Holiday package deals in Chicago

2 travellers
Exact dates
Boston (BOS)
Chicago, IL, United States
Mon 5/6
Mon 5/13

When is the best time to fly to Chicago?

Determine the best time to fly to Chicago based on the average flight price by month. Price data was last updated on Mon Apr 22 2024

January

£486

February

£502

March

£492

April

£503

May

£516

June

£622

July

£634

August

£575

September

£542

October

£525

November

£504

December

£509

Tips for booking hotels in Chicago

Gain useful insights to help choose a hotel in Chicago. Data was last updated on Mon Apr 22 2024.
Cheapest month:January
Most expensive month:October
Average price in Chicago:£194/night
Cheapest price found:£19/night
Cheapest day:Tuesday
Most expensive day:Friday
£126 - £278
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
£180 - £255
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 Mon Apr 22 2024.
909 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
£1,178
Avg. per night
163 East Walton Place, Chicago, IL, United States
0.0 mi from city centre
£1,155
Avg. per night
720 South Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,183
Avg. per night
701 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,042
Avg. per night
221 North Columbus Drive, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£1,348
Avg. per night
10 South Wabash Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,274
Avg. per night
505 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
£1,263
Avg. per night
230 North Michigan Avenue, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,286
Avg. per night
166 East Superior Street, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
£1,127
Avg. per night
See all

Where to stay in Chicago

Utilise the map to find the perfect place to stay for your trip to Chicago. There are 142 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 Wrigley Field 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.