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

Find Transport to Chicago

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There are 6 ways to get from Cheyenne 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 Cheyenne Airport to Chicago O'Hare International Airport

    best
    1. Fly from Cheyenne Airport (CYS) to Chicago O'Hare International Airport (ORD)plane plane CYS - ORD
    5h 30m
    $77–368

  2. Bus, train

    1. Take the bus from Cheyenne to Denver Union Stationbus bus Greyhound US0560S
    2. Take the train from Denver to Chicago Union Stationtrain train California Zephyr
    21h 30m
    $308–657

  3. Bus

    1. Take the bus from Cheyenne to Denver Union Stationbus bus Greyhound US0560S
    2. Take the bus from Denver Union Station to Chicago Bus Stationbus bus Greyhound US0123S
    23h 20m
    $198–307

  4. Drive  958.6 mi

    1. Drive from Cheyenne to Chicagocar car 958.6 mi
    15h 10m
    $175–253

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

    1. Take the bus from Warren AFB to Denver International Airport Pickupsbus bus
    2. Fly from Denver (DEN) to Chicago Midway International Airport (MDW)plane plane DEN - MDW
    6h 16m
    $185–286

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

    1. Take the bus from Warren AFB to Denver International Airport Pickupsbus bus
    2. Fly from Denver (DEN) to Chicago O'Hare International Airport (ORD)plane plane DEN - ORD
    6h 35m
    $115–496

Cheyenne to Chicago by bus and train

Calendar7Weekly Services
Duration21h 30mAverage Duration
Ticket$308Cheapest Price
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Comparing Your Travel Options

Map of how to get from Cheyenne to Chicago.ExpandLaunch map view
  • Distance: 892.8 mi
  • Duration: 5h 30m

What companies run services between Cheyenne, WY, USA and Chicago, IL, USA?

United Airlines flies from Cheyenne Airport (CYS) to Chicago O'Hare International Airport (ORD) 3 times a day. Alternatively, you can take a bus from Cheyenne to Chicago Bus Station via Denver Union Station in around 23h 20m.

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Need to know: Greyhound

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