There are 5 ways to get from Chicago to Windsor 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 from Chicago Midway International Airport
best- Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane MDW - BDL
4h 40m$136–709Fly from Chicago O'Hare International Airport
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane ORD - BDL
5h 8m$96–489Train (Amtrak)
- Take the train from Chicago Union Station to Springfieldtrain Lake Shore Limited
20h 44m$516–794Bus (Flixbus)
- Take the bus from Chicago Bus Station to New York Midtownbus FlixBus N2640 / ...
- Take the bus from New York Midtown to Hartford Union Stationbus FlixBus 2610
24h 32m$173–257Drive 896.4 mi
- Drive from Chicago to Windsorcar 896.4 mi
15h 3m$164–237
Chicago to Windsor by train (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chicago to Windsor is to drive which costs $160 - $240 and takes 15h 3m.
The fastest way to get from Chicago to Windsor is to fly which takes 4h 40m and costs $130 - $750.
No, there is no direct bus from Chicago station to Windsor. However, there are services departing from Chicago Bus Station and arriving at Central St @ Broad St via New York Midtown, Hartford Union Station and Central Row South Side @ Travelers. The journey, including transfers, takes approximately 24h 32m.
No, there is no direct train from Chicago station to Windsor. However, there are services departing from Chicago Union Station and arriving at Windsor via Springfield. The journey, including transfers, takes approximately 20h 44m.
The distance between Chicago and Windsor is 797 miles. The road distance is 901.6 miles.
The best way to get from Chicago to Windsor without a car is to train which takes 20h 44m and costs $500 - $800.
It takes approximately 4h 40m to get from Chicago to Windsor, including transfers.
Chicago to Windsor bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Windsor train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Windsor is to fly which takes 4h 40m and costs $130 - $750. Alternatively, you can train, which costs $500 - $800 and takes 20h 44m, you could also bus, which costs $170 - $260 and takes 24h 32m.
What companies run services between Chicago, IL, USA and Windsor, CT, USA?
Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL) 5 times a day. Alternatively, Amtrak operates a train from Chicago Union Station to Springfield once daily. Tickets cost $500–800 and the journey takes 19h 19m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Bradley International Airport
- Ave. Duration
- 2h 7m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago Midway International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 15m
- When
- Saturday, Tuesday, Wednesday, and Sunday
- Estimated price
- $140–750
- Website
- aa.com
Flights from Chicago O'Hare International Airport to Bradley International Airport
- Ave. Duration
- 2h 25m
- When
- Every day
- Estimated price
- $90–480
Flights from Chicago O'Hare International Airport to Bradley International Airport via Reagan Washington
- Ave. Duration
- 4h 29m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
Flights from Chicago O'Hare International Airport to Bradley International Airport via Philadelphia
- Ave. Duration
- 4h 39m
- When
- Every day
- Estimated price
- $95–500
- Website
- united.com
Flights from Chicago O'Hare International Airport to Bradley International Airport
- Ave. Duration
- 2h 19m
- When
- Every day
- Estimated price
- $90–480
Flights from Chicago O'Hare International Airport to Bradley International Airport via Washington Dulles
- Ave. Duration
- 4h 47m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $100–550
- Website
- delta.com
Flights from Chicago Midway International Airport to Bradley International Airport via Detroit
- Ave. Duration
- 3h 48m
- When
- Every day
- Estimated price
- $130–700
Flights from Chicago O'Hare International Airport to Bradley International Airport via Detroit
- Ave. Duration
- 4h 10m
- When
- Every day
- Estimated price
- $90–480
Rome2Rio's guide to Amtrak
Contact DetailsContact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Chicago Union Station to Springfield
- Ave. Duration
- 19h 19m
- Frequency
- Once daily
- Estimated price
- $500–800
- Website
- Amtrak
- Phone
- +1 (855) 626-8585
- Website
- Flixbus USA
Bus from Chicago Bus Station to New York Midtown
- Ave. Duration
- 20h 10m
- Frequency
- Twice daily
- Estimated price
- $150–230
- Schedules at
- Flixbus USA
Bus from New York Midtown to Hartford Union Station
- Ave. Duration
- 2h 25m
- Frequency
- Twice daily
- Estimated price
- $17–27
- 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.
Related travel guides
Travelling to the US: What do I need to know?
Read the travel guide
Why you should take the train in the US
Read the travel guide
Italian Lakes: Getting around by train
Read the travel guide
Booking & Getting There
Chicago to Windsor bus services, operated by Flixbus USA, arrive at New York Midtown station.
Windsor is 1h ahead of Chicago. It is currently 11:05 PM in Chicago and 12:05 AM in Windsor.
Chicago to Windsor train services, operated by Amtrak, arrive at Springfield station.
Yes, the driving distance between Chicago to Windsor is 902 miles. It takes approximately 15h 3m to drive from Chicago to Windsor.
Book your Chicago to Windsor train tickets online with Omio.
There are 133+ hotels available in Windsor.