There are 5 ways to get from Windsor to Chicago by plane, train (Amtrak), bus (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.
Fly to Chicago Midway International Airport
best- Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane BDL - MDW
4h 42m$80–390Fly to Chicago O'Hare International Airport
cheapest- Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane BDL - ORD
5h 16m$70–330Train (Amtrak)
- Take the train from Springfield to Chicago Union Stationtrain Lake Shore Limited
21h 17m$296–612Bus
- Take the bus from Hartford Union Station to New York Midtownbus FlixBus 2610
- Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2641 / ...
22h 10m$160–273Drive 895.6 mi
- Drive from Windsor to Chicagocar 895.6 mi
15h 1m$164–237
Windsor to Chicago by train (Amtrak)
Questions & Answers
The cheapest way to get from Windsor to Chicago is to fly which costs $70 - $330 and takes 5h 16m.
The fastest way to get from Windsor to Chicago is to fly which takes 4h 42m and costs $80 - $390.
No, there is no direct bus from Windsor to Chicago station. However, there are services departing from Central St @ Broad St and arriving at Chicago Bus Station via Hartford Union Station and New York Midtown. The journey, including transfers, takes approximately 22h 10m.
No, there is no direct train from Windsor to Chicago station. However, there are services departing from Windsor and arriving at Chicago Union Station via Springfield. The journey, including transfers, takes approximately 21h 17m.
The distance between Windsor and Chicago is 797 miles. The road distance is 900.8 miles.
The best way to get from Windsor to Chicago without a car is to train which takes 21h 17m and costs $290 - $650.
It takes approximately 4h 42m to get from Windsor to Chicago, including transfers.
Windsor to Chicago bus services, operated by FlixBus-us, depart from Hartford Union Station.
Windsor to Chicago train services, operated by Amtrak, depart from Springfield station.
The best way to get from Windsor to Chicago is to fly which takes 4h 42m and costs $80 - $390. Alternatively, you can train, which costs $290 - $650 and takes 21h 17m, you could also bus, which costs $160 - $280 and takes 22h 10m.
What companies run services between Windsor, CT, USA and Chicago, IL, USA?
Southwest Airlines and Delta fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Amtrak operates a train from Springfield to Chicago Union Station once daily. Tickets cost $290–600 and the journey takes 19h 46m.
- Website
- southwest.com
Flights from Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $75–380
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 26m
- When
- Tuesday and Wednesday
- Estimated price
- $85–400
- Website
- united.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 45m
- When
- Every day
- Estimated price
- $65–320
Flights from Bradley International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 42m
- When
- Every day
- Estimated price
- $70–350
- Website
- aa.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 57m
- When
- Every day
- Estimated price
- $65–320
Flights from Bradley International Airport to Chicago O'Hare International Airport via Philadelphia
- Ave. Duration
- 5h 28m
- When
- Every day
- Estimated price
- $70–340
- Website
- delta.com
Flights from Bradley International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 47m
- When
- Every day
- Estimated price
- $75–380
Flights from Bradley International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 16m
- When
- Every day
- Estimated price
- $65–320
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Springfield to Chicago Union Station
- Ave. Duration
- 19h 46m
- Frequency
- Once daily
- Estimated price
- $290–600
- Website
- https://www.amtrak.com/home.html
- Website
- flixbus.com
Bus from Hartford Union Station to New York Midtown
- Ave. Duration
- 2h 40m
- Frequency
- Once daily
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Once daily
- Schedules at
- flixbus.com
- Phone
- +1 (855) 626-8585
- Website
- https://www.flixbus.com
Bus from Hartford Union Station to New York Midtown
- Ave. Duration
- 2h 40m
- Frequency
- 6 times a week
- Estimated price
- $18–30
- Schedules at
- flixbus.com
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 16h 55m
- Frequency
- Twice daily
- Estimated price
- $140–240
- Schedules at
- flixbus.com
Want to know more about travelling around United States
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More Questions & Answers
Windsor to Chicago bus services, operated by FlixBus-us, arrive at New York Midtown station.
Chicago is 1h behind Windsor. It is currently 4:16 AM in Windsor and 3:16 AM in Chicago.
Windsor to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Windsor to Chicago is 901 miles. It takes approximately 15h 1m to drive from Windsor to Chicago.
Book your Windsor to Chicago train tickets online with Omio.
Book your Windsor to Chicago bus tickets online with Omio.
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