Rome2Rio

How to get fromFort Sam Houston to Chicagoby plane, bus, train (Amtrak) or car

Find Transport to Chicago

See all options

There are 7 ways to get from Fort Sam Houston to Chicago by plane, bus, train (Amtrak), or car

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 San Antonio International Airport to Chicago Midway International Airport

    best
    1. Fly from San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW)planeSAT - MDW
    5h 28m
    $100–488

  2. Bus

    1. Take the bus from Tornado Bus Co - San Antonio to ChicagobusQuerétaro
    25h 29m
    $197–361

  3. Train (Amtrak)

    1. Take the train from San Antonio Station to Chicago Union StationtrainTexas Eagle
    31h 7m
    $163–828

  4. Drive 1,189.4 mi

    1. Drive from Fort Sam Houston to Chicagocar1,189.4 mi
    19h 37m
    $218–314

  5. Fly San Antonio International Airport to Chicago O'Hare International Airport

    1. Fly from San Antonio International Airport (SAT) to Chicago O'Hare International Airport (ORD)planeSAT - ORD
    5h 49m
    $155–418

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

    1. Take the bus from San Antonio Bus Station to Austin Eastside Bus Plazabus
    2. Fly from Austin-Bergstrom International Airport (AUS) to Chicago Midway International Airport (MDW)planeAUS - MDW
    7h 15m
    $116–645

  7. Bus to Austin-Bergstrom International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from San Antonio Bus Station to Austin Eastside Bus Plazabus
    2. Fly from Austin-Bergstrom International Airport (AUS) to Chicago O'Hare International Airport (ORD)planeAUS - ORD
    7h 36m
    $111–475

San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) flights

Calendar35Weekly Planes
Duration3h 45mAverage Duration
Ticket$97Cheapest Price
See schedules

Questions & Answers

What companies run services between Fort Sam Houston, TX, USA and Chicago, IL, USA?

Southwest Airlines flies from San Antonio International Airport (SAT) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, Tornado Bus Company operates a bus from Tornado Bus Co - San Antonio to Chicago once daily. Tickets cost $180–340 and the journey takes 23h 15m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Where to next?

Trips from Fort Sam Houston

Trips to Chicago

Popular routes