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

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

    best
    1. Take the train from Wakefield to North Stationtrain train
    2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 25m
    $87–415

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

    cheapest
    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    7h 49m
    $80–349

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    23h 49m
    $334–709

  4. Bus

    1. Take the bus from Boston to Newark Penn Stationbus bus Greyhound US0235 / ...
    2. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus FlixBus N2641 / ...
    24h 15m
    $175–317

  5. Drive 987.8 mi

    1. Drive from Wakefield to Chicagocar car 987.8 mi
    16h 58m
    $181–261

  6. Fly Boston Logan Airport to Chicago O'Hare International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 50m
    $607–915

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

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    6h 48m
    $104–480

  8. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from Ruggles to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 18m
    $90–409

  9. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    7h 22m
    $89–410

  10. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 52m
    $684–3,384

Wakefield to Chicago by train and subway (Amtrak)

Calendar7Weekly Services
Duration23h 49mAverage Duration
Ticket$334Cheapest Price
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Questions & Answers

Map of how to get from Wakefield to Chicago.ExpandLaunch map view
  • Distance: 882.2 mi
  • Duration: 5h 25m

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

Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $330–700 and the journey takes 22h 15m. Alternatively, you can take a bus from Main St @ Water St to Chicago Bus Station via Oak Grove Busway, Oak Grove, Downtown Crossing, Boston, and Newark Penn Station in around 24h 15m.

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