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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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, (1,390 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is ￥22,464
￥26,371 total
includes taxes & fees
Nov 22 - Nov 23
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, (75 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
The price is ￥25,256
￥37,871 total
includes taxes & fees
Nov 4 - Nov 5
Kasa Lake Shore Chicago
A wooden dining table with two chairs, a potted plant, and a painting on the wall.

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 ￥16,694
￥42,903 total
includes taxes & fees
Nov 10 - Nov 11
Chic Studio in the Heart of the Gold Coast
A room with a round table, two chairs, a vase with flowers, a plate with food, and a window with blinds.

4. LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United States
Jason P.
The price is ￥25,884
￥34,457 total
includes taxes & fees
Nov 1 - Nov 2
LIVN Millennium Park Downtown Chicago Studio
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (48 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is ￥23,296
￥27,349 total
includes taxes & fees
Oct 28 - Oct 29
Wrigleyville Suites
A rooftop terrace with a brick wall, large windows, and a metal railing.

6. 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, (30 reviews)
"Very nice and clean place in a great location if you are going to Wrigley"
United States
Paul J.
The price is ￥11,765
￥42,102 total
includes taxes & fees
Nov 4 - Nov 5
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

7. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
10.0 out of 10, Exceptional, (72 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 ￥16,146
￥32,835 total
includes taxes & fees
Nov 9 - Nov 10
Chic Urban Retreat Near Wrigley Field w/Parking
A modern kitchen with a large island, bar stools, and a city view.

8. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (551 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ￥36,935
￥47,229 total
includes taxes & fees
Nov 1 - Nov 2
Level Chicago – Old Town
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 ￥11,765
￥42,681 total
includes taxes & fees
Oct 29 - Oct 30
Artistic 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.

10. 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 ￥19,766
￥45,232 total
includes taxes & fees
Nov 2 - Nov 3
3BR Complete and Spacious Apartment in Ideal Spot
A desk with a computer monitor, keyboard, mouse, a lamp, a mug, a plant, and a clock.

11. Private Workspace • Sleeps 4 • Modern and Stylish

Private Workspace • Sleeps 4 • Modern and Stylish
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 ￥6,902
￥43,586 total
includes taxes & fees
Nov 3 - Nov 4
Private Workspace • Sleeps 4 • Modern and Stylish
A modern living room with a spiral staircase, a green sofa, a round coffee table, and a large abstract painting on the wall.

12. 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 ￥23,531
￥73,329 total
includes taxes & fees
Nov 16 - Nov 17
Luxury River North Loft | Walk to Mag Mile, Riverwalk & Top Restaurants
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 ￥28,080
￥75,511 total
includes taxes & fees
Nov 1 - Nov 2
South Loop Rooftop With In and Out Parking 2
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.

14. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (28 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 ￥30,119
￥40,589 total
includes taxes & fees
Oct 30 - Oct 31
LIVN West Loop Chicago Queen Superior Studio
A modern kitchen with a central island, stainless steel dishwasher, pendant lighting, and hardwood flooring.

15. Flexhome West Town · Spacious 2BR Duplex · Sleeps 8

Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
West Town
10.0 out of 10, Exceptional, (3 reviews)
"Thank you. We had a wonderful stay."
United States
Janice G.
The price is ￥14,683
￥29,799 total
includes taxes & fees
Nov 17 - Nov 18
Flexhome West Town · Spacious 2BR Duplex · Sleeps 8
A hotel room with a large bed, a desk, a chair, a lamp, and artwork on the wall.

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 ￥12,664
￥29,178 total
includes taxes & fees
Nov 2 - Nov 3
Flexhome Ukrainian Village • 2BR • Walkable + Private Balcony · Sleeps 6
A modern kitchen with stainless steel appliances, white cabinetry, and a black stove.

17. 2BR Apt with 2 Baths & Laundry

2BR Apt with 2 Baths & Laundry
Near West Side
10.0 out of 10, Exceptional, (2 reviews)
"This made our stay in Chicago very relaxing. Everything was as expected and I do not have any complaints! Would definitely stay here again!"
United States
Matthew H.
The price is ￥22,276
￥46,603 total
includes taxes & fees
Nov 2 - Nov 3
2BR Apt with 2 Baths & Laundry
A modern living room with a blue sofa, a patterned rug, and a television.

18. 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 ￥10,394
￥33,208 total
includes taxes & fees
Nov 10 - Nov 11
Great Area Logan Square Apt Games Pets - Sleeps 5
A modern balcony with wicker furniture, a glass table, and a city skyline view.

19. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
Wabash 4BR - Pool, Free In & Out Parking 1
A modern kitchen with a large island, a built-in refrigerator, and a view of the city through large windows.

20. River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
River North Private Balcony With In and Out Parking
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 Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"L"
Barbara 1-night trip
Posted 3 hours ago
The Royal Sonesta 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!

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.