Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Chicago vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,172 reviews)
"Spacious apartment with stunning view. A great stay!!"
United States
Tina
The price is ￥24,222
￥33,105 total
includes taxes & fees
May 26 - May 27
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (480 reviews)
"Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again. "
Canada
Lissa
The price is ￥26,947
￥35,561 total
includes taxes & fees
May 26 - May 27
Level Chicago – Old Town
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (763 reviews)
"Great place to stay."
United States
Benedictine
The price is ￥24,179
￥37,725 total
includes taxes & fees
May 25 - May 26
Kasa Magnificent Mile Chicago
Desk, iron/ironing board, travel crib, WiFi

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, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is ￥15,759
￥31,940 total
includes taxes & fees
May 25 - May 26
Chic Studio in the Heart of the Gold Coast
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (23 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is ￥49,027
￥123,966 total
includes taxes & fees
Jun 17 - Jun 18
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Cute little place with all the necessities - old city feel with mlodern conveniences"
United States
Mary D.
The price is ￥25,628
￥34,017 total
includes taxes & fees
May 25 - May 26
LIVN Millennium Park Downtown Chicago Superior 1BR
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is ￥16,077
￥34,688 total
includes taxes & fees
May 26 - May 27
West Loop Living – Bright 1BR
Interior

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is ￥29,289
￥54,911 total
includes taxes & fees
May 25 - May 26
Stylish Japanese-Themed 2BR Apt Close to Downtown
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is ￥42,183
￥96,852 total
includes taxes & fees
May 25 - May 26
River North Rooftop With In and Out Parking 3
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ￥16,077
￥34,688 total
includes taxes & fees
May 26 - May 27
Sunlit 1BR Apartment | Warm & Welcoming Space
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥20,057
￥39,943 total
includes taxes & fees
May 26 - May 27
1BR Modern Luxe Apt with In-Unit Laundry
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Super clean, great communication! Thanks for a great stay."
United States
Tracey L.
The price is ￥26,583
￥35,137 total
includes taxes & fees
May 25 - May 26
LIVN West Loop Chicago 2 BR City View
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (193 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is ￥32,807
￥51,593 total
includes taxes & fees
May 26 - May 27
Kasa River North Chicago
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (17 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ￥109,675
￥192,891 total
includes taxes & fees
Jun 18 - Jun 19
Spacious 4BR Central Apartment w/ Skyline Views
2 bedrooms, desk, iron/ironing board, travel crib

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is ￥42,501
￥97,050 total
includes taxes & fees
May 31 - Jun 1
South Loop Rooftop With In & Out Parking 1
Terrace/patio

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is ￥108,561
￥187,000 total
includes taxes & fees
Jun 12 - Jun 13
Modern 3BR Apartment Near North Ave Shops
TV, offices

Downtown Chicago Stay with Free In & Out Parking 2

Downtown Chicago Stay with Free In & Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location and the in/out parking was very convenient. The apartment was clean and had plenty of room. The Host was very attentive to our needs. "
United States
Patty H.
The price is ￥69,880
￥140,709 total
includes taxes & fees
May 31 - Jun 1
Downtown Chicago Stay with Free In & Out Parking 2
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the location."
United States
Nicoll M.
The price is ￥28,334
￥37,192 total
includes taxes & fees
May 25 - May 26
LIVN Millennium Park Downtown Chicago Superior 2 BR
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is ￥23,877
￥32,159 total
includes taxes & fees
May 27 - May 28
LIVN Millennium Park Downtown Chicago Prem Studio
Interior

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ￥26,583
￥35,137 total
includes taxes & fees
May 25 - May 26
LIVN Millennium Park Downtown Chicago 2BR
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

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

8/10 Good
"Excellent location within walking distance of bars , restaurants and transit. Clean and spacious rooms."
Devin 1-night trip
Posted 1 hour ago
The Chicago Hotel Collection - Magnificent Mile

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 entertainment choices. 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated vacation home rental in Chicago is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable 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 Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed and Warm & Spacious 4BR Home Long Stays Welcome.

How many vacation rentals are there in Chicago?

With 934 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 Wrigley 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.