Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from Connecticut to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 Bradley International Airport to Chicago Midway International Airport

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    4h 49m
    $99–498

  2. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 52m
    $65–308

  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
    $128–709

  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
    $103–287

  5. Drive 839.6 mi

    1. Drive from Bridgeport to Chicagocar car 839.6 mi
    14h
    $154–222

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

    1. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    5h 10m
    $394–708

  7. Train to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 46m
    $95–478

  8. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Stamford 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 30m
    $826–1,040

  9. Fly Westchester County Airport to Chicago O'Hare International Airport

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 32m
    $72–362

  10. 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
    25h 22m
    $122–345

Connecticut to Chicago by train (Amtrak)

Calendar10Weekly Trains
Duration21h 48mAverage Duration
Ticket$128Cheapest Price
See schedules

Questions & Answers

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

Southwest Airlines and Delta fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, 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.

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

Where to next?

Trips from Connecticut

Trips to Chicago

Popular routes