
House holiday rentals in Downtown Chicago
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Top-rated house rentals in Downtown Chicago
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Downtown Chicago
House rentals with a pool

2BR w/ Stunning Views and Resort-Style Amenities

Luxury fenced in modern ranch

Elmhurst Luxury 4BR w/ Pool, Fenced Yard, Downtown

Stunning Home in Prime Chicago with Private Pool

Rosemont 4BD2BA house with Pool

Lucky #7 w/ pool & gym

Downtown 2BR: Unique Amenities, Ideal for Tourism

Luxury Loft with Private Pool and Movie Theater
Weekly house rentals

The Modern Muse of Chicago! Close to everything!

Gold Coast Home|Rooftop |PoolTable |Parking |Views

The Architectural Haven

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

Vibrant, Spacious Chinatown Home

Windy City White House (3br/2ba) *New Listing*

Private Downtown Retreat with Rooftop Oasis

Mid-Century Gem By United Center: Hot Tub & Sauna
Private house rentals

CasaNova Modern City Living

3 bd/ 2ba with Free Parking Spot by McCormick

The Grand Vic: Large 5BD/3BA Home (+Garage)

jane's house - a boutique flat in west town -2b/1b

WrigleyRoost <5 min to Cubs/train/lake!

Lux LoganHouse w/garage, Sleeps 12, & rooftop deck

Walk to the Beach! Theater-Coffee Bar-Games-Gym

Bright, Modern Home: Chef’s Kitchen & Free Parking
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Traverse City Holiday rentals
- Wisconsin River Holiday rentals
- Townhouse rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Waterfront rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- House rentals Cook County
- House rentals Illinois
- House rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Washington Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club
- The 606
- Things to do Downtown Chicago
- Sightseeing Downtown Chicago
- Nature and outdoors Downtown Chicago
- Art and culture Downtown Chicago
- Tours Downtown Chicago
- Food and drink Downtown Chicago
- Sports activities Downtown Chicago
- Things to do Cook County
- Sports activities Cook County
- Art and culture Cook County
- Tours Cook County
- Sightseeing Cook County
- Nature and outdoors Cook County
- Food and drink Cook County
- Things to do Illinois
- Tours Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Sports activities Illinois
- Art and culture Illinois
- Nature and outdoors Illinois
- Things to do United States
- Wellness United States
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- Entertainment United States
- Nature and outdoors United States
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