Rome2Rio

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

Find Transport to Chicago

See all options

There are 9 ways to get from Annaheim to Chicago by car, plane, train, or bus

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

  1. Drive to Saskatoon John G. Diefenbaker International Airport, fly to Chicago O'Hare International Airport

    best
    1. Drive from Annaheim to Saskatoon-Airport-YXEcar car
    2. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD)plane plane YXE - ORD
    8h 40m
    $263–836

  2. Drive to Regina, fly to Chicago Midway International Airport

    cheapest
    1. Drive from Annaheim to Regina-Airport-YQRcar car
    2. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    10h 8m
    $165–752

  3. Drive, train via Detroit

    1. Drive from Annaheim to Watrouscar car
    2. Take the train from Watrous to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Windsortrain train
    4. Take the train from Detroit to Chicago Union Stationtrain train
    2d 17h
    $302–571

  4. Drive 1,270.6 mi

    1. Drive from Annaheim to Chicagocar car 1,270.6 mi
    21h 58m
    $291–420

  5. Drive to Saskatoon John G. Diefenbaker International Airport, fly to Chicago Midway International Airport

    1. Drive from Annaheim to Saskatoon-Airport-YXEcar car
    2. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago Midway International Airport (MDW)plane plane YXE - MDW
    7h 44m
    $343–1,436

  6. Drive to Regina, fly to Chicago O'Hare International Airport

    1. Drive from Annaheim to Regina-Airport-YQRcar car
    2. Fly from Regina (YQR) to Chicago O'Hare International Airport (ORD)plane plane YQR - ORD
    9h 56m
    $205–852

  7. Drive to Saskatoon John G. Diefenbaker International Airport, fly to General Mitchell International Airport, train

    1. Drive from Annaheim to Saskatoon-Airport-YXEcar car
    2. Fly from Saskatoon John G. Diefenbaker International Airport (YXE) to General Mitchell International Airport (MKE)plane plane YXE - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    11h 46m
    $547–2,400

  8. Drive, train, bus

    1. Drive from Annaheim to Watrouscar car
    2. Take the train from Watrous to Toronto Union Stationtrain train
    3. Take the bus from Toronto to Detroit Bus Stationbus bus
    4. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    2d 20h
    $251–443

  9. Drive, train

    1. Drive from Annaheim to Watrouscar car
    2. Take the train from Watrous to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Buffalotrain train
    4. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    2d 22h
    $359–708

Saskatoon John G. Diefenbaker International Airport (YXE) to Chicago O'Hare International Airport (ORD) flights

Calendar36Weekly Planes
Duration6h 58mAverage Duration
Ticket$134Cheapest Price
See schedules

Questions & Answers

What companies run services between Annaheim, SK, Canada and Chicago, IL, USA?

There is no direct connection from Annaheim to Chicago. However, you can drive to Saskatoon-Airport-YXE airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take a vehicle from Annaheim to Chicago Union Station via Watrous, Toronto Union Station, Windsor, and Detroit in around 2d 17h.

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 Annaheim

Trips to Chicago

Popular routes