Rome2Rio

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

Find Transport to Chicago

See all options

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

    best
    1. Take the train from Chappaqua to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 36m
    $105–578

  2. Fly Westchester County Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 27m
    $62–320

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 40m
    $209–493

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    24h 15m
    $120–217

  5. Drive 811.9 mi

    1. Drive from Chappaqua to Chicagocar car 811.9 mi
    13h 38m
    $149–214

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

    1. Take the train from Chappaqua to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 58m
    $65–308

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Chappaqua to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 14m
    $726–1,040

  8. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Chappaqua to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 37m
    $88–347

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

    1. Take the train from Chappaqua 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
    8h 10m
    $224–572

  10. Train, bus

    1. Take the train from Chappaqua to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    24h 48m
    $163–319

Chappaqua to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 40mAverage Duration
Ticket$209Cheapest Price
See schedules

Questions & Answers

What companies run services between Chappaqua, NY, USA and Chicago, IL, USA?

Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $200–480 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $110–200 and the journey takes 20h 25m.

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

Where to next?

Trips from Chappaqua

Trips to Chicago

Popular routes