There are 5 ways to get from Windsor Locks 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 10m$94–487Fly to Chicago O'Hare International Airport
cheapest- Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane BDL - ORD
4h 44m$69–367Train (Amtrak)
- Take the train from Springfield to Chicago Union Stationtrain Lake Shore Limited
21h 14m$520–828Bus (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 / ...
26h 7m$172–271Drive 889.6 mi
- Drive from Windsor Locks to Chicagocar 889.6 mi
15h 33m$163–235
Windsor Locks to Chicago by bus (Flixbus)
Comparing Your Travel Options
The cheapest way to get from Windsor Locks to Chicago is to fly which costs $65 - $370 and takes 4h 44m.
The fastest way to get from Windsor Locks to Chicago is to fly which takes 4h 10m and costs $90 - $490.
No, there is no direct bus from Windsor Locks to Chicago station. However, there are services departing from Elm St @ West St and arriving at Chicago Bus Station via Bradley Int'l Airport @ Terminal A, Hartford Union Station and New York Midtown. The journey, including transfers, takes approximately 26h 7m.
No, there is no direct train from Windsor Locks to Chicago station. However, there are services departing from Windsor Locks and arriving at Chicago Union Station via Springfield. The journey, including transfers, takes approximately 21h 14m.
The distance between Windsor Locks and Chicago is 792 miles. The road distance is 894.8 miles.
The best way to get from Windsor Locks to Chicago without a car is to train which takes 21h 14m and costs $500 - $850.
It takes approximately 4h 10m to get from Windsor Locks to Chicago, including transfers.
Windsor Locks to Chicago bus services, operated by Flixbus USA, depart from Hartford Union Station.
Windsor Locks to Chicago train services, operated by Amtrak, depart from Springfield station.
The best way to get from Windsor Locks to Chicago is to fly which takes 4h 10m and costs $90 - $490. Alternatively, you can train, which costs $500 - $850 and takes 21h 14m, you could also bus, which costs $170 - $280 and takes 26h 7m.
What companies run services between Windsor Locks, 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 23m
- When
- Every day
- Estimated price
- $90–480
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 31m
- When
- Monday, Thursday, Friday, and Sunday
- Estimated price
- $95–500
- Website
- united.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 50m
- When
- Every day
- Estimated price
- $65–360
Flights from Bradley International Airport to Chicago O'Hare International Airport via Washington Dulles
- Ave. Duration
- 4h 49m
- When
- Every day
- Estimated price
- $75–380
- Website
- aa.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 56m
- When
- Every day
- Estimated price
- $65–360
- Website
- delta.com
Flights from Bradley International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 4h 36m
- When
- Every day
- Estimated price
- $90–480
Flights from Bradley International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 4h 37m
- When
- Every day
- Estimated price
- $65–360
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
- 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
- $18–27
- Schedules at
- Flixbus USA
Bus from New York Midtown to Chicago Bus Station
- Ave. Duration
- 20h 25m
- Frequency
- Twice daily
- Estimated price
- $150–240
- Schedules at
- Flixbus USA
Want to know more about travelling around United States
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Booking & Getting There
Windsor Locks to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind Windsor Locks. It is currently 12:54 AM in Windsor Locks and 11:54 PM in Chicago.
Windsor Locks to Chicago train services, operated by Amtrak, arrive at Chicago Union Station.
Yes, the driving distance between Windsor Locks to Chicago is 895 miles. It takes approximately 15h 33m to drive from Windsor Locks to Chicago.
Book your Windsor Locks to Chicago train tickets online with Omio.
There are 1298+ hotels available in Chicago.