Rome2Rio

How to get fromCalgary to Chicagoby plane, bus, car or train

Find Transport to Chicago

See all options

There are 5 ways to get from Calgary to Chicago by plane, bus, car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly to Chicago O'Hare International Airport

    best
    1. Fly from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD)plane plane YYC - ORD
    6h 48m
    $100–558

  2. Bus, drive, train

    1. Take the bus from Calgary - Deerfoot Inn & Casino* to Lethbridge - U of Lbus bus
    2. Drive from Lethbridge - U of L to Port of Sweet Grasscar car
    3. Take the bus from Port of Sweet Grass to Shelby Transit Centerbus bus
    4. Take the train from Shelby Amtrak Station to Chicago Union Stationtrain train
    34h 47m

  3. Drive 1,592.9 mi

    1. Drive from Calgary to Chicagocar car 1,592.9 mi
    27h 27m
    $365–527

  4. Fly to Chicago Midway International Airport

    1. Fly from Calgary International Airport (YYC) to Chicago Midway International Airport (MDW)plane plane YYC - MDW
    9h 7m
    $265–658

  5. Bus, drive, train via Saint Paul

    1. Take the bus from Calgary - Downtown Ticket Office to Lethbridge - U of Lbus bus
    2. Drive from Lethbridge - U of L to Port of Sweet Grasscar car
    3. Take the bus from Port of Sweet Grass to Shelby Transit Centerbus bus
    4. Take the train from Shelby Amtrak Station to St. Paul-Minneapolistrain train
    5. Take the bus from Saint Paul Union Depot to Chicago Bus Stationbus bus
    35h 40m

Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) flights

Calendar45Weekly Planes
Duration5h 34mAverage Duration
Ticket$74Cheapest Price
See schedules

Questions & Answers

What companies run services between Calgary, AB, Canada and Chicago, IL, USA?

WestJet, American Airlines, and two other airlines fly from Calgary International Airport (YYC) to Chicago O'Hare International Airport (ORD) every 4 hours.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Where to next?

Trips from Calgary

Trips to Chicago

Popular routes