (USD)
VRBO
🌟Spacious|Inviting 2BR Heart of Lively Lincoln Sq🌟
- 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 $235 per night (USD)VRBO
- From $500 per night (USD)
Expedia
3BR\/2.1BA TOWNHOUSE IN THE HEART OF WEST LOOP
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Location, Location, Location! Welcome to our amazing 3 BD/2.1 BA townhome located in the most desirable West Loop neighb ...
From $500 per night (USD)Expedia
- From $977 per night (USD)
VRBO
Elevate Your Experience: PH#1, A Penthouse Above the Rest in Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Imagine yourself in PH#1, a spectacular and one-of-a-kind rental perched 55 stories above the pulse of Chicago. Picture ...
From $977 per night (USD)VRBO
- From $346 per night (USD)
Expedia
52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This Downtown Chicago Penthouse unit is towering 52 stories above the city, with floor to ceiling windows in the living ...
From $346 per night (USD)Expedia
- From $430 per night (USD)
VRBO
53rd Floor MagMile Penthouse - VIEWS, Balcony, Pool, WiFi, & Fitness Center
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Penthouse level unit is a magnificent unique rental in Chicago. Towering 50+ Floors above the city, this Penthouse ...
From $430 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Belmont House, Classy & Chic\/walk to Wrigley Field
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous home is smack-dab in one of the hottest neighborhoods in Chicago, a 3/4 mile 15 minute walk to Wrigley Fie ...
From $184 per night (USD)Expedia
- From $571 per night (USD)
VRBO
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: Why pay $$$ Chi parking when you have a 2 CAR GARAGE DOWNTOWN? Our 4br/3.5ba rowhome has 4 levels & 2 ROOFTOPS; ...
From $571 per night (USD)VRBO
- From $290 per night (USD)
Expedia
312Riverhouse with private patio comfy beds!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Close to Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop sits between Chicago River & Fo ...
From $290 per night (USD)Expedia
- From $177 per night (USD)
VRBO
Mod 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 $177 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Trendy 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 stylish one bedroom Blueground apartment. You’ll love coming ...
From $174 per night (USD)Expedia
- From $308 per night (USD)
VRBO
Private Historic Coach House Wicker Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Location, location, location! Private quiet clean coach house with two bedrooms and one bath in the heart of Wicker Park ...
From $308 per night (USD)VRBO
- From $117 per night (USD)
Expedia
Tasteful Wicker Park 1BR w\/ W\/D, 1 block to L, Six Corners, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Wicker Park. with views over the city. It’ll be easy to ...
From $117 per night (USD)Expedia
- From $423 per night (USD)
VRBO
Spectacular Corner 2BR Penthouse in the Loop | Roof Deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With ...
From $423 per night (USD)VRBO
- From $174 per night (USD)
Expedia
Airy 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 comfortable River North furnished one bedroom ...
From $174 per night (USD)Expedia
- From $899 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 $899 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Serene West Loop 1BR w\/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming West Loop furnished one bedroom apar ...
From $116 per night (USD)Expedia
- From $655 per night (USD)
VRBO
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Perfectly located in the heart of Chicago in the River North neighborhood. You will experience Chicago easily from here ...
From $655 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Sunny 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 balcony views over the city. It’ll be e ...
From $116 per night (USD)Expedia
- From $114 per night (USD)
VRBO
Lovely 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 $114 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Bright West Loop 1BR w\/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming West Loop furnished one bedroom apar ...
From $116 per night (USD)Expedia
- From $114 per night (USD)
VRBO
Trendy West Loop 1BR w\/ Gym & Pool in heart of Greektown, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cozy West Loop furnished one bedroom apartmen ...
From $114 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Sweet West Loop 1BR w\/ Gym & Pool in heart of Greektown, 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 $116 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Roomy Gold Coast 1BR w\/ Walk-up, near L & Mariano Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Gold Coast furnished one bedroo ...
From $165 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Quaint River North 1BR w\/ Gym + 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 high floor views over the city. It’ll ...
From $215 per night (USD)Expedia
- From $130 per night (USD)
VRBO
Bright Loop 1BR w\/Gym, Roofdeck, W\/D, nr West Loop & the L 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 $130 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Ideal Loop 1BR w\/ Gym, Roofdeck, W\/D, nr West Loop & the , 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 $144 per night (USD)Expedia
- From $243 per night (USD)
VRBO
Ideal River North 2BR w\/ Gym, W\/D, near Magnificent Mile, by Blueground
- Bedrooms:
- 2
- 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 ...
From $243 per night (USD)VRBO
- From $151 per night (USD)
Expedia
Ideal Loop 2BR w\/ Gym, Pool, near Millennium Park, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this bright two bedroom Blueground apartment. You’ll love coming h ...
From $151 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Roomy Loop 1BR w\/ Fitness center near West Loop & the L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in The Loop. with high floor views over the city. It’ll be ...
From $144 per night (USD)VRBO
- From $116 per night (USD)
Expedia
Amazing West Loop 1BR w\/ Gym & Pool in heart of Greektown, 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 $116 per night (USD)Expedia
- From $163 per night (USD)
VRBO
Dreamy West Loop 2BR w\/ Gym & Pool in heart of Greektown, 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 $163 per night (USD)VRBO
- Click For Pricing
Expedia
Perfect 4 Bedroom + 2 Bath unit on 2 separate floors, Free parking, CUBS
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy Chicago in this lovely and very spacious home! Entire 2 floors of space for guests to enjoy! 4 total bedrooms with ...
Click For PricingExpedia
- From $48 per night (USD)
VRBO
Home sweet home in Northwest Chicago, almost a sole unit for you, great location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Full cozy, clean, and private garden suite for a pleasant stay. The home is located on a beautiful tree-lined residentia ...
From $48 per night (USD)VRBO
- From $462 per night (USD)
Expedia
Beautiful Downtown 3BR with Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
A beautiful and modern three bedroom two bath apartment located in the heart of Fulton Market in downtown Chicago. You'l ...
From $462 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Charming 3-BR House in Logan Sq
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Discover this exquisite treasure nestled in the heart of Logan Square. Guests adore this residence for its 2-level, glas ...
From $500 per night (USD)VRBO
- From $273 per night (USD)
VRBO
Cozy Garden Unit Located in North Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
My home is located on a charming tree-lined street in the North Center/Lakeview neighborhood. The featured space is a qu ...
From $273 per night (USD)VRBO