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How to get fromOdessa to Chicagoby plane, bus, train, or car

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There are 6 ways to get from Odessa to Chicago 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 to Chicago Midway International Airport

    best
    1. Fly from Midland International Airport (MAF) to Chicago Midway International Airport (MDW)plane plane MAF - MDW
    5h 33m
    $131–495

  2. Fly to Chicago O'Hare International Airport

    cheapest
    1. Fly from Midland International Airport (MAF) to Chicago O'Hare International Airport (ORD)plane plane MAF - ORD
    6h 17m
    $116–435

  3. Bus

    1. Take the bus from Stripes gas station - Odessa, TX to Dallasbus bus Dallas / ...
    2. Take the bus from Dallas Jefferson to Chicagobus bus Querétaro
    25h 30m
    $227–473

  4. Bus, train

    1. Take the bus from Stripes gas station - Odessa, TX to Fort Worth - La Gran Plazabus bus Dallas
    2. Take the train from Fort Worth to Chicago Union Stationtrain train Texas Eagle
    30h
    $394–792

  5. Drive 1,220.2 mi

    1. Drive from Odessa to Chicagocar car 1,220.2 mi
    20h 38m
    $223–322

  6. Bus, train via Midland

    1. Take the bus from Midland to Ft Worth Bus Stationbus bus Greyhound US1000
    2. Take the train from Fort Worth to Chicago Union Stationtrain train Texas Eagle
    30h 50m
    $403–837

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

Calendar37Weekly Planes
Duration6h 12mAverage Duration
Ticket$99Cheapest Price
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Questions & Answers

Map of how to get from Odessa to Chicago.ExpandLaunch map view
  • Distance: 1,070.2 mi
  • Duration: 5h 33m

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

Southwest Airlines flies from Midland International Airport (MAF) to Chicago Midway International Airport (MDW) 5 times a day. Alternatively, you can take a bus from Stripes gas station - Odessa, TX to Dearborn & Harrison via Dallas, Dallas Jefferson, California & 35th Street, and 35th/Archer Orange Line Station in around 25h 30m.

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