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Chicago Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Chicago holiday rentals

Exterior

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,327 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is HK$1,194
HK$1,631 total
includes taxes & fees
27 Sept - 28 Sept
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (34 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
The price is HK$1,412
HK$2,145 total
includes taxes & fees
5 Oct - 6 Oct
Kasa Lake Shore Chicago
Full-sized fridge, microwave, oven, stovetop

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$2,310
HK$2,905 total
includes taxes & fees
28 Sept - 29 Sept
Level Chicago – Old Town
TV, offices

4. 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$3,828
HK$5,133 total
includes taxes & fees
25 Sept - 26 Sept
LIVN West Loop Chicago 2 BR City View
TV, offices

5. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (12 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is HK$2,416
HK$3,253 total
includes taxes & fees
24 Sept - 25 Sept
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

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, (12 reviews)
"Perfect place for my family’s visit to Chicago."
United States
Jason L.
The price is HK$2,079
HK$4,744 total
includes taxes & fees
27 Sept - 28 Sept
Downtown Chicago Stay with Free In & Out Parking 3
Coffee/tea maker, fridge, microwave, oven

7. 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, (7 reviews)
"Everything was amazing"
United States
Kimberly R.
River North Rooftop With In and Out Parking 5
Interior

8. 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$1,255
HK$3,563 total
includes taxes & fees
14 Oct - 15 Oct
South Loop Rooftop With In and Out Parking 3
Living area

9. 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$3,758
HK$8,509 total
includes taxes & fees
21 Sept - 22 Sept
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
TV, offices

10. 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, (6 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$2,644
HK$5,039 total
includes taxes & fees
29 Sept - 30 Sept
River North Private Balcony With In and Out Parking
Beach nearby

11. 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$3,138
HK$7,386 total
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Interior

12. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (43 reviews)
"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...
United States
Andrea M.
The price is HK$1,922
HK$4,347 total
includes taxes & fees
22 Sept - 23 Sept
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
2 bedrooms, iron/ironing board, travel cot, free WiFi

13. Zen City Escape | Patio + Free Parking

Zen City Escape | Patio + Free Parking
West Town
10.0 out of 10, Exceptional, (4 reviews)
"I had an amazing stay at Tracee's place. It was quiet, clean, plenty of parking and served all of my needs. Tracee was responsive and very accommodating of my stay."
United States
Denise R.
The price is HK$1,415
HK$3,620 total
includes taxes & fees
22 Sept - 23 Sept
Zen City Escape | Patio + Free Parking
Outdoor dining

14. 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$2,704 total
includes taxes & fees
28 Sept - 29 Sept
2R- ❤️ Stylish and Cozy 2BR in Logan Square!
Property grounds

15. Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.8 out of 10, Exceptional, (102 reviews)
"We really enjoyed the space, and it was perfect for us."
United States
Nate T.
The price is HK$998
HK$2,519 total
includes taxes & fees
21 Sept - 22 Sept
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
Fireplace

16. Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.6 out of 10, Exceptional, (33 reviews)
"This place was perfect for our quick weekend getaway!"
United States
Kate P.
The price is HK$3,758
HK$8,509 total
includes taxes & fees
21 Sept - 22 Sept
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
TV

17. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.2 out of 10, Very good, (22 reviews)
"absolutely would stay here again. Great property and great communcation"
United States
Daniel J.
The price is HK$628
HK$1,762 total
includes taxes & fees
21 Sept - 22 Sept
3BR Complete and Spacious Apartment in Ideal Spot
Coffee/tea maker, fridge, microwave, oven

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

Wabash 4BR - Pool, Free In & Out Parking 4
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Nice place to stay."
United States
William H.
The price is HK$1,946
HK$5,509 total
includes taxes & fees
29 Sept - 30 Sept
Wabash 4BR - Pool, Free In & Out Parking 4
Beach

19. Luxury Lincoln Park Gem with Gourmet Kitchen & City Views

Luxury Lincoln Park Gem with Gourmet Kitchen & City Views
Lincoln Park
10.0 out of 10, Exceptional, (15 reviews)
"Home was well maintained and clean. Location was fantastic with an easy walk to shops and restaurants. "
United States
Nikki R.
The price is HK$4,487
HK$20,522 total
includes taxes & fees
5 Oct - 6 Oct
Luxury Lincoln Park Gem with Gourmet Kitchen & City Views
Dining

20. The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Lakeview
10.0 out of 10, Exceptional, (4 reviews)
"Great location in Wrigleyville! Comfortable, clean, and very nicely decorated. Will definitely be back!"
United States
Rhonda B.
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
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 Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

8/10 Good
"It was good for what we needed, there was a leak in the room but the problem was quickly addressed."
Samantha 3-night trip
Posted less than an hour ago
The Allegro Royal Sonesta Hotel Chicago Loop

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 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 919 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.