A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chicago holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,336 reviews)
"Great venue"
United States
Arthur Noel
The price is HK$1,194
HK$1,631 total
includes taxes & fees
27 Sept - 28 Sept
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (38 reviews)
"The property was in a very nice location."
United Kingdom
Nehal Manish
The price is HK$1,694
HK$2,481 total
includes taxes & fees
1 Oct - 2 Oct
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (527 reviews)
"Location and facility was very nice"
United States
Brian
The price is HK$2,376
HK$2,983 total
includes taxes & fees
27 Sept - 28 Sept
Level Chicago – Old Town
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

4. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$2,157
HK$2,871 total
includes taxes & fees
27 Sept - 28 Sept
LIVN Millennium Park Downtown Chicago 2BR
A modern room with a sofa, a dining table, and a window with a view of buildings.

5. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great property"
United States
duane
The price is HK$2,251
HK$3,001 total
includes taxes & fees
27 Sept - 28 Sept
LIVN West Loop Chicago 2 BR City View
A modern lounge area with a black leather sofa, a small table, and chairs. There is a television mounted on the wall and an exit sign above the door.

6. Downtown Chicago Stay with Free In & Out Parking 3

Downtown Chicago Stay with Free In & Out Parking 3
Downtown Chicago
10.0 out of 10, Exceptional, (13 reviews)
"Best location"
United States
Eric Dallas
The price is HK$1,992
HK$4,589 total
includes taxes & fees
27 Sept - 28 Sept
Downtown Chicago Stay with Free In & Out Parking 3
A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a gray sofa and patterned cushions.

7. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is HK$2,086
HK$4,534 total
includes taxes & fees
29 Sept - 30 Sept
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern kitchen with a central island, bar stools, and a dining table.

8. River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (15 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
River North Private Deck With In and Out Parking
A modern living room with a sectional sofa, a coffee table, and a dining area with chairs and a table.

9. Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.6 out of 10, Exceptional, (11 reviews)
"Great location, lots of food options, park near by for children. Great communication with hosts."
United States
Jackie S.
Modern West Loop Gem-City Views & Prime Location 2
A spacious lobby with a sectional sofa, a dining area, and large windows.

10. South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is HK$1,310
HK$3,641 total
includes taxes & fees
14 Oct - 15 Oct
South Loop Rooftop With In and Out Parking 3
A living room with a large arched window, a fireplace, and a sofa with patterned cushions.

11. Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
9.8 out of 10, Exceptional, (28 reviews)
"Location cannot be beat! So close to Wrigley and so fun! "
United States
Celia A
The price is HK$3,757
HK$8,508 total
includes taxes & fees
28 Sept - 29 Sept
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

12. Bronzeville Gem: Balcony, Gym & Rooftop Deck

Bronzeville Gem: Balcony, Gym & Rooftop Deck
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
The price is HK$2,958
HK$6,080 total
includes taxes & fees
26 Sept - 27 Sept
Bronzeville Gem: Balcony, Gym & Rooftop Deck

13. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
9.6 out of 10, Exceptional, (9 reviews)
"Great location with large beds which made it amazing for our group. Easy access to public transport and a cute neighborhood"
United States
Kortnee
The price is HK$2,761
HK$5,808 total
includes taxes & fees
27 Sept - 28 Sept
Premium Urban 4BR - Perfect Mix of Comfort & Location
A spacious room with exposed brick walls, a large window with a city view, a gray sofa, a dining table with chairs, and a small side table.

14. River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.6 out of 10, Exceptional, (13 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is HK$2,212
HK$4,390 total
includes taxes & fees
7 Oct - 8 Oct
River North Rooftop With In and Out Parking 1
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

15. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is HK$3,530
HK$7,927 total
includes taxes & fees
29 Sept - 30 Sept
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

16. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
8.8 out of 10, Excellent, (15 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is HK$1,044
HK$2,015 total
includes taxes & fees
1 Oct - 2 Oct
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (23 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street
A living room with a sofa, coffee table, TV, and a ceiling fan.

18. Newly Remodeled Gem | Heart of Chicago

Newly Remodeled Gem | Heart of Chicago
Humboldt Park
9.6 out of 10, Exceptional, (7 reviews)
"Super clean, comfortable beds, easy to access, easy checkout, and a very communicable host. Overall a great stay. "
United States
Kevin R.
The price is HK$5,255
HK$9,478 total
includes taxes & fees
11 Oct - 12 Oct
Newly Remodeled Gem | Heart of Chicago
A living room with a sofa, armchair, coffee table, and a TV mounted on the wall.

19. 5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly

5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
Lakeview
9.6 out of 10, Exceptional, (11 reviews)
"Great location. Nice big unit. Very good place for a group. Beds were comfortable Kitchen was big Parking in garage was good. Lots of stuff to walk too… Great transit location."
United States
Jason D.
The price is HK$1,553
HK$3,457 total
includes taxes & fees
24 Sept - 25 Sept
5 Mins to Wrigley and Beach - Games - Garage - Sleeps 10 - Pet Friendly
A balcony with a wooden table and chairs, a potted plant, and a lattice screen.

20. 2R- ❤️ Stylish and Cozy 2BR in Logan Square!

2R- ❤️ Stylish and Cozy 2BR in Logan Square!
Logan Square
10.0 out of 10, Exceptional, (58 reviews)
"Excellent stay. Nice location"
United States
Daniel R.
The price is HK$1,412
HK$2,733 total
includes taxes & fees
28 Sept - 29 Sept
2R- ❤️ Stylish and Cozy 2BR in Logan Square!
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 Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Great Stay"
Johny 1-night trip
Posted 3 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

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!

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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 LUXE 3 BR, 2 BA + Hot Tub and Cozy 3-bedroom house in family-oriented Melrose Park..

How many holiday rentals are there in Chicago?

With 934 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.