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How to get fromEnterprise to Chicagoby taxi, plane, bus, car, or train

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There are 12 ways to get from Enterprise to Chicago by taxi, plane, bus, car, or train

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

  1. Taxi to Dothan Regional Airport, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Enterprise to Dothan Regional Airport (DHN)taxi taxi
    2. Fly from Dothan Regional Airport (DHN) to Chicago Midway International Airport (MDW)plane plane DHN - MDW
    5h 23m
    $86–405

  2. Drive to Pensacola International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Enterprise to Pensacola-Airport-PNScar car
    2. Fly from Pensacola International Airport (PNS) to Chicago O'Hare International Airport (ORD)plane plane PNS - ORD
    5h 55m
    $78–325

  3. Taxi, bus

    1. Take the taxi from Enterprise to Dothantaxi taxi
    2. Take the bus from Dothan to Nashville Bus Stationbus bus
    3. Take the bus from Nashville Bus Station to Chicago Bus Stationbus bus
    19h 44m
    $134–270

  4. Drive 795.3 mi

    1. Drive from Enterprise to Chicagocar car 795.3 mi
    14h 49m
    $146–210

  5. Drive to Northwest Florida Beaches International Airport, fly to Chicago Midway International Airport

    1. Drive from Enterprise to Northwest Florida Beaches International Airport (ECP)car car
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago Midway International Airport (MDW)plane plane ECP - MDW
    4h 41m
    $93–418

  6. Drive to Northwest Florida Beaches International Airport, fly to Chicago O'Hare International Airport

    1. Drive from Enterprise to Northwest Florida Beaches International Airport (ECP)car car
    2. Fly from Northwest Florida Beaches International Airport (ECP) to Chicago O'Hare International Airport (ORD)plane plane ECP - ORD
    5h 17m
    $83–368

  7. Drive to Pensacola International Airport, fly to Chicago Midway International Airport

    1. Drive from Enterprise to Pensacola-Airport-PNScar car
    2. Fly from Pensacola International Airport (PNS) to Chicago Midway International Airport (MDW)plane plane PNS - MDW
    7h 1m
    $88–375

  8. Drive to Birmingham–Shuttlesworth International Airport, fly to Chicago Midway International Airport

    1. Drive from Enterprise to Birmingham-Airport-BHMcar car
    2. Fly from Birmingham–Shuttlesworth International Airport (BHM) to Chicago Midway International Airport (MDW)plane plane BHM - MDW
    5h 55m
    $114–502

  9. Drive to Destin–Fort Walton Beach Airport, fly to Chicago O'Hare International Airport

    1. Drive from Enterprise to Destin–Fort Walton Beach Airport (VPS)car car
    2. Fly from Destin–Fort Walton Beach Airport (VPS) to Chicago O'Hare International Airport (ORD)plane plane VPS - ORD
    5h 34m
    $82–357

  10. Taxi, bus, train via Nashville

    1. Take the taxi from Enterprise to Dothantaxi taxi
    2. Take the bus from Dothan to Nashville Bus Stationbus bus
    3. Take the bus from Nashville Bus Station to Carbondale Intermodal Stationbus bus
    4. Take the train from Carbondale to Chicago Union Stationtrain train
    20h 9m
    $189–395

  11. Taxi, bus via Lafayette

    1. Take the taxi from Enterprise to Dothantaxi taxi
    2. Take the bus from Dothan to Nashville Bus Stationbus bus
    3. Take the bus from Nashville to Lafayette Amtrak Stationbus bus
    4. Take the bus from Lafayette Amtrak Station to Chicago Union Stationbus bus
    20h 24m
    $138–245

  12. Taxi, bus, train

    1. Take the taxi from Enterprise to Dothantaxi taxi
    2. Take the bus from Dothan to Montgomery Intermodal Centerbus bus
    3. Take the bus from Montgomery Intermodal Center to Indianapolis Union Stationbus bus
    4. Take the train from Indianapolis to Chicago Union Stationtrain train
    23h 54m
    $174–350

Dothan Regional Airport (DHN) to Chicago Midway International Airport (MDW) flights

Calendar27Weekly Planes
Duration4h 57mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

Map of how to get from Enterprise to Chicago.ExpandLaunch map view
  • Distance: 773.1 mi
  • Duration: 5h 23m

What companies run services between Enterprise, Coffee County, AL, USA and Chicago, IL, USA?

There is no direct connection from Enterprise to Chicago. However, you can take the taxi to Dothan Regional Airport (DHN) airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take the taxi to Dothan, take the bus to Nashville Bus Station, then take the bus to Chicago Bus Station.

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