Rome2Rio

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

Find Transport to Bridgeport

See all options

There are 11 ways to get from Chicago to Bridgeport by plane, train, train (Amtrak), bus (Flixbus, Greyhound), 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. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    5h 53m
    $98–474

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    7h 1m
    $62–505

  3. Train

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train
    2. Take the train from Croton-Harmon to 125th Street - Harlemtrain train
    3. Take the train from 125th Street - Harlem to Bridgeporttrain train
    22h 13m
    $160–317

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    23h 21m
    $109–175

  5. Drive 839.7 mi

    1. Drive from Chicago to Bridgeportcar car 839.7 mi
    14h 10m
    $154–222

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    6h 16m
    $68–284

  7. 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)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Bridgeporttrain train
    6h 32m
    $780–1,046

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

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    6h 41m
    $122–1,008

  9. 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)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus bus
    3. Take the train from Stamford to Bridgeporttrain train
    7h 25m
    $94–682

  10. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 12m
    $86–828

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Bridgeporttrain train
    23h 37m
    $125–278

Chicago to Bridgeport by train

Calendar7Weekly Trains
Duration22h 13mAverage Duration
Ticket$160Cheapest Price
See schedules

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.

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

More Questions & Answers

Trips from Chicago

Trips to Bridgeport

Popular routes