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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chicago holiday rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,272 reviews)
"Nice stay"
United States
Heather
The price is HK$1,186
HK$1,623 total
includes taxes & fees
31 Aug - 1 Sept
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.0 out of 10, Very good, (15 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,334
HK$2,052 total
includes taxes & fees
19 Aug - 20 Aug
Kasa Lake Shore Chicago
TV, offices

3. LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is HK$1,592
HK$2,150 total
includes taxes & fees
23 Aug - 24 Aug
LIVN Millennium Park Downtown Chicago Superior 1BR
Full-sized fridge, microwave, oven, stovetop

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (518 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is HK$1,866
HK$2,385 total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
1 bedroom, iron/ironing board, travel cot, WiFi

5. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (18 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$1,373
HK$1,805 total
includes taxes & fees
20 Aug - 21 Aug
LIVN West Loop Chicago Queen Superior Studio
Interior

6. River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.0 out of 10, Wonderful, (9 reviews)
"Not a bad thing to say about this experience. Host was extremely responsive and helpful, looked exactly like the pictures, had everything we needed, location was perfect and the included parking was such a perk! Highly recommend staying here. I hope to be back! "
United States
Kara B.
The price is HK$1,404
HK$3,824 total
includes taxes & fees
8 Sept - 9 Sept
River North Rooftop With In and Out Parking 3
Interior

7. Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
9.6 out of 10, Exceptional, (8 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$1,679
HK$5,093 total
includes taxes & fees
19 Aug - 20 Aug
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

8. 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, (10 reviews)
"Perfect Stay!"
United States
Miyauna G.
Downtown Chicago Stay with Free In & Out Parking 3
Interior

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

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
10.0 out of 10, Exceptional, (3 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$3,475
HK$6,574 total
includes taxes & fees
20 Aug - 21 Aug
Plymouth Collection: 3BD 2BA High Floor with Gym
1 bedroom, iron/ironing board, travel cot, WiFi

10. 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$1,820
HK$2,446 total
includes taxes & fees
19 Aug - 20 Aug
LIVN West Loop Chicago King Studio
TV, offices

11. 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$1,310
HK$1,732 total
includes taxes & fees
20 Aug - 21 Aug
LIVN Millennium Park Downtown Chicago 1 BR
1 bedroom, iron/ironing board, travel cot, WiFi

12. LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay. Great area and very happy with everything"
United States
Abigail B.
The price is HK$1,483
HK$2,002 total
includes taxes & fees
23 Aug - 24 Aug
LIVN West Loop Chicago Classic Queen Studio
Exterior

13. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
The price is HK$4,722
HK$8,635 total
includes taxes & fees
27 Aug - 28 Aug
Envitae Hotel, 4BR Modern Sleek Apartment
Dining

14. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
LIVN Millennium Park Downtown Chicago Studio
Dining

15. LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is HK$1,592
HK$2,150 total
includes taxes & fees
23 Aug - 24 Aug
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

16. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is HK$1,388
HK$3,345 total
includes taxes & fees
30 Aug - 31 Aug
River North Private Balcony With In and Out Parking
TV, offices

17. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is HK$1,483
HK$1,954 total
includes taxes & fees
20 Aug - 21 Aug
LIVN West Loop Chicago 2 BR City View
TV, offices

18. LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (8 reviews)
"We loved the location."
United States
Nicoll M.
The price is HK$2,369
HK$3,197 total
includes taxes & fees
24 Aug - 25 Aug
LIVN Millennium Park Downtown Chicago Superior 2 BR
1 bedroom, iron/ironing board, travel cot, WiFi

19. LIVN West Loop Chicago 1 BR

LIVN West Loop Chicago 1 BR
Downtown Chicago
2.0 out of 10, (1 review)
"Unfortunately, this property was in disrepair and the surroundings were so loud that it was impossible to sleep."
United States
Brittany C.
LIVN West Loop Chicago 1 BR
TV, offices

20. Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
9.0 out of 10, Wonderful, (4 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
The price is HK$1,804
HK$5,315 total
includes taxes & fees
1 Sept - 2 Sept
Modern West Loop Gem-City Views & Prime Location 1
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Great location. Nice hotel"
Michael 4-night trip
Posted less than an hour ago
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!

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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 Vintage Escape 1BR Two Blocks Away From Beach.

How many holiday rentals are there in Chicago?

With 926 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.