Vacation Packages in Chicago

2 travelers
Boston (BOS)
Chicago, IL
mié. 6/5
mié. 6/12

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 Wed May 22 2024

January

$248

February

$244

March

$280

April

$258

May

$278

June

$330

July

$324

August

$274

September

$258

October

$248

November

$269

December

$248

Tips for booking hotels in Chicago

Gain useful insights to help choose a hotel in Chicago. Data was last updated on Wed May 22 2024.
Cheapest month:January
Most expensive month:October
Average price in Chicago:$238/night
Cheapest price found:$24/night
Cheapest day:Sunday
Most expensive day:Tuesday
$165 - $332
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$236 - $297
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 vacation package deals more than any other. Data was last updated on Wed May 22 2024.
22 W. Monroe, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$1,530
Avg. per night
Chicago, IL, United States
0.0 mi from city centre
$619
Avg. per night
See all

Where to stay in Chicago

Utilize the map to find the perfect place to stay for your trip to Chicago. There are 174 hotels to choose from in Chicago.

FAQ about Chicago vacation packages

Find answers to frequently asked questions Cheapflights users have about Chicago vacation packages.
  • How much are vacation packages to Chicago?

    The cheapest price of a Chicago vacation package is currently $59.

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

    Chicago vacation packages in January typically cost around $143.

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

    Yes! Vacation packages on Cheapflights are designed to help users save money by bundling their flight, car rental, and hotel.

  • What are some things to do in Chicago?

    Above all, travelers to Chicago trend to visit Aragon Ballroom most frequently.

  • What other destinations does Chicago have vacation pages to?

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

See more FAQs