Rome2Rio

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

Find Transport to Chicago

See all options

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 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 4m
    $220–686

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

    cheapest
    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 8m
    $118–517

  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
    $532–900

  4. 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 N2640 / ...
    23h 56m
    $150–245

  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 21m
    $150–586

  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 train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 56m
    $342–897

  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 45m
    $118–631

  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 41m
    $124–441

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

    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 38m
    $205–920

  11. 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
    26h 15m
    $174–282

Bridgeport to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 48mAverage Duration
Ticket$532Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Bridgeport to Chicago.ExpandLaunch map view
  • Distance: 792.4 mi
  • Duration: 6h 4m

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.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There