Chicago Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 3 - Oct 5
In two months
Nov 14 - Nov 16
In three months
Dec 12 - Dec 14
In four months
Jan 9 - Jan 11

Vacation Rentals in Chicago

Our top choices for Chicago vacation rentals

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (922)
"This area is perfect we will definitely be back."
The price is P8,681
P11,865 total
includes taxes & fees
Sep 22 - Sep 23
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (520)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (355)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (659)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is P9,072
P10,650 total
includes taxes & fees
Sep 23 - Sep 24
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (202)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (360)
"Great stay!"
The price is P7,360
P8,640 total
includes taxes & fees
Sep 21 - Sep 22
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (342)
"Fantastic property with an amazing view. Easy walk to food, shopping and the lake. Would absolutely stay again "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (221)
"Great location and lovely amenities. "
The price is P8,901
P10,449 total
includes taxes & fees
Sep 20 - Sep 21
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.2 out of 10, Very Good, (48)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is P9,651
P11,329 total
includes taxes & fees
Oct 19 - Oct 20
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (167)
"This place has everything for a multi-night stay."
Kasa River North Chicago
The Gem Museum Suites
Private kitchen

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (89)
"Super nice hotel and staff "
The price is P12,134
P13,891 total
includes taxes & fees
Sep 24 - Sep 25
The Gem Museum Suites
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is P7,424
P11,559 total
includes taxes & fees
Sep 21 - Sep 22
Wrigleyville Suites
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Desk, laptop workspace, blackout drapes, free WiFi

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (60)
"Good "
The price is P4,813
P5,437 total
includes taxes & fees
Sep 24 - Sep 25
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (179)
"Great location!!!"
The price is P8,476
P9,950 total
includes taxes & fees
Sep 21 - Sep 22
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (137)
"Overall, our stay was wonderful! The staff was friendly, everything was clean, and the service was excellent. The only downside was that we had some issues with the AC. Luckily, the weather wasn’t too hot, so it wasn’t unbearable, but it was a little uncomfortable at times. Other than that, everything was perfect, and we really enjoyed our stay!"
The price is P9,864
P11,580 total
includes taxes & fees
Oct 5 - Oct 6
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy Greektown Apartments
Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (62)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is P14,207
P16,678 total
includes taxes & fees
Oct 2 - Oct 3
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is P3,839
P8,262 total
includes taxes & fees
Sep 30 - Oct 1
Ground Floor Studios in Chicago by 747 Lofts
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great!"
Ashley 3-night trip
Posted 2 days ago
Hilton Chicago/Magnificent Mile Suites

Find out more about 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!

Explore a world of travel with Expedia

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.

How many vacation rentals are there in Chicago?

With 1119 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 Michigan Avenue 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.