Vacation Packages in Chicago

2 travellers

Tips for booking hotels in Chicago

Gain useful insights to help choose a hotel in Chicago. Data was last updated on Tue Apr 29 2025.
Cheapest month:December
Most expensive month:October
Average price in Chicago:C$ 295/night
Cheapest price found:C$ 46/night
Cheapest day:Monday
Most expensive day:Tuesday
C$ 181 - C$ 405
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
C$ 259 - C$ 353
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 Tue Apr 29 2025.
9625 South 76th Avenue, Bridgeview, IL, United States
0.0 km from city centre
Free Wi-Fi
Parking
C$ 800
Avg. per night
1550 McConnor Parkway, Schaumburg, IL, United States
0.0 km from city centre
Pool
Free Wi-Fi
Parking
C$ 1,333
Avg. per night
10 East Grand Avenue, Chicago, IL, United States
0.0 km from city centre
Pool
Free Wi-Fi
C$ 1,534
Avg. per night
6650 South Cicero Avenue, Bedford Park, IL, United States
0.0 km from city centre
Free Wi-Fi
Air Conditioning
C$ 1,016
Avg. per night
1150 North Arlington Heights Road, Itasca, IL, United States
0.0 km from city centre
Pool
Free Wi-Fi
Parking
C$ 1,210
Avg. per night
2881 Touhy Avenue, Elk Grove Village, IL, United States
0.0 km from city centre
Free Wi-Fi
Parking
Air Conditioning
C$ 747
Avg. per night
1801 Milwaukee Avenue, Glenview, IL, United States
0.0 km from city centre
Pool
Free Wi-Fi
Parking
C$ 1,368
Avg. per night
108 East Superior Street, Chicago, IL, United States
0.0 km from city centre
Pool
Free Wi-Fi
C$ 6,039
Avg. per night
5500 North River Road, Rosemont, IL, United States
0.0 km from city centre
Pool
C$ 1,713
Avg. per night
6630 South Cicero Avenue, Bedford Park, IL, United States
0.0 km from city centre
Pool
Free Wi-Fi
C$ 1,404
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 156 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 C$ 539.

  • 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 deal with Cheapflights?

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

  • What are some things to do in Chicago?

    Above all, travellers to Chicago trend to visit Wrigley Field most frequently.

  • What other destinations does Chicago have holiday packages to?

    In addition to Chicago, Cheapflights also offers holiday packages to Illinois

See more FAQs