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

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There are 10 ways to get from Southbury to Chicago by bus, plane, train (Amtrak), bus (Flixbus), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

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

    best
    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 58m
    $86–448

  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
    7h 17m
    $66–358

  3. Train (Amtrak)

    1. Take the train from Meriden to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    24h 9m
    $233–582

  4. Bus

    1. Take the bus from W Main St @ Leavenworth St to Asylum St @ Bushnell Parkbus bus 928
    2. Take the bus from Hartford Union Station to New York Midtownbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    27h 5m
    $170–264

  5. Drive  849.8 mi

    1. Drive from Southbury to Chicagocar car 849.8 mi
    14h 6m
    $156–224

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

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    8h 27m
    $163–607

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

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport to 125th Street - Harlemtrain train
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    8h 17m
    $233–707

  8. Line 229 bus to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from W Main St @ Leavenworth St to Temple St @ New Haven Greenbus bus
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    7h 28m
    $126–426

  9. Line 480 bus, train, line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Heritage Rd @ opp Pomperaug Woods to S Main St @ E Main Stbus bus
    2. Take the train from Waterbury to Bridgeporttrain train
    3. Take the train from Bridgeport to Stamfordtrain train
    4. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    5. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 48m
    $119–596

  10. Train via New York

    1. Take the train from Waterbury to Bridgeporttrain train
    2. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train
    3. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train
    24h 43m
    $257–606

Southbury to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration24h 9mAverage Duration
Ticket$233Cheapest Price
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Comparing Your Travel Options

Map of how to get from Southbury to Chicago.ExpandLaunch map view
  • Distance: 842.4 mi
  • Duration: 6h 58m

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

You can take a bus from Heritage Rd @ opp Pomperaug Woods to Chicago Union Station via S Main St @ E Main St, W Main St @ Leavenworth St, State St @ Meriden Transit Center, Meriden, and Springfield in around 24h 9m. Alternatively, you can take a bus from Heritage Rd @ opp Pomperaug Woods to Chicago Bus Station via S Main St @ E Main St, W Main St @ Leavenworth St, Asylum St @ Bushnell Park, Hartford Union Station, and New York Midtown in around 27h 5m.

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