Chicago Vacation Rentals

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Vacation Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (607)
"This is an apartment unit for rent. It had a full kitchen and nice bathroom. The room was clean and the bed was soft. It has directv and the staff was nice. Parking was good but you have to walk around the corner to come inside and it was more inconvenient than just walking in after parking."
The price is P6,319
P9,138 total
includes taxes & fees
Dec 10 - Dec 11
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (216)
"I love everything about Sonder hotels! Great location to catch the subway. We were able to park on the street with no issues. My only complaint was that we were on the second floor and one night the nightclub below was so loud that it seemed like the whole room was thumping! So beware if you book Thursday, Friday, Saturday! "
The price is P4,707
P5,525 total
includes taxes & fees
Dec 24 - Dec 25
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (401)
"The location was perfect: close to grocery, public transportation and expressways. Unfortunately there is only street parking available, but I knew this when I booked. Had trouble getting in the front door which was VERY frustrating, but was able to speak to an agent easily. It did take them a while to remedy., and they gave a small credit for that. The layout of the 2 bedroom was nice; the furniture was what you might expect in a mid-range hotel: we had to put bed pillows on the sofa for...
The price is P8,651
P10,156 total
includes taxes & fees
Dec 8 - Dec 9
Sonder South Wabash
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, (336)
"Had a great stay at Kasa! The place had everything necessary to make ourselves right at home. 10/10 looking forward to coming back in the future! "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (106)
"Comfortably accommodated all in our party. In suite laundry was very helpful. Kitchen had all supplies needed for our stay. I would highly recommend. "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (270)
"We had parking included. Very secure building and parking ramp. Quiet. Housekeeping very attentive. Front desk staff friendly. Shout out to Eric (he was there a lot, friendly, professional and available for questions or concerns). Great views. 8th floor has a workout room, sauna, steam room, massage room, pool table, ping pong, arcade games, outdoor area with basketball court, pickle ball, dog area. There’s a pool and hot tub but closed for the season. We def will be back. Great location to...
The price is P9,798
P12,672 total
includes taxes & fees
Dec 10 - Dec 11
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (177)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is P7,557
P8,871 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (117)
"Great place to stay, really clean and quiet. Beautiful space to sleep . Great aesthetic!"
The price is P8,593
P10,087 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (237)
"This was a great place and deserves the exceptional rating. The first night our oven didn’t work and they had it fixed first thing in the morning! All communication was quick and it had all we needed."
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very Good, (134)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is P8,571
P10,061 total
includes taxes & fees
Dec 29 - Dec 30
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (105)
"Had a great time and Kosa was awesome! Staff was excellent and the communication along the way was very organized."
The price is P5,140
P6,033 total
includes taxes & fees
Dec 9 - Dec 10
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very Good, (86)
"Great stay. Bedroom temperature didn’t seem to work great but otherwise very nice stay. "
The price is P6,479
P7,606 total
includes taxes & fees
Dec 29 - Dec 30
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very Good, (26)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is P6,747
P7,920 total
includes taxes & fees
Dec 16 - Dec 17
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (34)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is P9,776
P11,476 total
includes taxes & fees
Dec 27 - Dec 28
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
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.
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Other types of properties in Chicago you may be interested in

Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8190)
"Steve, the doorman was amazing. He went above and beyond to ensure our stay was great. He made sure to offer assistance even when we didn't request any. The room was clean and comfortable. If you are looking for the character and a little history of Chicago you will find it at the Congress Plaza Hotel. "
The price is P6,127
P7,193 total
includes taxes & fees
Dec 8 - Dec 9
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3580)
"Always great stay"
The price is P5,979
P7,018 total
includes taxes & fees
Jan 2 - Jan 3, 2025
River Hotel
The Westin Michigan Avenue Chicago
View from property

The Westin Michigan Avenue Chicago

4.5 star property
8.6 out of 10, Excellent, (1001)
"Nice place, extremely overpriced. Great location!"
The price is P7,922
P10,765 total
includes taxes & fees
Jan 2 - Jan 3, 2025
The Westin Michigan Avenue Chicago
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.

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Field Museum of Natural History, 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 1278 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 Wrigley 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.