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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
    2. Fly from Birmingham–Shuttlesworth International Airport (BHM) to Chicago Midway International Airport (MDW)planeBHM - MDW
    4h 52m
    $136–690

  2. Fly Tupelo Regional Airport to Chicago Midway International Airport

    cheapest
    1. Fly from Tupelo Regional Airport (TUP) to Chicago Midway International Airport (MDW)planeTUP - MDW
    5h 50m
    $83–404

  3. Bus

    1. Take the bus from Tupelo to Memphis Bus StationbusGreyhound US0610
    2. Take the bus from Memphis Bus Station to Chicago Bus StationbusGreyhound US0125
    12h 24m
    $109–242

  4. Drive 583.2 mi

    1. Drive from Tupelo to Chicagocar583.2 mi
    10h 31m
    $107–154

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

    1. Drive from Tupelo to Huntsville International Airport-Carl T Jones Field (HSV)car
    2. Fly from Huntsville International Airport-Carl T Jones Field (HSV) to Chicago O'Hare International Airport (ORD)planeHSV - ORD
    5h 30m
    $90–408

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

    1. Take the bus from Tupelo to Memphis Bus Stationbus
    2. Fly from Memphis (MEM) to Chicago Midway International Airport (MDW)planeMEM - MDW
    6h 18m
    $127–568

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

    1. Take the bus from Tupelo to Memphis Bus Stationbus
    2. Fly from Memphis (MEM) to Chicago O'Hare International Airport (ORD)planeMEM - ORD
    6h 50m
    $192–568

  8. Bus, train

    1. Take the bus from Tupelo to Memphis Bus Stationbus
    2. Take the bus from Memphis Bus Station to St Louis Bus Stationbus
    3. Take the train from St. Louis to Chicago Union Stationtrain
    14h 4m
    $124–487

  9. Bus via Champaign

    1. Take the bus from Tupelo to Memphis Bus Stationbus
    2. Take the bus from Memphis Bus Station to Champaign Intermodal Trans Ctrbus
    3. Take the bus from Champaign Intermodal Trans Ctr to Chicago Bus Stationbus
    15h 9m
    $121–232

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

Calendar22Weekly Planes
Duration2h 38mAverage Duration
Ticket$111Cheapest Price
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Questions & Answers

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 24m. Alternatively, Corporate Flight Management Inc and Southwest Airlines fly from Tupelo Regional Airport (TUP) to Chicago Midway International Airport (MDW) twice daily.

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