Rome2Rio

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

Find Transport to Tupelo

See all options

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 37m
    $156–845

  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 9m
    $96–460

  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
    $108–275

  4. Drive 583 mi

    1. Drive from Chicago to Tupelocar car 583 mi
    10h 33m
    $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 41m
    $192–568

  6. 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
    6h 29m
    $128–675

  7. 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 19m
    $142–728

  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
    $110–403

  9. 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 Bus Station to Tupelobus bus
    15h 53m
    $118–212

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

Calendar25Weekly Planes
Duration3h 18mAverage Duration
Ticket$135Cheapest Price
See schedules

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

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Trips from Chicago

Trips to Tupelo

Popular routes