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How to get fromChicago to Odessaby plane, bus, train, or car

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There are 8 ways to get from Chicago to Odessa by plane, bus, train, 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 from Chicago Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Midland International Airport (MAF)plane plane MDW - MAF
    6h 27m
    $158–650

  2. Fly from Chicago O'Hare International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Midland International Airport (MAF)plane plane ORD - MAF
    6h 48m
    $138–510

  3. Bus

    1. Take the bus from Chicago to Dallas Jeffersonbus bus Chicago
    2. Take the bus from Dallas to Stripes gas station - Odessa, TXbus bus Dallas / ...
    26h 30m
    $222–472

  4. Train, bus

    1. Take the train from Chicago Union Station to Fort Worthtrain train Texas Eagle
    2. Take the bus from Fort Worth - La Gran Plaza to Stripes gas station - Odessa, TXbus bus Dallas
    30h 14m
    $396–760

  5. Drive 1,223.5 mi

    1. Drive from Chicago to Odessacar car 1,223.5 mi
    20h 39m
    $224–323

  6. Train to General Mitchell International Airport, fly

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Midland International Airport (MAF)plane plane MKE - MAF
    7h 55m
    $214–815

  7. Train to South Bend, fly

    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Midland International Airport (MAF)plane plane SBN - MAF
    8h 17m
    $168–659

  8. Train, bus via Midland

    1. Take the train from Chicago Union Station to Fort Worthtrain train Texas Eagle
    2. Take the bus from Ft Worth Bus Station to Midlandbus bus Greyhound US1000
    31h 19m
    $404–808

Chicago Midway International Airport (MDW) to Midland International Airport (MAF) flights

Calendar36Weekly Planes
Duration6h 4mAverage Duration
Ticket$127Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Odessa.ExpandLaunch map view
  • Distance: 1,070.9 mi
  • Duration: 6h 27m

What companies run services between Chicago, IL, USA and Odessa, TX, USA?

Southwest Airlines flies from Chicago Midway International Airport (MDW) to Midland International Airport (MAF) 5 times a day. Alternatively, you can take a bus from State & Harrison/Ida B Wells Drive to Stripes gas station - Odessa, TX via 35th/Archer Orange Line Station, California & 35th Street, Chicago, Dallas Jefferson, and Dallas in around 26h 30m.

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