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How to get fromConnecticut to ChicagoBy plane, bus (Greyhound, Flixbus), train (Amtrak), car, train, or bus

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There are 10 ways to get from Connecticut to Chicago by plane, bus (Greyhound, Flixbus), train (Amtrak), 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 Bradley International Airport to Chicago Midway International Airport

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    4h 39m
    $89–478

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

    cheapest
    1. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    5h 1m
    $74–408

  3. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    20h 26m
    $119–218

  4. Train (Amtrak)

    1. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    21h 48m
    $276–635

  5. Drive 839.6 mi

    1. Drive from Bridgeport to Chicagocar car 839.6 mi
    14h 10m
    $154–222

  6. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 38m
    $95–488

  7. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 52m
    $80–318

  8. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Stamford to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 24m
    $527–1,240

  9. Fly Westchester County Airport to Chicago O'Hare International Airport

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 25m
    $447–612

  10. Train, bus

    1. Take the train from Bridgeport to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 25m
    $182–360

Connecticut to Chicago by bus and foot

Calendar7Weekly Services
Duration20h 26mAverage Duration
Ticket$119Cheapest Price
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Questions & Answers

What companies run services between Connecticut, 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 bus from Bridgeport Bus Stop to Chicago Bus Station via Port Authority Bus Terminal and New York Midtown in around 20h 26m.

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