Chicago Vacation Rentals

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Check prices for these dates

Tonight
Jun 16 - Jun 17
Tomorrow
Jun 17 - Jun 18
This weekend
Jun 20 - Jun 22
Next weekend
Jun 27 - Jun 29

Vacation Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (785)
"Great place, great view. Would stay again."
The price is P8,548
P11,683 total
includes taxes & fees
Jun 29 - Jun 30
Sentral Michigan Avenue
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
8.8 out of 10, Excellent, (537)
" The check in process was smooth and easy. Good location, walkable to many places. This was our 4th stay and we will be back!!!!"
The price is P7,975
P9,362 total
includes taxes & fees
Jun 30 - Jul 1
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
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
8.6 out of 10, Excellent, (302)
"Super cool spot in a great part of the city."
The price is P6,160
P7,232 total
includes taxes & fees
Jul 8 - Jul 9
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (320)
"Hotel was nice"
The price is P18,509
P22,982 total
includes taxes & fees
Jul 17 - Jul 18
Level Chicago – Old Town
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, (423)
"We had an amazing week staying here. Highly recommend!!"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
2 bedrooms, premium bedding, individually decorated

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (182)
"Easy and great for extended stay."
The price is P10,888
P12,781 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.4 out of 10, Very Good, (106)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is P7,115
P8,353 total
includes taxes & fees
Jul 3 - Jul 4
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (68)
"Wonderful stay ! Amazing stuff & their hospitality! Old building but maintained well. Great experience overall."
The price is P12,843
P14,703 total
includes taxes & fees
Jun 23 - Jun 24
The Gem Museum Suites
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (166)
"Great room, well decorated and appointed. Great location!"
The Neighborhood Hotel-Little Italy
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
8.4 out of 10, Very Good, (162)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is P8,548
P10,034 total
includes taxes & fees
Jul 1 - Jul 2
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Opal Apartments River North
2 bedrooms, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (40)
"This is a perfect location to walk around downtown, have dining options at walking distance. Everything was perfect for my family trip. The only issue is the noise its close to walgreens that gets deliveries at like 5am and the noise is so bad it wakes you up."
The price is P7,115
P8,353 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa South Loop Chicago
City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (305)
"Nice place to stay"
Kasa South Loop Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
1 bedroom, desk, laptop workspace, blackout drapes

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

2.5 star property
3.6 out of 10, (36)
"Nice inside room but it’s not safe outside area"
The price is P4,753
P5,370 total
includes taxes & fees
Jun 24 - Jun 25
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
8.8 out of 10, Excellent, (5)
The price is P5,562
P9,338 total
includes taxes & fees
Jun 17 - Jun 18
Wrigleyville Suites
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (150)
"Great stay, clean room!"
Kasa River North Chicago
Sonder by Marriott Bonvoy Greektown Apartments
40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (53)
"Great location, easy stay!"
The price is P10,458
P12,277 total
includes taxes & fees
Jun 29 - Jun 30
Sonder by Marriott Bonvoy Greektown Apartments
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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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.

How many vacation rentals are there in Chicago?

With 1453 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 Soldier Field.

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.