Rome2Rio

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

Find Transport to Connecticut

See all options

There are 11 ways to get from Chicago to Connecticut by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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 O'Hare International Airport to Bradley International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    4h 41m
    $84–439

  2. 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
    $270–575

  3. 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
    $160–241

  4. Drive  839.7 mi

    1. Drive from Chicago to Bridgeportcar car 839.7 mi
    14h 12m
    $154–222

  5. Fly Chicago Midway International Airport to Bradley International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    4h 28m
    $114–609

  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 Stamfordtrain train
    5h 27m
    $146–580

  7. Fly Chicago Midway International Airport to Laguardia Airport, train

    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 Stamfordtrain train
    5h 13m
    $216–680

  8. 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 Stamfordtrain train
    6h 9m
    $338–891

  9. 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 Ny Moynihan Train Hall At Penn Station to Stamford Amtrak Stationtrain train
    6h 6m
    $152–1,433

  10. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus

    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 Main St @ Atlantic Stbus bus
    6h 36m
    $92–462

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to Bridgeporttrain train
    24h 21m
    $182–304

Chicago to Connecticut by train

Calendar7Weekly Trains
Duration22h 13mAverage Duration
Ticket$270Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Connecticut.ExpandLaunch map view
  • Distance: 813.2 mi
  • Duration: 4h 41m

What companies run services between Chicago, IL, USA and Connecticut, USA?

American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL) hourly. Alternatively, you can take a train from Chicago Union Station to Bridgeport via Croton-Harmon and 125th Street - Harlem in around 22h 13m.

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

More Questions & Answers