There are 6 ways to get from Windsor to Chicago by plane, train (Amtrak), bus (Flixbus), car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly Bradley International Airport to Chicago Midway International Airport
best- Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane BDL - MDW
4h 47m$91–469Fly Bradley International Airport to Chicago O'Hare International Airport
cheapest- Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane BDL - ORD
5h 18m$71–369Train (Amtrak)
- Take the train from Springfield to Chicago Union Stationtrain Lake Shore Limited
21h 17m$510–816Bus (Flixbus)
- 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 N2640 / ...
25h 38m$169–259Drive 895.6 mi
- Drive from Windsor to Chicagocar 895.6 mi
15h 2m$164–237Train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport
- Take the train from Windsor to New Haventrain
- Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane HVN - ORD
6h 27m$137–443
Windsor to Chicago by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Windsor to Chicago is to drive which costs $160 - $240 and takes 15h 2m.
The fastest way to get from Windsor to Chicago is to fly which takes 4h 47m and costs $90 - $470.
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 25h 38m.
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 $500 - $850.
It takes approximately 4h 47m to get from Windsor to Chicago, including transfers.
Windsor to Chicago bus services, operated by Flixbus USA, 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 47m and costs $90 - $470. Alternatively, you can train, which costs $500 - $850 and takes 21h 17m, you could also bus, which costs $160 - $260 and takes 25h 38m.
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) every 4 hours. Alternatively, Amtrak operates a train from Springfield to Chicago Union Station once daily. Tickets cost $500–800 and the journey takes 19h 46m.
- Website
- southwest.com
Flights from Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 20m
- When
- Every day
- Estimated price
- $85–460
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 30m
- When
- Tuesday to Saturday
- Estimated price
- $95–480
- Website
- united.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 47m
- When
- Every day
- Estimated price
- $65–360
Flights from Bradley International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 43m
- When
- Every day
- Estimated price
- $75–380
- Website
- delta.com
Flights from Bradley International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 36m
- When
- Every day
- Estimated price
- $85–460
Flights from Bradley International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 6m
- When
- Every day
- Estimated price
- $65–360
- Website
- aa.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 59m
- When
- Every day
- Estimated price
- $65–360
- Website
- aveloair.com
Flights from Tweed-New Haven Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 53m
- When
- Monday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $110–400
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Springfield to Chicago Union Station
- Ave. Duration
- 19h 46m
- Frequency
- Once daily
- Estimated price
- $500–800
- Website
- Amtrak
Train from Windsor to New Haven
- Ave. Duration
- 50 min
- Frequency
- Every 4 hours
- Estimated price
- $23–40
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Hartford Union Station to New York Midtown
- Ave. Duration
- 2h 40m
- Frequency
- Twice daily
- Estimated price
- $17–27
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $150–230
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.
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Booking & Getting There
Windsor to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Windsor. It is currently 12:31 PM in Windsor and 11:31 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 2m to drive from Windsor to Chicago.
Book your Windsor to Chicago train tickets online with Omio.
There are 1127+ hotels available in Chicago.