Chicago Holiday Rentals

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Check prices for these dates

Tonight
5 Aug - 6 Aug
Tomorrow
6 Aug - 7 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

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, (860)
"Great stay!"
The price is AU$352
includes taxes & fees
3 Sept - 4 Sept
Sentral Michigan Avenue
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
8.2 out of 10, Very good, (339)
"The property canceled on us 4 hours prior to check in"
The price is AU$230
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
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, (335)
"A lot of good food options walkable distance. "
Level Chicago – Old Town
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
9.4 out of 10, Exceptional, (460)
"Kasa apartments are two blocks away from Magnificent mile street. It is a really nice area and there are a lot of attractions close by. We had a wonderful time!!"
Kasa Magnificent Mile Chicago
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, (182)
"Definitely will back soon, very clean and spacious."
The Neighborhood Hotel-Little Italy
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, (605)
"I would stay again. "
The price is AU$259
includes taxes & fees
25 Aug - 26 Aug
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, (325)
"Great stay"
Kasa South Loop Chicago
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
9.6 out of 10, Exceptional, (82)
"Super nice hotel and staff "
The price is AU$371
includes taxes & fees
14 Aug - 15 Aug
The Gem Museum Suites
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
7.8 out of 10, Good, (127)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is AU$291
includes taxes & fees
21 Aug - 22 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
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, (201)
"Clean, new, spacious "
The price is AU$307
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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, (171)
"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 AU$276
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
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
9.0 out of 10, Wonderful, (13)
"Excellent location and very clean! Would stay again!"
The price is AU$220
includes taxes & fees
7 Aug - 8 Aug
Wrigleyville Suites
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, (159)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
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
3.6 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 AU$148
includes taxes & fees
11 Aug - 12 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
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, (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 AU$245
includes taxes & fees
26 Aug - 27 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North
Clean & Equipped 1BR Apt
Relax in comfort with a large bed, featuring a dark headboard and crisp white bedding, and a cozy throw blanket.

Clean & Equipped 1BR Apt

7.6 out of 10, Good, (9)
The price is AU$321
includes taxes & fees
7 Aug - 8 Aug
Clean & Equipped 1BR Apt
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop

Lakeview 2BR Apartment

9.0 out of 10, Wonderful, (10)
"Great experience overall. Check-in was easy and the unit was very well kept. Very happy that we were so close to so much public transportation. It is a little noisy for those who aren’t used to hearing the L train nearby. Parking is hard to find, but there is paid parking nearby and easy to access public transit. If you plan on parking your car for the full time you’re there."
The price is AU$345
includes taxes & fees
11 Aug - 12 Aug
Lakeview 2BR Apartment
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

9.4 out of 10, Exceptional, (9)
"Great place! 15 min walk to Wrigley "
The price is AU$321
includes taxes & fees
7 Aug - 8 Aug
Cozy, Fully Set-Up 1BR Space
Stylish 1BR in Lakeview Chicago
Fridge, microwave, oven, stovetop

Stylish 1BR in Lakeview Chicago

8.0 out of 10, Very good, (6)
"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 AU$346
includes taxes & fees
3 Sept - 4 Sept
Stylish 1BR in Lakeview Chicago
Charming 2BR in Vibrant Lakeview
Cozy retreat with a large bed and a bedside table.

Charming 2BR in Vibrant Lakeview

9.8 out of 10, Exceptional, (7)
The price is AU$352
includes taxes & fees
11 Aug - 12 Aug
Charming 2BR in Vibrant Lakeview
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
"Great North river hotel with a fantastic breakfast."
Vic 2-night trip
Posted 2 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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. Another good choice for your trip to Chicago is Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed.

How many holiday rentals are there in Chicago?

With 1520 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.