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How to get fromTupelo to Chicagoby car, plane, bus (Greyhound, Flixbus), bus, or train

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There are 9 ways to get from Tupelo to Chicago by car, plane, 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. Drive to Birmingham–Shuttlesworth International Airport, fly to Chicago Midway International Airport

    best
    1. Drive from Tupelo to Birmingham-Airport-BHMcar car
    2. Fly from Birmingham–Shuttlesworth International Airport (BHM) to Chicago Midway International Airport (MDW)plane plane BHM - MDW
    4h 54m
    $95–448

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

    cheapest
    1. Drive from Tupelo to Huntsville International Airport-Carl T Jones Field (HSV)car car
    2. Fly from Huntsville International Airport-Carl T Jones Field (HSV) to Chicago O'Hare International Airport (ORD)plane plane HSV - ORD
    5h 29m
    $69–316

  3. Bus

    1. Take the bus from Tupelo to Memphis Bus Stationbus bus Greyhound US0610
    2. Take the bus from Memphis Bus Station to Chicago Bus Stationbus bus Greyhound US0125
    12h 34m
    $114–191

  4. Drive  583.5 mi

    1. Drive from Tupelo to Chicagocar car 583.5 mi
    10h 21m
    $100–144

  5. Bus to Memphis, fly to Chicago Midway International Airport

    1. Take the bus from Tupelo to Memphis Bus Stationbus bus
    2. Fly from Memphis (MEM) to Chicago Midway International Airport (MDW)plane plane MEM - MDW
    6h 25m
    $117–547

  6. Bus to Memphis, fly to Chicago O'Hare International Airport

    1. Take the bus from Tupelo to Memphis Bus Stationbus bus
    2. Fly from Memphis (MEM) to Chicago O'Hare International Airport (ORD)plane plane MEM - ORD
    6h 51m
    $92–407

  7. Fly Tupelo Regional Airport to Chicago Midway International Airport

    1. Fly from Tupelo Regional Airport (TUP) to Chicago Midway International Airport (MDW)plane plane TUP - MDW
    4h 35m
    $87–432

  8. Bus, train

    1. Take the bus from Tupelo to Memphis Bus Stationbus bus
    2. Take the bus from Memphis Bus Station to St Louis Bus Stationbus bus
    3. Take the train from St. Louis to Chicago Union Stationtrain train
    14h 4m
    $224–361

  9. Bus via Champaign

    1. Take the bus from Tupelo to Memphis Bus Stationbus bus
    2. Take the bus from Memphis Bus Station to Champaign Intermodal Trans Ctrbus bus
    3. Take the bus from Champaign Intermodal Trans Ctr to Chicago Bus Stationbus bus
    14h 49m
    $149–221

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

Calendar24Weekly Planes
Duration3h 1mAverage Duration
Ticket$72Cheapest Price
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Comparing Your Travel Options

Map of how to get from Tupelo to Chicago.ExpandLaunch map view
  • Distance: 716 mi
  • Duration: 4h 54m

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

You can take a vehicle from Tupelo to Chicago Bus Station via Tupelo and Memphis Bus Station in around 12h 34m. Alternatively, Corporate Flight Management Inc and Southwest Airlines fly from Tupelo Regional Airport (TUP) to Chicago Midway International Airport (MDW) once daily.

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