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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 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, (1,285 reviews)
"Nice stay"
United States
Heather
The price is HK$1,193
HK$1,630 total
includes taxes & fees
30 Aug - 31 Aug
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (20 reviews)
"Great location and super clean!"
United States
Erica
The price is HK$1,387
HK$2,115 total
includes taxes & fees
7 Sept - 8 Sept
Kasa Lake Shore Chicago
1 bedroom, iron/ironing board, travel cot, WiFi

3. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Highly recommend! Will be staying here again."
United States
Sheila M.
The price is HK$1,082
HK$1,463 total
includes taxes & fees
31 Aug - 1 Sept
LIVN West Loop Chicago Queen Superior Studio
Dining

4. 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$1,050
HK$1,427 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago Studio
Full-sized fridge, microwave, oven, stovetop

5. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (520 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$1,892
HK$2,414 total
includes taxes & fees
31 Aug - 1 Sept
Level Chicago – Old Town
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$1,254
HK$3,618 total
includes taxes & fees
8 Sept - 9 Sept
River North Rooftop With In and Out Parking 3
TV, offices

7. 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)
The price is HK$2,257
HK$4,953 total
includes taxes & fees
27 Sept - 28 Sept
Downtown Chicago Stay with Free In & Out Parking 3
Interior

8. 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$1,983
HK$4,442 total
includes taxes & fees
2 Sept - 3 Sept
Plymouth Collection: 3BD 2BA High Floor with Gym
Fitness facility

9. South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is HK$1,819
HK$4,412 total
includes taxes & fees
3 Sept - 4 Sept
South Loop Rooftop With In & Out Parking 1
TV, offices

10. 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$1,309
HK$1,740 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago 1 BR
Property grounds

11. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
The price is HK$4,499
HK$8,319 total
includes taxes & fees
16 Sept - 17 Sept
ENVITAE Hotel, 4BR Luxury Modern Apartments
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$1,223
HK$1,629 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago Superior 1BR
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$3,762
HK$7,255 total
includes taxes & fees
28 Sept - 29 Sept
Envitae Hotel, 4BR Modern Sleek Apartment
1 bedroom, iron/ironing board, travel cot, WiFi

14. 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$1,097
HK$1,482 total
includes taxes & fees
31 Aug - 1 Sept
LIVN West Loop Chicago Classic Queen Studio
Coffee/tea maker, fridge, microwave, oven

15. 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, (12 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is HK$5,228
HK$9,444 total
includes taxes & fees
6 Sept - 7 Sept
River North Private Deck With In and Out Parking
TV, offices

16. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$1,568
HK$2,121 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago 2BR
Dining

17. 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$1,458
HK$1,934 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

18. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great property"
United States
duane
The price is HK$1,482
HK$1,962 total
includes taxes & fees
31 Aug - 1 Sept
LIVN West Loop Chicago 2 BR City View
1 bedroom, iron/ironing board, travel cot, WiFi

19. 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$1,599
HK$2,158 total
includes taxes & fees
31 Aug - 1 Sept
LIVN West Loop Chicago King Studio
TV, offices

20. 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$1,568
HK$2,121 total
includes taxes & fees
31 Aug - 1 Sept
LIVN Millennium Park Downtown Chicago Superior 2 BR
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

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"They were so accommodating. I thoroughly enjoyed the stay."
Karen 3-night trip
Posted 4 hours ago
Fairmont Chicago at Millennium Park

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!

Explore a world of travel with Expedia

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 929 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.