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

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There are 10 ways to get from Lexington to Chicago by plane, bus (Flixbus), train (Amtrak), car, bus, 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 Boston Logan Airport to Chicago Midway International Airport

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    5h 57m
    $88–415

  2. Train to Theodore Francis Green State Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago O'Hare International Airport (ORD)plane plane PVD - ORD
    8h 4m
    $81–348

  3. Bus

    1. Take the bus from Cambridge to Manhattanbus bus Acb 1311
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    23h 35m
    $182–294

  4. Train (Amtrak)

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    24h 6m
    $335–707

  5. Drive 977.3 mi

    1. Drive from Lexington to Chicagocar car 977.3 mi
    16h 46m
    $179–258

  6. Fly Boston Logan Airport to Chicago O'Hare International Airport

    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    6h 22m
    $608–915

  7. Bus to Manchester Airport, fly to Chicago Midway International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    6h 55m
    $105–478

  8. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport

    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    7h 33m
    $91–408

  9. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    7h 30m
    $90–408

  10. Fly Boston Logan Airport to General Mitchell International Airport, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 24m
    $685–3,384

Lexington to Chicago by bus and foot

Calendar22Weekly Services
Duration23h 35mAverage Duration
Ticket$182Cheapest Price
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Questions & Answers

Map of how to get from Lexington to Chicago.ExpandLaunch map view
  • Distance: 885.6 mi
  • Duration: 5h 57m

What companies run services between Lexington, MA, USA and Chicago, IL, USA?

Southwest Airlines and Delta fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW) every 4 hours. Alternatively, you can take a bus from Massachusetts Ave opp Grant St to Chicago Bus Station via Alewife, Cambridge, Manhattan, and New York Midtown in around 23h 35m.

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