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

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There are 10 ways to get from Bridgeport to Chicago by train, plane, train (Amtrak), bus, car, or bus (Greyhound, Flixbus)

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 Midway International Airport

    best
    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 7m
    $113–524

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

    cheapest
    1. Take the train from Bridgeport 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 53m
    $86–326

  3. 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
    $308–637

  4. 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
    $172–370

  5. Drive 839.6 mi

    1. Drive from Bridgeport to Chicagocar car 839.6 mi
    14h 9m
    $154–222

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

    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 23m
    $108–294

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

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 3m
    $102–458

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

    1. Take the train from Bridgeport to Stamfordtrain train
    2. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 41m
    $93–436

  9. Fly Tweed-New Haven Airport to Chicago O'Hare International Airport

    1. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 35m
    $180–508

  10. 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 N2642 / ...
    25h 56m
    $149–256

Bridgeport to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 48mAverage Duration
Ticket$308Cheapest Price
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Questions & Answers

Map of how to get from Bridgeport to Chicago.ExpandLaunch map view
  • Distance: 792.5 mi
  • Duration: 6h 7m

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, Avelo Airlines flies from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD) 4 times a week.

Airlines
Train operators
Bus operators

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