
House holiday rentals in Downtown Chicago
Find and book unique houses on Airbnb
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

Pardizes Suites

Glen Ellyn Home

2BR w/ Stunning Views and Resort-Style Amenities

Rosemont 4BD2BA house with Pool

Downtown 2BR: Unique Amenities, Ideal for Tourism

Luxury Loft with Private Pool and Movie Theater

Luxury fenced in modern ranch

Stunning Home in Prime Chicago with Private Pool
Weekly house rentals

The Architectural Haven

NEW! 3BR/2.5B Duplex in Noble Sq

Charming 3bd Bungalow In Vibrant Andersonville

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

Vibrant, Spacious Chinatown Home

Modern Victorian Charm | A+ Location in OP

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

Beautiful Lincoln Park House
Private house rentals

The Modern Muse of Chicago! Close to everything!

*King bed *Outdoor Living *Sought-After Area

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

Big house in the BEST Location!

Culinary DREAM - Pizza Oven/BBQ/Smoker

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

Beverly House

Sophisticated Twnhm in Prestigious S. Lincoln Park
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
- Wisconsin River Holiday rentals
- Windsor Holiday rentals
- Apartment rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with beach access Downtown Chicago
- Townhouse rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Waterfront rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a sauna 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
- Illinois Beach State Park
- Wicker Park
- Garfield Park Conservatory
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
- Art and culture Downtown Chicago
- Food and drink Downtown Chicago
- Sightseeing Downtown Chicago
- Nature and outdoors Downtown Chicago
- Sports activities Downtown Chicago
- Tours Downtown Chicago
- Things to do Cook County
- Tours Cook County
- Art and culture Cook County
- Sightseeing Cook County
- Sports activities Cook County
- Food and drink Cook County
- Things to do Illinois
- Sports activities Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Art and culture Illinois
- Tours Illinois
- Nature and outdoors Illinois
- Things to do United States
- Entertainment United States
- Wellness United States
- Art and culture United States
- Sports activities United States
- Food and drink United States
- Nature and outdoors United States
- Tours United States
- Sightseeing United States