A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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, (1,371 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
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, (66 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is HK$1,405
HK$2,137 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is HK$2,175
HK$2,747 total
includes taxes & fees
1 Nov - 2 Nov
Level Chicago – Old Town
A modern living room with a brick wall, large windows, a flat-screen TV, a sofa, a coffee table, and a side table.

4. 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$824
HK$3,013 total
includes taxes & fees
3 Nov - 4 Nov
River North Rooftop With In and Out Parking 6
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

5. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great location"
United States
Jason P.
The price is HK$2,111
HK$2,817 total
includes taxes & fees
15 Oct - 16 Oct
LIVN Millennium Park Downtown Chicago Studio
A spacious lobby with a sectional sofa, a dining area, and large windows.

6. 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
South Loop Rooftop With In and Out Parking 3
A hotel room with a bed, two bedside lamps, a wall-mounted artwork, and a small table with a lamp.

7. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is HK$1,099
HK$2,293 total
includes taxes & fees
2 Nov - 3 Nov
2BR Apt with 2 Baths & Laundry
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

8. Downtown Chicago Stay with Free In & Out Parking 1

Downtown Chicago Stay with Free In & Out Parking 1
Downtown Chicago
9.4 out of 10, Exceptional, (6 reviews)
"Spacious, free parking, family friendly"
United States
Majid
The price is HK$1,428
HK$4,081 total
includes taxes & fees
29 Oct - 30 Oct
Downtown Chicago Stay with Free In & Out Parking 1
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

9. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (64 reviews)
"terrible experience i need my money back, I cant check in at all please give me back my money"
United States
Jainul
The price is HK$1,243
HK$1,459 total
includes taxes & fees
3 Nov - 4 Nov
Wrigleyville Suites
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (69 reviews)
"Hosts were great, location is great, and it was a great stay."
United States
Ryan G.
The price is HK$797
HK$1,657 total
includes taxes & fees
2 Nov - 3 Nov
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

11. 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, (10 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$1,256
HK$3,623 total
includes taxes & fees
3 Nov - 4 Nov
River North Rooftop With In and Out Parking 3
A rooftop terrace with a brick wall, large windows, and a metal railing.

12. 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.
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a fire pit, seating area, and a city skyline view.

13. 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
9.8 out of 10, Exceptional, (6 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$872
HK$1,878 total
includes taxes & fees
4 Nov - 5 Nov
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A bedroom with a bed, bedside tables, a ceiling fan, framed pictures, and a window.

14. Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is HK$1,201
HK$2,726 total
includes taxes & fees
9 Nov - 10 Nov
Stylish Gold Coast 1BR with Vintage Flair
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

15. Flexhome East Village • Modern 2BR • Quiet Street

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (26 reviews)
"Great location! "
United States
Andrea B.
Flexhome East Village • Modern 2BR • Quiet Street
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$518
HK$1,317 total
includes taxes & fees
2 Nov - 3 Nov
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with white cabinets, a central island with stools, a microwave, and a refrigerator.

17. 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$816
HK$2,012 total
includes taxes & fees
20 Oct - 21 Oct
3BR Complete and Spacious Apartment in Ideal Spot
A hotel room with a bed, two bedside tables, and three wall-mounted paintings.

18. Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is HK$1,240
HK$2,439 total
includes taxes & fees
2 Nov - 3 Nov
Stylish Japanese-Themed 2BR Apt Close to Downtown
A modern bedroom with a bed, a sofa, and a hanging plant.

19. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (102 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$494
HK$1,094 total
includes taxes & fees
2 Nov - 3 Nov
Cozy studio in Andersonville Chicago
A hotel room with a bed, a view of a cityscape, and a window with curtains.

20. Elegant Style Loft Montrose|13 mins DT|4 mins Lake

Elegant Style Loft Montrose|13 mins DT|4 mins Lake
Uptown
8.6 out of 10, Excellent, (11 reviews)
"Great location and great place! "
United States
Ryinne P.
The price is HK$1,271
HK$2,640 total
includes taxes & fees
20 Oct - 21 Oct
Elegant Style Loft Montrose|13 mins DT|4 mins Lake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chicago Hotel Reviews

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

10/10 Excellent
"Amazing locations and staff!"
Sarah 2-night trip
Posted 3 hours ago
The Godfrey Hotel Chicago

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 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.