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How to get fromBridgeport to Chicagoby train, plane, train (Amtrak), bus (Greyhound, Flixbus), car or bus

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There are 11 ways to get from Bridgeport to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), car, 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. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Bridgeport to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    6h 23m
    $73–284

  2. Train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Bridgeport to New Haventrain
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)planeHVN - ORD
    6h 23m
    $41–676

  3. Train (Amtrak)

    1. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn StationtrainNortheast Regional
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union StationtrainLake Shore Limited / ...
    21h 48m
    $138–759

  4. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus TerminalbusGreyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    23h 56m
    $108–245

  5. Drive 839.6 mi

    1. Drive from Bridgeport to Chicagocar839.6 mi
    14h
    $154–222

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

    1. Take the train from Bridgeport to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    6h 12m
    $93–444

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

    1. Take the train from Bridgeport to Grand Central Terminaltrain
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    6h 58m
    $830–1,046

  8. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from New Haven to Windsor Lockstrain
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)planeBDL - MDW
    7h 20m
    $106–896

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

    1. Take the train from Bridgeport to Stamfordtrain
    2. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    7h 48m
    $79–573

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Bridgeport to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 45m
    $202–634

  11. Train, bus

    1. Take the train from Bridgeport to Grand Central Terminaltrain
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
    25h 23m
    $127–355

Bridgeport to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 48mAverage Duration
Ticket$138Cheapest Price
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Questions & Answers

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

You can take a train from Bridgeport Amtrak Station to Chicago Union Station via Ny Moynihan Train Hall At Penn Station in around 21h 48m. 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 23h 56m.

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