Search Vacation Homes in Central Chicago
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Vacation Homes in Central Chicago

Beautiful, Remodeled Penthouse Unit in Old Town!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.4 out of 10, Exceptional, (24)

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.2 out of 10, Wonderful, (57)

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, (97)

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
9.2 out of 10, Wonderful, (17)

Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
10.0 out of 10, Exceptional, (2)

Luxury House in the heart of Old Town with Parking
Luxury House in the heart of Old Town with Parking
10.0 out of 10, Exceptional, (50)

Secure, Quiet, Solo Traveler's Fave, Free Coffee!
Secure, Quiet, Solo Traveler's Fave, Free Coffee!

Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
Ideal Group Getaway: Prime Location, Parking, Backyard, Sunroom & Pet-Friendly
10.0 out of 10, Exceptional, (3)
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
Top Central Chicago Hotel Reviews

Hotel Felix River North/Magnificent Mile
10/10 Excellent
Find out more about Central Chicago
Find out more about Central Chicago
Central Chicago Vacation Homes information
Number of reviews | 455 |
---|---|
Accommodation | 68 Vacation Homes |
Lowest Price | ¥26,710 |
Highest Price | ¥80,352 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Vacation Homes in Tokyo
- Vacation Homes in Osaka
- Vacation Homes in Kyoto
- Vacation Homes in Okinawa
- Vacation Homes in Nagoya
- Vacation Homes in Fukuoka
- Vacation Homes in Hatsushima
- Vacation Homes in Sapporo
- Vacation Homes in Yokohama
- Vacation Homes in Karuizawa
- Vacation Homes in Hiroshima
- Vacation Homes in Kamakura
- Vacation Homes in North Okinawa
- Vacation Homes in Izu Peninsula
- Vacation Homes in Ishigaki
- Vacation Homes in Awaji Island
- Vacation Homes in Urayasu
- Vacation Homes in Naha
- Vacation Homes in Asahikawa
- Vacation Homes in Kanto
More ways to book
Expedia's Latest Trends
Hotels
- Toyohashi Station Hotel
- Hotels in Fujiyoshida
- Apartments Senju-Ohashi Station
- Southern Beach Hotel & Resort OKINAWA
- Hilton Bangkok Grande Asoke
- Lunar Cappadocia Hotel
- Hotel Associa Shin-Yokohama
- Apartments Saitama
- Kyoto Tower Hotel
- Toyoko Inn Tokyo Fussa Station Higashi
- Hotels near Hottarakashi Onsen Hot Spring
- The HO Hotel
- Minn Chitose
- Hotels in Hiroshima City Centre
- Apartments Shin-Urayasu Station
- Hotels near Mukogaoka-Yuen Station
- Hotels near Tanashi Station
- Holiday Inn Resort Kandooma Maldives - Kids Stay & Eat Free and DIVE FREE for Certified Divers for a minimum 3 nights stay
- Daiwa Roynet Hotel Kanazawa Miyabi
- Hilton Sydney
Flights
Activities
Packages
General