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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (1,388 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,123
HK$1,318 total
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (74 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is HK$1,263
HK$1,893 total
includes taxes & fees
4 Nov - 5 Nov
Kasa Lake Shore Chicago
A bedroom with a bed, bedside tables, a desk, and a chair. There are windows with blinds, a ceiling fan, and a rug on the floor.

3. Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great little spot in a fun area of downtown Chicago. Lots of bars & restaurants within walking distance."
United States
Ryan
The price is HK$902
HK$2,219 total
includes taxes & fees
8 Nov - 9 Nov
Chic Studio in the Heart of the Gold Coast
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

4. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Jason P.
The price is HK$1,874
HK$2,530 total
includes taxes & fees
31 Oct - 1 Nov
LIVN Millennium Park Downtown Chicago Studio
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (47 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is HK$1,165
HK$1,367 total
includes taxes & fees
26 Oct - 27 Oct
Wrigleyville Suites
A rooftop terrace with a brick wall, large windows, and a metal railing.

6. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
9.2 out of 10, Wonderful, (30 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is HK$520
HK$2,061 total
includes taxes & fees
26 Oct - 27 Oct
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

7. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (71 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is HK$796
HK$1,656 total
includes taxes & fees
8 Nov - 9 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a large island, bar stools, and a city view.

8. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (549 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is HK$1,871
HK$2,390 total
includes taxes & fees
1 Nov - 2 Nov
Level Chicago – Old Town
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (60 reviews)
"Clean, efficient, and conveniently located to plenty of transportation and culture."
United States
Michael S.
The price is HK$716
HK$2,258 total
includes taxes & fees
29 Oct - 30 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A laundry room with a front-loading washer and dryer, a white door with a vent, and a wooden floor.

10. 3BR Complete and Spacious Apartment in Ideal Spot

3BR Complete and Spacious Apartment in Ideal Spot
West Town
8.4 out of 10, Very good, (23 reviews)
"My wife and I stayed here when we came to town for a concert at the united center. We actually walked to the venue and it was about 45 mins, a lovely walk. It was a very convenient location, lovely apartment, and the host communicated very well. Check in and out was easy. Great neighborhood. Would definitely stay here again."
United States
Francis
The price is HK$1,004
HK$2,270 total
includes taxes & fees
27 Oct - 28 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A bathroom with a glass shower enclosure and a white washing machine.

11. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"The apartment was just as described, modern, comfortable, very clean and perfect for two people for our five night stay. Very comfortable bed and we especially appreciated the easy entry lock. Great location. Good communication with property manager but we had zero complaints. We would stay again!"
United States
Margaret N.
The price is HK$428
HK$2,286 total
includes taxes & fees
3 Nov - 4 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
A modern kitchen with stainless steel appliances, a dining area with a wooden table, and a spiral staircase.

12. Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants

Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
Downtown Chicago
The price is HK$2,808
HK$5,927 total
includes taxes & fees
8 Nov - 9 Nov
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
A narrow hallway with a concrete wall, a wooden floor, a small table, and a large mirror on the right.

13. 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$1,388
HK$3,794 total
includes taxes & fees
1 Nov - 2 Nov
South Loop Rooftop With In and Out Parking 2
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.

14. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (27 reviews)
"Clean, comfortable, effortless check-in and checkout process, and in a very convenient location. Would stay again!"
United States
Tara H.
The price is HK$1,435
HK$1,937 total
includes taxes & fees
26 Oct - 27 Oct
LIVN West Loop Chicago Queen Superior Studio
A modern kitchen with a dishwasher, a sink, and a large island. There is a trash can and a dining area with a table and chairs.

15. Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is HK$734
HK$1,490 total
includes taxes & fees
26 Oct - 27 Oct
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A hotel room with a geometric-patterned wall, a bed with white bedding and a beige throw, two bedside lamps, and a window with blinds.

16. Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6

Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
West Town
9.0 out of 10, Wonderful, (16 reviews)
"Great location! Comfortable and quiet. "
United States
Jonalyn B.
The price is HK$633
HK$1,459 total
includes taxes & fees
16 Nov - 17 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

17. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (2 reviews)
"This made our stay in Chicago very relaxing. Everything was as expected and I do not have any complaints! Would definitely stay here again!"
United States
Matthew H.
The price is HK$1,208
HK$2,450 total
includes taxes & fees
8 Nov - 9 Nov
2BR Apt with 2 Baths & Laundry
A modern living room with a blue sofa, a patterned rug, and a television.

18. Great Area Logan Square Apt Games Pets - Sleeps 5

Great Area Logan Square Apt Games Pets - Sleeps 5
Avondale
10.0 out of 10, Exceptional, (2 reviews)
"Place was nice and clean. Great communication from the host! Would stay here again!"
United States
Deborah J.
The price is HK$471
HK$1,592 total
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern balcony with wicker furniture, a glass table, and a city skyline view.

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

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
The price is HK$1,176
HK$4,414 total
includes taxes & fees
26 Oct - 27 Oct
Wabash 4BR - Pool, Free In & Out Parking 1
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

20. 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.
River North Private Balcony With In and Out Parking
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Pleasant stay great location"
Sam 2-night trip
Posted 1 hour ago
Congress Plaza Hotel

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 Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

How many holiday rentals are there in Chicago?

With 933 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.