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

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

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 18m
    $208–597

  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 24m
    $88–369

  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 / ...
    22h 2m
    $221–317

  4. 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 16m
    $332–1,256

  5. Drive 876 mi

    1. Drive from Madison to Chicagocar car 876 mi
    14h 52m
    $160–231

  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
    6h 50m
    $98–429

  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 2m
    $108–344

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

    1. Take the train from Madison to Stamford Amtrak Stationtrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 13m
    $116–501

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

    1. Take the train from Madison 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 14m
    $104–444

  10. 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 35m
    $315–646

  11. Bus via Baltimore

    1. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    27h 8m
    $228–351

Madison to Chicago by bus and foot

Calendar22Weekly Services
Duration22h 2mAverage Duration
Ticket$221Cheapest Price
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Questions & Answers

Map of how to get from Madison to Chicago.ExpandLaunch map view
  • Distance: 829.9 mi
  • Duration: 7h 18m

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

You can take a bus from Boston Post Rd @ Durham Rd to Chicago Bus Station via Church St @ George St, George St @ opp Orange St, Union Ave @ Union Station, New Haven Union Station, Port Authority Bus Terminal, and New York Midtown in around 22h 2m. Alternatively, you can take a train from Madison to Chicago Union Station via New Haven and Ny Moynihan Train Hall At Penn Station in around 23h 16m.

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