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
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chicago holiday rentals

A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (91 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is HK$1,192
HK$1,884 total
includes taxes & fees
25 Nov - 26 Nov
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,415 reviews)
"Great for extended stays."
United States
Jeff
The price is HK$1,500
HK$1,761 total
includes taxes & fees
13 Dec - 14 Dec
Sentral Michigan Avenue
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is HK$932
HK$1,094 total
includes taxes & fees
15 Nov - 16 Nov
Wrigleyville Suites
A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (563 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is HK$1,334
HK$1,760 total
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
LIVN Millennium Park entrance at 19 S Wabash Ave

5. LIVN Millennium Park Downtown Chicago 1 BR

LIVN Millennium Park Downtown Chicago 1 BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location to sights, shops, and food."
United States
Adrianna W.
The price is HK$1,279
HK$1,637 total
includes taxes & fees
16 Nov - 17 Nov
LIVN Millennium Park Downtown Chicago 1 BR
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

6. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (25 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is HK$643
HK$1,683 total
includes taxes & fees
16 Nov - 17 Nov
3BR Complete and Spacious Apartment in Ideal Spot
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

7. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (29 reviews)
"Great location! "
United States
Andrea B.
The price is HK$601
HK$1,342 total
includes taxes & fees
9 Dec - 10 Dec
Flexhome East Village • Modern 2BR • Quiet Street
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

8. 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, (1 review)
"Great little spot in a fun area of downtown Chicago. Lots of bars & restaurants within walking distance."
United States
Ryan
The price is HK$737
HK$1,882 total
includes taxes & fees
14 Dec - 15 Dec
Chic Studio in the Heart of the Gold Coast
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

9. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is HK$796
HK$3,352 total
includes taxes & fees
30 Nov - 1 Dec
Chic Urban Retreat Near Wrigley Field w/Parking
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

10. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is HK$549
HK$1,230 total
includes taxes & fees
15 Nov - 16 Nov
Hyde Park Trendy Studio Apartment in Good Spot
A rooftop terrace with a brick wall, large windows, and a metal railing.

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

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is HK$588
HK$2,047 total
includes taxes & fees
17 Nov - 18 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

12. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is HK$708
HK$2,535 total
includes taxes & fees
21 Nov - 22 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
A neatly made bed with a headboard, two bedside tables with lamps, a wall-mounted artwork, and a patterned rug.

13. West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
The price is HK$1,004
HK$2,321 total
includes taxes & fees
16 Nov - 17 Nov
West Loop Living – Bright 1BR
A modern bedroom with a bed, a sofa, and a hanging plant.

14. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is HK$565
HK$1,026 total
includes taxes & fees
10 Dec - 11 Dec
Cozy studio in Andersonville Chicago
A building with a stone facade and a sign that reads 'LIVN WEST LOOP'.

15. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (29 reviews)
"Location was amazing, and check in was super simple."
United States
Dale H.
The price is HK$1,216
HK$1,544 total
includes taxes & fees
15 Nov - 16 Nov
LIVN West Loop Chicago Queen Superior Studio
A modern kitchen with a built-in microwave, a dining area with a black sofa, and a large window offering a city view.

16. Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is HK$894
HK$1,879 total
includes taxes & fees
17 Nov - 18 Nov
Stylish Japanese-Themed 2BR Apt Close to Downtown
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

17. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
The price is HK$601
HK$1,342 total
includes taxes & fees
15 Nov - 16 Nov
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A living room with a flat-screen TV on a wooden cabinet, a dark sofa, a coffee table, a floor lamp, and a potted plant.

18. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (14 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is HK$494
HK$1,244 total
includes taxes & fees
17 Nov - 18 Nov
1BR/1BA City Comfort
A hotel room with a large bed, a window with blinds, a projector screen displaying a castle, and a neatly made bed with towels.

19. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is HK$745
HK$2,570 total
includes taxes & fees
16 Nov - 17 Nov
Sleeps 7 • Huge Projector • Designated Workspace
A living room with a dark blue sofa, a small coffee table, a floor lamp, and a ceiling fan. There are two windows with blinds, a radiator, and a potted plant on the windowsill.

20. Beautifully Set Up 2BR Space

Beautifully Set Up 2BR Space
Lakeview
9.0 out of 10, Wonderful, (2 reviews)
"Approval/check-in process was a little more laborous than expected but great deal for a really nice place and location. Would stay again!"
United States
Tavia S.
The price is HK$886
HK$1,870 total
includes taxes & fees
16 Nov - 17 Nov
Beautifully Set Up 2BR Space
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

Find holiday rentals that suit your style

apart-hotel image
Aparthotels
Aparthotels
Apartment image
Apartments
Apartments

Top Chicago Hotel Reviews

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
Downtown Chicago

10/10 Excellent

very good hotel and nearby the shopping area
Hong Kong SAR China
Kwok Tai
Reviewed March 7, 2025
Hotel Riu Plaza 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated holiday home rental in Chicago is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease 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 Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

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 Soldier Field and Navy Pier.

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.

Explore a world of travel with Expedia