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

Find Transport to Tupelo

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There are 8 ways to get from Chicago to Tupelo by plane, car, bus (Greyhound, Flixbus), bus, 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. Fly Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport, drive

    best
    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 Tupelocar car
    5h 32m
    $176–945

  2. Fly Chicago O'Hare International Airport to Huntsville International Airport-Carl T Jones Field, drive

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Huntsville International Airport-Carl T Jones Field (HSV)plane plane ORD - HSV
    2. Drive from Huntsville International Airport-Carl T Jones Field (HSV) to Tupelocar car
    6h 5m
    $90–440

  3. Bus

    1. Take the bus from Chicago Bus Station to Memphis Bus Stationbus bus Greyhound US0125
    2. Take the bus from Memphis Bus Station to Tupelobus bus Greyhound US0610
    12h 14m
    $100–224

  4. Drive 583.3 mi

    1. Drive from Chicago to Tupelocar car 583.3 mi
    10h 19m
    $107–154

  5. 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 Bus Station to Tupelobus bus
    7h 44m
    $302–555

  6. 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 Bus Station to Tupelobus bus
    7h 14m
    $132–705

  7. Fly Chicago Midway International Airport to Tupelo Regional Airport

    1. Fly from Chicago Midway International Airport (MDW) to Tupelo Regional Airport (TUP)plane plane MDW - TUP
    5h 44m
    $102–513

  8. Train, bus

    1. Take the train from Chicago Union Station to St. Louistrain train
    2. Take the bus from St Louis Bus Station to Memphis Bus Stationbus bus
    3. Take the bus from Memphis Bus Station to Tupelobus bus
    13h 15m
    $142–316

Chicago Midway International Airport (MDW) to Birmingham–Shuttlesworth International Airport (BHM) flights

Calendar28Weekly Planes
Duration3h 7mAverage Duration
Ticket$151Cheapest Price
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Questions & Answers

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

You can take a bus from Chicago Bus Station to Tupelo via Memphis Bus Station and Tupelo in around 12h 14m. Alternatively, Southwest Airlines and Corporate Flight Management Inc fly from Chicago Midway International Airport (MDW) to Tupelo Regional Airport (TUP) twice daily.

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