Chicago Vacation Rentals

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Check prices for these dates

Tonight
Nov 4 - Nov 5
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Nov 5 - Nov 6
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Vacation Rentals in Chicago

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (972)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P7,884
P10,981 total
includes taxes & fees
Nov 10 - Nov 11
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (604)
"Great place close to downtown. Well equipped and super clean. "
United States
Mauricio
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (375)
"Great place to stay. Loved it!"
United States
Peter
The price is P12,114
P15,533 total
includes taxes & fees
Nov 10 - Nov 11
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very Good, (397)
"Quite and low key spot"
United States
Shunica
The price is P5,942
P6,976 total
includes taxes & fees
Nov 20 - Nov 21
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (249)
"Great stay. "
United States
Teresa
The price is P7,446
P8,741 total
includes taxes & fees
Nov 30 - Dec 1
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (706)
"Location was nice."
United States
Juliet
The price is P7,940
P9,320 total
includes taxes & fees
Nov 20 - Nov 21
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (369)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (215)
"excellent room, beds - great communication and very stylish- only issue is parking can be complicated "
United States
chris
The Neighborhood Hotel-Little Italy
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very Good, (56)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
United States
Swastika
The price is P6,941
P8,148 total
includes taxes & fees
Nov 20 - Nov 21
Sonder by Marriott Bonvoy The Opal Apartments River North
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very Good, (187)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is P6,442
P7,562 total
includes taxes & fees
Nov 20 - Nov 21
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business center
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
The price is P9,752
P16,965 total
includes taxes & fees
Nov 18 - Nov 19
Kasa River North Chicago
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is P4,656
P5,466 total
includes taxes & fees
Nov 5 - Nov 6
Wrigleyville Suites
Living room
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"I enjoyed my stay! Thanks!"
United States
Jonathan
The price is P6,941
P8,148 total
includes taxes & fees
Nov 20 - Nov 21
Sonder by Marriott Bonvoy Greektown Apartments
Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is P14,628
P23,241 total
includes taxes & fees
Nov 9 - Nov 10
Stylish Apartment near Chicago Downtown
Interior
Art Villa
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is P31,665
P60,549 total
includes taxes & fees
Nov 5 - Nov 6
Art Villa
Free WiFi
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is P58,747
P68,963 total
includes taxes & fees
Nov 12 - Nov 13
Chicago luxury home suites
Iron/ironing board, free WiFi
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (21)
"This property is excellent!"
United States
Philip
The price is P3,481
P7,875 total
includes taxes & fees
Nov 5 - Nov 6
Ground Floor Studios in Chicago by 747 Lofts
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.
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Top Chicago Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Room was spacious, walking distance to just about anything you’d want to do in Chicago. Would highly recommend."
Anthony 3-night trip
Posted 1 day ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Chicago
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

Look no further and take a look at our great range of rental properties in Chicago!

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed theater scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many vacation rentals are there in Chicago?

With 1140 Expedia vacation rentals, you're sure to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Michigan Avenue and Navy Pier.

What are vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.