Chicago Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 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, (1,152 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$1,191
HK$1,628 total
includes taxes & fees
25 May - 26 May
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, (473 reviews)
"Love the amenities. Great location too"
United States
Paul
The price is HK$1,782
HK$2,285 total
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town
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$971
HK$1,800 total
includes taxes & fees
11 May - 12 May
Chic Studio in the Heart of the Gold Coast
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 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$1,378
HK$2,452 total
includes taxes & fees
10 May - 11 May
West Loop Living – Bright 1BR
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, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is HK$1,198
HK$4,387 total
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,284
HK$1,710 total
includes taxes & fees
13 May - 14 May
LIVN Millennium Park Downtown Chicago 2BR
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is HK$1,170
HK$2,016 total
includes taxes & fees
10 May - 11 May
Kasa River North Chicago
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$1,041
HK$2,009 total
includes taxes & fees
10 May - 11 May
Modern Comfort: 1BR Unit w/ Laundry
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$2,075
HK$4,706 total
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3
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$1,464
HK$2,572 total
includes taxes & fees
10 May - 11 May
Sunlit 1BR Apartment | Warm & Welcoming Space
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$1,191
HK$2,185 total
includes taxes & fees
11 May - 12 May
Chicago-Themed 1BR in a Central Spot near Downtown
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,229
HK$3,710 total
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views
1 bedroom, iron/ironing board, travel cot, WiFi

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is HK$1,010
HK$1,379 total
includes taxes & fees
10 May - 11 May
LIVN West Loop Chicago King Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is HK$1,754
HK$5,170 total
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 5
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, (7 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.
The price is HK$1,182
HK$4,426 total
includes taxes & fees
20 May - 21 May
Modern West Loop Gem-City Views & Prime Location 3
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (36 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is HK$1,093
HK$1,283 total
includes taxes & fees
10 May - 11 May
Wrigleyville Suites
Iron/ironing board, WiFi

Uptown Studio Gem Sum

Uptown Studio Gem Sum
Uptown
7.8 out of 10, Good, (7 reviews)
"This studio is very clean and is located in a neighborhood with access to anything you would want to do or see. The stairway and halls are not pristine, but studio is good. Neighbors were quiet and seldom seen during my stay. Excellent restaurant right across the street and grocery nearby. Wrigley Field is easy walk. Check in was confusing for me, but it worked out. "
United States
Leah W.
The price is HK$752
HK$1,543 total
includes taxes & fees
26 May - 27 May
Uptown Studio Gem Sum
TV, offices

Stylish and Roomy 2BR in Chicago

Stylish and Roomy 2BR in Chicago
Edgewater
9.2 out of 10, Wonderful, (18 reviews)
"Really great location. Clark street is great but can be a little noisy at night. "
United States
Adam
The price is HK$1,378
HK$2,569 total
includes taxes & fees
11 May - 12 May
Stylish and Roomy 2BR in Chicago
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place and reasonable price."
United States
Maya K.
The price is HK$1,370
HK$1,802 total
includes taxes & fees
10 May - 11 May
LIVN Millennium Park Downtown Chicago Superior 2 BR
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,448
HK$1,952 total
includes taxes & fees
14 May - 15 May
LIVN Millennium Park Downtown Chicago Studio
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

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

2/10 Terrible
"Staff was not consistent with hospitality. Room service was out of most items after 10pm. I believe the colleague’s name was Jo… she was rude and called my room several times after my order was placed. I spoke to front desk about my complaints and was told that my Hospitality Fee would be waived. That did not happen, I was still charged and have not gotten a call back from Management after calling multiple times. The facility is beautiful but staff is lacking In consistency of service. I do not recommend."
ERIKA 1-night trip
Posted 1 hour ago
The Westin Michigan Avenue Chicago

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 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated holiday home rental in Chicago is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. 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 Luxury Home Away From Your Home and Warm & Spacious 4BR Home Long Stays Welcome.

How many holiday rentals are there in Chicago?

With 933 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.