There are 7 ways to get from Lenox 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 Lenox to Albanybus
- Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane ALB - MDW
6h 17m$115–624Bus to Bradley International Airport, fly to Chicago O'Hare International Airport
cheapest- Take the bus from Lenox to Springfieldbus
- Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane BDL - ORD
7h 7m$80–383Train (Amtrak)
- Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain Lake Shore Limited
20h$222–503Bus
- Take the bus from Lenox to New Yorkbus
- Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus 108
- Take the bus from Newark Penn Station to Chicago Bus Stationbus
25h 17m$164–297Drive 853.6 mi
- Drive from Lenox to Chicagocar 853.6 mi
14h 44m$156–225Bus to Albany County Airport, fly to Chicago O'Hare International Airport
- Take the bus from Lenox to Albanybus
- Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane ALB - ORD
6h 39m$105–494Bus to Bradley International Airport, fly to Chicago Midway International Airport
- Take the bus from Lenox to Springfieldbus
- Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane BDL - MDW
6h 50m$95–453
Lenox to Chicago by bus and train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Lenox to Chicago is to drive which costs $150 - $230 and takes 14h 44m.
The fastest way to get from Lenox to Chicago is to bus and fly which takes 6h 17m and costs $110 - $650.
No, there is no direct bus from Lenox to Chicago station. However, there are services departing from Lenox and arriving at Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station. The journey, including transfers, takes approximately 25h 17m.
No, there is no direct train from Lenox station to Chicago station. However, there are services departing from Pittsfield Amtrak Station and arriving at Chicago Union Station via . The journey, including transfers, takes approximately 20h.
The distance between Lenox and Chicago is 784 miles. The road distance is 858.6 miles.
The best way to get from Lenox to Chicago without a car is to train which takes 20h and costs $220 - $550.
It takes approximately 6h 17m to get from Lenox to Chicago, including transfers.
Lenox to Chicago bus services, operated by Peter Pan Bus Lines, depart from Lenox station.
Lenox to Chicago train services, operated by Amtrak, depart from Pittsfield Amtrak Station.
The best way to get from Lenox to Chicago is to train which takes 20h and costs $220 - $550. Alternatively, you can bus, which costs $160 - $300 and takes 25h 17m.
What companies run services between Lenox, MA, USA and Chicago, IL, USA?
Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $220–500 and the journey takes 18h 30m. Alternatively, you can take a bus from Lenox to Chicago Bus Station via New York, Port Authority Bus Terminal, and Newark Penn Station in around 25h 17m.
- Website
- southwest.com
Flights from Albany County Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 8m
- When
- Every day
- Estimated price
- $100–600
Flights from Albany County Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $120–650
Flights from Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 23m
- When
- Every day
- Estimated price
- $80–420
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 26m
- When
- Tuesday, Wednesday, Monday, Thursday, Friday, and Sunday
- Estimated price
- $85–440
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Pittsfield Amtrak Station to Chicago Union Station
- Ave. Duration
- 18h 30m
- Frequency
- Once daily
- Estimated price
- $220–500
- Website
- Amtrak
- Phone
- 1-800-343-9999
- Website
- Peter Pan
Bus from Lenox to Albany
- Ave. Duration
- 1h 15m
- Frequency
- 6 times a week
- Estimated price
- $8–15
- Website
- Peter Pan
Bus from Lenox to New York
- Ave. Duration
- 3h 45m
- Frequency
- 5 times a week
- Estimated price
- $27–50
- Website
- Peter Pan
Bus from Lenox to Albany
- Ave. Duration
- 1h 15m
- Frequency
- 6 times a week
- Estimated price
- $8–15
- Website
- Peter Pan
Bus from Lenox to Springfield
- Ave. Duration
- 1h
- Frequency
- 6 times a week
- Estimated price
- $9–16
- Website
- Peter Pan
Bus from Lenox to Springfield
- Ave. Duration
- 1h
- Frequency
- 6 times a week
- Estimated price
- $9–16
- Website
- Peter Pan
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Booking & Getting There
Lenox to Chicago bus services, operated by Peter Pan Bus Lines, arrive at New York station.
Chicago is 1h behind Lenox. It is currently 1:14 AM in Lenox and 12:14 AM in Chicago.
Lenox to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Lenox to Chicago is 859 miles. It takes approximately 14h 44m to drive from Lenox to Chicago.
There are 1284+ hotels available in Chicago.