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How to get fromChicago Midway Airport (MDW) to South Sideby plane, bus, subway, train (Amtrak), bus (Amtrak, Greyhound), bus (Flixbus), rideshare, or car

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There are 7 ways to get from Chicago Midway Airport (MDW) to South Side by plane, bus, subway, train (Amtrak), bus (Amtrak, Greyhound), bus (Flixbus), rideshare, 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 from Chicago Midway International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Pittsburgh International Airport (PIT)plane plane MDW - PIT
    2. Take the bus from Pittsburgh International Airport to Liberty Ave + Wood Stbus bus
    3h 22m

  2. Drive 462.5 mi

    cheapest
    1. Drive from Chicago Midway Airport (MDW) to South Sidecar car 462.5 mi
    7h 44m
    $85–122

  3. Subway to Chicago O'Hare International Airport, fly, bus, line 48 bus

    1. Take the subway from Midway to Clark/Lakesubway subway
    2. Fly from Chicago O'Hare International Airport (ORD) to Pittsburgh International Airport (PIT)plane plane ORD - PIT
    3. Take the bus from Pittsburgh International Airport to Liberty Ave + Wood Stbus bus
    4. Take the bus from Wood St + Sixth Ave to E Carson St + 21St Stbus bus
    5h 55m

  4. Train (Amtrak)

    1. Take the train from Chicago Union Station to Pittsburgh Amtrak Stationtrain train Floridian
    11h 28m
    $146–328

  5. Bus via Toledo

    1. Take the bus from Chicago Union Station to Toledobus bus Amtrak Thruway Connecting Service
    2. Take the bus from Toledo Bus Stop to Pittsburgh Intermodal Stationbus bus Greyhound US0420 / ...
    11h 35m
    $120–198

  6. Bus (Flixbus)

    1. Take the bus from Chicago to Pittsburgh Intermodal Stationbus bus FlixBus N2640
    13h 56m
    $86–146

  7. Airport Transfer

    1. Take the rideshare from Chicago Midway-MDW to South Siderideshare rideshare 462.5 mi
    7h 44m

Chicago Midway Airport (MDW) to South Side by subway, foot, bus, and train (Amtrak)

Calendar7Weekly Services
Duration11h 28mAverage Duration
Ticket$146Cheapest Price
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Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to South Side.ExpandLaunch map view
  • Distance: 427.1 mi
  • Duration: 3h 22m

What companies run services between Chicago Midway Airport (MDW), USA and South Side, PA, USA?

Amtrak operates a train from Chicago Union Station to Pittsburgh Amtrak Station once daily. Tickets cost $140–320 and the journey takes 9h 25m. Alternatively, you can take a subway from Midway to E Carson St + 21St St via Adams/Wabash, Adams & Wabash, Union Station Transit Center, Chicago Union Station, Toledo Bus Stop, Pittsburgh Intermodal Station, and Bedford Ave At Logan St in around 11h 35m.

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