Search Holiday Rentals in Chicago

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Find properties with these dates

Tonight
May 12 - May 13
Tomorrow
May 13 - May 14
Next weekend
May 17 - May 19

Top Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (395)
"The facility is fantastic. Really enjoyed the gym and pool. Our premium apartment was not the best. Although the corner suite offered a fantastic view the apartment was dirty and run down. Trains are very loud. Not sure that I would stay here again. For the same price you can book something in the north or downtown. "
The price is ₹11,949
per night
27 May - 28 May
Sentral Michigan Avenue
Sonder Market Hall
Apartment, 1 Bedroom, City View | Private kitchen | Full-sized fridge, stovetop, dishwasher, electric kettle
Sonder Market Hall
3.5 star property
8.2 out of 10, Very good, (77)
"Gorgeous rooms. Simple and quiet property. "
The price is ₹10,302
per night
27 May - 28 May
Sonder Market Hall
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, (221)
"Kasa is good overall. However, the cleaning lady just barged in my room without knocking and pretended to be checking the place. Not good at all. No proper MANNER. There is only one person in the lobby checking in guests as well as taking luggages for storage. It would be helpful to have a separate person designated so guests are not waiting."
Kasa Magnificent Mile Chicago
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Sonder South Wabash
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is ₹16,203
per night
13 May - 14 May
Sonder South Wabash
Sonder The Burnham
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (51)
"We loved the space, very clean, great amenities, looks like a perfect combo of a cozy apartment and a hotel room. The only problem is that it’s not very soundproof, and you can hear people using restrooms or showering in the neighboring rooms. But would definitely stay again!"
The price is ₹16,924
per night
28 May - 29 May
Sonder The Burnham
Found Chicago powered by Sonder
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (125)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is ₹17,975
per night
6 Jun - 7 Jun
Found Chicago powered by Sonder
Level Chicago – Old Town
Front of property – evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is ₹22,059
per night
13 May - 14 May
Level Chicago – Old Town
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (27)
"Great location, Great Neighborhood, plenty of dining options within walking distance. You can park by the hotel to unload and load and there is limited time meter parking or late night early am free parking streetside... When you can find it. There is a parking garage at the corner of Taylor and Paulina that is only $9 if in after 3p and out before 8a... Which is a steal by Chicago parking costs. It's a short 3 block walk to the hotel... Well lit and sidewalks. The only nitpick I can even...
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
1 bedroom, premium bedding, pillowtop beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is ₹6,011
per night
13 May - 14 May
WoodSpring Suites Chicago Addison
Sonder Jewelers Row
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very good, (98)
"This is an overall very convenient, clean and well maintained apartment hotel. Transportation is convenient, there are restaurants and other amenities nearby, and the facilities within the hotel are also good. However, the only downside is that it is close to the station and there is construction nearby, so it is very noisy. However, if I had the chance to choose again, I would choose this hotel. I am satisfied."
The price is ₹17,457
per night
28 May - 29 May
Sonder Jewelers Row
Kasa River North Chicago
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Kasa South Loop Chicago
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | Smart TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Sonder The Plymouth
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very good, (66)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ₹21,985
per night
27 May - 28 May
Sonder The Plymouth
Sonder The Opal
Full-sized fridge, oven, stovetop, dishwasher
Sonder The Opal
3.5 star property
8.0 out of 10, Very good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is ₹19,017
per night
28 May - 29 May
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (29)
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is ₹23,957
per night
29 May - 30 May
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (6)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is ₹6,739
per night
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Don't see what you're looking for?
See all available properties in 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.

Other types of properties in Chicago you may be interested in

Congress Plaza Hotel
Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6713)
"A great hotel to start our Drive on Route 66. Perfectly located to see a lot of Chicago. Just need more lights in the room"
The price is ₹11,816
per night
13 May - 14 May
Congress Plaza Hotel
Warwick Allerton - Chicago
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2577)
"Great location near shops, food outlet’s, etc"
The price is ₹9,602
per night
27 May - 28 May
Warwick Allerton - Chicago
The Westin Michigan Avenue Chicago
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1006)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
The price is ₹15,698
per night
28 May - 29 May
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.

Holiday Rentals in Chicago

Search for holiday rentals in Chicago on Expedia.co.uk! 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 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 fascinating museums. The array of shops and acclaimed art scene are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1366 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 Art Institute of Chicago and CIBC Theatre, whereas Grant Park and Millennium Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Navy Pier and Wrigley 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.

Recent reviews of Chicago properties
Expedia verified reviews

citizenM Chicago Downtown

citizenM Chicago Downtown

5/5 Excellent
"Would totally stay here again. Easy access to great food, museums and the Chicago River!"
A verified traveller stayed at citizenM Chicago Downtown
Posted 21 hours ago
citizenM Chicago Downtown