Rome2Rio

How to get fromBrookfield to Chicagoby train, plane, bus, or car

Find Transport to Chicago

See all options
QR code to download the Rome2Rio app

Download the Rome2Rio travel app

Scan QR code with your phone to download the app

Download on the App StoreGet it on Google Play

There are 10 ways to get from Brookfield to Chicago by train, plane, bus, or car

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 Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Brewster to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    8h 1m
    $219–685

  2. Train, train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from South Norwalk to New Haventrain train
    2. Take the train from New Haven to Hartford Amtrak Stationtrain train
    3. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    11h 12m
    $108–434

  3. Bus, train

    1. Take the bus from Cousins Cafe to Poughkeepsie Train Stationbus bus E
    2. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 47m
    $537–817

  4. Train, bus

    1. Take the train from Brewster to White Plainstrain train Harlem
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    26h 47m
    $165–262

  5. Drive  840.3 mi

    1. Drive from Brookfield to Chicagocar car 840.3 mi
    14h
    $139–201

  6. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Brewster to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h 19m
    $139–495

  7. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Brewster to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 3m
    $126–674

  8. Line 9 bus, train, train to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Strikers Bar & Grill to Pulse Pointbus bus
    2. Take the train from Danbury to South Norwalktrain train
    3. Take the train from Stamford Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    4. Take the train from New York Penn Station to Newark Airport Railroad Stationtrain train
    5. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    9h 43m

  9. Train, train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from South Norwalk to New Haventrain train
    2. Take the train from New Haven to Hartford Amtrak Stationtrain train
    3. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    10h 44m
    $138–624

  10. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Brewster to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    10h 35m
    $204–869

Brookfield to Chicago by bus and train

Calendar7Weekly Services
Duration26h 47mAverage Duration
Ticket$165Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Brookfield to Chicago.ExpandLaunch map view
  • Distance: 807.2 mi
  • Duration: 8h 1m

What companies run services between Brookfield, CT, USA and Chicago, IL, USA?

There is no direct connection from Brookfield to Chicago. However, you can take the line 9 bus to PC Richards, walk to Federal Road Park & Ride, take the line 12 bus to Brewster Village Mta, walk to Brewster, take the train to 125th Street - Harlem, walk to E 125 St/Lexington Av, take the bus to Laguardia Rd/94 St, walk to New-York-La-Guardia-Airport-LGA airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take a vehicle from Brookfield to Chicago Union Station via Cousins Cafe, Poughkeepsie Train Station, and Poughkeepsie Amtrak Station in around 20h 47m.

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