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

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There are 9 ways to get from Brookline to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), 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 O'Hare International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    5h 1m
    $561–1,014

  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 19m
    $81–380

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    22h 15m
    $550–900

  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 N2640 / ...
    27h 8m
    $192–299

  5. Drive  977.3 mi

    1. Drive from Brookline to Chicagocar car 977.3 mi
    16h 46m
    $167–242

  6. Fly Boston Logan Airport to Chicago Midway International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    4h 49m
    $111–564

  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 46m
    $106–510

  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 50m
    $98–471

  9. 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 3m
    $186–798

Brookline to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration22h 15mAverage Duration
Ticket$550Cheapest Price
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Comparing Your Travel Options

Map of how to get from Brookline to Chicago.ExpandLaunch map view
  • Distance: 886.9 mi
  • Duration: 5h 1m

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

American Airlines, JetBlue Airways, and two other airlines fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $550–900 and the journey takes 22h 15m.

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