House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago house rentals
House rentals with a pool
Home in Glen Ellyn
Glen Ellyn Home
Home in Schaumburg
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
Luxury Cabin in Lakeview
Home in Bloomingdale
Whole House in Bloomingdale, IL
Home in Chicago
2Bed+2Bath PentHouse in South Loop
Home in Lisle
Cozy Lisle Home w/ Fenced Backyard: Pets Welcome!
Home in Riverwoods
Riverwoods Nature Retreat
Weekly house rentals
Home in Chicago
The Evergreen House
Home in Chicago
Lincoln Park - DePaul House w/Patio Free Parking
Home in Bolingbrook
The Sunshine Spot
Home in Des Plaines
Urban Farmhouse near O'Hare
Home in Berwyn
Retro Modern Bungalow | free parking | fire pit
Home in Chicago
Boho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
Chicago getaway for two!
Home in Chicago
Lakeview Condo
Private house rentals
Home in Wilmette
Unique porcelain-enamel paneled "Lustron" home
Home in Chicago
Cozy, Quiet, Riverwalk Sanctuary
Home in Chicago
Chicago Home by Midway near Downtown Attractions
Home in Chicago
City Cottage in Logan Square-Avondale
Home in Chicago
1-bedroom with full kitchen, washer/dryer inside
Home in Chicago
Cozy Haven
Home in Chicago
Cozy space in Wicker Park
Home in Chicago Ridge
Quiet cul-de-sac with huge fenced in backyard
Destinations to explore
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Townhouse rentals United States
- Guesthouse rentals United States
- Earth house rentals United States
- Lighthouse rentals United States
- House rentals United States
- Lakehouse rentals Chicago
- Townhouse rentals Chicago
- House rentals Chicago
- Rentals with a patio Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with a washer and dryer Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Rentals with pools Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with lake access Downtown Chicago
- Condo rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Waterfront rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a home theater Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- House rentals Milwaukee
- Lakehouse rentals Milwaukee
- Lakehouse rentals Lake Geneva
- House rentals Lake Geneva
- Lakehouse rentals Illinois
- House rentals Illinois
- Guesthouse rentals Illinois
- Treehouse rentals Illinois
- Townhouse rentals Illinois
- Tiny house rentals Illinois
- House rentals Cook County
- Townhouse rentals Cook County
- Guesthouse rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom