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

Find Transport to Tupelo

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There are 9 ways to get from Chicago to Tupelo by plane, car, bus (Greyhound, Flixbus), bus, train, or bus (Flixbus, Greyhound)

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 35m
    $156–795

  2. Fly Chicago Midway International Airport to Tupelo Regional Airport

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Tupelo Regional Airport (TUP)plane plane MDW - TUP
    5h 57m
    $92–453

  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 9m
    $108–197

  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 Huntsville International Airport-Carl T Jones Field, drive

    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
    $100–470

  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 17m
    $150–799

  7. 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 42m
    $130–649

  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
    14h 5m
    $156–313

  9. Bus via Champaign

    1. Take the bus from Chicago Bus Station 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 Bus Station to Tupelobus bus
    14h 44m
    $146–233

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

Calendar35Weekly Planes
Duration3h 10mAverage Duration
Ticket$137Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Tupelo.ExpandLaunch map view
  • Distance: 716.6 mi
  • Duration: 5h 35m

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 9m. Alternatively, Southwest Airlines and Corporate Flight Management Inc fly from Chicago Midway International Airport (MDW) to Tupelo Regional Airport (TUP) 4 times a week.

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