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

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

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    4h 32m
    $104–559

  2. Fly Chicago O'Hare International Airport to Bradley International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    5h
    $84–419

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    20h 16m
    $138–229

  4. 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
    $330–633

  5. Drive 839.7 mi

    1. Drive from Chicago to Bridgeportcar car 839.7 mi
    14h 9m
    $154–222

  6. 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
    $134–679

  7. 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 34m
    $104–359

  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
    $458–891

  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 10m
    $120–1,033

  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 40m
    $102–562

  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 41m
    $176–359

Chicago to Connecticut by bus and foot

Calendar7Weekly Services
Duration20h 16mAverage Duration
Ticket$138Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Connecticut.ExpandLaunch map view
  • Distance: 799.3 mi
  • Duration: 4h 32m

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

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL) 5 times a day. 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 20h 16m.

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