Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from Brookline to Chicago by plane, train (Amtrak), bus (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 Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)planeBOS - MDW
    4h 48m
    $96–454

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

    cheapest
    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)planePVD - ORD
    6h 13m
    $59–853

  3. Train (Amtrak)

    1. Take the train from Boston to Chicago Union StationtrainLake Shore Limited
    22h 15m
    $150–750

  4. Bus (Flixbus)

    1. Take the bus from Brookline to New York MidtownbusFlixBus N2610 / ...
    2. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    25h 25m
    $127–278

  5. Drive 978.1 mi

    1. Drive from Brookline to Chicagocar978.1 mi
    16h 36m
    $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)planeBOS - ORD
    5h 9m
    $111–324

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

    1. Take the train from Boston to Providencetrain
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)planePVD - MDW
    5h 41m
    $79–943

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)planeMHT - MDW
    6h 25m
    $117–589

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

    1. Take the bus from Boston to Boston Manchester Airportbus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)planeMHT - ORD
    6h 52m
    $92–449

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

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)planeBOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain
    6h 54m
    $293–729

Brookline to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration22h 15mAverage Duration
Ticket$150Cheapest Price
See schedules

Questions & Answers

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) 4 times a day. Alternatively, Amtrak operates a train from Boston to Chicago Union Station once daily. Tickets cost $150–750 and the journey takes 22h 15m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Where to next?

Trips from Brookline

Trips to Chicago

Popular routes