Chicago Holiday Rentals

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Check prices for these dates

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (808)
"Great stay!"
The price is HK$1,194
HK$1,632 total
includes taxes & fees
7 Jul - 8 Jul
Sentral Michigan Avenue
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (322)
"Hotel was nice"
The price is HK$3,515
HK$4,301 total
includes taxes & fees
30 Jul - 31 Jul
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (314)
"Super cool spot in a great part of the city."
The price is HK$1,091
HK$1,281 total
includes taxes & fees
9 Jul - 10 Jul
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (558)
"Great place and location. "
The price is HK$1,170
HK$1,373 total
includes taxes & fees
7 Jul - 8 Jul
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
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, (436)
"We had an amazing week staying here. Highly recommend!!"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
2 bedrooms, premium bedding, individually decorated

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (192)
"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 HK$2,088
HK$2,451 total
includes taxes & fees
27 Jul - 28 Jul
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (69)
"Very clean, the room was very spacious and everyone was very friendly and the complementary breakfast was good. We also like the location. "
The price is HK$1,646
HK$1,884 total
includes taxes & fees
7 Jul - 8 Jul
The Gem Museum Suites
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very good, (109)
"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 HK$894
HK$1,050 total
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (173)
"Great spot. "
The Neighborhood Hotel-Little Italy
Kasa South Loop Chicago
City view

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 Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (40)
"Our stay was amazing. "
The price is HK$1,528
HK$1,794 total
includes taxes & fees
20 Jul - 21 Jul
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

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 HK$1,327
HK$1,557 total
includes taxes & fees
7 Jul - 8 Jul
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

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 HK$689
HK$1,202 total
includes taxes & fees
7 Jul - 8 Jul
Wrigleyville Suites
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (152)
"Great stay, clean room!"
Kasa River North Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
1 bedroom, desk, laptop workspace, blackout curtains

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

2.5 star property
3.8 out of 10, (42)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is HK$738
HK$834 total
includes taxes & fees
7 Jul - 8 Jul
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Huge Projector and Designated Workspace - Near Wrigley!
2 bedrooms, desk, iron/ironing board, free WiFi

Huge Projector and Designated Workspace - Near Wrigley!

The price is HK$1,040
HK$2,966 total
includes taxes & fees
14 Jul - 15 Jul
Huge Projector and Designated Workspace - Near Wrigley!
Sonder by Marriott Bonvoy Greektown Apartments
40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is HK$1,728
HK$2,029 total
includes taxes & fees
27 Jul - 28 Jul
Sonder by Marriott Bonvoy Greektown Apartments
Luxurious 3 Bedroom Apartment in Chicago
Microwave, oven, stovetop, dishwasher

Luxurious 3 Bedroom Apartment in Chicago

10.0 out of 10, Exceptional, (11)
"Great property! Would visit again!"
Luxurious 3 Bedroom Apartment in Chicago
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Bar (on property)

"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "

5.2 out of 10, (5)
"Room clean, fitness room awful!! Have to request house keeping but they do not change sheets. Bar and restaurant bare minimum. They have a nice bar next to hotel(Not the-one located in the hotel) Would not stay again!"
The price is HK$1,091
HK$1,261 total
includes taxes & fees
7 Jul - 8 Jul
"Cozy Rooms with WiFi, Fitness Room & On-Site Restaurant/Bar in Schaumburg "
Cozy studio in Andersonville Chicago
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

9.8 out of 10, Exceptional, (8)
"I thought I was in a $300 night hotel, private, and serene surrounding"
The price is HK$706
HK$1,337 total
includes taxes & fees
7 Jul - 8 Jul
Cozy studio in Andersonville 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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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 entertainment choices. 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?

Stylish 3bd w/ backyard patio mins from Downtown! : This highly rated holiday home rental in Chicago offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 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 Your Next Vacation Home.

How many holiday rentals are there in Chicago?

With 1451 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 Art Institute of Chicago and CIBC Theatre, 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.