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How to get fromChicago to Anguillaby plane, car, train, taxi, or bus

Find Transport to Anguilla

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There are 9 ways to get from Chicago to Anguilla by plane, car, train, taxi, or bus

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 Chicago O'Hare International Airport to Bill And Hillary Clinton National Airport, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Bill And Hillary Clinton National Airport (LIT)plane plane ORD - LIT
    2. Drive from Bill And Hillary Clinton National Airport (LIT) to Anguillacar car
    7h 3m
    $88–375

  2. Train, taxi (Amtrak)

    1. Take the train from Chicago Union Station to Yazoo City Amtrak Stationtrain train City of New Orleans
    2. Take the taxi from Yazoo City Amtrak Station to Anguillataxi taxi
    15h 4m
    $509–746

  3. Bus, train, taxi

    1. Take the bus from Chicago Bus Station to Memphis Bus Stationbus bus
    2. Take the bus from Memphis Bus Station to Jacksonbus bus
    3. Take the train from Jackson to Yazoo City Amtrak Stationtrain train
    4. Take the taxi from Yazoo City Amtrak Station to Anguillataxi taxi
    17h 4m
    $261–382

  4. Drive  699 mi

    1. Drive from Chicago to Anguillacar car 699 mi
    11h 47m
    $128–185

  5. Fly Chicago Midway International Airport to Jackson/Vicksburg, train, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN)plane plane MDW - JAN
    2. Take the train from Jackson to Yazoo City Amtrak Stationtrain train
    3. Take the taxi from Yazoo City Amtrak Station to Anguillataxi taxi
    8h 15m
    $278–735

  6. Fly Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport, drive

    1. Fly from Chicago Midway International Airport (MDW) to Birmingham–Shuttlesworth International Airport (BHM)plane plane MDW - BHM
    2. Drive from Birmingham-Airport-BHM to Anguillacar car
    8h 51m
    $192–935

  7. Fly Chicago Midway International Airport to Greenville International Airport, taxi

    1. Fly from Chicago Midway International Airport (MDW) to Greenville International Airport (GLH)plane plane MDW - GLH
    2. Take the taxi from Greenville International Airport (GLH) to Anguillataxi taxi
    7h 32m
    $272–765

  8. Fly Chicago O'Hare International Airport to Greenville International Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Greenville International Airport (GLH)plane plane ORD - GLH
    2. Take the taxi from Greenville International Airport (GLH) to Anguillataxi taxi
    7h 19m
    $248–605

  9. Fly Chicago O'Hare International Airport to Birmingham–Shuttlesworth International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Birmingham–Shuttlesworth International Airport (BHM)plane plane ORD - BHM
    2. Drive from Birmingham-Airport-BHM to Anguillacar car
    9h 25m
    $152–685

Chicago O'Hare International Airport (ORD) to Bill And Hillary Clinton National Airport (LIT) flights

Calendar60Weekly Planes
Duration3h 7mAverage Duration
Ticket$54Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Anguilla.ExpandLaunch map view
  • Distance: 749.3 mi
  • Duration: 7h 3m

What companies run services between Chicago, IL, USA and Anguilla, MS, USA?

There is no direct connection from Chicago to Anguilla. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Bill And Hillary Clinton National Airport (LIT), then drive to Anguilla. Alternatively, you can take the train to Yazoo City Amtrak Station then take the taxi to Anguilla.

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