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How to get fromNewtown to Chicagoby taxi, plane, bus, train, or car

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There are 10 ways to get from Newtown to Chicago by taxi, plane, bus, train, 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. Taxi to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the taxi from Newtown to New-Haven-Airport-HVNtaxi taxi
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    4h 27m
    $191–441

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

    cheapest
    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    6h 47m
    $122–398

  3. Taxi, bus

    1. Take the taxi from Newtown to New Haven Union Stationtaxi taxi
    2. Take the bus from New Haven Union Station to Port Authority Bus Terminalbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    20h 38m
    $230–384

  4. Taxi, bus, train

    1. Take the taxi from Newtown to Chamber of Commercetaxi taxi
    2. Take the bus from Chamber of Commerce to Poughkeepsie Train Stationbus bus E
    3. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train
    20h 45m
    $351–684

  5. Drive 842 mi

    1. Drive from Newtown to Chicagocar car 842 mi
    14h 2m
    $154–222

  6. Bus to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the bus from W Main St @ Leavenworth St to Central Row South Side @ Travelersbus bus
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    6h 13m
    $132–458

  7. Train to Laguardia Airport, fly to Chicago Midway International Airport

    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
    6h 51m
    $223–614

  8. 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
    7h 11m
    $253–714

  9. 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
    7h 50m
    $129–504

  10. Train, bus

    1. Take the train from Brewster 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
    26h 14m
    $197–410

Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD) flights

Calendar4Weekly Planes
Duration2h 53mAverage Duration
Ticket$101Cheapest Price
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Questions & Answers

Map of how to get from Newtown to Chicago.ExpandLaunch map view
  • Distance: 822.7 mi
  • Duration: 4h 27m

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

There is no direct connection from Newtown to Chicago. However, you can take the taxi to New-Haven-Airport-HVN airport, fly to Chicago O'Hare International Airport (ORD), walk to O'Hare, then take the subway to Jackson-Blue. Alternatively, you can take the taxi to New Haven Union Station, take the bus to Port Authority Bus Terminal, walk to New York Midtown, then take the bus to Chicago Bus Station.

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