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

Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chicago vacation rentals

A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (89 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is ￥24,018
￥37,949 total
includes taxes & fees
Dec 3 - Dec 4
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,414 reviews)
"Great for extended stays."
United States
Jeff
The price is ￥30,347
￥35,624 total
includes taxes & fees
Nov 24 - Nov 25
Sentral Michigan Avenue
A neatly arranged bedroom with a bed, a bedside table, a wall-mounted artwork, and a patterned wallpaper.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (50 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is ￥18,583
￥21,815 total
includes taxes & fees
Dec 8 - Dec 9
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, (562 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ￥27,284
￥35,946 total
includes taxes & fees
Nov 22 - Nov 23
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 ￥30,316
￥38,531 total
includes taxes & fees
Nov 15 - Nov 16
LIVN Millennium Park Downtown Chicago 1 BR
A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

6. 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, (25 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 ￥13,273
￥34,276 total
includes taxes & fees
Nov 12 - Nov 13
3BR Complete and Spacious Apartment in Ideal Spot
A modern kitchen with white cabinets, a stainless steel refrigerator, a built-in oven, and a window above the sink.

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

Flexhome East Village • Modern 2BR • Quiet Street
West Town
9.6 out of 10, Exceptional, (29 reviews)
"Great location! "
United States
Andrea B.
The price is ￥12,102
￥27,023 total
includes taxes & fees
Dec 9 - Dec 10
Flexhome East Village • Modern 2BR • Quiet Street
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

8. 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 ￥11,110
￥33,413 total
includes taxes & fees
Nov 16 - Nov 17
Chic Studio in the Heart of the Gold Coast
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

9. 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 ￥16,110
￥67,815 total
includes taxes & fees
Nov 30 - Dec 1
Chic Urban Retreat Near Wrigley Field w/Parking
A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

10. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
The price is ￥11,428
￥25,260 total
includes taxes & fees
Nov 16 - Nov 17
Hyde Park Trendy Studio Apartment in Good Spot
A rooftop terrace with a brick wall, large windows, and a metal railing.

11. 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 ￥11,851
￥41,042 total
includes taxes & fees
Nov 12 - Nov 13
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

12. 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 ￥14,928
￥52,008 total
includes taxes & fees
Nov 21 - Nov 22
Private Workspace • Sleeps 4 • Modern and Stylish
A neatly made bed with a headboard, two bedside tables with lamps, a wall-mounted artwork, and a patterned rug.

13. West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
The price is ￥16,507
￥41,909 total
includes taxes & fees
Nov 12 - Nov 13
West Loop Living – Bright 1BR
A modern bedroom with a bed, a sofa, and a hanging plant.

14. Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (110 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 ￥11,428
￥20,759 total
includes taxes & fees
Dec 10 - Dec 11
Cozy studio in Andersonville Chicago
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.

15. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (29 reviews)
"Location was amazing, and check in was super simple."
United States
Dale H.
The price is ￥25,756
￥32,775 total
includes taxes & fees
Nov 12 - Nov 13
LIVN West Loop Chicago Queen Superior Studio
A modern kitchen with a built-in microwave, a dining area with a black sofa, and a large window offering a city view.

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

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is ￥18,412
￥38,388 total
includes taxes & fees
Nov 17 - Nov 18
Stylish Japanese-Themed 2BR Apt Close to Downtown
A bedroom with a bed, a desk, a chair, a TV, and a window with blinds.

17. Flexhome Wicker Park • Stylish 2BR • Sleeps 6

Flexhome Wicker Park • Stylish 2BR • Sleeps 6
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Wouldn’t change a thing. Great location to downtown and all the things that we wanted to do."
United States
beth m.
The price is ￥12,156
￥27,144 total
includes taxes & fees
Nov 24 - Nov 25
Flexhome Wicker Park • Stylish 2BR • Sleeps 6
A living room with a flat-screen TV on a wooden cabinet, a dark sofa, a coffee table, a floor lamp, and a potted plant.

18. 1BR/1BA City Comfort

1BR/1BA City Comfort
Lincoln Square
8.6 out of 10, Excellent, (13 reviews)
"good place to stay clean and comfortable!"
United States
patricia r.
The price is ￥9,999
￥25,174 total
includes taxes & fees
Nov 16 - Nov 17
1BR/1BA City Comfort
A hotel room with a large bed, a window with blinds, a projector screen displaying a castle, and a neatly made bed with towels.

19. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is ￥15,380
￥52,346 total
includes taxes & fees
Nov 17 - Nov 18
Sleeps 7 • Huge Projector • Designated Workspace
A living room with a dark blue sofa, a small coffee table, a floor lamp, and a ceiling fan. There are two windows with blinds, a radiator, and a potted plant on the windowsill.

20. Beautifully Set Up 2BR Space

Beautifully Set Up 2BR Space
Lakeview
9.0 out of 10, Wonderful, (2 reviews)
"Approval/check-in process was a little more laborous than expected but great deal for a really nice place and location. Would stay again!"
United States
Tavia S.
The price is ￥18,253
￥38,203 total
includes taxes & fees
Nov 16 - Nov 17
Beautifully Set Up 2BR Space
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

8/10 Good
"Honestly not my favorite stay, but it was in a super convenient location. We stayed three nights, and checked in pretty late. The hotel is very old in a sense of no modern amenities, no microwave in the room but has a great and comfortable vintage aesthetic. Was also told that it’s haunted with lore of a little ghost boy roaming the halls of the 10th floor.. lol. Staff and security were super friendly and great to converse with about things to do in the city. Would I stay again? Probably not, but wasn’t the worst place to stay."
Nevaeh 3-night trip
Posted 3 hours 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 vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed theater 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 vacation rentals in Chicago?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, 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 you can cook with friends or family. Other favorite homes for rent in Chicago are Sleeps 18 • 8BR • Game Room • Gym • Theater and LUXE 3 BR, 2 BA + Hot Tub.

How many vacation rentals are there in Chicago?

With 933 Expedia vacation rentals, you're sure 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 vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.