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

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There are 12 ways to get from Chicago to Monroe by plane, taxi, train (Amtrak), bus (Flixbus, Greyhound), 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 Chicago O'Hare International Airport to Westchester County Airport, taxi

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the taxi from White-Plains-Airport-HPN to Monroetaxi taxi
    5h 1m
    $192–575

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

    cheapest
    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
    $150–578

  3. Train via Springfield (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 2m
    $318–749

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640 / ...
    2. Take the bus from Port Authority Bus Terminal to Bridgeport Bus Stopbus bus Greyhound US0255s
    24h 53m
    $168–249

  5. Drive  852.2 mi

    1. Drive from Chicago to Monroecar car 852.2 mi
    14h 16m
    $156–225

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

    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 Bridgeporttrain train
    6h 19m
    $256–731

  7. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    6h 37m
    $186–631

  8. 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
    4h 52m
    $158–435

  9. 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
    6h 30m
    $186–808

  10. 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 Newark Liberty International Airport to Bridgeport Amtrak Stationtrain train
    7h 22m
    $176–950

  11. Train (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 Bridgeport Amtrak Stationtrain train Northeast Regional / ...
    24h 10m
    $288–722

  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 Bridgeporttrain train
    26h 2m
    $195–318

Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN) flights

Calendar54Weekly Planes
Duration3h 26mAverage Duration
Ticket$80Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Monroe.ExpandLaunch map view
  • Distance: 792.6 mi
  • Duration: 5h 1m

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

You can take a train from Chicago Union Station to Monroe via Springfield and New Haven in around 22h 2m. Alternatively, you can take a bus from Chicago Bus Station to Monroe via New York Midtown, Port Authority Bus Terminal, Bridgeport Bus Stop, Bridgeport Transportation Center, and Monroe Tpk. at Stop & Shop in around 24h 53m.

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