Chicago holiday rentals

Find and compare great deals on holiday rentals in Chicago from hundreds of travel sites

Chicago, IL, United States
27 Jan — 28 Jan2
Chicago, IL, United States
Thu 27/1
Fri 28/1
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Popular Holiday Rentals in Chicago

The Chicago Hotel Collection Millennium Park
The Chicago Hotel Collection Millennium Park
6.2 Good
55 East Washington Street, Chicago, IL, United States
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0.5 mi from city centre, Chicago, IL, United States 
GoodBased on 39 reviews
6.2

Strategically located in the middle of the city, this 3-star property makes for an ideal base in Chicago. It also provides free Wi-Fi, valet parking and a swimming pool.

Ginosi 747 Apartel
Ginosi 747 Apartel
Chicago, IL, United States
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2.0 mi from city centre, Chicago, IL, United States 

Ginosi 747 Apartel is located in Chicago and features complimentary Wi-Fi. It is situated a brief walk from the Polish Museum of America.

Furnished Suites in South Loop Chicago
Furnished Suites in South Loop Chicago
Chicago, IL, United States
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0.8 mi from city centre, Chicago, IL, United States 

Strategically located in the heart of the city, this 4.5-star property makes for an ideal base in Chicago. It also offers laundry facilities, a concierge and free Wi-Fi.

Tips for booking a Chicago holiday rental

Cheapest month:February
Most expensive month:November
Average price in Chicago:£146/night
Absolute cheapest price found:£14/night
Cheapest day:Thursday
Most expensive day:Friday
£46 - £316
Average price per night. Prices are not fixed and may vary with time.
£15 - £282
Average price per night. Prices are not fixed and may vary with time.

Top rated Chicago vacation rentals

Show all 2,080 vacation rentals
1
The Chicago Hotel Collection Millennium Park
The Chicago Hotel Collection Millennium Park
6.2 Good
55 East Washington Street, Chicago, IL, United States
Show on map
0.5 mi from city centre, Chicago, IL, United States 

Strategically located in the middle of the city, this 3-star property makes for an ideal base in Chicago. It also provides free Wi-Fi, valet parking and a swimming pool.

Cheapest holiday rentals in Chicago

Show all 2,080 vacation rentals
Ginosi 747 Apartel
Ginosi 747 Apartel
Chicago, IL, United States
Show on map
2.0 mi from city centre, Chicago, IL, United States 

Ginosi 747 Apartel is located in Chicago and features complimentary Wi-Fi. It is situated a brief walk from the Polish Museum of America.

£56
Avg. per night
The Chicago Hotel Collection Millennium Park
The Chicago Hotel Collection Millennium Park
6.2 Good
55 East Washington Street, Chicago, IL, United States
Show on map
0.5 mi from city centre, Chicago, IL, United States 

Strategically located in the middle of the city, this 3-star property makes for an ideal base in Chicago. It also provides free Wi-Fi, valet parking and a swimming pool.

£110
Avg. per night
Furnished Suites in South Loop Chicago
Furnished Suites in South Loop Chicago
Chicago, IL, United States
Show on map
0.8 mi from city centre, Chicago, IL, United States 

Strategically located in the heart of the city, this 4.5-star property makes for an ideal base in Chicago. It also offers laundry facilities, a concierge and free Wi-Fi.

£115
Avg. per night

Where to stay in Chicago

Chicago vacation rental FAQs

  • How much does a holiday rental in Chicago cost?

    Chicago holiday rentals are £147/night on average. However, you may find that prices fluctuate depending on the time of year. For example, August is the most expensive month to book a holiday rental in Chicago, and November is often the cheapest month to book. Recently, our users found rentals for £14/night - which is currently the cheapest price. Keep in mind that anything £94/night or less is still considered a good deal.

  • What is the best Chicago holiday rental?

    While there may be other great holiday rentals in Chicago to choose from, The Chicago Hotel Collection Millennium Park is currently considered the best, based on 39 HotelsCombined reviews and an average rating of 6.2/10.

  • What’s the closest holiday rental to Chicago O'Hare Intl Airport?

    If you’re looking for Chicago holiday rentals that are close to Chicago O'Hare Intl Airport, then the nearest one is Ginosi 747 Apartel which is 14.0 mi away.

  • What’s the most popular holiday rental in Chicago near Navy Pier?

    While there may be several Chicago holiday rentals near Navy Pier, The Chicago Hotel Collection Millennium Park happens to be the most popular among our users. The Chicago Hotel Collection Millennium Park has a current rating of 6.2 from 39 HotelsCombined travellers. Navy Pier is also conveniently located just 1.3 mi from this holiday rental.