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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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, (1,300 reviews)
"A great place"
United States
Lahiru
The price is ￥24,158
￥33,018 total
includes taxes & fees
Sep 7 - Sep 8
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (25 reviews)
"Great location and super clean!"
United States
Erica
The price is ￥26,516
￥40,963 total
includes taxes & fees
Sep 7 - Sep 8
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, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is ￥43,675
￥55,187 total
includes taxes & fees
Sep 7 - Sep 8
Level Chicago – Old Town
A brick building with a sign for 'Irish Declans' Pub' and outdoor seating with metal chairs and tables.

4. Scott C.H.

Scott C.H.
2.0 star property
Near North Side
The price is ￥120,516
￥204,847 total
includes taxes & fees
Sep 8 - Sep 9
Scott C.H.
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.

5. LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.6 out of 10, Exceptional, (21 reviews)
"Incredible location, very clean and easy! Would book again!"
United States
Andrea K.
The price is ￥29,216
￥39,002 total
includes taxes & fees
Sep 7 - Sep 8
LIVN West Loop Chicago Queen Superior 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
The price is ￥52,715
￥110,328 total
includes taxes & fees
Sep 13 - Sep 14
South Loop Rooftop With In and Out Parking 3

7. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, very quite loved having 3 bathrooms, had everything you’d need for your stay"
Canada
LM
The price is ￥68,593
￥135,195 total
includes taxes & fees
Sep 13 - Sep 14
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

8. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (25 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
The price is ￥85,106
￥158,510 total
includes taxes & fees
Sep 16 - Sep 17
ENVITAE Hotel, 4BR Luxury Modern Apartments

9. Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
9.4 out of 10, Exceptional, (6 reviews)
"Nice place, clean property, great views "
United States
Zach L.
The price is ￥68,117
￥132,845 total
includes taxes & fees
Sep 27 - Sep 28
Premium Urban 4BR - Perfect Mix of Comfort & Location
A modern kitchen with a central island, bar stools, and a dining table.

10. River North Private Deck With In and Out Parking

River North Private Deck With In and Out Parking
Downtown Chicago
9.8 out of 10, Exceptional, (14 reviews)
"Excellent location, very clean, spacious."
United States
John David K.
The price is ￥43,665
￥101,953 total
includes taxes & fees
Sep 29 - Sep 30
River North Private Deck With In and Out Parking
A kitchen with white cabinets, a microwave, a kettle, and a toaster.

11. Plymouth Collection: 3BD 2BA High Floor with Gym

Plymouth Collection: 3BD 2BA High Floor with Gym
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"The suite was excellent. Clean and very well furnished. The building is located within walking distance to many of the things that we did. We would stay in this place again in a heartbeat. Very pleased with our experience"
United States
Derek M.
The price is ￥25,564
￥68,258 total
includes taxes & fees
Sep 8 - Sep 9
Plymouth Collection: 3BD 2BA High Floor with Gym
A modern living room with a dining area, a large window, a flat-screen TV, and a piece of abstract art on the wall.

12. LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ￥30,168
￥40,317 total
includes taxes & fees
Sep 7 - Sep 8
LIVN Millennium Park Downtown Chicago 2BR
A bedroom with a bed, a nightstand, a lamp, and a window with blinds.

13. 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, (3 reviews)
"Spacious, free parking, family friendly"
United States
Majid
The price is ￥42,712
￥100,778 total
includes taxes & fees
Sep 21 - Sep 22
Downtown Chicago Stay with Free In & Out Parking 1
A modern building with a glass facade, surrounded by a parking area and greenery.

14. Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (31 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ￥26,834
￥76,024 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 4BR Central Apartment w/ Skyline Views
A modern kitchen with a marble island, wooden cabinets, and a dining area with a table and chairs.

15. 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, (9 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 ￥25,405
￥72,118 total
includes taxes & fees
Sep 8 - Sep 9
River North Rooftop With In and Out Parking 3
A modern living room with a grey sofa, a coffee table, and a small round table. There are abstract wall art pieces and a large window with a view of a building and greenery.

16. Wabash 4BR - Pool, Free In & Out Parking 2

Wabash 4BR - Pool, Free In & Out Parking 2
Downtown Chicago
The price is ￥41,283
￥58,193 total
includes taxes & fees
Sep 13 - Sep 14
Wabash 4BR - Pool, Free In & Out Parking 2
A modern living room with a flat-screen TV, a grey sofa, a round coffee table, and a large window with a view of a building.

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

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
Wabash 4BR - Pool, Free In & Out Parking 1
A modern room with a sofa, a dining table, and a window with a view of buildings.

18. LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (11 reviews)
"Great property"
United States
duane
The price is ￥33,026
￥44,064 total
includes taxes & fees
Sep 7 - Sep 8
LIVN West Loop Chicago 2 BR City View
A modern bedroom with a brick wall, a large bed, a sofa, a nightstand, and a mirror.

19. LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is ￥28,263
￥37,688 total
includes taxes & fees
Sep 7 - Sep 8
LIVN West Loop Chicago King Studio

20. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.6 out of 10, Exceptional, (4 reviews)
The price is ￥108,142
￥190,977 total
includes taxes & fees
Sep 18 - Sep 19
Modern 3BR Apartment Near North Ave Shops
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Would stay there again."
Steve 1-night trip
Posted 1 hour ago
Hyatt Regency 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!

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 ENVITAE Hotel, 4BR Luxury Modern Apartments and Vintage Escape 1BR Two Blocks Away From Beach.

How many vacation rentals are there in Chicago?

With 919 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.