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

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There are 12 ways to get from Chicago to Madison by plane, train, train (Amtrak), bus (Flixbus, Greyhound), car, 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 Laguardia Airport, train

    best
    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 New Haventrain train
    7h 50m
    $228–697

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from Stamford to New Haventrain train
    9h 20m
    $96–1,026

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to New Haventrain train Amtrak Hartford Line / ...
    22h 49m
    $542–840

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from Port Authority Bus Terminal to New Haven Bus Stopbus bus
    3. Take the bus from Church St @ George St to Boston Post Rd @ Meigs Avebus bus 201
    25h 26m
    $172–253

  5. Drive  875.6 mi

    1. Drive from Chicago to Madisoncar car 875.6 mi
    14h 54m
    $160–231

  6. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 18m
    $164–758

  7. 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 New Haventrain train
    8h 1m
    $166–1,490

  8. Fly Chicago O'Hare International Airport to Bradley International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the train from Windsor Locks to New Haventrain train
    7h 47m
    $124–538

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    7h 37m
    $160–565

  10. Fly Chicago Midway International Airport to Theodore Francis Green State Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Theodore Francis Green State Airport (PVD)plane plane MDW - PVD
    2. Take the train from Providence to New Londontrain train
    3. Take the train from New London to Madisontrain train
    8h 39m
    $114–475

  11. Train via New York (Amtrak)

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train Lake Shore Limited / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to New Haventrain train Northeast Regional / ...
    23h 39m
    $551–1,419

  12. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore to New Yorkbus bus
    3. Take the train from Grand Central Terminal to New Haventrain train
    26h 8m
    $205–325

Chicago to Madison by train (Amtrak)

Calendar7Weekly Trains
Duration22h 49mAverage Duration
Ticket$542Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Madison.ExpandLaunch map view
  • Distance: 829.6 mi
  • Duration: 7h 50m

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

You can take a train from Chicago Union Station to Madison via Springfield and New Haven in around 22h 49m. Alternatively, you can take a bus from Chicago Bus Station to Boston Post Rd @ Meigs Ave via New York Midtown, Port Authority Bus Terminal, New Haven Bus Stop, Union Ave @ Union Station, Church St @ Chapel St, and Church St @ George St in around 25h 26m.

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