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How to get fromColorado Springs to Chicagoby plane, bus, train, bus (Greyhound) or car

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There are 7 ways to get from Colorado Springs to Chicago by plane, bus, train, bus (Greyhound), 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 Colorado Springs Airport to Chicago Midway International Airport

    best
    1. Fly from Colorado Springs Airport (COS) to Chicago Midway International Airport (MDW)plane plane COS - MDW
    5h 12m
    $136–709

  2. Bus

    cheapest
    1. Take the bus from Colorado Springs Downtown Station to Union Stationbus bus South
    2. Take the bus from Denver Union Station to Chicago Bus Stationbus bus Greyhound US0123
    23h 50m
    $92–266

  3. Bus, train

    1. Take the bus from Colorado Springs Downtown Station to Union Stationbus bus South
    2. Take the train from Denver to Chicago Union Stationtrain train California Zephyr
    21h 55m
    $122–276

  4. Drive 1,026.4 mi

    1. Drive from Colorado Springs to Chicagocar car 1,026.4 mi
    17h 28m
    $188–271

  5. Fly Colorado Springs Airport to Chicago O'Hare International Airport

    1. Fly from Colorado Springs Airport (COS) to Chicago O'Hare International Airport (ORD)plane plane COS - ORD
    5h 47m
    $96–499

  6. Bus to Denver, fly to Chicago Midway International Airport

    1. Take the bus from The Antlers; S. Cascade to Denver International Airportbus bus
    2. Fly from Denver (DEN) to Chicago Midway International Airport (MDW)plane plane DEN - MDW
    5h 56m
    $137–610

  7. Bus to Denver, fly to Chicago O'Hare International Airport

    1. Take the bus from The Antlers; S. Cascade to Denver International Airportbus bus
    2. Fly from Denver (DEN) to Chicago O'Hare International Airport (ORD)plane plane DEN - ORD
    6h 13m
    $312–760

Colorado Springs to Chicago by bus and train

Calendar7Weekly Services
Duration21h 55mAverage Duration
Ticket$122Cheapest Price
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Questions & Answers

What companies run services between Colorado Springs, CO, USA and Chicago, IL, USA?

Southwest Airlines flies from Colorado Springs Airport (COS) to Chicago Midway International Airport (MDW) twice daily. Alternatively, you can take a bus from Colorado Springs Downtown Station to Chicago Bus Station via Denver Union Station in around 23h 50m.

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