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 Downtown Chicago house rentals
House rentals with a pool
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Chicago
4.87 out of 5 average rating, 39 reviewsLuxury Cabin in Lakeview
Home in Lisle
5.0 out of 5 average rating, 3 reviewsWelcoming, cozy, and a fur baby paradise.
Home in Chicago
4.82 out of 5 average rating, 17 reviews2Bed+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 Berwyn
4.99 out of 5 average rating, 84 reviewsRetro Modern Bungalow | free parking | fire pit
Home in Chicago
4.86 out of 5 average rating, 70 reviewsChicago getaway for two!
Home in Chicago
4.85 out of 5 average rating, 84 reviewsFree parking, close to public transit, dining
Home in Chicago
4.97 out of 5 average rating, 31 reviewsLakeview Condo
Home in Chicago
4.91 out of 5 average rating, 92 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Home in Chicago
5.0 out of 5 average rating, 6 reviews1-bedroom with full kitchen, washer/dryer inside
Home in Chicago
4.98 out of 5 average rating, 59 reviews2BD/1 BA with summer patio in quiet Roscoe Village
Home in Chicago
5.0 out of 5 average rating, 53 reviewsCharming 3-BED in Lincoln Park/ Old Town & Parking
Private house rentals
Home in Chicago
4.89 out of 5 average rating, 36 reviewsBrand New Spacious Duplex
Home in Chicago
5.0 out of 5 average rating, 19 reviewsChicago Home by Midway near Downtown Attractions
Home in Chicago
4.96 out of 5 average rating, 26 reviewsCharming and Classic Brick Home in Bridgeport
Home in Munster
5.0 out of 5 average rating, 18 reviewsCozy Farmhouse in Munster
Home in Chicago
4.86 out of 5 average rating, 69 reviewsLive Like a Local + Roomy home by Mexican Museum
Home in Chicago
4.93 out of 5 average rating, 75 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Home in Chicago
4.94 out of 5 average rating, 49 reviewsCozy space in Wicker Park
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family-Friendly Home in the Heart of Pilsen
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Lighthouse rentals United States
- House rentals United States
- Earth house rentals United States
- Townhouse rentals United States
- Guesthouse rentals United States
- Lakehouse rentals Chicago
- House rentals Chicago
- Townhouse rentals Chicago
- Guesthouse rentals Chicago
- Apartment rentals Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Beachfront rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a patio Downtown Chicago
- Condo rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Monthly Rentals Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Rentals with lake access Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Lakehouse rentals Milwaukee
- House rentals Milwaukee
- House rentals Lake Geneva
- Lakehouse rentals Lake Geneva
- Tiny house rentals Illinois
- Tree house rentals Illinois
- Lakehouse rentals Illinois
- House rentals Illinois
- Guesthouse rentals Illinois
- Townhouse rentals Illinois
- Townhouse rentals Cook County
- House 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