Chicago Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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, (1,148 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$1,192
HK$1,629 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, (472 reviews)
"Very clean and nice place"
United States
Hector
The price is HK$1,713
HK$2,205 total
includes taxes & fees
26 May - 27 May
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Having a kitchen is great."
United States
Mark
The price is HK$1,262
HK$2,217 total
includes taxes & fees
10 May - 11 May
Kasa River North Chicago
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, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is HK$2,640
HK$6,469 total
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 6
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$1,042
HK$2,040 total
includes taxes & fees
26 May - 27 May
Modern Comfort: 1BR Unit w/ Laundry
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$1,097
HK$2,006 total
includes taxes & fees
3 Jun - 4 Jun
Chic Studio in the Heart of the Gold Coast
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,332
HK$3,858 total
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views
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$1,379
HK$2,463 total
includes taxes & fees
10 May - 11 May
West Loop Living – Bright 1BR
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is HK$2,374
HK$5,144 total
includes taxes & fees
19 May - 20 May
River North Rooftop With In and Out Parking 6
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$1,387
HK$2,473 total
includes taxes & fees
10 May - 11 May
Sunlit 1BR Apartment | Warm & Welcoming Space
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$1,606
HK$2,118 total
includes taxes & fees
6 May - 7 May
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We spent most of this trip discussing our NEXT trip - this stay was one of the simplest, easiest, and most satisfying we've ever experienced with a short-term rental. Hands-down will stay again!Unit incredibly clean, close proximity to the areas we needed to be in, and the host was next-level communicative and kind! Thank you for making it so easy for us!"
United States
Stephanie G.
The price is HK$1,536
HK$2,006 total
includes taxes & fees
7 May - 8 May
LIVN West Loop Chicago 2 BR City View
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$2,076
HK$4,738 total
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3
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.
The price is HK$1,713
HK$4,338 total
includes taxes & fees
6 May - 7 May
Premium Urban 4BR - Perfect Mix of Comfort & Location
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$1,199
HK$2,252 total
includes taxes & fees
12 May - 13 May
Chicago-Themed 1BR in a Central Spot near Downtown
Terrace/patio

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.0 out of 10, Wonderful, (20 reviews)
"Convenient check in and good amenities made this a pleasant place to stay near our relative in Chicago. "
United States
Laura O.
The price is HK$959
HK$2,519 total
includes taxes & fees
7 May - 8 May
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (72 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is HK$599
HK$1,223 total
includes taxes & fees
20 May - 21 May
Cozy studio in Andersonville Chicago
Fridge, microwave, oven, stovetop

Cozy Boho Chicago - 10 Minutes to Downtown Chicago

Cozy Boho Chicago - 10 Minutes to Downtown Chicago
Lawndale
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful space and convenient location. Really responsive host and super quiet neighborhood! "
United States
Jess S.
Cozy Boho Chicago - 10 Minutes to Downtown Chicago
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$4,121
HK$8,557 total
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 5
Smart TV, video games

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is HK$776
HK$2,102 total
includes taxes & fees
18 May - 19 May
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"."
Claudia 1-night trip
Posted 4 hours ago
Club Quarters Hotel, Central Loop, 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 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?

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 Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! and HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony.

How many holiday rentals are there in Chicago?

With 927 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.