Chicago

Vacation Packages in Chicago

From
Boston (BOS)
To
Chicago, United States
2 adults, no children
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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 Thu Feb 13 2025

January

$252

February

$257

March

$321

April

$258

May

$292

June

$312

July

$298

August

$245

September

$259

October

$254

November

$263

December

$274

Tips for booking hotels in Chicago

Gain useful insights to help choose a hotel in Chicago. Data was last updated on Thu Feb 13 2025.
Cheapest month:January
Most expensive month:October
Average price in Chicago:$257/night
Cheapest price found:$24/night
Cheapest day:Sunday
Most expensive day:Friday
$160 - $369
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$176 - $199
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 Thu Feb 13 2025.
9625 South 76th Avenue, Bridgeview, IL, United States
0.0 mi from city centre
Free Wi-Fi
Parking
$482
Avg. per night
1550 McConnor Parkway, Schaumburg, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
$805
Avg. per night
10 East Grand Avenue, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$792
Avg. per night
6650 South Cicero Avenue, Bedford Park, IL, United States
0.0 mi from city centre
Free Wi-Fi
Air Conditioning
$689
Avg. per night
1150 North Arlington Heights Road, Itasca, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
$691
Avg. per night
2881 Touhy Avenue, Elk Grove Village, IL, United States
0.0 mi from city centre
Free Wi-Fi
Parking
Air Conditioning
$489
Avg. per night
108 East Superior Street, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$3,684
Avg. per night
1251 American Lane, Schaumburg, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
Parking
$721
Avg. per night
5500 North River Road, Rosemont, IL, United States
0.0 mi from city centre
Pool
$1,042
Avg. per night
8535 West Higgins Road, Chicago, IL, United States
0.0 mi from city centre
Pool
Free Wi-Fi
$1,403
Avg. per night

Where to stay in Chicago

Utilize the map to find the perfect place to stay for your trip to Chicago. There are 177 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 $482.

  • 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