Holiday Rentals in Chicago, IL

Search and compare Chicago, IL vacation rentals from hundreds of travel sites and save.

Chicago, IL, United States
5 Apr — 6 Apr2
Chicago, IL, United States
Fri 5/4
Sat 6/4
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Popular holiday rental in Chicago

Discover well-known properties in Chicago that are favoured by visitors more than others. There are 3,023 hotels in Chicago and price data was last updated on 29 March 2024. The average price for a hotel in Chicago is ₹ 8,931/night.
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540 North State Street, Chicago, IL, United States
Conveniently located in the middle of the city, this 4-star property makes for an excellent base in Chicago. It also offers a sauna, an outdoor pool and free Wi-Fi.
Free Wi-Fi
9.2
Excellent
63 reviews
Location
1.8 km from city centre
₹ 35,935
Chicago, IL, United States
This comfortable property in Chicago offers complimentary wireless internet, as well as an outdoor pool and a swimming pool. It is conveniently located in the city centre.
Air conditioning
Location
2.5 km from city centre
₹ 19,495

Tips for booking holiday rentals in Chicago

Gain useful insights and advice for booking the perfect stay in Chicago. Price data is based on averages over the past 12 months and was last updated on 29 March 2024.
Cheapest month:July
Most expensive month:June
Average price in Chicago:₹ 8,931/night
Cheapest price found:₹ 3,252/night
₹ 3,260 - ₹ 17,953
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Cheapest holiday rentals in Chicago, Illinois

Discover affordable stays in Chicago that provide a quality experience without breaking the bank. Hotels in Chicago can be found for as low as ₹ 7,837 per night. There is currently one property in Chicago that can be booked for this price. Corporate Suites in the Heart of Magnificent Mile is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 29 March 2024
For those on a budget, these are the cheapest vacation rentals available in Chicago for the selected dates. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Show all 3,023 holiday rentals
Chicago, IL, United States
1.8 km from city centre
Air conditioning
Free Wi-Fi
₹ 7,837
Avg. per night
55 East Washington Street, Chicago, IL, United States
0.8 km from city centre
Free Wi-Fi
Airport shuttle
₹ 14,174
Avg. per night
Chicago, IL, United States
1.2 km from city centre
Air conditioning
₹ 15,424
Avg. per night
Chicago, IL, United States
8.6 km from city centre
Air conditioning
₹ 17,342
Avg. per night

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,023 hotels in Chicago and price data was last updated on 29 March 2024. The average price for a hotel in Chicago is ₹ 8,931/night.
Show all 3,023 stays
310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air conditioning
₹ 12,430
Avg. per night
3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
₹ 3,442
Avg. per night
1 West Washington Street, Chicago, IL, United States
0.8 km from city centre
Free Wi-Fi
₹ 13,083
Avg. per night
225 North Wabash Avenue, Chicago, IL, United States
1.2 km from city centre
₹ 16,806
Avg. per night
800 North Michigan Avenue, Chicago, IL, United States
2.4 km from city centre
Pool
Free Wi-Fi
₹ 34,491
Avg. per night

Where to stay in Chicago

Explore different neighbourhoods and areas within Chicago to find the perfect location for your stay. Map data was last updated on 29 March 2024.
Navigate to the areas in Chicago you plan to visit to find vacation rentals that are close by. You can find more information on a particular vacation rental within the map by clicking on its name.

Facts about staying in Chicago

Find useful tips and insights about staying in Chicago to help you make the most of your experience. FAQs were last updated on 29 March 2024.
  • How much does a holiday rental in Chicago cost?

    A holiday rental in Chicago will cost ₹ 8,932 per night on average. However some users found rentals for as low as ₹ 3,260 per night. A good deal on a Chicago holiday rental would be anything for ₹ 8,799 per night or less. Keep in mind that booking December may be more expensive, whereas booking July is the cheapest month of the year to book.

  • What is the best Chicago holiday rental?

    The Chicago Hotel Collection - Millennium Park is considered the best Chicago holiday rental based on HotelsCombined user data. The Chicago Hotel Collection - Millennium Park has an average rating of 3.7/10 and 8 reviews.

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

    The Chicago Hotel Collection - Millennium Park is the closest Chicago holiday rental to Chicago O'Hare Intl Airport at a distance of 25.4 km.

  • What part of Chicago is best to stay in?

    Downtown is the best part of the city to stay in if you’re looking for a holiday rental in Chicago. The 4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Chicago, 4% of HotelsCombined users searched for rentals in Downtown in the past 12 months, making it a popular choice.

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

    The most popular holiday rental near Chicago’s Navy Pier is The Chicago Hotel Collection - Millennium Park. The Chicago Hotel Collection - Millennium Park has a review score of 3.7/10 from 8 HotelsCombined users and it’s located just 2.0 km from Navy Pier.

  • Are there any Aparthotel holiday rentals in Chicago?

    50 Aparthotel holiday rentals are available in Chicago. Based on our user data, the most popular is Sentral Michigan Avenue - so we recommend seeing if this property is available for your travel dates before looking at other Aparthotel options in Chicago.

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