Chicago Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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, (1,405 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is HK$997
HK$1,171 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (85 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is HK$1,192
HK$1,883 total
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
The price is HK$1,164
HK$1,367 total
includes taxes & fees
9 Nov - 10 Nov
Wrigleyville Suites
A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (558 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is HK$1,333
HK$1,759 total
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A hotel room with a large grey sofa, a small table with a copper pot, a red lamp, and a bed with white linens.

5. 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$1,176
HK$1,458 total
includes taxes & fees
8 Nov - 9 Nov
LIVN Millennium Park Downtown Chicago 1 BR
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

6. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (79 reviews)
"We had a very nice stay, the place was comfortable and clean, beautifully decorated. We only wish we would’ve had more time! And bonus it came with a parking spot. We hope to come back again!"
United States
Rachael
The price is HK$796
HK$3,369 total
includes taxes & fees
11 Nov - 12 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A rooftop terrace with a brick wall, large windows, and a metal railing.

7. 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, (32 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is HK$588
HK$1,978 total
includes taxes & fees
8 Nov - 9 Nov
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

8. 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, (24 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$627
HK$1,654 total
includes taxes & fees
8 Nov - 9 Nov
3BR Complete and Spacious Apartment in Ideal Spot
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$588
HK$1,949 total
includes taxes & fees
9 Nov - 10 Nov
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

10. 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$580
HK$1,697 total
includes taxes & fees
16 Nov - 17 Nov
Chic Studio in the Heart of the Gold Coast
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

11. 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$510
HK$1,183 total
includes taxes & fees
12 Nov - 13 Nov
Hyde Park Trendy Studio Apartment in Good Spot
A modern living room with a blue sofa, a patterned rug, and a television.

12. 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$470
HK$1,446 total
includes taxes & fees
9 Nov - 10 Nov
Great Area Logan Square Apt Games Pets - Sleeps 5
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

13. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"We really enjoyed our stay here. The communication was great. Check-in was flawless. We were able to find free parking close by. The listing is accurate, and the location was perfect for our visit to Chicago. We would definitely stay again. Well-equipped kitchen, in-unit laundry, plug strips and extra bedding all were appreciated."
United States
Karin S.
The price is HK$767
HK$2,536 total
includes taxes & fees
21 Nov - 22 Nov
Private Workspace • Sleeps 4 • Modern and Stylish
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

14. 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.
River North Rooftop With In and Out Parking 6
A neatly made bed with pillows, a bedside lamp, a small plant, and a stack of towels on the nightstand.

15. 1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
The price is HK$1,505
HK$2,956 total
includes taxes & fees
14 Nov - 15 Nov
1BR Modern Luxe Apt with In-Unit Laundry
A rooftop terrace with a fire pit, seating area, and a city skyline view.

16. Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6

Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
West Town
9.6 out of 10, Exceptional, (8 reviews)
"Very happy with our stay. Loved the rooftop views! The host was very friendly and welcoming."
United States
Jessica C.
The price is HK$1,211
HK$2,193 total
includes taxes & fees
3 Dec - 4 Dec
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
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.

17. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (29 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$1,176
HK$1,439 total
includes taxes & fees
9 Nov - 10 Nov
LIVN West Loop Chicago Queen Superior Studio
A spacious room with exposed brick walls, a large window with a city view, a gray sofa, a dining table with chairs, and a small side table.

18. River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is HK$1,051
HK$2,676 total
includes taxes & fees
16 Nov - 17 Nov
River North Rooftop With In and Out Parking 1
A modern living room with a green sofa, a coffee table, a chair, and a TV. There is a ceiling fan, a window with blinds, and a lamp on a side table.

19. 1BR Well-Equipped Apartment

1BR Well-Equipped Apartment
Lakeview
8.4 out of 10, Very good, (12 reviews)
"Very good location "
United States
wendy h.
The price is HK$494
HK$1,655 total
includes taxes & fees
8 Nov - 9 Nov
1BR Well-Equipped Apartment
A modern living room with a spiral staircase, a green sofa, a round coffee table, and a large abstract painting on the wall.

20. 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$1,312
HK$3,676 total
includes taxes & fees
7 Dec - 8 Dec
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
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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Find holiday rentals that suit your style

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Top Chicago Hotel Reviews

A modern building with a colorful facade and a red circular seating area.
citizenM Chicago Downtown

citizenM Chicago Downtown

citizenM Chicago Downtown
Downtown Chicago

8/10 Good

Good hotel
Hong Kong SAR China
TAO
Reviewed February 7, 2024
citizenM Chicago Downtown

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!

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.

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