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How to get fromChicago to Connecticutby plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, or bus

Find Transport to Connecticut

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There are 11 ways to get from Chicago to Connecticut by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly Chicago Midway International Airport to Bradley International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    4h 24m
    $124–659

  2. Fly Chicago O'Hare International Airport to Bradley International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    5h 1m
    $84–449

  3. Train via Springfield (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to New Haventrain train Amtrak Hartford Line / ...
    22h 19m
    $284–611

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    23h 21m
    $141–238

  5. Drive 839.7 mi

    1. Drive from Chicago to Bridgeportcar car 839.7 mi
    14h 10m
    $154–222

  6. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Stamfordtrain train
    5h 31m
    $124–679

  7. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Stamfordtrain train
    5h 59m
    $84–349

  8. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Stamfordtrain train
    6h 8m
    $88–371

  9. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Main St @ Atlantic Stbus bus
    6h 41m
    $446–612

  10. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain train Northeast Regional / ...
    22h 28m
    $290–625

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Bridgeporttrain train
    23h 45m
    $187–379

Chicago to Connecticut by train (Amtrak)

Calendar7Weekly Trains
Duration22h 19mAverage Duration
Ticket$284Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Connecticut, USA?

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL) every 4 hours. Alternatively, you can take a train from Chicago Union Station to Bridgeport via Springfield and New Haven in around 22h 19m.

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