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How to get fromGlendive to Chicagoby car, plane, bus, train, bus (Greyhound) or bus (Greyhound, Flixbus)

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There are 8 ways to get from Glendive to Chicago by car, plane, bus, train, bus (Greyhound), or bus (Greyhound, Flixbus)

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 Ring Rock Ranch Airport, fly to Chicago O'Hare International Airport

    best
    1. Drive from Glendive to Ring Rock Ranch Airport (XWA)car car
    2. Fly from Ring Rock Ranch Airport (XWA) to Chicago O'Hare International Airport (ORD)plane plane XWA - ORD
    8h 38m
    $81–353

  2. Bus, train

    1. Take the bus from Glendive to Dickinsonbus bus
    2. Take the bus from Dickinson to Minneapolisbus bus
    3. Take the train from St. Paul-Minneapolis to Chicago Union Stationtrain train
    21h 8m
    $111–470

  3. Drive 1,026.3 mi

    1. Drive from Glendive to Chicagocar car 1,026.3 mi
    16h 1m
    $188–271

  4. Drive to Ring Rock Ranch Airport, fly to Chicago Midway International Airport

    1. Drive from Glendive to Ring Rock Ranch Airport (XWA)car car
    2. Fly from Ring Rock Ranch Airport (XWA) to Chicago Midway International Airport (MDW)plane plane XWA - MDW
    8h 47m
    $106–493

  5. Fly Dawson Community Airport to Chicago O'Hare International Airport

    1. Fly from Dawson Community Airport (GDV) to Chicago O'Hare International Airport (ORD)plane plane GDV - ORD
    8h 42m
    $90–391

  6. Drive to Ring Rock Ranch Airport, fly to General Mitchell International Airport, train

    1. Drive from Glendive to Ring Rock Ranch Airport (XWA)car car
    2. Fly from Ring Rock Ranch Airport (XWA) to General Mitchell International Airport (MKE)plane plane XWA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    11h 12m
    $193–998

  7. Bus via Chicago

    1. Take the bus from Glendive to Dickinsonbus bus
    2. Take the bus from Dickinson to Minneapolisbus bus
    3. Take the bus from Minneapolis Bus Station to Chicagobus bus
    21h 20m
    $102–365

  8. Bus

    1. Take the bus from Glendive to Dickinsonbus bus
    2. Take the bus from Dickinson to Minneapolisbus bus
    3. Take the bus from Minneapolis Bus Station to Chicago Bus Stationbus bus
    21h 30m
    $100–345

Glendive to Chicago by bus and train

Calendar7Weekly Services
Duration21h 8mAverage Duration
Ticket$111Cheapest Price
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Questions & Answers

What companies run services between Glendive, MT, USA and Chicago, IL, USA?

Cape Air, American Airlines, and two other airlines fly from Dawson Community Airport (GDV) to Chicago O'Hare International Airport (ORD) 3 times a day. Alternatively, you can take a bus from Glendive to Jackson-Blue via Dickinson, Minneapolis Bus Station, Chicago, and Cumberland in around 21h 20m.

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