Holiday package deals in Chicago

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Tips for booking hotels in Chicago

Gain useful insights to help choose a hotel in Chicago. Data was last updated on Wed Apr 30 2025.
Cheapest month:January
Most expensive month:July
Average price in Chicago:£163/night
Cheapest price found:£13/night
Cheapest day:Friday
Most expensive day:Sunday
£108 - £220
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£163 - £207
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 Wed Apr 30 2025.
Intercontinental Chicago Magnificent Mile, An IHG Hotel
Intercontinental Chicago Magnificent Mile, An IHG Hotel

Intercontinental Chicago Magnificent Mile, An IHG Hotel

505 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£1,163
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
£1,085
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
£1,090
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
£1,064
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
Free Wi-Fi
£1,038
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
£960
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
£1,185
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
£1,174
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
Free Wi-Fi
£1,242
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 139 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 £1,287.

  • 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 Illinois

Consider booking a Flight+Hotel in one of these other areas of Illinois.
Illinois holidays
Schaumburg holidays
Elk Grove Village holidays
Bloomington holidays
Rosemont holidays