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

Chicago Vacation 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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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, (1,377 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ￥22,629
￥26,564 total
includes taxes & fees
Nov 9 - Nov 10
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, (72 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ￥24,043
￥36,484 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥19,594
￥46,965 total
includes taxes & fees
Nov 9 - Nov 10
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 ￥7,648
￥44,724 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥16,908
￥60,657 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥8,091
￥31,219 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥9,481
￥32,078 total
includes taxes & fees
Nov 10 - Nov 11
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 ￥16,200
￥33,336 total
includes taxes & fees
Nov 3 - Nov 4
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, (29 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is ￥13,463
￥45,707 total
includes taxes & fees
Oct 26 - Oct 27
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 ￥11,377
￥42,622 total
includes taxes & fees
Oct 21 - Oct 22
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, (543 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is ￥42,059
￥53,273 total
includes taxes & fees
Nov 3 - Nov 4
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, (1 review)
"The property was very clean and perfect for our overnight stay. Thank you"
United States
michele
The price is ￥17,224
￥40,053 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥28,444
￥77,038 total
includes taxes & fees
Nov 1 - Nov 2
South Loop Rooftop With In and Out Parking 2
A bedroom with a bed, a closet with shelves, and a vacuum cleaner.

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 ￥11,994
￥28,450 total
includes taxes & fees
Nov 2 - Nov 3
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.

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 ￥17,382
￥42,011 total
includes taxes & fees
Oct 26 - Oct 27
3BR Complete and Spacious Apartment in Ideal Spot
A modern living room with a grey sectional sofa, a white coffee table, and a small potted plant.

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 ￥13,489
￥52,375 total
includes taxes & fees
Oct 22 - Oct 23
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 ￥11,061
￥26,338 total
includes taxes & fees
Oct 28 - Oct 29
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, (104 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 ￥9,955
￥22,034 total
includes taxes & fees
Nov 2 - Nov 3
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, (2 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is ￥13,906
￥29,000 total
includes taxes & fees
Nov 17 - Nov 18
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 ￥14,064
￥39,196 total
includes taxes & fees
Nov 1 - Nov 2
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.
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

River Hotel

River Hotel

8/10 Good
"I wish there were ice on the 2nd floor with the coffee and water station. Also would have liked some non-caffeinated tea options. Overall the stay was nice. A great central location for walking to many different places. It felt safe to be outside at night and the river view was nice."
Nicole 4-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!

Explore a world of travel with Expedia

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.