Rome2Rio

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

Find Transport to Bridgeport

See all options

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 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
    6h 4m
    $148–734

  2. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    cheapest
    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 40m
    $92–346

  3. Train via Springfield (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to New Haventrain train Amtrak Hartford Line / ...
    22h 20m
    $300–619

  4. 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 45m
    $174–350

  5. Drive 839.7 mi

    1. Drive from Chicago to Bridgeportcar car 839.7 mi
    14h 9m
    $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 26m
    $98–374

  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)plane plane ORD - EWR
    2. Take the train from Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    7h 8m
    $114–380

  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 54m
    $142–699

  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 35m
    $102–496

  10. Train (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain train Northeast Regional / ...
    22h 28m
    $307–633

  11. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2642 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    25h 51m
    $148–246

Chicago to Bridgeport by train (Amtrak)

Calendar7Weekly Trains
Duration22h 20mAverage Duration
Ticket$300Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Bridgeport.ExpandLaunch map view
  • Distance: 792.1 mi
  • Duration: 6h 4m

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

You can take a train from Chicago Union Station to Bridgeport via Springfield and New Haven in around 22h 20m. 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 25h 51m.

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