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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 6 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
    $153–680

  2. 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 5m
    $210–384

  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
    26h 51m
    $369–733

  4. Drive 1,091.6 mi

    1. Drive from Sugar Land to Chicagocar car 1,091.6 mi
    18h 29m
    $200–288

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

    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
    6h 3m
    $173–413

  6. 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
    $439–913

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 Sugar Land to Chicago.ExpandLaunch map view
  • Distance: 979 mi
  • Duration: 5h 16m

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 3 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 5m.

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