Chicago Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 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, (1,130 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$1,124
HK$1,549 total
includes taxes & fees
26 Apr - 27 Apr
Sentral Michigan Avenue
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is HK$837
HK$1,673 total
includes taxes & fees
28 Apr - 29 Apr
Chic Studio in the Heart of the Gold Coast
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (18 reviews)
"Great place"
United States
Daniel L.
The price is HK$1,614
HK$4,970 total
includes taxes & fees
19 Apr - 20 Apr
Modern West Loop Gem-City Views & Prime Location 6
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is HK$884
HK$1,825 total
includes taxes & fees
21 Apr - 22 Apr
West Loop Living – Bright 1BR
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$1,252
HK$3,554 total
includes taxes & fees
29 Apr - 30 Apr
River North Rooftop With In and Out Parking 3
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, (465 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is HK$1,204
HK$1,607 total
includes taxes & fees
19 Apr - 20 Apr
Level Chicago – Old Town
Exterior

Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
The price is HK$1,330
HK$3,834 total
includes taxes & fees
13 May - 14 May
Envitae Hotel, 4BR Modern Sleek Apartment
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (190 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
The price is HK$1,261
HK$2,215 total
includes taxes & fees
30 Apr - 1 May
Kasa River North Chicago
Room

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
The price is HK$1,199
HK$1,601 total
includes taxes & fees
19 Apr - 20 Apr
LIVN West Loop Chicago King Studio
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$884
HK$1,777 total
includes taxes & fees
27 Apr - 28 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is HK$1,581
HK$4,076 total
includes taxes & fees
22 Apr - 23 Apr
Downtown Chicago Stay with Free In & Out Parking 5
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is HK$885
HK$1,779 total
includes taxes & fees
19 Apr - 20 Apr
Chicago-Themed 1BR in a Central Spot near Downtown
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$564
HK$1,402 total
includes taxes & fees
19 Apr - 20 Apr
Modern Comfort: 1BR Unit w/ Laundry
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (14 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,839
HK$4,510 total
includes taxes & fees
30 Apr - 1 May
Spacious 4BR Central Apartment w/ Skyline Views
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
Premium Urban 4BR - Perfect Mix of Comfort & Location
Living area

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
The price is HK$2,311
HK$3,110 total
includes taxes & fees
19 Apr - 20 Apr
LIVN Millennium Park Downtown Chicago 2BR
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (34 reviews)
"Great location and space ! Will use again "
United States
Vanessa
The price is HK$1,136
HK$1,333 total
includes taxes & fees
19 Apr - 20 Apr
Wrigleyville Suites
TV, offices

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is HK$1,355
HK$3,703 total
includes taxes & fees
28 Apr - 29 Apr
Downtown Chicago Stay with Free In & Out Parking 4
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (67 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is HK$1,049
HK$2,550 total
includes taxes & fees
28 Apr - 29 Apr
2-bedroom apartment just 2 minutes drive to Wrigley Field
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

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

6/10 Okay
"Clean and comfortable room, overall clean and well kept facility. Bar staff was entertaining. Easy check in and out. Central location with plenty of bars and restaurants around. The building is not sound-proof AT ALL. The room I was in had a door to the room next to it, and the people in that room had the TV on almost the entire night. You can hear every noise in the hallway. The doors slam very loudly. The housekeeping staff was extremely unaware that they were being so loud. I wasn’t able to join zoom meetings in the room due to the noise level, ended up going to a nearby coffee shop. People were up and down the hall til 2am the second night and you could hear every word they were saying. I am not one to complain, I understand everyone is paying to stay there - there is just no sound proofing at all inside the room. Maybe look into designated “quiet floors” or something for those needing to work, study or who have early mornings. And inform the staff, especially the housekeeping crew, how loud it is inside the rooms so they can be mindful - they may not realize it’s an issue. "
Wesley 4-night trip
Posted 1 hour ago
Aloft Chicago Mag 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 931 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.