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

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There are 11 ways to get from Guilford to Chicago by train, plane, train (Amtrak), bus (Greyhound, Flixbus), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

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

    best
    1. Take the train from New Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 17m
    $227–696

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

    cheapest
    1. Take the train from New Haven to Hartford Amtrak Stationtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 36m
    $92–407

  3. Train (Amtrak)

    1. Take the train from New Haven to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    23h 28m
    $534–860

  4. Bus

    1. Take the bus from New Haven Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0230 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    25h 37m
    $167–264

  5. Drive  871.2 mi

    1. Drive from Guilford to Chicagocar car 871.2 mi
    14h 47m
    $159–230

  6. Fly Tweed-New Haven Airport to Chicago O'Hare International Airport

    1. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    5h 47m
    $118–422

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

    1. Take the train from New Haven to Hartford Amtrak Stationtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 2m
    $117–527

  8. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from New Haven to Stamfordtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 53m
    $130–1,215

  9. Train, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Guilford to New Londontrain train
    2. Take the train from New London to Providencetrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    8h 24m
    $134–625

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from New Haven to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    9h 52m
    $212–930

  11. Train via New York (Amtrak)

    1. Take the train from New Haven 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 / ...
    23h 37m
    $521–1,454

Guilford to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration23h 28mAverage Duration
Ticket$534Cheapest Price
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Comparing Your Travel Options

Map of how to get from Guilford to Chicago.ExpandLaunch map view
  • Distance: 825.9 mi
  • Duration: 7h 17m

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

You can take a train from Guilford to Chicago Union Station via New Haven and Springfield in around 23h 28m. Alternatively, you can take a bus from State St @ Boston Post Rd to Chicago Bus Station via Church St @ George St, George St @ opp Orange St, Union Ave @ Union Station, New Haven Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 25h 37m.

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