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

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There are 10 ways to get from Cheshire to Chicago by train, plane, bus (Greyhound, Flixbus), train (Amtrak), 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 34m
    $226–597

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

    cheapest
    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 41m
    $84–386

  3. Bus

    1. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus Providence
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 52m
    $154–291

  4. Train (Amtrak)

    1. Take the train from Meriden to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    21h 59m
    $314–692

  5. Drive 870.3 mi

    1. Drive from Cheshire to Chicagocar car 870.3 mi
    14h 31m
    $159–230

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

    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 7m
    $94–446

  7. 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
    6h 14m
    $175–491

  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
    9h 8m
    $108–1,088

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

    1. Take the train from New Haven to Providencetrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    9h 5m
    $107–1,058

  10. 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 42m
    $320–1,256

Cheshire to Chicago by bus and foot

Calendar30Weekly Services
Duration21h 52mAverage Duration
Ticket$154Cheapest Price
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Questions & Answers

Map of how to get from Cheshire to Chicago.ExpandLaunch map view
  • Distance: 824 mi
  • Duration: 7h 34m

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

You can take a bus from S Main St @ Cheshire Town Hall to Chicago Bus Station via Temple St @ Chapel St, New Haven Union Station, Port Authority Bus Terminal, and New York Midtown in around 21h 52m. Alternatively, you can take a vehicle from Cheshire to Chicago Union Station via Meriden and Springfield in around 21h 59m.

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