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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chicago holiday rentals

Indoor pool

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,249 reviews)
"Great property and location."
United States
Michael
The price is HK$1,249
HK$1,696 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Full-sized fridge, microwave, oven, stovetop

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (515 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$1,847
HK$2,361 total
includes taxes & fees
1 Sept - 2 Sept
Level Chicago – Old Town
TV, offices

3. 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.
LIVN Millennium Park Downtown Chicago 1 BR
Lake

4. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (13 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,930
HK$2,761 total
includes taxes & fees
7 Sept - 8 Sept
Kasa Lake Shore Chicago
Interior

5. 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$1,420
HK$3,805 total
includes taxes & fees
8 Sept - 9 Sept
River North Rooftop With In and Out Parking 3
1 bedroom, iron/ironing board, travel cot, WiFi

6. 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$1,695
HK$2,289 total
includes taxes & fees
16 Aug - 17 Aug
LIVN West Loop Chicago Classic Queen Studio
3 bedrooms, iron/ironing board, WiFi, bed sheets

7. 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$1,012
HK$3,021 total
includes taxes & fees
11 Aug - 12 Aug
Plymouth Collection: 3BD 2BA High Floor with Gym
Coffee/tea maker, fridge, microwave, oven

8. River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is HK$1,898
HK$4,033 total
includes taxes & fees
16 Aug - 17 Aug
River North Rooftop With In and Out Parking 5
TV, offices

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)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
The price is HK$1,883
HK$5,383 total
includes taxes & fees
16 Aug - 17 Aug
Modern West Loop Gem-City Views & Prime Location 2
TV, offices

10. 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.
The price is HK$3,130
HK$6,235 total
includes taxes & fees
2 Sept - 3 Sept
Downtown Chicago Stay with Free In & Out Parking 3
Interior

11. 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$2,652
HK$5,586 total
includes taxes & fees
3 Sept - 4 Sept
South Loop Rooftop With In and Out Parking 2
TV, offices

12. 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$1,930
HK$2,605 total
includes taxes & fees
13 Aug - 14 Aug
LIVN Millennium Park Downtown Chicago Superior 1BR
Dining

13. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.6 out of 10, Exceptional, (8 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is HK$1,695
HK$2,289 total
includes taxes & fees
17 Aug - 18 Aug
LIVN Millennium Park Downtown Chicago Studio
TV, offices

14. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,922
HK$2,595 total
includes taxes & fees
13 Aug - 14 Aug
LIVN Millennium Park Downtown Chicago 2BR
1 bedroom, iron/ironing board, travel cot, WiFi

15. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.4 out of 10, Exceptional, (17 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$1,577
HK$2,122 total
includes taxes & fees
16 Aug - 17 Aug
LIVN West Loop Chicago Queen Superior Studio
Exterior

16. 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$4,244
HK$7,861 total
includes taxes & fees
22 Aug - 23 Aug
Envitae Hotel, 4BR Modern Sleek Apartment
1 bedroom, iron/ironing board, travel cot, WiFi

17. 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$2,134
HK$2,883 total
includes taxes & fees
13 Aug - 14 Aug
LIVN West Loop Chicago King Studio
Living area

18. Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (15 reviews)
"i loved this place! would definitely come again"
United States
adrian
The price is HK$769
HK$1,191 total
includes taxes & fees
12 Aug - 13 Aug
Chicago Second Floor Studio by 747 Lofts
Dining

19. 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$1,679
HK$2,271 total
includes taxes & fees
13 Aug - 14 Aug
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

20. 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$1,726
HK$2,336 total
includes taxes & fees
17 Aug - 18 Aug
LIVN West Loop Chicago 2 BR City View
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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Very convenient location and well maintained"
Masakazu 2-night trip
Posted less than an hour ago
Eurostars Magnificent Mile

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 930 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.