There are 9 ways to get from Chicago to Southbury by plane, taxi, train (Amtrak), bus (Flixbus), car, bus, 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 Chicago O'Hare International Airport to Tweed-New Haven Airport, taxi
best- Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane ORD - HVN
- Take the taxi from New-Haven-Airport-HVN to Southburytaxi
4h 49m$198–650Fly Chicago O'Hare International Airport to Bradley International Airport, bus
cheapest- Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane ORD - BDL
- Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus
7h 40m$86–449Train (Amtrak)
- Take the train from Chicago Union Station to Springfieldtrain Lake Shore Limited
- Take the train from Springfield to Meridentrain Amtrak Hartford Line / ...
23h 32m$251–557Bus
- Take the bus from Chicago Bus Station to New York Midtownbus
- Take the bus from New York to New Havenbus
- Take the bus from Church St @ Chapel St to W Main St @ Waterbury Greenbus 229
26h 32m$168–263Drive 850.5 mi
- Drive from Chicago to Southburycar 850.5 mi
14h 8m$156–225Fly Chicago Midway International Airport to Bradley International Airport, bus
- Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane MDW - BDL
- Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus
7h 26m$116–619Fly Chicago O'Hare International Airport to Laguardia Airport, train
- Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane ORD - LGA
- Take the train from 125th Street - Harlem to Bridgeporttrain
- Take the train from Bridgeport to Waterburytrain
9h 10m$162–608Fly Chicago Midway International Airport to Laguardia Airport, train
- Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane MDW - LGA
- Take the train from 125th Street - Harlem to Bridgeporttrain
- Take the train from Bridgeport to Waterburytrain
8h 55m$232–708Train via New York
- Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain
- Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain
- Take the train from Bridgeport to Waterburytrain
25h 25m$276–604
Chicago to Southbury by train and bus (Amtrak)
Comparing Your Travel Options
The cheapest way to get from Chicago to Southbury is to drive which costs $150 - $230 and takes 14h 8m.
The fastest way to get from Chicago to Southbury is to fly and taxi which takes 4h 49m and costs $190 - $650.
No, there is no direct bus from Chicago station to Southbury. However, there are services departing from Chicago Bus Station and arriving at Heritage Rd @ Pomperaug Woods via 8 Av/W 31 St, New York, Church St @ Chapel St and Waterbury Green @ North Main. The journey, including transfers, takes approximately 26h 32m.
No, there is no direct train from Chicago station to Southbury. However, there are services departing from Chicago Union Station and arriving at Meriden via Springfield. The journey, including transfers, takes approximately 23h 32m.
The distance between Chicago and Southbury is 824 miles. The road distance is 855.5 miles.
The best way to get from Chicago to Southbury without a car is to train which takes 23h 32m and costs $250 - $600.
It takes approximately 4h 49m to get from Chicago to Southbury, including transfers.
Chicago to Southbury bus services, operated by Flixbus USA, depart from Chicago Bus Station.
Chicago to Southbury train services, operated by Amtrak, depart from Chicago Union Station.
The best way to get from Chicago to Southbury is to train which takes 23h 32m and costs $250 - $600. Alternatively, you can bus, which costs $160 - $270 and takes 26h 32m.
What companies run services between Chicago, IL, USA and Southbury, CT, USA?
You can take a train from Chicago Union Station to Heritage Rd @ Pomperaug Woods via Springfield, Meriden, State St @ Meriden Transit Center, E Main St @ Phoenix St, and Waterbury Green @ North Main in around 23h 32m. Alternatively, you can take a bus from Chicago Bus Station to Heritage Rd @ Pomperaug Woods via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, New York, New Haven, Church St @ Chapel St, W Main St @ Waterbury Green, and Waterbury Green @ North Main in around 26h 32m.
- Website
- southwest.com
Flights from Chicago Midway International Airport to Bradley International Airport
- Ave. Duration
- 2h 3m
- When
- Every day
- Estimated price
- $110–600
Flights from Chicago Midway International Airport to Bradley International Airport via Baltimore
- Ave. Duration
- 4h 36m
- When
- Monday to Saturday
- Estimated price
- $120–650
Flights from Chicago Midway International Airport to Laguardia Airport
- Ave. Duration
- 2h 6m
- When
- Every day
- Estimated price
- $130–700
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
- $230–550
- Website
- Amtrak
Train from Springfield to Meriden
- Ave. Duration
- 54 min
- Frequency
- Every 3 hours
- Estimated price
- $11–25
- Website
- Amtrak
Train from Chicago Union Station to Ny Moynihan Train Hall At Penn Station
- Ave. Duration
- 20h 12m
- Frequency
- Once daily
- Estimated price
- $240–550
- Website
- Amtrak
Train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Station
- Ave. Duration
- 1h 20m
- Frequency
- Hourly
- Estimated price
- $15–35
- 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
- $140–220
- Schedules at
- Flixbus USA
- Ave. Duration
- 41 min
- Estimated price
- $75–95
Norwalk Taxi & Car Service
- Phone
- +1 203-855-1764
- Website
- norwalktaxi.com
Yellow Cab
- Phone
- +1 203-334-2121
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
Chicago to Southbury bus services, operated by Flixbus USA, arrive at New York Midtown station.
Southbury is 1h ahead of Chicago. It is currently 2:01 PM in Chicago and 3:01 PM in Southbury.
Chicago to Southbury train services, operated by Amtrak, arrive at Springfield station.
Yes, the driving distance between Chicago to Southbury is 855 miles. It takes approximately 14h 8m to drive from Chicago to Southbury.
There are 83+ hotels available in Southbury.




