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How to get fromConnecticut to Chicago Midway Airport (MDW)by plane, bus (Greyhound, Flixbus), train (Amtrak), train, bus, subway, or car

Find Transport to Chicago Midway Airport (MDW)

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There are 10 ways to get from Connecticut to Chicago Midway Airport (MDW) by plane, bus (Greyhound, Flixbus), train (Amtrak), train, bus, subway, 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. Fly Bradley International Airport to Chicago Midway International Airport

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    3h 48m
    $82–423

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

    cheapest
    1. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    5h 32m
    $71–363

  3. Bus

    1. Take the bus from Bridgeport Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0255s
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 52m
    $145–252

  4. Train (Amtrak)

    1. Take the train from Bridgeport Amtrak Station to Ny Moynihan Train Hall At Penn Stationtrain train Northeast Regional / ...
    2. Take the train from Ny Moynihan Train Hall At Penn Station to Chicago Union Stationtrain train Lake Shore Limited / ...
    22h 29m
    $313–696

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

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    4h 50m
    $213–574

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

    1. Take the train from Stamford to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 21m
    $147–684

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

    1. Take the train from Stamford 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 49m
    $339–895

  8. Line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport, subway

    1. Take the bus from Main St @ Atlantic St to South Broadway @ Main Stbus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    3. Take the subway from Clark/Lake to Midwaysubway subway
    6h 50m
    $104–567

  9. Train, bus

    1. Take the train from Bridgeport 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 52m
    $180–388

  10. Drive 839.9 mi

    1. Drive from Bridgeport to Chicago Midway Airport (MDW)car car 839.9 mi
    14h 12m
    $154–222

Connecticut to Chicago Midway Airport (MDW) by bus and foot

Calendar7Weekly Services
Duration21h 52mAverage Duration
Ticket$145Cheapest Price
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Questions & Answers

Map of how to get from Connecticut to Chicago Midway Airport (MDW).ExpandLaunch map view
  • Distance: 788.3 mi
  • Duration: 3h 48m

What companies run services between Connecticut, USA and Chicago Midway Airport (MDW), USA?

Southwest Airlines and Delta fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from Bridgeport Bus Stop to Midway Orange Line Station via Port Authority Bus Terminal, New York Midtown, Chicago Bus Station, Harrison & Jefferson, and Cicero & 24th Place in around 21h 52m.

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