Chicago Vacation Rentals

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Check prices for these dates

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

Vacation Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (689)
"Check in was very easy and the front desk staff were very friendly. The room could’ve been cleaner but overall will recommend this place to others! "
The price is P7,344
P10,324 total
includes taxes & fees
Mar 9 - Mar 10
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (442)
"Amazing space - I'll be requesting the same one in the summer :) Spacious and clean! Absolutely loved the view of Willis Tower from our room. Excellent stay!"
The price is P5,731
P6,728 total
includes taxes & fees
Mar 10 - Mar 11
Sonder South Wabash
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is P7,777
P9,130 total
includes taxes & fees
Mar 5 - Mar 6
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (144)
"Beautiful apartment! Very quiet area "
The price is P7,269
P8,533 total
includes taxes & fees
Apr 1 - Apr 2
Sonder The Burnham Apartments
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (367)
"Conveniently located, and an excellent option for a longer stay. "
Kasa Magnificent Mile Chicago
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (258)
"wonderful easy accessible ideal for people have stsycation"
The price is P6,543
P7,681 total
includes taxes & fees
Apr 1 - Apr 2
Sonder Market Hall
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (289)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is P9,952
P12,975 total
includes taxes & fees
Mar 5 - Mar 6
Level Chicago – Old Town
Comfort Inn Chicago Wind Creek Casino
Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.0 out of 10, (5)
"HVAC did not work, no microwave no refrigerator. Only one sheet on bed Had to provide a security deposit not mentioned on reservation did not provide breakfast broken glass door on side of hotel Very noisy "
The price is P5,444
P6,150 total
includes taxes & fees
Mar 5 - Mar 6
Comfort Inn Chicago Wind Creek Casino
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (127)
"I booked this last minute for a new year’s getaway. The young lady at the front desk assisted me with the check in process. I also asked if I could check in early and was accommodated. The room was perfect and clean. I liked the bathroom and the bench in the shower. The view was great as well. It was located in a nice area and a lot of attractions were nearby. The next time I’m in Chicago I’ll stay here again."
The price is P6,321
P7,420 total
includes taxes & fees
Mar 5 - Mar 6
Kasa River North Chicago
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (262)
"realy great place and very close to everything"
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very Good, (139)
"Loved it Had to leave early but loved "
The price is P5,938
P6,971 total
includes taxes & fees
Mar 27 - Mar 28
Sonder Jewelers Row
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (134)
"The hotel itself is pretty great, but its impossible to get ahold of customer service and have any support there is no one available on-site, and parking is very limited. "
The Neighborhood Hotel-Little Italy
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very Good, (92)
"This is the best Sonder property we've ever stayed at!! The location is perfect for Chicago. We had a few different questions during our stay and we always received immediate and thorough answers by using the chat button in the app. Would definitely stay here again!"
The price is P5,989
P7,030 total
includes taxes & fees
Apr 1 - Apr 2
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (29)
"Our stay was amazing. "
The price is P6,949
P8,157 total
includes taxes & fees
Mar 12 - Mar 13
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (42)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is P7,298
P8,567 total
includes taxes & fees
Mar 25 - Mar 26
Sonder Greektown
Wrigleyville Suites
Living area

Wrigleyville Suites

2.5 star property
10.0 out of 10, Exceptional, (2)
The price is P4,488
P19,766 total
includes taxes & fees
Mar 5 - Mar 6
Wrigleyville Suites
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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Other types of properties in Chicago you may be interested in

Congress Plaza Hotel
Aerial view

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8576)
"I always love this place. "
The price is P6,630
P7,783 total
includes taxes & fees
Mar 9 - Mar 10
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3852)
"This hotel is beautiful. Staff were nice & friendly helped me check in & out at a promptly time. Many lounge area to relax at. Even have a coffee room. I would definitely recommend 10/10. I’m visiting Chicago in 3months & definitely will be staying here again !"
The price is P4,726
P5,547 total
includes taxes & fees
Mar 23 - Mar 24
River Hotel
L7 Chicago by LOTTE
Exterior

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1765)
"I appreciate this property for such a pleasant experience. Antonio the concierge greeted us with great customer service and giving us recommendations in town. I definitely recommend this location. "
The price is P9,498
P11,149 total
includes taxes & fees
Mar 6 - Mar 7
L7 Chicago by LOTTE
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.

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 entertainment choices. 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 1331 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 Soldier Field.

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.