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

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There are 6 ways to get from Glastonbury to Chicago by plane, bus (Flixbus), train (Amtrak), car, or bus (Greyhound)

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 to Chicago Midway International Airport

    best
    1. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    5h 4m
    $85–432

  2. Fly 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 38m
    $70–362

  3. Bus

    1. Take the bus from Hartford Union Station to Port Authority Bus Terminalbus bus Boston
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    21h 59m
    $156–298

  4. Train (Amtrak)

    1. Take the train from Hartford Amtrak Station to Springfieldtrain train Amtrak Hartford Line / ...
    2. Take the train from Springfield to Chicago Union Stationtrain train Lake Shore Limited
    22h 41m
    $289–620

  5. Drive 893.1 mi

    1. Drive from Glastonbury to Chicagocar car 893.1 mi
    14h 54m
    $163–236

  6. Bus via Baltimore

    1. Take the bus from Hartford to New Yorkbus bus
    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
    27h 52m
    $181–418

Glastonbury to Chicago by bus and foot

Calendar15Weekly Services
Duration21h 59mAverage Duration
Ticket$156Cheapest Price
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Questions & Answers

Map of how to get from Glastonbury to Chicago.ExpandLaunch map view
  • Distance: 804.5 mi
  • Duration: 5h 4m

What companies run services between Glastonbury, CT, USA and Chicago, IL, 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 Main St @ Hebron Ave to Chicago Bus Station via Asylum St @ Union Pl, Hartford Union Station, Port Authority Bus Terminal, and New York Midtown in around 21h 59m.

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