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 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chicago vacation 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, (1,407 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is ￥20,158
￥23,662 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

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 ￥24,089
￥38,062 total
includes taxes & fees
Nov 22 - Nov 23
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 ￥23,299
￥27,350 total
includes taxes & fees
Nov 9 - Nov 10
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, (559 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ￥27,099
￥35,722 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town
A multi-story building with a fire escape, a pedestrian bridge, and a train on an elevated track.

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 ￥24,564
￥30,013 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥16,247
￥68,273 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥11,886
￥39,406 total
includes taxes & fees
Nov 9 - Nov 10
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a sofa, a TV, and a dining area with stools.

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, (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 ￥11,252
￥30,201 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥11,886
￥39,406 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥11,252
￥33,742 total
includes taxes & fees
Nov 16 - Nov 17
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 ￥10,301
￥23,922 total
includes taxes & fees
Nov 12 - Nov 13
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 ￥9,509
￥29,235 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥15,507
￥51,270 total
includes taxes & fees
Nov 21 - Nov 22
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 ￥21,870
￥48,938 total
includes taxes & fees
Dec 7 - Dec 8
1BR Modern Luxe Apt with In-Unit Laundry
A laundry room with a stacked washer and dryer, shelves with cleaning supplies, and two propane tanks.

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 ￥24,476
￥44,329 total
includes taxes & fees
Dec 3 - Dec 4
Penthouse and Private Rooftop with Skyline Views, Grill, and Fire Pit - Sleeps 6
A spacious lobby with high ceilings and a skylight, featuring marble columns and a central staircase.

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 ￥23,297
￥28,524 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥44,095
￥82,763 total
includes taxes & fees
Dec 6 - Dec 7
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 ￥12,995
￥37,564 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥21,385
￥67,441 total
includes taxes & fees
Nov 16 - Nov 17
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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Top Chicago Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Rooms were cleaned and remodeled. Would stay here again"
Daisy 3-night trip
Posted less than an 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 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.