Chicago Holiday Rentals

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Check prices for these dates

Tonight
11 Jul - 12 Jul
Tomorrow
12 Jul - 13 Jul
This weekend
11 Jul - 13 Jul
Next weekend
18 Jul - 20 Jul

Holiday Rentals in Chicago

Sentral Michigan Avenue
Relax in a spacious area with comfortable seating and lush greenery.

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (815)
"Great stay!"
The price is NZ$427
includes taxes & fees
16 July - 17 July
Sentral Michigan Avenue
Level Chicago – Old Town
Located in a bustling urban area, this high-rise building offers stunning city views.

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (325)
"Hotel was nice"
The price is NZ$907
includes taxes & fees
30 July - 31 July
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Enjoy a minimalist retreat with a large bed, desk, and compact kitchenette.

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (320)
"Super cool spot in a great part of the city."
The price is NZ$348
includes taxes & fees
13 July - 14 July
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Kasa Magnificent Mile Chicago
Relax on the spacious balcony with a city view, featuring a sofa, armchair, and outdoor seating area.

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (441)
"Overall experience was great"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Enjoy a city view from the large window, with a comfortable sofa and potted plant adding to the inviting atmosphere.

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (562)
"Great place and location. "
The price is NZ$362
includes taxes & fees
24 July - 25 July
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
Enjoy the city view from this balcony with a comfortable Adirondack chair and a small table.

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (317)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Relax in style with plush armchairs and a natural centerpiece, surrounded by a contemporary design.

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (194)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is NZ$444
includes taxes & fees
26 July - 27 July
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Enjoy the city view from this stylish balcony with a sofa, chair, and table.

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very good, (111)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is NZ$205
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Gem Museum Suites
Kitchen area with dining space, featuring a refrigerator, round table, and two chairs.

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (71)
"Good people great breakfast "
The price is NZ$433
includes taxes & fees
17 July - 18 July
The Gem Museum Suites
The Neighborhood Hotel-Little Italy
Welcome to The Neighborhood Hotel, where guests enter through a distinctive black brick facade with the hotel's name prominently displayed.

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (173)
"Great spot. "
The Neighborhood Hotel-Little Italy
Kasa River North Chicago
Meetings take place around a large, rectangular table surrounded by six chairs with chrome legs.

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (154)
"Great stay, clean room!"
Kasa River North Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the city outside.

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is NZ$345
includes taxes & fees
7 Aug - 8 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Opal Apartments River North
Enjoy a panoramic city view from this rooftop terrace, featuring a round table, wicker chairs, and a sofa with a throw blanket.

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is NZ$387
includes taxes & fees
13 July - 14 July
Sonder by Marriott Bonvoy The Opal Apartments River North
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Two single beds with white linens, a small armchair, and a bedside table with a lamp.

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

2.5 star property
3.8 out of 10, (44)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is NZ$158
includes taxes & fees
24 July - 25 July
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Wrigleyville Suites
Enjoy meals in this cozy dining area with a long table and six chairs, surrounded by framed photographs and a potted plant.

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is NZ$367
includes taxes & fees
12 July - 13 July
Wrigleyville Suites
Sonder by Marriott Bonvoy Greektown Apartments
Relax in this stylish living space with a sofa, armchair, and dining area.

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is NZ$444
includes taxes & fees
7 Aug - 8 Aug
Sonder by Marriott Bonvoy Greektown Apartments
Huge Projector and Designated Workspace - Near Wrigley!
Restful retreat with a neatly made bed and a bedside lamp.

Huge Projector and Designated Workspace - Near Wrigley!

Huge Projector and Designated Workspace - Near Wrigley!
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

10.0 out of 10, Exceptional, (1)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is NZ$337
includes taxes & fees
14 July - 15 July
Lakeview 2BR Apartment
Clean & Equipped 1BR Apt
Relax in this stylish room with a large bed, flat-screen TV, and seating area.

Clean & Equipped 1BR Apt

The price is NZ$318
includes taxes & fees
15 July - 16 July
Clean & Equipped 1BR Apt
Cozy, Fully Set-Up 1BR Space
Enjoy cooking and entertaining in this well-equipped kitchen with stainless steel appliances and sleek cabinetry.

Cozy, Fully Set-Up 1BR Space

10.0 out of 10, Exceptional, (1)
"Great communication, location, and would love to stay here again "
The price is NZ$310
includes taxes & fees
23 July - 24 July
Cozy, Fully Set-Up 1BR Space
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 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 Lincoln Park Living - Suite 2! and Great 3 bedroom rental unit near Logan Square.

How many holiday rentals are there in Chicago?

With 1463 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.