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

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There are 10 ways to get from Chicago to Montgomery by plane, bus, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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. Fly Chicago Midway International Airport to Laguardia Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from Broadway & W 167th St to Union St & Ward St - Montgomerybus bus
    7h 38m
    $224–601

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

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from White Plains, Ny to Newburghbus bus
    9h 13m
    $118–551

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    19h 32m
    $374–704

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to New Yorkbus bus
    3. Take the bus from W 179th St & Broadway to Union St & Ward St - Montgomerybus bus
    20h 50m
    $156–268

  5. Drive 786.1 mi

    1. Drive from Chicago to Montgomerycar car 786.1 mi
    13h 3m
    $144–208

  6. Fly Chicago O'Hare International Airport to Laguardia Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the bus from Broadway & W 167th St to Union St & Ward St - Montgomerybus bus
    7h 59m
    $234–701

  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 Secaucus Lower Level to Campbell Halltrain train
    7h
    $184–955

  8. Fly Chicago Midway International Airport to Albany County Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany to Newburghbus bus
    8h 47m
    $168–828

  9. Fly Chicago Midway International Airport to Philadelphia International Airport, train, bus

    1. Fly from Chicago Midway International Airport (MDW) to Philadelphia International Airport (PHL)plane plane MDW - PHL
    2. Take the train from 30th Street Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the bus from Broadway & W 167th St to Union St & Ward St - Montgomerybus bus
    9h 20m
    $184–1,016

  10. Bus via Baltimore

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the bus from Broadway & W 167th St to Union St & Ward St - Montgomerybus bus
    24h 58m
    $179–384

Chicago to Montgomery by bus

Calendar20Weekly Buses
Duration20h 50mAverage Duration
Ticket$156Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Montgomery.ExpandLaunch map view
  • Distance: 833.6 mi
  • Duration: 7h 38m

What companies run services between Chicago, IL, USA and Montgomery, NY, USA?

Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $280–600 and the journey takes 18h 43m. Alternatively, you can take a bus from Chicago Bus Station to Union St & Ward St - Montgomery via Newark Penn Station, New York, and W 179th St & Broadway in around 20h 50m.

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