Search Vacation Homes in Chicago
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 900 Vacation Homes in Chicago with updated reviews, rates, and availability.

Great 3 bedroom rental unit near Logan Square
Great 3 bedroom rental unit near Logan Square
9.4 out of 10, Exceptional, (27)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
10.0 out of 10, Exceptional, (164)

Cozy Home Sweet Homewood.
Cozy Home Sweet Homewood.
9.8 out of 10, Exceptional, (20)

Modern 3Bd Townhome Near Beach & Base
Modern 3Bd Townhome Near Beach & Base
9.8 out of 10, Exceptional, (18)

Cozy 3-bedroom house in family-oriented Melrose Park.
Cozy 3-bedroom house in family-oriented Melrose Park.
10.0 out of 10, Exceptional, (5)

Updated Forest Park 3 BR Bungalow
Updated Forest Park 3 BR Bungalow
10.0 out of 10, Exceptional, (100)

Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East
10.0 out of 10, Exceptional, (2)

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (88)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Chicago

Sentral Michigan Avenue
Sentral Michigan Avenue
9.2 out of 10, Wonderful, (706)
The price is AED 465
AED 654 total
includes taxes & fees
20 Apr - 21 Apr

Sonder South Wabash
Sonder South Wabash
9.0 out of 10, Wonderful, (454)
The price is AED 345
AED 405 total
includes taxes & fees
20 Apr - 21 Apr

Sonder Market Hall
Sonder Market Hall
8.6 out of 10, Excellent, (267)
The price is AED 392
AED 460 total
includes taxes & fees
22 Apr - 23 Apr
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.
Recent reviews of Chicago hotels
Recent reviews of Chicago hotels

Embassy Suites by Hilton Chicago Downtown River North
5/5 Excellent
Great place
"We actually were supposed to stay at another hotel in town and it was awful. Found this one on a whim and it was great! Clean, friendly staff, free breakfast"
A verified traveler stayed at Embassy Suites by Hilton Chicago Downtown River North
Posted 7 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
- Vacation Homes in Gurnee
- Vacation Homes in Schaumburg
- Vacation Homes in Evanston
- Vacation Homes in Downers Grove
- Vacation Homes in Skokie
- Vacation Homes in Willowbrook
- Vacation Homes in Glenview
- Vacation Homes in Rosemont
- Vacation Homes in Schiller Park
- Vacation Homes in Lombard
- Vacation Homes in Oak Park
- Vacation Homes in Des Plaines
- Vacation Homes in Elk Grove Village
- Vacation Homes in Oak Brook
- Vacation Homes in Arlington Heights