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

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There are 8 ways to get from Middlebury (village) to Chicago by bus, plane, train (Amtrak), bus (Greyhound), car, train, or bus (Flixbus)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus to Burlington International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Storrs Ave SB at Franklin St next to Davis Family Library to Burlington International Airportbus bus
    2. Fly from Burlington International Airport (BTV) to Chicago O'Hare International Airport (ORD)plane plane BTV - ORD
    5h 28m
    $88–433

  2. Train (Amtrak)

    1. Take the train from Middlebury to Schenectadytrain train Ethan Allen Express
    2. Take the train from Schenectady to Chicago Union Stationtrain train Lake Shore Limited
    19h 54m
    $298–627

  3. Bus via Brook Park

    1. Take the bus from Storrs Ave SB at Franklin St next to Davis Family Library to Greyhound \ Trailways Terminalbus bus 7
    2. Take the bus from Albany Bus Terminal, NY to Cleveland Bus Stationbus bus
    3. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    23h 18m
    $153–300

  4. Drive 877.3 mi

    1. Drive from Middlebury (village) to Chicagocar car 877.3 mi
    15h 45m
    $161–232

  5. Bus to Burlington International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Storrs Ave SB at Franklin St next to Davis Family Library to Burlington International Airportbus bus
    2. Fly from Burlington International Airport (BTV) to Chicago Midway International Airport (MDW)plane plane BTV - MDW
    7h 40m
    $103–503

  6. Train, bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the train from Middlebury to Saratoga Springs Amtrak Stationtrain train
    2. Take the bus from Saratoga Springs to Albanybus bus
    3. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 5m
    $156–653

  7. Train, bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Middlebury to Saratoga Springs Amtrak Stationtrain train
    2. Take the bus from Saratoga Springs to Albanybus bus
    3. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    8h 34m
    $136–573

  8. Bus

    1. Take the bus from Storrs Ave SB at Franklin St next to Davis Family Library to AMTRAK Station Rensselaerbus bus 7
    2. Take the bus from Albany-Rensselaer to New York, NYbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    25h 14m
    $182–319

Middlebury (village) to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration19h 54mAverage Duration
Ticket$298Cheapest Price
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Questions & Answers

Map of how to get from Middlebury (village) to Chicago.ExpandLaunch map view
  • Distance: 815.9 mi
  • Duration: 5h 28m

What companies run services between Middlebury (village), VT, USA and Chicago, IL, USA?

You can take a train from Middlebury to Chicago Union Station via Schenectady in around 19h 54m. Alternatively, you can take a bus from Storrs Ave SB at Franklin St next to Davis Family Library to Chicago Bus Station via Albany Bus Terminal, NY and Cleveland Bus Station in around 23h 18m.

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