There are 11 ways to get from Naylor to Chicago by car, plane, bus, train (Amtrak), train, or taxi
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Drive to Cape Girardeau Municipal Airport, fly to Chicago O'Hare International Airport
best- Drive from Naylor to Cape Girardeau Municipal Airport (CGI)
- Fly from Cape Girardeau Municipal Airport (CGI) to Chicago O'Hare International Airport (ORD)CGI - ORD
4h 39m$98–199Drive 461.9 mi
cheapest- Drive from Naylor to Chicago461.9 mi
7h 52m$85–122Drive, bus
- Drive from Naylor to Flying J - Matthews
- Take the bus from Flying J - Matthews to Tornado Bus Co - ChicagoMilwaukee
9h 53m$92–213Train (Amtrak)
- Take the train from Poplar Bluff Station to Chicago Union StationTexas Eagle
11h 40m$96–154Drive to Barkley Regional Airport, fly to Chicago O'Hare International Airport
- Drive from Naylor to Barkley Regional Airport (PAH)
- Fly from Barkley Regional Airport (PAH) to Chicago O'Hare International Airport (ORD)PAH - ORD
5h 9m$234–1,737Drive, bus to Williamson County Regional Airport, fly to Chicago O'Hare International Airport
- Drive from Naylor to Flying J - Matthews
- Take the bus from Flying J - Matthews to Marathon Gas Station - Marion
- Fly from Williamson County Regional Airport (MWA) to Chicago O'Hare International Airport (ORD)MWA - ORD
6h 38m$125–346Train to Lambert–St. Louis International Airport, fly to Chicago Midway International Airport
- Take the train from Poplar Bluff Station to St. Louis
- Fly from Lambert–St. Louis International Airport (STL) to Chicago Midway International Airport (MDW)STL - MDW
8h 56m$138–547Train to Lambert–St. Louis International Airport, fly to Chicago O'Hare International Airport
- Take the train from Poplar Bluff Station to St. Louis
- Fly from Lambert–St. Louis International Airport (STL) to Chicago O'Hare International Airport (ORD)STL - ORD
9h 20m$208–587Taxi, bus to Memphis, fly to Chicago O'Hare International Airport
- Take the taxi from Naylor to Jonesboro
- Take the bus from Jonesboro to Memphis Bus Station
- Fly from Memphis (MEM) to Chicago O'Hare International Airport (ORD)MEM - ORD
8h 7m$288–670Taxi, bus to Memphis, fly to Chicago Midway International Airport
- Take the taxi from Naylor to Jonesboro
- Take the bus from Jonesboro to Memphis Bus Station
- Fly from Memphis (MEM) to Chicago Midway International Airport (MDW)MEM - MDW
7h 41m$233–670Train, bus
- Take the train from Poplar Bluff Station to St. LouisTexas Eagle
- Take the bus from St Louis Bus Station to Chicago Bus StationFlixBus N2521 / ...
12h 41m$103–179
Cape Girardeau Municipal Airport (CGI) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Naylor to Chicago is to drive which costs $80 - $130 and takes 7h 52m.
The fastest way to get from Naylor to Chicago is to drive and fly which takes 4h 39m and costs $95 - $200.
The distance between Naylor and Chicago is 450 miles. The road distance is 464.6 miles.
The best way to get from Naylor to Chicago without a car is to train which takes 11h 40m and costs $95 - $160.
It takes approximately 4h 39m to get from Naylor to Chicago, including transfers.
Yes, the driving distance between Naylor to Chicago is 465 miles. It takes approximately 7h 52m to drive from Naylor to Chicago.
There are 1267+ hotels available in Chicago.
What companies run services between Naylor, MO, USA and Chicago, IL, USA?
Amtrak operates a train from Poplar Bluff Station to Chicago Union Station once daily. Tickets cost $50–100 and the journey takes 11h.
Transport is disrupted due to the Russia-Ukraine war. Read more
- Website
- united.com
Flights from Barkley Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 45m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $80–490
Flights from Lambert–St. Louis International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 28m
- When
- Every day
- Estimated price
- $50–340
Flights from Memphis to Chicago O'Hare International Airport
- Ave. Duration
- 2h 1m
- When
- Every day
- Estimated price
- $60–360
- Website
- southwest.com
Flights from Lambert–St. Louis International Airport to Chicago Midway International Airport
- Ave. Duration
- 1h 9m
- When
- Every day
- Estimated price
- $70–450
Flights from Memphis to Chicago Midway International Airport
- Ave. Duration
- 1h 40m
- When
- Every day
- Estimated price
- $85–490
- Website
- aa.com
Flights from Lambert–St. Louis International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 32m
- When
- Every day
- Estimated price
- $50–340
Flights from Memphis to Chicago O'Hare International Airport
- Ave. Duration
- 1h 59m
- When
- Every day
- Estimated price
- $60–360
- Website
- contouraviation.com
Flights from Cape Girardeau Municipal Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 40m
- When
- Every day
- Estimated price
- $80–170
Flights from Williamson County Regional Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 35m
- When
- Every day
- Estimated price
- $60–170
- Website
- gojetairlines.com
Flights from Lambert–St. Louis International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 1h 29m
- When
- Every day
- Estimated price
- $50–340
- Website
- delta.com
Flights from Memphis to Chicago O'Hare International Airport via Atlanta
- Ave. Duration
- 4h 40m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $90–460
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Poplar Bluff Station to Chicago Union Station
- Ave. Duration
- 11h
- Frequency
- Once daily
- Estimated price
- $50–100
- Website
- https://www.amtrak.com/home.html
Train from Poplar Bluff Station to St. Louis
- Ave. Duration
- 4h 46m
- Frequency
- Once daily
- Estimated price
- $17–35
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 888 358 6762
- info@tornadobus.com
- Website
- tornadobus.com
Bus from Flying J - Matthews to Tornado Bus Co - Chicago
- Ave. Duration
- 7h 24m
- Frequency
- Once daily
- Estimated price
- $75–190
- Schedules at
- tornadobus.com
- Adults 11-59
- $75–190
Bus from Flying J - Matthews to Marathon Gas Station - Marion
- Ave. Duration
- 1h 30m
- Frequency
- Once daily
- Estimated price
- $40–140
- Schedules at
- tornadobus.com
- Adults 11-59
- $40–140
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Jonesboro to Memphis Bus Station
- Ave. Duration
- 1h 35m
- Frequency
- Once daily
- Estimated price
- $14–19
- Website
- https://www.greyhound.com/
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from St Louis Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 15m
- Frequency
- 3 times a day
- Estimated price
- $40–90
- Schedules at
- flixbus.com
- Ave. Duration
- 1h 42m
- Estimated price
- $130–160
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