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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 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, (1,313 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is HK$1,193
HK$1,631 total
includes taxes & fees
21 Sept - 22 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, (27 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,529
HK$2,284 total
includes taxes & fees
20 Sept - 21 Sept
Kasa Lake Shore Chicago
A narrow hallway with a concrete wall, a wooden floor, a small table, and a large mirror on the right.

3. South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is HK$823
HK$2,962 total
includes taxes & fees
21 Sept - 22 Sept
South Loop Rooftop With In and Out Parking 2
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, (524 reviews)
"Location and facility was very nice"
United States
Brian
The price is HK$2,389
HK$2,998 total
includes taxes & fees
27 Sept - 28 Sept
Level Chicago – Old Town
A hotel room with a large bed, a window with a view of buildings, a nightstand with a lamp, and two framed pictures on the wall.

5. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is HK$3,192
HK$4,250 total
includes taxes & fees
18 Sept - 19 Sept
LIVN West Loop Chicago Queen Superior Studio
A modern bar area with high stools, a counter, and a flat-screen TV.

6. Downtown Chicago Stay with Free In & Out Parking-2

Downtown Chicago Stay with Free In & Out Parking-2
Downtown Chicago
The price is HK$1,521
HK$4,106 total
includes taxes & fees
30 Sept - 1 Oct
Downtown Chicago Stay with Free In & Out Parking-2
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

7. 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$2,996
HK$3,856 total
includes taxes & fees
17 Sept - 18 Sept
LIVN Millennium Park Downtown Chicago 1 BR
A modern lobby with a seating area, a reception desk, and a large plant.

8. Wabash 4BR - Pool, Free In & Out Parking 2

Wabash 4BR - Pool, Free In & Out Parking 2
Downtown Chicago
Wabash 4BR - Pool, Free In & Out Parking 2
A modern building with a glass facade, surrounded by a parking area and greenery.

9. Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (32 reviews)
"Property was comfortable and clean. Perfect for our night stay and we could all hang out together. Thank you!"
United States
Marceen N.
The price is HK$1,349
HK$3,794 total
includes taxes & fees
29 Sept - 30 Sept
Spacious 4BR Central Apartment w/ Skyline Views
A modern kitchen with a central island, bar stools, and a dining table.

10. 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, (14 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is HK$2,368
HK$5,355 total
includes taxes & fees
29 Sept - 30 Sept
River North Private Deck With In and Out Parking
A billiards room with multiple tables, large windows, and a high ceiling with exposed ductwork.

11. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is HK$3,937
HK$5,303 total
includes taxes & fees
8 Oct - 9 Oct
Wabash 4BR - Pool, Free In & Out Parking 1
A modern living room with a sectional sofa, a dining table with chairs, and large windows offering city views.

12. Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
9.4 out of 10, Exceptional, (14 reviews)
"Amazing accommodation"
United States
Jiri N.
Modern West Loop Gem-City Views & Prime Location 4

13. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.4 out of 10, Exceptional, (22 reviews)
"Very clean, very quite loved having 3 bathrooms, had everything you’d need for your stay"
Canada
LM
The price is HK$3,451
HK$6,542 total
includes taxes & fees
17 Sept - 18 Sept
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

14. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.8 out of 10, Exceptional, (6 reviews)
Modern 3BR Apartment Near North Ave Shops

15. 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, (8 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$2,886
HK$5,777 total
includes taxes & fees
27 Sept - 28 Sept
Premium Urban 4BR - Perfect Mix of Comfort & Location
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

16. Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Spacious, free parking, family friendly"
United States
Majid
The price is HK$1,616
HK$4,252 total
includes taxes & fees
21 Sept - 22 Sept
Downtown Chicago Stay with Free In & Out Parking 1
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

17. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.2 out of 10, Wonderful, (10 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$2,957
HK$3,945 total
includes taxes & fees
19 Sept - 20 Sept
LIVN Millennium Park Downtown Chicago Studio
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

18. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is HK$2,964
HK$3,945 total
includes taxes & fees
18 Sept - 19 Sept
LIVN West Loop Chicago King Studio
A modern living room with a blue sofa, a leather armchair, and a geometric coffee table.

19. LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
8.6 out of 10, Excellent, (10 reviews)
"We loved the location."
United States
Nicoll M.
The price is HK$3,529
HK$4,540 total
includes taxes & fees
17 Sept - 18 Sept
LIVN Millennium Park Downtown Chicago Superior 2 BR
A modern gym with various exercise equipment, including a bench press, dumbbells, and a treadmill.

20. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is HK$14,634
HK$31,716 total
includes taxes & fees
29 Sept - 30 Sept
Brand New 12 Bedroom Mansion
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

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Excellent hotel. Very clean, modern, friendly staff and great location"
Tom 4-night trip
Posted 5 hours ago
Hilton 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!

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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 ENVITAE Hotel, 4BR Luxury Modern Apartments and LUXE 3 BR, 2 BA + Hot Tub.

How many holiday rentals are there in Chicago?

With 918 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.