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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, (1,385 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is HK$1,124
HK$1,319 total
includes taxes & fees
22 Nov - 23 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, (73 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$1,894 total
includes taxes & fees
5 Nov - 6 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$832
HK$2,138 total
includes taxes & fees
10 Nov - 11 Nov
Chic Studio in the Heart of the Gold Coast
A hotel room with a bed, a wall-mounted mirror, a television displaying a space-themed image, and a window with curtains.

4. Private Workspace • Sleeps4 • Modern Stylish Stay

Private Workspace • Sleeps4 • Modern Stylish Stay
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$359
HK$2,168 total
includes taxes & fees
25 Oct - 26 Oct
Private Workspace • Sleeps4 • Modern Stylish Stay
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

5. River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is HK$1,051
HK$3,283 total
includes taxes & fees
18 Nov - 19 Nov
River North Rooftop With In and Out Parking 6
A corner room with a green upholstered chair, a small round table with a potted plant, and a framed picture on the wall.

6. Cozy Urban View Retreat Near Downtown - Sleeps 7

Cozy Urban View Retreat Near Downtown - Sleeps 7
Lawndale
10.0 out of 10, Exceptional, (1 review)
The price is HK$439
HK$1,592 total
includes taxes & fees
3 Nov - 4 Nov
Cozy Urban View Retreat Near Downtown - Sleeps 7
A modern living room with a blue sofa, a patterned rug, and a television.

7. 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$487
HK$1,610 total
includes taxes & fees
10 Nov - 11 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

8. 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)
"The app isn’t letting me give 5 stars but I would give 5 stars for all categories. It was perfect for our needs. Two adults and two kids. Perfect location and easy to get in and out with our car off the street. Beds were comfy and the main rooms were spacious. They were super responsive for our last minute booking. Would definitely stay here again!"
United States
Bridget
The price is HK$796
HK$1,647 total
includes taxes & fees
3 Nov - 4 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

9. 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$565
HK$2,107 total
includes taxes & fees
25 Oct - 26 Oct
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.

10. 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$697
HK$2,217 total
includes taxes & fees
29 Oct - 30 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A modern kitchen with a large island, bar stools, and a city view.

11. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (545 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is HK$1,888
HK$2,410 total
includes taxes & fees
1 Nov - 2 Nov
Level Chicago – Old Town
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

12. 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$1,051
HK$2,248 total
includes taxes & fees
2 Nov - 3 Nov
2BR Apt with 2 Baths & Laundry
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$1,538
HK$4,009 total
includes taxes & fees
1 Nov - 2 Nov
South Loop Rooftop With In and Out Parking 2
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.

14. 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$1,460 total
includes taxes & fees
2 Nov - 3 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with white cabinets, stainless steel appliances, and a bar area with stools.

15. 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$895
HK$2,133 total
includes taxes & fees
2 Nov - 3 Nov
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a white coffee table, a vase with flowers, a bottle of wine, and a cheese board with snacks.

16. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
9.4 out of 10, Exceptional, (8 reviews)
"Great property in a central location. Neighborhood was quiet and safe with good parks nearby. Apartment had good amenities and perfect for our stay. Communication with host was excellent"
United States
Carey M.
The price is HK$773
HK$2,752 total
includes taxes & fees
28 Oct - 29 Oct
2BR Fitness Pad • Private Gym • Sleeps 7
A modern kitchen with a stainless steel refrigerator, a stove, and white cabinets.

17. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Such a cozy stay! Definitely recommend!"
United States
Angelina
The price is HK$636
HK$1,419 total
includes taxes & fees
11 Nov - 12 Nov
Hyde Park Trendy Studio Apartment in Good Spot
A modern bedroom with a bed, a sofa, and a hanging plant.

18. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (105 reviews)
"Great location for us near the Edgewood neighborhood. Property was very clean, bed comfy, and owner responsive. We’d stay here again!"
United States
Sherry M.
The price is HK$742
HK$1,399 total
includes taxes & fees
5 Nov - 6 Nov
Cozy studio in Andersonville Chicago
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.

19. 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$735
HK$1,491 total
includes taxes & fees
17 Nov - 18 Nov
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A living room with a flat-screen TV, a sofa, a coffee table, and a staircase leading to another room.

20. Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6

Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
Brighton Park
8.6 out of 10, Excellent, (21 reviews)
"Excellent location and go anywhere so close."
United States
Yiu S.
The price is HK$596
HK$1,814 total
includes taxes & fees
27 Oct - 28 Oct
Sunflower Apt 10 Min from Downtown Chicago - Sleeps up to 6
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

River Hotel

River Hotel

10/10 Excellent
"Clean room staff is very courteous even with late check ins. Very well located. Breakfast included is the best option."
Jocelyn 2-night trip
Posted 1 hour ago
River 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.