Rome2Rio

How to get fromChicago to Woodburyby plane, bus, bus (Flixbus, Greyhound), train (Amtrak), car, taxi, or train

Find Transport to Woodbury

See all options

There are 11 ways to get from Chicago to Woodbury by plane, bus, bus (Flixbus, Greyhound), train (Amtrak), car, taxi, 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. Fly Chicago Midway International Airport to Bradley International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus bus
    6h 25m
    $116–528

  2. Fly Chicago O'Hare International Airport to Bradley International Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Bradley International Airport (BDL)plane plane ORD - BDL
    2. Take the bus from Main St @ Atheneum Sq to E Main St @ Phoenix Stbus bus
    6h 56m
    $90–428

  3. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from Port Authority Bus Terminal to New Haven Bus Stopbus bus
    3. Take the bus from Church St @ Chapel St to Grand St @ State Stbus bus 229
    22h 18m
    $165–296

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Springfieldtrain train Lake Shore Limited
    2. Take the train from Springfield to Meridentrain train Amtrak Hartford Line / ...
    22h 31m
    $317–649

  5. Drive 855 mi

    1. Drive from Chicago to Woodburycar car 855 mi
    14h 14m
    $156–226

  6. Fly Chicago O'Hare International Airport to Tweed-New Haven Airport, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Tweed-New Haven Airport (HVN)plane plane ORD - HVN
    2. Take the taxi from New-Haven-Airport-HVN to Woodburytaxi taxi
    5h 5m
    $262–595

  7. Fly Chicago Midway International Airport to Laguardia Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    3. Take the train from Bridgeport to Waterburytrain train
    7h 24m
    $242–617

  8. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Bridgeporttrain train
    3. Take the train from Bridgeport to Waterburytrain train
    7h 45m
    $252–717

  9. Fly Chicago O'Hare International Airport to Westchester County Airport, line 971 bus, train, taxi

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from Main St @ South Broadway to Stamford Transportation Center @ Bay Abus bus
    3. Take the train from Stamford to Bridgeporttrain train
    4. Take the train from Bridgeport to Waterburytrain train
    5. Take the taxi from Waterbury to Woodburytaxi taxi
    8h 57m
    $130–558

  10. Train via New York

    1. Take the train from Chicago Union Station to Ny Moynihan Train Hall At Penn Stationtrain train
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Bridgeport Amtrak Stationtrain train
    3. Take the train from Bridgeport to Waterburytrain train
    23h 57m
    $345–700

  11. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Bridgeporttrain train
    4. Take the train from Bridgeport to Waterburytrain train
    24h 53m
    $200–409

Chicago Midway International Airport (MDW) to Bradley International Airport (BDL) flights

Calendar41Weekly Planes
Duration3h 13mAverage Duration
Ticket$100Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Woodbury.ExpandLaunch map view
  • Distance: 842.7 mi
  • Duration: 6h 25m

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

You can take a bus from Chicago Bus Station to Woodbury via New York Midtown, Port Authority Bus Terminal, New Haven Bus Stop, Church St @ Chapel St, and Grand St @ State St in around 22h 18m. Alternatively, you can take a train from Chicago Union Station to Woodbury via Springfield, Meriden, State St @ Meriden Transit Center, and E Main St @ Phoenix St in around 22h 31m.

Airlines
Train operators
Bus operators
Other 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