Holiday Homes in Chicago
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chicago holiday homes
Near Lake and Museum • Pool Table • Game Area
Near Lake and Museum • Pool Table • Game AreaSouth Shore
The price is AU$672
includes taxes & fees
20 Jan - 21 Jan
The price is AU$711
includes taxes & fees
20 Jan - 21 Jan
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private BackyardOak Park
The price is AU$368
includes taxes & fees
10 Feb - 11 Feb
Newly remodeled-Near Lake 4BR w/ Hot Tub & Games
Newly remodeled-Near Lake 4BR w/ Hot Tub & GamesGages Lake
10.0 out of 10, Exceptional, (1 review)
"The property was beautiful and relaxing. Our host was wonderful and responded quickly to any questions we had. "
Danielle S.
The price is AU$797
includes taxes & fees
18 Jan - 19 Jan
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Guesthouse Gem 2BR, Smart TVs, W/D, & ParkingLa Grange Highlands
10.0 out of 10, Exceptional, (3 reviews)
"Was amazing "
Tyvon I.
The price is AU$387
includes taxes & fees
19 Jan - 20 Jan
Quaint Bungalow, near Great Lakes Naval Base
Quaint Bungalow, near Great Lakes Naval BaseMundelein
9.8 out of 10, Exceptional, (68 reviews)
"Super cozy!! The neighborhood is so so so lovely! "
Andrea M.
The price is AU$494
includes taxes & fees
18 Jan - 19 Jan
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Back Unit Patio, Balcony, Yard, Smart TVs, W/DWestmont
The price is AU$419
includes taxes & fees
18 Jan - 19 Jan
Cozy Estate in charming Willow Springs 20 minutes from Downtown and Beaches
Cozy Estate in charming Willow Springs 20 minutes from Downtown and BeachesWillow Springs
10.0 out of 10, Exceptional, (1 review)
"Host was great at communicating throughout the process. House was perfect. Great yard for the dogs and looks to be recently updated and very clean. Wasn’t a fan of being forced into the insurance or they take a big deposit when you book but don’t know if that is this listing or a VRBO thing. Still besides that it was perfect. Would definitely stay again. "
Raymond H.
The price is AU$472
includes taxes & fees
19 Jan - 20 Jan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chicago Hotel Reviews
Embassy Suites by Hilton Chicago Downtown River North
10/10 Excellent
Find out more about Chicago
Chicago Holiday Homes information
Number of reviews | 213 |
|---|---|
Accommodation | 822 Holiday Homes |
Lowest Price | AU$294 |
Highest Price | AU$1,563 |
Explore a world of travel with Expedia
- Hotels near Aon Center
- Hotels near Art Institute of Chicago
- Hotels near Auditorium Building and Theatre
- Apartments in Belmont Station
- Motels in Belmont Station
- Resort in Belmont Station
- Motels in Berwyn
- Apartments in Broadview
- Resort in Broadview
- Hotels near Buckingham Fountain
- B&B in Burbank
- Hotels near Cadillac Palace Theatre
- Apartments in Central Chicago
- B&B in Central Chicago
- Luxury Hotels in Central Chicago
- Apartments in Chicago 63rd Street Station
- Hotels near Chicago Cultural Center
- B&B in Chicago Halsted Station
- Inns in Chicago McCormick Place Station
- Hotels near Chicago Museum Campus-11th Street Station
- Holiday Homes in Chicago Norwood Park Station
- Hotels near Chicago Riverwalk
- Condo Rentals in Chicago Station
- Holiday Homes in Chicago Station
- Hotels near Chicago Symphony Orchestra
- Hotels near Chicago Theatre
- Hotels near Chicago Union Station
- Resort in Clark-Lake Station
- Hotels near Cloud Gate
- Hotels near Daley Plaza
- Beach Hotels in Downtown Chicago
- Boutique Hotels in Downtown Chicago
- Cheap Hotels in Downtown Chicago
- Hilton Hotels in Downtown Chicago
- Historic Hotels in Downtown Chicago
- Hotels with Parking in Downtown Chicago
- Lgbt Welcoming Hotels in Downtown Chicago
- Luxury Hotels in Downtown Chicago
- Spa Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Apartments in Evanston
- B&B in Evanston
- Hostels in Evanston
- Inns in Evanston
- Holiday Homes in Forest View
- Four Seasons Hotels in Gold Coast
- Hotels near Goodman Theater
- Hotels near Grant Park
- Motels in Hines
- Hotels near House of Blues Chicago
- Hotels near James M. Nederlander Theatre
- Hotels near LaSalle Street Station
- Hotels near Lollapalooza
- Farmstay in Lyons
- Hotels near Madison-Wabash Station
- Hotels near Michigan Avenue Bridge
- Hotels near Michigan Avenue
- Hotels near Millennium Park
- Motels in Oak Park
- Printers Row Hotels
- Hotels near Randolph-Wabash Station
- Apartments in Ridgeland Station
- Motels in River Grove
- All Inclusive Hotels in River North
- Cheap Hotels in River North
- Hotels with Parking in River North
- Luxury Hotels in River North
- River North Hotels
- B&B in Riverside
- Residences in Riverside
- Hotels near Ronald McDonald House near Lurie Children’s
- Hotels near Roosevelt University
- Hotels near State Street
- Inns in Stickney
- Boutique Hotels in The Loop
- Luxury Hotels in The Loop
- Ski Hotels in The Loop
- The Loop Hotels
- Theatre District Hotels
- Cabin Rentals in West Side
- Hotels near Willis Tower