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Top Holiday Rentals in Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (768)
"we enjoyed the stay"
The price is ₹13,738
₹18,637 total
includes taxes & fees
29 Jun - 30 Jun
Sentral Michigan Avenue

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (523)
"Love the place "
The price is ₹10,141
₹11,905 total
includes taxes & fees
1 Jul - 2 Jul
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.6 out of 10, Excellent, (291)
"Great location for traveling! There’s two bars walking distance and everything else is about a 10-15 min drive. Rooms are also spacious and clean."
The price is ₹10,839
₹12,724 total
includes taxes & fees
29 Jun - 30 Jun
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (177)
"Easy and great for extended stay."
The price is ₹17,780
₹20,871 total
includes taxes & fees
1 Jul - 2 Jul
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (317)
"The staff were amazing. The view was gorgeous and location can’t be beat. "
The price is ₹23,473
₹29,464 total
includes taxes & fees
4 Jun - 5 Jun
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (408)
"Great stay "
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (162)
"wonderful stay- loved this place incredibly clean and great communication "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.4 out of 10, Very good, (157)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is ₹11,489
₹13,487 total
includes taxes & fees
1 Jul - 2 Jul
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (66)
"Wonderful stay ! Amazing stuff & their hospitality! Old building but maintained well. Great experience overall."
The price is ₹19,025
₹21,779 total
includes taxes & fees
1 Jul - 2 Jul
The Gem Museum Suites

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.8 out of 10, (34)
"Nice inside room but it’s not safe outside area"
The price is ₹6,270
₹7,084 total
includes taxes & fees
20 Jun - 21 Jun
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Wrigleyville Suites

2.0 star property
8.0 out of 10, Very good, (6)
The price is ₹9,467
₹15,389 total
includes taxes & fees
1 Jun - 2 Jun
Wrigleyville Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.4 out of 10, Very good, (103)
"Awesome"
The price is ₹14,688
₹17,242 total
includes taxes & fees
22 Jun - 23 Jun
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.8 out of 10, Excellent, (38)
"This is a perfect location to walk around downtown, have dining options at walking distance. Everything was perfect for my family trip. The only issue is the noise its close to walgreens that gets deliveries at like 5am and the noise is so bad it wakes you up."
The price is ₹15,020
₹17,631 total
includes taxes & fees
1 Jul - 2 Jul
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.4 out of 10, Exceptional, (142)
"i really enjoyed this cozy apartment, it had all the amenities and friendly staff to help me through the check-in process. "
The price is ₹19,669
₹29,213 total
includes taxes & fees
4 Jun - 5 Jun
Kasa River North Chicago

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (294)
"Great stay will be back "
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (51)
"Great location, easy stay!"
The price is ₹17,253
₹20,253 total
includes taxes & fees
29 Jun - 30 Jun
Sonder by Marriott Bonvoy Greektown Apartments

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (13)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is ₹9,823
₹24,845 total
includes taxes & fees
5 Jun - 6 Jun
Ground Floor Studios in Chicago by 747 Lofts

Skokie 2BR Apt - Bright & Central

3.0 star property
Skokie 2BR Apt - Bright & Central
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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Frequently asked questions

Can I find holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed theatre scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1455 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.