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

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There are 7 ways to get from Pearland to Chicago by plane, bus, train, bus (Flixbus), car, 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 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
    $196–895

  2. Fly to Chicago O'Hare International Airport

    cheapest
    1. Fly from William P. Hobby Airport (HOU) to Chicago O'Hare International Airport (ORD)plane plane HOU - ORD
    5h 25m
    $146–645

  3. 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

  4. Bus

    1. Take the bus from Downtown Houston to Downtown Dallas / Deep Ellumbus bus FlixBus 2240 / ...
    2. Take the bus from Dallas Jefferson to Chicagobus bus Querétaro
    26h 16m
    $206–407

  5. Drive 1,086.2 mi

    1. Drive from Pearland to Chicagocar car 1,086.2 mi
    18h 43m
    $199–287

  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
    $196–492

  7. 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
    $227–380

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

Calendar58Weekly Planes
Duration3h 37mAverage Duration
Ticket$162Cheapest Price
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Questions & Answers

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 4 hours. Alternatively, you can take a vehicle from Pearland to Dearborn & Harrison via Fuqua Park & Ride, St Joseph Pkwy @ Travis St, Downtown Houston, Downtown Dallas / Deep Ellum, Gaston @ Good Latimer - S- Ns, Jefferson @ Marsalis - W - Ns, Dallas Jefferson, California & 35th Street, and 35th/Archer Orange Line Station in around 26h 16m.

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