There are 8 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.
Fly Chicago O'Hare International Airport to Huntsville International Airport-Carl T Jones Field, drive
best- Fly from Chicago O'Hare International Airport (ORD) to Huntsville International Airport-Carl T Jones Field (HSV)plane ORD - HSV
- Drive from Huntsville International Airport-Carl T Jones Field (HSV) to Tupelocar
6h 1m$96–450Bus
- Take the bus from Chicago Bus Station to Memphis Bus Stationbus Greyhound US0125
- Take the bus from Memphis Bus Station to Tupelobus Greyhound US0610
12h 24m$106–171Drive 583.3 mi
- Drive from Chicago to Tupelocar 583.3 mi
10h 19m$107–154Fly Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport, drive
- Fly from Chicago Midway International Airport (MDW) to Birmingham–Shuttlesworth International Airport (BHM)plane MDW - BHM
- Drive from Birmingham-Airport-BHM to Tupelocar
5h 35m$176–895Fly Chicago Midway International Airport to Memphis, bus
- Fly from Chicago Midway International Airport (MDW) to Memphis (MEM)plane MDW - MEM
- Take the bus from Memphis Bus Station to Tupelobus
7h 17m$160–845Fly Chicago O'Hare International Airport to Memphis, bus
- Fly from Chicago O'Hare International Airport (ORD) to Memphis (MEM)plane ORD - MEM
- Take the bus from Memphis Bus Station to Tupelobus
7h 39m$124–645Train, bus
- Take the train from Chicago Union Station to St. Louistrain
- Take the bus from St Louis Bus Station to Memphis Bus Stationbus
- Take the bus from Memphis Bus Station to Tupelobus
14h 5m$139–273Bus via Champaign
- Take the bus from Downtown Chicago to Illinois Terminalbus
- Take the bus from Champaign Intermodal Trans Ctr to Memphis Bus Stationbus
- Take the bus from Memphis Bus Station to Tupelobus
15h 4m$116–179
Chicago O'Hare International Airport (ORD) to Huntsville International Airport-Carl T Jones Field (HSV) flights
Comparing Your Travel Options
The cheapest way to get from Chicago to Tupelo is to drive which costs $100 - $160 and takes 10h 19m.
The fastest way to get from Chicago to Tupelo is to fly and drive which takes 5h 35m and costs $170 - $900.
No, there is no direct bus from Chicago station to Tupelo. However, there are services departing from Chicago Bus Station and arriving at Tupelo via Memphis Bus Station. The journey, including transfers, takes approximately 12h 24m.
The distance between Chicago and Tupelo is 659 miles. The road distance is 586.7 miles.
The best way to get from Chicago to Tupelo without a car is to bus which takes 12h 24m and costs $100 - $180.
It takes approximately 6h 1m to get from Chicago to Tupelo, including transfers.
Chicago to Tupelo bus services, operated by Greyhound USA, depart from Chicago Bus Station.
Chicago to Tupelo bus services, operated by Greyhound USA, arrive at Memphis Bus Station.
Yes, the driving distance between Chicago to Tupelo is 587 miles. It takes approximately 10h 19m to drive from Chicago to Tupelo.
Book your Chicago to Tupelo bus tickets online with Omio.
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 24m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport
- Ave. Duration
- 1h 41m
- When
- Every day
- Estimated price
- $150–850
Flights from Chicago Midway International Airport to Birmingham–Shuttlesworth International Airport via Nashville
- Ave. Duration
- 3h 40m
- When
- Tuesday and Wednesday
- Estimated price
- $150–850
Flights from Chicago Midway International Airport to Memphis
- Ave. Duration
- 1h 39m
- When
- Every day
- Estimated price
- $130–800
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to St. Louis
- Ave. Duration
- 4h 46m
- Frequency
- 5 times a day
- Estimated price
- $70–160
- Website
- Amtrak
Rome2Rio's guide to Greyhound USA
Contact DetailsContact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- Greyhound
Bus from Chicago Bus Station to Memphis Bus Station
- Ave. Duration
- 9h 35m
- Frequency
- Once daily
- Estimated price
- $80–140
- Website
- Greyhound
Bus from Memphis Bus Station to Tupelo
- Ave. Duration
- 1h 45m
- Frequency
- Twice daily
- Estimated price
- $15–25
- Website
- Greyhound
Bus from Memphis Bus Station to Tupelo
- Ave. Duration
- 1h 45m
- Frequency
- Twice daily
- Estimated price
- $15–25
- Website
- Greyhound
Bus from Memphis Bus Station to Tupelo
- Ave. Duration
- 1h 45m
- Frequency
- Twice daily
- Estimated price
- $15–25
- Website
- Greyhound
Bus from St Louis Bus Station to Memphis Bus Station
- Ave. Duration
- 5h 30m
- Frequency
- Once daily
- Estimated price
- $45–75
- Website
- Greyhound
Bus from Memphis Bus Station to Tupelo
- Ave. Duration
- 1h 45m
- Frequency
- Twice daily
- Estimated price
- $15–25
- Website
- Greyhound
Bus from Memphis Bus Station to Tupelo
- Ave. Duration
- 1h 45m
- Frequency
- Twice daily
- Estimated price
- $15–25
- Website
- Greyhound
Want to know more about travelling around United States
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Booking & Getting There
There are 34+ hotels available in Tupelo.








