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How to get fromChicago to Anguillaby plane, train, taxi, bus (Greyhound, Flixbus), car, bus, or bus (Flixbus)

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There are 11 ways to get from Chicago to Anguilla by plane, train, taxi, bus (Greyhound, Flixbus), car, bus, or bus (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. Fly Chicago Midway International Airport to Jackson/Vicksburg, train, taxi

    best
    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
    $272–725

  2. Drive 699 mi

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

  3. Bus

    1. Take the bus from Chicago Bus Station to Memphis Bus Stationbus bus Greyhound US0125
    2. Take the bus from Memphis to Rolling Forkbus bus Dea 3
    14h 30m

  4. 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
    $349–608

  5. Fly Chicago Midway International Airport to Memphis, bus

    1. Fly from Chicago Midway International Airport (MDW) to Memphis (MEM)plane plane MDW - MEM
    2. Take the bus from Memphis to Rolling Forkbus bus
    9h 38m

  6. Fly Chicago O'Hare International Airport to Memphis, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Memphis (MEM)plane plane ORD - MEM
    2. Take the bus from Memphis to Rolling Forkbus bus
    10h 4m

  7. 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
    $182–835

  8. 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
    8h 13m
    $282–765

  9. 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
    8h 29m
    $262–645

  10. 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 23m
    $162–685

  11. Bus via Champaign

    1. Take the bus from Chicago to Champaign Intermodal Trans Ctrbus bus
    2. Take the bus from Champaign Intermodal Trans Ctr to Memphis Bus Stationbus bus
    3. Take the bus from Memphis to Rolling Forkbus bus
    18h 19m

Chicago Midway International Airport (MDW) to Jackson/Vicksburg (JAN) flights

Calendar36Weekly Planes
Duration5h 39mAverage Duration
Ticket$97Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Anguilla.ExpandLaunch map view
  • Distance: 764.6 mi
  • Duration: 8h

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

You can take a bus from Chicago Bus Station to Anguilla via Memphis and Rolling Fork in around 14h 30m.

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