Holiday Rentals in Chicago

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Holiday Rentals in Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (852)
"Great stay!"
The price is €205
includes taxes & fees
4 Aug - 5 Aug
Sentral Michigan Avenue

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (332)
"Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice "
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (335)
"The property canceled on us 4 hours prior to check in"
The price is €128
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (456)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (599)
"I would stay again. "
The price is €145
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (200)
"Clean, new, spacious "
The price is €214
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (323)
"Great stay"
Kasa South Loop Chicago

The Gem Museum Suites

3.5 star property
9.6 out of 10, Exceptional, (81)
"Had a good and comfortable stay "
The price is €214
includes taxes & fees
26 Aug - 27 Aug
The Gem Museum Suites

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (124)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is €146
includes taxes & fees
5 Aug - 6 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (181)
"Great suite"
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is €146
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

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

2.5 star property
3.6 out of 10, (50)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is €83
includes taxes & fees
4 Aug - 5 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (12)
"Excellent location and very clean! Would stay again!"
The price is €196
includes taxes & fees
4 Aug - 5 Aug
Wrigleyville Suites

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (157)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (43)
"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."
The price is €144
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

Clean & Equipped 1BR Apt

7.6 out of 10, Good, (9)
The price is €186
includes taxes & fees
11 Aug - 12 Aug
Clean & Equipped 1BR Apt

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is €214
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Greektown Apartments

Lakeview 2BR Apartment

9.4 out of 10, Exceptional, (8)
The price is €195
includes taxes & fees
6 Aug - 7 Aug
Lakeview 2BR Apartment

Cozy, Fully Set-Up 1BR Space

9.2 out of 10, Wonderful, (7)
"Great place! 15 min walk to Wrigley "
The price is €186
includes taxes & fees
11 Aug - 12 Aug
Cozy, Fully Set-Up 1BR Space

Stylish 1BR in Lakeview Chicago

7.0 out of 10, Good, (4)
"This is a great apartment. It was very clean, well equipped kitchen and comfortable bed. Close to restaurants, grocery store, Starbucks and Wrigley Field. We could not find any parking on the street where the apartment is. I do recommend that you get in touch with the property owners couple of days prior to your visit because there is a vetting process prior to getting the keys to the apartment. "
The price is €201
includes taxes & fees
12 Aug - 13 Aug
Stylish 1BR in Lakeview Chicago
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

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 art scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

What are some of the best holiday rentals that Chicago has to offer?

Clarendon Hills Top Floor: This highly rated holiday home rental in Chicago is equipped with a BBQ, air conditioning and free WiFi to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Chicago are Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Lincoln Park Living - Suite 2!.

How many holiday rentals are there in Chicago?

With 1501 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 Navy Pier.

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.