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

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There are 7 ways to get from Chicago to Callicoon by plane, car, train, bus, bus (Flixbus), 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 O'Hare International Airport to Wilkes-Barre/Scranton International Airport, drive

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Wilkes-Barre/Scranton International Airport (AVP)plane plane ORD - AVP
    2. Drive from Wilkes-Barre/Scranton International Airport (AVP) to Callicooncar car
    5h 23m
    $70–345

  2. Train, bus

    1. Take the train from Chicago Union Station to Syracuse Regional Transportation Centertrain train
    2. Take the bus from Syracuse Bus Station to Binghamtonbus bus
    3. Take the bus from Binghamton ShortLine Terminal to 31 Cottage Streetbus bus
    18h 9m
    $150–331

  3. 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 Monticello ShortLine Terminalbus bus ShortLine Hudson
    25h 4m
    $144–330

  4. Drive 765.8 mi

    1. Drive from Chicago to Callicooncar car 765.8 mi
    13h 4m
    $140–202

  5. Fly Chicago Midway International Airport to Laguardia Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from Port Authority Bus Terminal to Monticello ShortLine Terminalbus bus
    8h 48m
    $124–482

  6. Train, drive (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    2. Drive from Poughkeepsie Amtrak Station to Callicooncar car
    20h 23m
    $180–357

  7. 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 Port Authority Bus Terminal to Monticello ShortLine Terminalbus bus
    26h 3m
    $152–318

Chicago O'Hare International Airport (ORD) to Wilkes-Barre/Scranton International Airport (AVP) flights

Calendar21Weekly Planes
Duration1h 53mAverage Duration
Ticket$59Cheapest Price
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Questions & Answers

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

You can take a bus from Chicago Bus Station to Callicoon via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, Port Authority Bus Terminal, Monticello ShortLine Terminal, Sullivan County Government Center, and CJ’s Deli in around 25h 4m.

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