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

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There are 8 ways to get from Sugar Land to Chicago by plane, bus (Flixbus), bus, train, 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
    5h 16m
    $183–930

  2. Line 265 bus, line 102 bus to George Bush Intercontinental Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from West Bellfort Park & Ride to Louisiana St @ Prairie Stbus bus
    2. Take the bus from Travis St @ Texas Ave 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
    5h 53m
    $98–293

  3. 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
    $203–369

  4. 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
    26h 51m
    $264–563

  5. Drive 1,091.6 mi

    1. Drive from Sugar Land to Chicagocar car 1,091.6 mi
    18h 34m
    $200–288

  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
    7h 20m
    $118–530

  7. Bus to Austin-Bergstrom International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Katy to Austin Eastside Bus Plazabus bus
    2. Fly from Austin-Bergstrom International Airport (AUS) to Chicago Midway International Airport (MDW)plane plane AUS - MDW
    7h 28m
    $184–700

  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
    31h 45m
    $299–693

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

Calendar55Weekly Planes
Duration2h 59mAverage Duration
Ticket$166Cheapest Price
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Questions & Answers

What companies run services between Sugar Land, 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 Sugar Land to Dearborn & Harrison via West Bellfort Park & Ride, Louisiana St @ St Joseph Pkwy, 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.

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