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

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

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 O'Hare International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)planeORD - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain
    6h 10m
    $68–294

  2. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain
    3. Take the train from 125th Street - Harlem to Bridgeporttrain
    22h 13m
    $123–328

  3. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus
    3. Take the train from Grand Central Terminal to Bridgeporttrain
    23h 21m
    $128–305

  4. Drive 839.7 mi

    1. Drive from Chicago to Bridgeportcar839.7 mi
    14h 1m
    $154–222

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

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)planeMDW - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain
    5h 53m
    $88–424

  6. 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)planeORD - JFK
    2. Take the train from Grand Central Terminal to Bridgeporttrain
    6h 30m
    $830–1,046

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)planeORD - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain
    7h 6m
    $68–515

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)planeORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus
    3. Take the train from Stamford to Bridgeporttrain
    7h 25m
    $94–662

  9. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)planeMDW - BDL
    2. Take the train from Windsor Locks to New Haventrain
    6h 46m
    $112–1,008

  10. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, line 206 bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)planeORD - HVN
    2. Take the bus from Lighthouse Park Terminus to Chapel St @ Orange Stbus
    3. Take the train from New Haven to Bridgeporttrain
    6h 51m
    $76–511

  11. Bus

    1. Take the bus from Chicago Bus Station to New York MidtownbusFlixBus N2640
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus StopbusGreyhound US0255s
    23h 21m
    $113–272

Chicago to Bridgeport by train

Calendar7Weekly Trains
Duration22h 13mAverage Duration
Ticket$123Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Bridgeport, CT, USA?

You can take a train from Chicago Union Station to Bridgeport via Croton-Harmon and 125th Street - Harlem in around 22h 13m. Alternatively, you can take a bus from Chicago Bus Station to Bridgeport Bus Stop via New York Midtown and Port Authority Bus Terminal in around 23h 21m.

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