Chicago Vacation Rentals

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In two weeks
Oct 31 - Nov 2
In two months
Dec 12 - Dec 14
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Jan 9 - Jan 11
In four months
Feb 6 - Feb 8

Vacation Rentals in Chicago

Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (955)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is ￥20,433
￥28,423 total
includes taxes & fees
Nov 11 - Nov 12
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (559)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (367)
"Friendly staff and great amenities "
The price is ￥23,190
￥30,624 total
includes taxes & fees
Nov 3 - Nov 4
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very Good, (383)
"Great stay!"
The price is ￥19,148
￥22,478 total
includes taxes & fees
Nov 11 - Nov 12
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (239)
"Great stay. "
The price is ￥20,433
￥23,986 total
includes taxes & fees
Nov 11 - Nov 12
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
3.5 star property
8.6 out of 10, Excellent, (687)
"great room, clean good space and close to places "
The price is ￥20,587
￥24,167 total
includes taxes & fees
Oct 29 - Oct 30
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (363)
"nice area, shops nearby"
Kasa South Loop Chicago
Front of property
The Neighborhood Hotel-Little Italy
The Neighborhood Hotel-Little Italy
4.0 star property
9.6 out of 10, Exceptional, (210)
"Perfect location and area was wonderful."
The Neighborhood Hotel-Little Italy
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy The Opal Apartments River North
3.5 star property
8.4 out of 10, Very Good, (53)
"Place was in a great location close to good restaurants "
The price is ￥20,433
￥23,986 total
includes taxes & fees
Nov 11 - Nov 12
Sonder by Marriott Bonvoy The Opal Apartments River North
Business center
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (171)
"This place has everything for a multi-night stay."
Kasa River North Chicago
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very Good, (184)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
The price is ￥17,863
￥20,969 total
includes taxes & fees
Nov 11 - Nov 12
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.8 out of 10, Exceptional, (21)
"Excellent location and very clean! Would stay again!"
The price is ￥9,563
￥18,841 total
includes taxes & fees
Oct 15 - Oct 16
Wrigleyville Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is ￥29,335
￥51,297 total
includes taxes & fees
Oct 23 - Oct 24
Stylish Apartment near Chicago Downtown
Property amenity
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
3.5 star property
7.6 out of 10, Good, (144)
"Very clean and affordable "
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt
Clean & Equipped 1BR Apt
9.2 out of 10, Wonderful, (27)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
The price is ￥11,793
￥28,129 total
includes taxes & fees
Nov 11 - Nov 12
Clean & Equipped 1BR Apt
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
The price is ￥25,767
￥30,249 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy Greektown Apartments
2 bedrooms, iron/ironing board, travel crib, WiFi
Charming 2BR in Vibrant Lakeview
Charming 2BR in Vibrant Lakeview
9.4 out of 10, Exceptional, (20)
"This place was great! Loved my stay!"
The price is ￥13,405
￥32,410 total
includes taxes & fees
Oct 20 - Oct 21
Charming 2BR in Vibrant Lakeview
Desk, iron/ironing board, WiFi, bed sheets
Relaxing Chicago Studio
Relaxing Chicago Studio
9.8 out of 10, Exceptional, (19)
"Had a great stay. Great location. "
The price is ￥11,339
￥26,118 total
includes taxes & fees
Nov 11 - Nov 12
Relaxing Chicago Studio
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University
Cozy Studio in Hyde Park-Walk to Lake & University
9.0 out of 10, Wonderful, (7)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is ￥12,034
￥26,996 total
includes taxes & fees
Oct 15 - Oct 16
Cozy Studio in Hyde Park-Walk to Lake & University
WiFi, bed sheets
Bright & Modern Lakeview Studio
Bright & Modern Lakeview Studio
9.0 out of 10, Wonderful, (10)
"The property wasn’t cleaned from the previous renters. bed unmade, dirty, all the towels were dirty and dishes still dirty"
The price is ￥13,607
￥28,743 total
includes taxes & fees
Nov 11 - Nov 12
Bright & Modern Lakeview Studio
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Great"
WENDY 3-night trip
Posted 2 hours ago
Hilton Chicago/Magnificent Mile Suites

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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This highly rated vacation home rental in Chicago is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Other favorite homes for rent in Chicago are Master qtr close to nature & easy urban facilities and Stunning / Spacious 6BD Home + garage - Bucktown!.

How many vacation rentals are there in Chicago?

With 1125 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.