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Check prices for these dates

Tonight
24 Apr - 25 Apr
Tomorrow
25 Apr - 26 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

Top Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (736)
"it was perfect will stay again"
The price is ₹11,545
₹16,060 total
includes taxes & fees
30 Apr - 1 May
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (482)
"Good place"
The price is ₹10,751
₹12,620 total
includes taxes & fees
26 May - 27 May
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (274)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is ₹11,343
₹13,316 total
includes taxes & fees
26 May - 27 May
Sonder Market Hall
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (162)
"Easy and great for extended stay."
The price is ₹13,102
₹15,381 total
includes taxes & fees
1 May - 2 May
Sonder The Burnham Apartments
Sonder Onterie
Miscellaneous

Sonder Onterie

3.5 star property
8.4 out of 10, Very good, (13)
"The stove, washer/drier, plates, silverwear, beds, everything was obviously cleaned throughly. Was very impressed with how spotless everything was"
The price is ₹14,006
₹16,442 total
includes taxes & fees
26 May - 27 May
Sonder Onterie
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (305)
"Front desk was very friendly and helpful. We had a corner unit and the view was great. The unit was very comfortable and clean."
The price is ₹19,134
₹24,368 total
includes taxes & fees
1 May - 2 May
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, (394)
"it was as it advertising. clean, tourist friendly "
Kasa Magnificent Mile Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.4 out of 10, Very good, (148)
"Stayed here before the start of our Route 66 trip. No reception and was sent check in instructions which were clear. Had 1 apartment and 1 studio. Close to everything and felt really safe. "
The price is ₹13,594
₹15,957 total
includes taxes & fees
26 May - 27 May
Sonder Jewelers Row
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (275)
"This property was spacious, clean, easy to access parking and very walkable to the "
Kasa South Loop Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (151)
"Another amazing stay in Little Italy!"
The Neighborhood Hotel-Little Italy
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (97)
"The apartment was perfect. Location made everything walkable. Super clean. Bright rooms. Bed was super comfy. I can’t say enough good things about this place. I loved it and would stay here again on my next trip to Chicago "
The price is ₹10,826
₹12,708 total
includes taxes & fees
26 May - 27 May
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (34)
"Great stay overall! The location was perfect—close to everything with plenty of nearby parking options. Check-in was smooth and easy. The unit had tall ceilings and floor-to-ceiling windows, which made the space feel bright and open. Contrary to some other reviews, we didn’t find the walls thin. It was a bit noisy, but that’s just city life. We stayed in a 3-bedroom unit that fit 5 adults, 2 kids, and a baby comfortably. We requested a crib and received it the next day, which was great. The...
The price is ₹9,877
₹11,594 total
includes taxes & fees
11 May - 12 May
Sonder The Opal
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (136)
"Easy, clean, affordable and great location. Great value too- kitchen, living room, washer/dryer, so much space!"
The price is ₹16,324
₹19,163 total
includes taxes & fees
30 Apr - 1 May
Kasa River North Chicago
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (47)
"The location was great for us. Close to where my daughter works and easy access to the Blue Line. I don't mind the lack of direct contact with staff people and we didn't have any unmet needs. It was very stormy the first night we were there and the windows made a great deal of noise. The storm abated the second night and it was much quieter."
The price is ₹16,051
₹18,842 total
includes taxes & fees
22 May - 23 May
Sonder Greektown
Comfort Inn Chicago Wind Creek Casino
Comfort Double Room | Desk, laptop workspace, blackout curtains, free WiFi

Comfort Inn Chicago Wind Creek Casino

2.5 star property
3.8 out of 10, (20)
"Lower level had a smell"
The price is ₹7,615
₹8,604 total
includes taxes & fees
27 Apr - 28 Apr
Comfort Inn Chicago Wind Creek Casino
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
8.6 out of 10, Excellent, (4)
"Very good place at a very good price! Communication is the only need for improvement in my opinion. "
Wrigleyville Suites
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.6 out of 10, Exceptional, (12)
"Overall for solo travel is recommended."
The price is ₹5,603
₹19,164 total
includes taxes & fees
5 May - 6 May
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

Embassy Suites by Hilton Chicago Downtown River North
Lobby

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very good, (3939)
"The staff was very helpful "
The price is ₹12,271
₹14,405 total
includes taxes & fees
1 May - 2 May
Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Front of property – evening/night

Swissotel - Chicago

4.5 star property
8.8 out of 10, Excellent, (2083)
"Clean rooms, great location, next to everything in the city. "
The price is ₹14,939
₹20,039 total
includes taxes & fees
2 May - 3 May
Swissotel - Chicago
Hilton Chicago/Magnificent Mile Suites
Exterior

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2159)
"。"
The price is ₹14,423
₹16,931 total
includes taxes & fees
21 May - 22 May
Hilton Chicago/Magnificent Mile Suites
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 holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed art scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1262 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.