Chicago Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,140 reviews)
"Thank you for the stay"
United States
Marco
The price is HK$1,059
HK$1,473 total
includes taxes & fees
27 Apr - 28 Apr
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (467 reviews)
"Very clean and nice place"
United States
Hector
The price is HK$1,269
HK$1,683 total
includes taxes & fees
26 Apr - 27 Apr
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (190 reviews)
"Having a kitchen is great."
United States
Mark
The price is HK$1,048
HK$1,966 total
includes taxes & fees
30 Apr - 1 May
Kasa River North Chicago
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (35 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is HK$1,082
HK$1,270 total
includes taxes & fees
26 Apr - 27 Apr
Wrigleyville Suites
Interior

River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts
2.0 star property
West Town
9.6 out of 10, Exceptional, (4 reviews)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveller
The price is HK$1,748
HK$4,933 total
includes taxes & fees
14 May - 15 May
River West, Second Floor Chicago by 747 Lofts
Interior

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (18 reviews)
"Cvs. Dunkin Donuts. Pizza pie all 1-2 blocks walking distance "
United States
Paul
The price is HK$1,405
HK$3,104 total
includes taxes & fees
3 May - 4 May
River West, Third Floor Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (21 reviews)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
United States
Susan
Ground Floor Studios in Chicago by 747 Lofts
Interior

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is HK$1,713
HK$4,873 total
includes taxes & fees
9 May - 10 May
Chicago Third Floor Studio by 747 Lofts
Living area

Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
8.8 out of 10, Excellent, (13 reviews)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is HK$1,298
HK$2,920 total
includes taxes & fees
20 May - 21 May
Chicago Second Floor Studio by 747 Lofts
Breakfast, lunch, dinner served; Greek cuisine

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (113 reviews)
"Great well taken care of boutique hotel. Loved the decoration and the quiet area of Evanston. Breakfast was great and a sit down service that was much appreciated."
United States
Michael
The price is HK$926
HK$1,061 total
includes taxes & fees
26 Apr - 27 Apr
The Gem Museum Suites
Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is HK$1,263
HK$2,315 total
includes taxes & fees
27 Apr - 28 Apr
The Oak Park Loft
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

4/10 Poor
"This property lacked cleanliness. The rugs in the rooms were nasty. I don’t know if they have ever cleaned them. They only do housekeeping every other day, and if you ask them to clean it on a day it isn’t scheduled. They give you resonses, in a nice way that it’s not your day. You have to be to the point if you want it done regularly. They also don’t give you new towels on your off day, unless you ask. Clean up on your day consist of fresh towels, bed made, change the trash will try and tell you when you last had house keeping. There is a $70 parking fee if you decide to rent a car. That wouldn’t have been an issue if we were told that there was a charge to park when we asked about parking. We were just told that they do have parking. Also if you park it has to be for the whole time tha you are there, which we weren’t told that as welll. If you park without the hotel validating your parking, it could be more expensive. in the beginning, but no one told us that, and we asked It is not the hotel’s garage."
Shauna Lorraine 6-night trip
Posted 1 hour ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

  • View our selection of featured holiday rentals in Chicago
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

Look no further and take a look at our great range of rental properties in Chicago!

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.

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

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This highly rated holiday home rental in Chicago is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease 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. Other favourite homes for rent in Chicago are Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! and A Home Away From Home!.

How many holiday rentals are there in Chicago?

With 928 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 Navy Pier and Wrigley 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.