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How to get fromOrleans to Chicagoby bus, plane, bus (Flixbus), train, car, or bus (Greyhound)

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There are 10 ways to get from Orleans to Chicago by bus, plane, bus (Flixbus), train, car, 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. Bus to Boston Logan Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    7h 37m
    $120–466

  2. Bus, train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus
    2. Take the train from South Station to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    10h 35m
    $96–402

  3. Bus

    1. Take the bus from Main Street/CVS/Mobil, Orleans to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the bus from Boston to New York Midtownbus bus
    4. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    27h 5m
    $205–348

  4. Bus, train

    1. Take the bus from Main Street/CVS/Mobil, Orleans to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the train from Boston to Chicago Union Stationtrain train
    27h 19m
    $360–738

  5. Drive 1,045.3 mi

    1. Drive from Orleans to Chicagocar car 1,045.3 mi
    18h 15m
    $191–276

  6. Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    8h 2m
    $635–1,056

  7. Bus, bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus
    2. Take the bus from Boston to Boston Manchester Airportbus bus
    3. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    9h 21m
    $124–541

  8. Bus to Boston Logan Airport, fly to General Mitchell International Airport, train

    1. Take the bus from Hyannis Transportation Center to Logan International Airportbus bus
    2. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 6m
    $712–2,025

  9. Bus, train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the bus from Hyannis Transportation Center to Boston South Stationbus bus
    2. Take the train from South Station to TF Green Airporttrain train
    3. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    10h 4m
    $106–462

  10. Bus via Brook Park

    1. Take the bus from Main Street/CVS/Mobil, Orleans to Hyannis Transportation Centerbus bus
    2. Take the bus from Hyannis Transportation Center to Boston South Busesbus bus
    3. Take the bus from Boston to Cleveland Bus Stationbus bus
    4. Take the bus from Cleveland Bus Station to Chicago Bus Stationbus bus
    27h 12m
    $180–338

Orleans to Chicago by bus

Calendar15Weekly Buses
Duration27h 5mAverage Duration
Ticket$205Cheapest Price
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Questions & Answers

Map of how to get from Orleans to Chicago.ExpandLaunch map view
  • Distance: 966.3 mi
  • Duration: 7h 37m

What companies run services between Orleans, MA, USA and Chicago, IL, USA?

You can take a bus from Main Street/CVS/Mobil, Orleans to Chicago Bus Station via Hyannis Transportation Center, Boston, South Station, Boston, and New York Midtown in around 27h 5m.

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