Rome2Rio

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

Find Transport to Chicago

See all options

There are 7 ways to get from Regina to Chicago by plane, bus, train, or car

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 Regina (YQR) to Chicago O'Hare International Airport (ORD)plane plane YQR - ORD
    6h 47m
    $129–792

  2. Fly to Chicago Midway International Airport

    cheapest
    1. Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane plane YQR - MDW
    6h 21m
    $124–586

  3. Bus, train via Detroit

    1. Take the bus from Regina, SK - 2820B Avonhurst to Portage la Prairie, MBbus bus
    2. Take the train from Portage la Prairie 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 16h
    $305–513

  4. Drive 1,147.8 mi

    1. Drive from Regina to Chicagocar car 1,147.8 mi
    19h 51m
    $263–380

  5. Fly to South Bend, train

    1. Fly from Regina (YQR) to South Bend (SBN)plane plane YQR - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    11h 3m
    $161–711

  6. Fly to General Mitchell International Airport, train

    1. Fly from Regina (YQR) to General Mitchell International Airport (MKE)plane plane YQR - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 34m
    $240–1,162

  7. Bus, train

    1. Take the bus from Regina, SK - 2820B Avonhurst to Portage la Prairie, MBbus bus
    2. Take the train from Portage la Prairie 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 18h
    $323–603

Regina (YQR) to Chicago O'Hare International Airport (ORD) flights

Calendar30Weekly Planes
Duration6h 45mAverage Duration
Ticket$119Cheapest Price
See schedules

Questions & Answers

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

Air Canada, United Airlines, and three other airlines fly from Regina (YQR) to Chicago O'Hare International Airport (ORD) 4 times a day.

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 Regina

Trips to Chicago

Popular routes