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

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There are 10 ways to get from Trumbull to Chicago by train, plane, bus (Greyhound, Flixbus), train (Amtrak), 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 Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 27m
    $222–688

  2. Train to Bradley International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the train from New Haven to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 28m
    $101–479

  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 36m
    $130–218

  4. Train

    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Take the train from 125th Street - Harlem to Croton-Harmontrain train
    3. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train
    22h 29m
    $277–592

  5. Drive 842.5 mi

    1. Drive from Trumbull to Chicagocar car 842.5 mi
    14h 15m
    $154–223

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

    1. Take the train from Bridgeport to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 47m
    $152–588

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

    1. Take the train from Bridgeport 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
    7h 14m
    $343–899

  8. Train, line 971 bus to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Bridgeport to Stamfordtrain train
    2. Take the bus from Stamford Transportation Center @ Bay A to South Broadway @ Main Stbus bus
    3. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    8h 4m
    $114–578

  9. Train to Tweed-New Haven Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Bridgeport to New Haventrain train
    2. Fly from Tweed-New Haven Airport (HVN) to Chicago O'Hare International Airport (ORD)plane plane HVN - ORD
    6h 52m
    $181–579

  10. 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 35m
    $150–299

Trumbull to Chicago by bus and foot

Calendar7Weekly Services
Duration21h 36mAverage Duration
Ticket$130Cheapest Price
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Questions & Answers

Map of how to get from Trumbull to Chicago.ExpandLaunch map view
  • Distance: 798 mi
  • Duration: 6h 27m

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

You can take a bus from White Plains Rd. at Trumbull Center to Chicago Bus Station via Bridgeport Transportation Center, Bridgeport Bus Stop, Port Authority Bus Terminal, and New York Midtown in around 21h 36m. Alternatively, you can take a bus from White Plains Rd. at Trumbull Center to Chicago Union Station via Bridgeport Transportation Center, Bridgeport, 125th Street - Harlem, and Croton-Harmon Amtrak Station in around 22h 29m.

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