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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 8 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 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 20m
    $206–945

  2. Line 247 bus, line 102 bus to George Bush Intercontinental Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Fuqua Park & Ride to Travis St @ Dallas Stbus bus
    2. Take the bus from Travis St @ Dallas St to Bush IAH Terminal Cbus bus
    3. Fly from George Bush Intercontinental Airport (IAH) to Chicago O'Hare International Airport (ORD)plane plane IAH - ORD
    6h 9m
    $90–286

  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
    $207–407

  5. Drive 1,086.4 mi

    1. Drive from Pearland to Chicagocar car 1,086.4 mi
    18h 32m
    $199–287

  6. Fly William P. Hobby Airport to Chicago O'Hare International Airport

    1. Fly from William P. Hobby Airport (HOU) to Chicago O'Hare International Airport (ORD)plane plane HOU - ORD
    5h 16m
    $146–645

  7. 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
    $191–392

  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
    $227–350

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

Calendar53Weekly Planes
Duration2h 57mAverage Duration
Ticket$177Cheapest 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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