Chicago Vacation Rentals

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Check prices for these dates

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Jul 5 - Jul 6
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Jul 6 - Jul 7
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Jul 11 - Jul 13
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Jul 18 - Jul 20

Vacation Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (808)
"Great stay!"
The price is P8,585
P11,734 total
includes taxes & fees
Jul 7 - Jul 8
Sentral Michigan Avenue
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (322)
"Hotel was nice"
The price is P25,266
P30,920 total
includes taxes & fees
Jul 30 - Jul 31
Level Chicago – Old Town
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
8.4 out of 10, Very Good, (314)
"Super cool spot in a great part of the city."
The price is P7,843
P9,207 total
includes taxes & fees
Jul 9 - Jul 10
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
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, (558)
"Great place and location. "
The price is P8,407
P9,870 total
includes taxes & fees
Jul 6 - Jul 7
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
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, (436)
"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, (192)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is P13,994
P16,427 total
includes taxes & fees
Jul 6 - Jul 7
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (69)
"Very clean, the room was very spacious and everyone was very friendly and the complementary breakfast was good. We also like the location. "
The price is P11,833
P13,546 total
includes taxes & fees
Jul 7 - Jul 8
The Gem Museum Suites
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very Good, (109)
"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 P6,427
P7,545 total
includes taxes & fees
Aug 4 - Aug 5
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (173)
"Great spot. "
The Neighborhood Hotel-Little Italy
Kasa South Loop Chicago
City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (317)
"Great stay"
Kasa South Loop Chicago
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
8.6 out of 10, Excellent, (40)
"Our stay was amazing. "
The price is P8,972
P10,532 total
includes taxes & fees
Jul 6 - Jul 7
Sonder by Marriott Bonvoy The Opal Apartments River North
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, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is P8,972
P10,532 total
includes taxes & fees
Jul 6 - Jul 7
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is P5,383
P9,140 total
includes taxes & fees
Jul 7 - Jul 8
Wrigleyville Suites
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (152)
"Great stay, clean room!"
Kasa River North 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
3.8 out of 10, (42)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is P5,288
P5,974 total
includes taxes & fees
Jul 6 - Jul 7
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
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
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is P12,422
P14,582 total
includes taxes & fees
Jul 27 - Jul 28
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 1451 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 Art Institute of Chicago and CIBC Theatre, 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.