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

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

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    4h 34m
    $96–424

  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
    6h 12m
    $76–350

  3. Bus (Flixbus)

    1. Take the bus from Brookline to New York Midtownbus bus FlixBus N2605 / ...
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    22h 5m
    $174–307

  4. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 15m
    $330–700

  5. Drive 977.3 mi

    1. Drive from Brookline to Chicagocar car 977.3 mi
    16h 46m
    $179–258

  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
    4h 58m
    $611–1,014

  7. 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
    5h 41m
    $86–410

  8. 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 16m
    $104–496

  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
    6h 51m
    $89–426

  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 2m
    $688–1,983

Brookline to Chicago by bus (Flixbus)

Calendar14Weekly Buses
Duration22h 5mAverage Duration
Ticket$174Cheapest Price
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Questions & Answers

Map of how to get from Brookline to Chicago.ExpandLaunch map view
  • Distance: 873.5 mi
  • Duration: 4h 34m

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

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Brookline to Chicago Bus Station via New York Midtown in around 22h 5m.

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