Holiday package deals in Chicago

2 travellers
Exact dates

Tips for booking hotels in Chicago

Gain useful insights to help choose a hotel in Chicago. Data was last updated on Sun Dec 28 2025.
Cheapest month:January
Most expensive month:October
Average price in Chicago:£182/night
Cheapest price found:£27/night
Cheapest day:Wednesday
Most expensive day:Friday
£107 - £270
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£165 - £226
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Popular Chicago vacation deals

Users browsing Cheapflights choose these holiday deals more than any other. Data was last updated on Sun Dec 28 2025.
Intercontinental Hotels Chicago Magnificent Mile By IHG
Intercontinental Hotels Chicago Magnificent Mile By IHG

Intercontinental Hotels Chicago Magnificent Mile By IHG

505 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£1,155
Avg. per night
View Deal
The Westin Michigan Avenue Chicago
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

909 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
£1,077
Avg. per night
View Deal
Hilton Chicago
Hilton Chicago

Hilton Chicago

720 South Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£1,082
Avg. per night
View Deal
Millennium Knickerbocker Chicago
Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

163 East Walton Place, Chicago, IL, United States
0.0 mi from city centre
£1,057
Avg. per night
View Deal
The Chicago Hotel Collection Magnificent Mile
The Chicago Hotel Collection Magnificent Mile

The Chicago Hotel Collection Magnificent Mile

166 East Superior Street, Chicago, IL, United States
0.0 mi from city centre
Air conditioning
£1,031
Avg. per night
View Deal
Warwick Allerton Chicago
Warwick Allerton Chicago

Warwick Allerton Chicago

701 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£953
Avg. per night
View Deal
Gale Chicago
Gale Chicago

Gale Chicago

201 East Delaware Place, Chicago, IL, United States
0.0 mi from city centre
£1,031
Avg. per night
View Deal
Pendry Chicago
Pendry Chicago

Pendry Chicago

230 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,176
Avg. per night
View Deal
Silversmith Hotel Chicago Downtown
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

10 South Wabash Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,165
Avg. per night
View Deal
Radisson Blu Aqua Hotel, Chicago, IL
Radisson Blu Aqua Hotel, Chicago, IL

Radisson Blu Aqua Hotel, Chicago, IL

221 North Columbus Drive, Chicago, IL, United States
0.0 mi from city centre
Pool
£1,233
Avg. per night
View Deal
See all

Where to stay in Chicago

Utilise the map to find the perfect place to stay for your trip to Chicago. There are 173 hotels to choose from in Chicago.

FAQ about Chicago holiday packages

Find answers to frequently asked questions Cheapflights users have about Chicago holiday deals.

  • How much are vacation packages to Chicago?

    Chicago holidays can be booked for as little as £953.

  • What is the cheapest time of year to travel to Chicago?

    If you're looking for the cheapest month of the year to book a holiday package to Chicago, January is ideal.

  • Can I save money on travel by booking a holiday package with Cheapflights?

    Make sure to check back regularly as prices are subject to change.

  • What are some things to do in Chicago?

    Many Chicago visitors also spend their time visiting National Museum of Mexican Art during their trip.

  • What other destinations does Chicago have flight+hotel deals to?

    Remember to check back often to keep track of all the enticing offers for holiday packages to Chicago and more.

See more FAQs

Other popular holiday deals in the United States

Consider booking a Flight+Hotel in one of these other areas of the United States.
Illinois holidays
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Atlanta holidays
Dallas holidays
Washington, D.C. holidays
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Memphis holidays
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Tampa holidays
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