There are 5 ways to get from South 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
5h 21m$101–559Fly to Chicago O'Hare International Airport
cheapest- Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane BDL - ORD
5h 50m$71–369Train (Amtrak)
- Take the train from Hartford Amtrak Station to Springfieldtrain Amtrak Hartford Line / ...
- Take the train from Springfield to Chicago Union Stationtrain Lake Shore Limited
21h 35m$550–864Bus (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 42m$172–271Drive 895.3 mi
- Drive from South Windsor to Chicagocar 895.3 mi
15h 5m$148–214
South Windsor to Chicago by bus (Flixbus)
Comparing Your Travel Options
The cheapest way to get from South Windsor to Chicago is to drive which costs $140 - $220 and takes 15h 5m.
The fastest way to get from South Windsor to Chicago is to fly which takes 5h 21m and costs $100 - $600.
No, there is no direct bus from South Windsor to Chicago station. However, there are services departing from Main St @ Opp Pleasant Valley Rd and arriving at Chicago Bus Station via Market St @ Temple St, Hartford Union Station and New York Midtown. The journey, including transfers, takes approximately 25h 42m.
No, there is no direct train from South Windsor station to Chicago station. However, there are services departing from Hartford Amtrak Station and arriving at Chicago Union Station via Springfield. The journey, including transfers, takes approximately 21h 35m.
The distance between South Windsor and Chicago is 809 miles. The road distance is 900.6 miles.
The best way to get from South Windsor to Chicago without a car is to train which takes 21h 35m and costs $550 - $900.
It takes approximately 5h 21m to get from South Windsor to Chicago, including transfers.
South Windsor to Chicago bus services, operated by Flixbus USA, depart from Hartford Union Station.
South Windsor to Chicago train services, operated by Amtrak, depart from Hartford Amtrak Station.
The best way to get from South Windsor to Chicago is to fly which takes 5h 21m and costs $100 - $600. Alternatively, you can train, which costs $550 - $900 and takes 21h 35m, you could also bus, which costs $170 - $280 and takes 25h 42m.
What companies run services between South 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, you can take a vehicle from South Windsor to Chicago Union Station via Hartford Amtrak Station and Springfield in around 21h 35m.
- Website
- southwest.com
Flights from Bradley International Airport to Chicago Midway International Airport
- Ave. Duration
- 2h 29m
- When
- Every day
- Estimated price
- $95–550
Flights from Bradley International Airport to Chicago Midway International Airport via Baltimore
- Ave. Duration
- 4h 51m
- When
- Monday, Thursday, Friday, Sunday, and Saturday
- Estimated price
- $100–550
- 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 57m
- When
- Every day
- Estimated price
- $75–380
- Website
- delta.com
Flights from Bradley International Airport to Chicago Midway International Airport via Detroit
- Ave. Duration
- 5h 16m
- When
- Every day
- Estimated price
- $95–550
Flights from Bradley International Airport to Chicago O'Hare International Airport via Detroit
- Ave. Duration
- 5h 15m
- When
- Every day
- Estimated price
- $65–360
- Website
- aa.com
Flights from Bradley International Airport to Chicago O'Hare International Airport
- Ave. Duration
- 2h 55m
- When
- Every day
- Estimated price
- $65–360
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- Amtrak
Train from Hartford Amtrak Station to Springfield
- Ave. Duration
- 37 min
- Frequency
- Every 3 hours
- Estimated price
- $14–22
- 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
South Windsor to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.
Chicago is 1h behind South Windsor. It is currently 6:27 AM in South Windsor and 5:27 AM in Chicago.
South Windsor to Chicago train services, operated by Amtrak, arrive at Springfield station.
Yes, the driving distance between South Windsor to Chicago is 901 miles. It takes approximately 15h 5m to drive from South Windsor to Chicago.
Book your South Windsor to Chicago train tickets online with Omio.
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