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

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There are 8 ways to get from Pearland to Chicago by plane, bus, train, car, bus (Flixbus), or train (Amtrak)

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 William P. Hobby Airport to Chicago Midway International Airport

    best
    1. Fly from William P. Hobby Airport (HOU) to Chicago Midway International Airport (MDW)plane plane HOU - MDW
    3h 15m
    $155–682

  2. Bus, train (Amtrak)

    1. Take the bus from Houston to Longviewbus bus Amtrak Thruway Connecting Service
    2. Take the train from Longview to Chicago Union Stationtrain train Texas Eagle
    25h 29m
    $397–765

  3. Bus

    1. Take the bus from Houston, TX - 808 Jefferson St to Dallas, TX - 1376 Marilla Stbus bus Houston
    2. Take the bus from Dallas Jefferson to Chicagobus bus Querétaro
    25h 46m
    $232–432

  4. Drive 1,086.4 mi

    1. Drive from Pearland to Chicagocar car 1,086.4 mi
    18h 27m
    $199–287

  5. Bus to George Bush Intercontinental Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Hobby Airport to Bush IAH Term E - Downtown Directbus bus
    2. Fly from George Bush Intercontinental Airport (IAH) to Chicago O'Hare International Airport (ORD)plane plane IAH - ORD
    6h 9m
    $177–414

  6. Bus, train via Hobby Airport

    1. Take the bus from Houston Bus Station to Longview Bus Stationbus bus Greyhound US1152
    2. Take the train from Longview to Chicago Union Stationtrain train Texas Eagle
    27h 10m
    $335–689

  7. Bus via New South Memphis

    1. Take the bus from Downtown Houston to Memphis Bus Stationbus bus
    2. Take the bus from Memphis Bus Station to Champaign Intermodal Trans Ctrbus bus
    3. Take the bus from Champaign Intermodal Trans Ctr to Chicago Bus Stationbus bus
    29h 11m
    $256–406

  8. Train (Amtrak)

    1. Take the train from Houston to New Orleans Union Passenger Terminaltrain train Sunset Limited
    2. Take the train from New Orleans Union Passenger Terminal to Chicago Union Stationtrain train City of New Orleans
    30h 23m
    $467–945

William P. Hobby Airport (HOU) to Chicago Midway International Airport (MDW) flights

Calendar64Weekly Planes
Duration3h 6mAverage Duration
Ticket$130Cheapest Price
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Questions & Answers

Map of how to get from Pearland to Chicago.ExpandLaunch map view
  • Distance: 956.6 mi
  • Duration: 3h 15m

What companies run services between Pearland, TX, USA and Chicago, IL, USA?

Southwest Airlines flies from William P. Hobby Airport (HOU) to Chicago Midway International Airport (MDW) every 3 hours. Alternatively, you can take a vehicle from Pearland to Dearborn & Harrison via Fuqua Park & Ride, Travis St @ Jefferson St, Houston, TX - 808 Jefferson St, Dallas, TX - 1376 Marilla St, Houston @ Young - S - Mb, Jefferson @ Marsalis - W - Ns, Dallas Jefferson, California & 35th Street, and 35th/Archer Orange Line Station in around 25h 46m.

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