There are 5 ways to get from Chesapeake to Chicago by plane, train (Amtrak), bus (Flixbus, Greyhound), or car
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago O'Hare International Airport
best- Fly from Norfolk International Airport (ORF) to Chicago O'Hare International Airport (ORD)plane ORF - ORD
3h 36m$150–588Bus
cheapest- Take the bus from Norfolk to Washington Union Stationbus FlixBus N2601
- Take the bus from Washington Union Station to Chicago Bus Stationbus Greyhound US0164
24h 32m$97–242Train (Amtrak)
- Take the train from Norfolk to Petersburg Amtrak Stationtrain Northeast Regional
- Take the train from Petersburg Amtrak Station to Chicago Union Stationtrain Floridian
24h 14m$202–872Drive 844.1 mi
- Drive from Chesapeake to Chicagocar 844.1 mi
15h 5m$154–223Fly to Chicago Midway International Airport
- Fly from Norfolk International Airport (ORF) to Chicago Midway International Airport (MDW)plane ORF - MDW
3h 11m$115–498
Chesapeake to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from Chesapeake to Chicago is to bus which costs $95 - $250 and takes 24h 32m.
The fastest way to get from Chesapeake to Chicago is to fly which takes 3h 11m and costs $110 - $500.
No, there is no direct bus from Chesapeake to Chicago station. However, there are services departing from Dntc and arriving at Chicago Bus Station via Military Circle Mall, Norfolk and Washington Union Station. The journey, including transfers, takes approximately 24h 32m.
No, there is no direct train from Chesapeake to Chicago station. However, there are services departing from Norfolk and arriving at Chicago Union Station via Petersburg Amtrak Station. The journey, including transfers, takes approximately 24h 14m.
The distance between Chesapeake and Chicago is 745 miles. The road distance is 849 miles.
The best way to get from Chesapeake to Chicago without a car is to train which takes 24h 14m and costs $200 - $900.
It takes approximately 3h 36m to get from Chesapeake to Chicago, including transfers.
Chesapeake to Chicago bus services, operated by Flixbus USA, depart from Norfolk station.
Chesapeake to Chicago train services, operated by Amtrak Northeast Regional, depart from Norfolk station.
The best way to get from Chesapeake to Chicago is to fly which takes 3h 36m and costs $150 - $600. Alternatively, you can train, which costs $200 - $900 and takes 24h 14m, you could also bus, which costs $95 - $250 and takes 24h 32m.
What companies run services between Chesapeake, City of Chesapeake, VA, USA and Chicago, IL, USA?
American Airlines, United Airlines, and Delta fly from Norfolk International Airport (ORF) to Chicago O'Hare International Airport (ORD) every 2 hours. Alternatively, you can take a train from Norfolk to Chicago Union Station via Petersburg Amtrak Station in around 24h 14m.
- Website
- united.com
Flights from Norfolk International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 34m
- When
- Every day
- Estimated price
- $60–340
Flights from Norfolk International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 40m
- When
- Every day
- Estimated price
- $65–340
- Website
- aa.com
Flights from Norfolk International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 38m
- When
- Every day
- Estimated price
- $60–340
Flights from Norfolk International Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 35m
- When
- Every day
- Estimated price
- $65–350
- Website
- southwest.com
Flights from Norfolk International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 15m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $85–460
Flights from Norfolk International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 18m
- When
- Thursday, Friday, and Sunday
- Estimated price
- $90–470
- Website
- delta.com
Flights from Norfolk International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 18m
- When
- Every day
- Estimated price
- $65–350
Rome2Rio's guide to Amtrak Northeast Regional
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Norfolk to Petersburg Amtrak Station
- Ave. Duration
- 1h 24m
- Frequency
- 3 times a day
- Estimated price
- $11–230
- Website
- https://www.amtrak.com/home
- Schedules at
- https://www.amtrak.com/northeast-regional-train
- Coach
- $11–230
- Business Class
- $55–260
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Petersburg Amtrak Station to Chicago Union Station
- Ave. Duration
- 21h 50m
- Frequency
- Once daily
- Estimated price
- $190–650
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Norfolk to Washington Union Station
- Ave. Duration
- 4h 25m
- Frequency
- 5 times a week
- Estimated price
- $30–60
- Schedules at
- flixbus.com
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Washington Union Station to Chicago Bus Station
- Ave. Duration
- 17h 25m
- Frequency
- Twice daily
- Estimated price
- $65–180
- Website
- https://www.greyhound.com/
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More Questions & Answers
Chesapeake to Chicago bus services, operated by Flixbus USA, arrive at Washington Union Station.
Chicago is 1h behind Chesapeake. It is currently 9:21 AM in Chesapeake and 8:21 AM in Chicago.
Chesapeake to Chicago train services, operated by Amtrak Northeast Regional, arrive at Petersburg Amtrak Station.
Yes, the driving distance between Chesapeake to Chicago is 849 miles. It takes approximately 15h 5m to drive from Chesapeake to Chicago.
Book your Chesapeake to Chicago train tickets online with Omio.
There are 1249+ hotels available in Chicago.