Search Vacation Homes in Chicago
- Be pickySearch almost a million properties worldwide
- Change your mindBook hotels with free cancellation
Plan, book, stay with confidence
Check availability on Vacation Homes in Chicago
Compare 495 Vacation Homes in Chicago with updated reviews, rates, and availability.
Lincoln Park Living - Suite 2!
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (2)
Luxury Downtown Penthouse with Private Rooftop!
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
Beautiful, Remodeled Penthouse Unit in Old Town!
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
Save an average of 15% on thousands of hotels when you're signed in
Your Next Vacation Home
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
The price is SAR 675
SAR 1,212 total
includes taxes & fees
3 Jum. II - 4 Jum. II
Breathtaking Downtown Penthouse B - Sleeps 11
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (2)
Luxury Home Away From Your Home
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
Breathtaking Downtown Penthouse A - Sleeps 11!
Breathtaking Downtown Penthouse A - Sleeps 11!
8.0 out of 10, Very Good, (1)
LUXE 3 BR, 2 BA + Hot Tub
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
The price is SAR 563
SAR 955 total
includes taxes & fees
21 Jum. I - 22 Jum. I
Relax & enjoy private house, green and quiet
Relax & enjoy private house, green and quiet
✽ Charming Cottage ✽ close to College/Town/Station
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (30)
The price is SAR 638
SAR 1,095 total
includes taxes & fees
20 Jum. I - 21 Jum. I
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
The price is SAR 770
SAR 1,596 total
includes taxes & fees
20 Jum. I - 21 Jum. I
Free Parking! Designed for Work and Play - Perfect for Any Traveler with 2 Work Spaces and Old Town Charm by RedAwning
Free Parking! Designed for Work and Play - Perfect for Any Traveler with 2 Work Spaces and Old Town Charm by RedAwning
8.8 out of 10, Excellent, (28)
Freshly Remodeled Cozy Home
Freshly Remodeled Cozy Home
10.0 out of 10, Exceptional, (15)
national historic home near downtown airports no parties no events
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
The price is SAR 1,125
SAR 1,296 total
includes taxes & fees
20 Jum. I - 21 Jum. I
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, (70)
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace
9.0 out of 10, Wonderful, (43)
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
The price is SAR 454
SAR 881 total
includes taxes & fees
26 Jum. I - 27 Jum. I
Fully Updated home. Great for the entire family!
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, (10)
Cozy, King bed with heated bathroom!
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
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.
Other property types in Chicago
Sentral Michigan Avenue
Sentral Michigan Avenue
9.2 out of 10, Wonderful, (404)
The price is SAR 521
SAR 722 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Sonder Market Hall
Sonder Market Hall
8.2 out of 10, Very Good, (80)
The price is SAR 344
SAR 397 total
includes taxes & fees
27 Jum. I - 28 Jum. I
Sonder South Wabash
Sonder South Wabash
8.8 out of 10, Excellent, (295)
The price is SAR 655
SAR 756 total
includes taxes & fees
10 Jum. II - 11 Jum. II
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 hotelsExpedia verified reviews
5/5 Excellent
"All has gone as planned. Check in was quick and the ice machine on the 7th floor works. What a bonus."
A verified traveler from ARLINGTON stayed at Congress Plaza Hotel
Posted 2 days ago
Popular Destinations
- Vacation Homes in Evanston
- Vacation Homes in Gurnee
- Vacation Homes in Bridgeview
- Vacation Homes in Oak Park
- Vacation Homes in Willowbrook
- Vacation Homes in Rosemont
- Vacation Homes in Schiller Park
- Vacation Homes in Downers Grove
- Vacation Homes in Oak Brook
- Vacation Homes in Lombard
- Vacation Homes in Skokie
- Vacation Homes in Elk Grove Village
- Vacation Homes in Schaumburg
- Vacation Homes in Des Plaines
- Vacation Homes in Arlington Heights
Top Vacation Homes in Other Destinations
More Accommodation Types in Chicago
Expedia's Latest Trends
Flights
Flights to SouldernFlights to ParFlights to KirkhamFlights to East GrimsteadFlights to Ash ShimasiyahFlights to MarsettFlights to Blackborough EndFlights to WendyFlights to HighwayFlights to DervaigFlights to BunburyFlights to Great MiltonFlights to SandtoftFlights to HalstockFlights to WithersfieldFlights to CoveFlights to MorleyFlights to WoodhurstFlights to LlanyreFlights to WitherslackFlights to AbergwiliFlights to LlanhamlachFlights to AbramFlights to Carlyon BayFlights to ElvingtonFlights to ElsteadFlights to Frome Saint QuintonFlights to Hemsworth