There are 7 ways to get from Lee to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), 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.
Bus to Albany County Airport, fly to Chicago Midway International Airport
best- Take the bus from Lee to Albany Bus Terminal, NY
- Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)ALB - MDW
6h 30m$130–660Bus
cheapest- Take the bus from Lee to Port Authority Bus Terminal
- Take the bus from Port Authority Bus Terminal to Newark Penn Station108
- Take the bus from Newark Penn Station to Chicago Bus Station
25h 6m$115–310Train (Amtrak)
- Take the train from Pittsfield Amtrak Station to Chicago Union StationLake Shore Limited
20h 14m$222–302Drive 858.5 mi
- Drive from Lee to Chicago858.5 mi
14h 30m$157–227Bus to Albany County Airport, fly to Chicago O'Hare International Airport
- Take the bus from Lee to Albany Bus Terminal, NY
- Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)ALB - ORD
7h 7m$230–610Bus to Bradley International Airport, fly to Chicago Midway International Airport
- Take the bus from Lee to Springfield Union Station
- Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)BDL - MDW
6h 45m$119–729Bus to Bradley International Airport, fly to Chicago O'Hare International Airport
- Take the bus from Lee to Springfield Union Station
- Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)BDL - ORD
7h 11m$389–899
Lee to Chicago by bus and train (Amtrak)
Questions & Answers
The cheapest way to get from Lee to Chicago is to drive which costs $150 - $230 and takes 14h 30m.
The fastest way to get from Lee to Chicago is to bus and fly which takes 6h 30m and costs $130 - $700.
No, there is no direct bus from Lee to Chicago station. However, there are services departing from Lee and arriving at Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station. The journey, including transfers, takes approximately 25h 6m.
The distance between Lee and Chicago is 787 miles. The road distance is 863.5 miles.
The best way to get from Lee to Chicago without a car is to train which takes 20h 14m and costs $220 - $310.
It takes approximately 6h 30m to get from Lee to Chicago, including transfers.
Lee to Chicago bus services, operated by Peter Pan Bus Lines, depart from Lee station.
The best way to get from Lee to Chicago is to train which takes 20h 14m and costs $220 - $310. Alternatively, you can bus, which costs $110 - $310 and takes 25h 6m.
Lee to Chicago bus services, operated by Peter Pan Bus Lines, arrive at Port Authority Bus Terminal station.
Chicago is 1h behind Lee. It is currently 4:15 AM in Lee and 3:15 AM in Chicago.
What companies run services between Lee, MA, USA and Chicago, IL, USA?
Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $220–300 and the journey takes 18h 30m. Alternatively, you can take a bus from Lee to Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station in around 25h 6m.
- Website
- southwest.com
Flights from Albany County Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 16m
- When
- Every day
- Estimated price
- $100–600
Flights from Albany County Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 48m
- When
- Every day
- Estimated price
- $120–650
Flights from Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 30m
- When
- Every day
- Estimated price
- $90–480
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 43m
- When
- Monday, Tuesday, Wednesday, Friday, Saturday, and Sunday
- Estimated price
- $100–500
- Website
- aa.com
Flights from Albany County Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 51m
- When
- Every day
- Estimated price
- $80–430
Flights from Albany County Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 5m
- When
- Every day
- Estimated price
- $90–460
Flights from Albany County Airport to Chicago O'Hare International Airport via Reagan Washington
- Ave. Duration
- 5h 5m
- When
- Every day
- Estimated price
- $95–470
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $70–360
Flights from Bradley International Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 51m
- When
- Every day
- Estimated price
- $75–380
- Website
- united.com
Flights from Albany County Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $80–430
Flights from Albany County Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 7m
- When
- Every day
- Estimated price
- $90–460
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $70–360
Flights from Bradley International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 5h 2m
- When
- Every day
- Estimated price
- $75–380
- Website
- delta.com
Flights from Albany County Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 9m
- When
- Every day
- Estimated price
- $100–600
Flights from Albany County Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 21m
- When
- Every day
- Estimated price
- $80–430
Flights from Bradley International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 38m
- When
- Every day
- Estimated price
- $90–480
Flights from Bradley International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 1m
- When
- Every day
- Estimated price
- $70–360
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Pittsfield Amtrak Station to Chicago Union Station
- Ave. Duration
- 18h 30m
- Frequency
- Once daily
- Estimated price
- $220–300
- Website
- https://www.amtrak.com/home.html
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Lee to Albany Bus Terminal, NY
- Ave. Duration
- 1h 25m
- Frequency
- Once daily
- Estimated price
- $24–55
- Website
- https://www.greyhound.com/
Bus from Port Authority Bus Terminal to Newark Penn Station
- Ave. Duration
- 25 min
- Frequency
- Hourly
- Estimated price
- $7–17
- Website
- https://www.greyhound.com/
Bus from Lee to Springfield Union Station
- Ave. Duration
- 45 min
- Frequency
- Once daily
- Estimated price
- $23–55
- Website
- https://www.greyhound.com/
- Phone
- 1-800-343-9999
- Website
- peterpanbus.com
Bus from Lee to Port Authority Bus Terminal
- Ave. Duration
- 3h 35m
- Frequency
- Once daily
- Estimated price
- $18–60
- Website
- https://peterpanbus.com
- Adult
- $18–60
- Phone
- +1 973-275-5555
- Website
- njtransit.com
Bus from Port Authority Bus Terminal to Newark Penn Station
- Ave. Duration
- 34 min
- Frequency
- Hourly
- Estimated price
- $7–24
- Website
- https://www.njtransit.com/
- Schedules at
- https://www.njtransit.com/bus-to
- Adults
- $7–24
- Phone
- +1 800-858-8555
- Website
- trailways.com
Bus from Port Authority Bus Terminal to Newark Penn Station
- Ave. Duration
- 30 min
- Frequency
- Once daily
- Estimated price
- $17–38
- Website
- https://trailways.com
- Schedules at
- https://trailways.com/schedules/
- Saver
- $17–35
- Flexible
- $35–38
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Newark Penn Station to Chicago Bus Station
- Ave. Duration
- 19h 40m
- Frequency
- Once daily
- Estimated price
- $90–210
- Schedules at
- flixbus.com
Want to know more about travelling around United States
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More Questions & Answers
Yes, the driving distance between Lee to Chicago is 863 miles. It takes approximately 14h 30m to drive from Lee to Chicago.
There are 1245+ hotels available in Chicago.

















