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How to get fromChicago to Oldsmarby plane, bus (Greyhound, Flixbus), train (Amtrak), car, or train

Find Transport to Oldsmar

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There are 6 ways to get from Chicago to Oldsmar by plane, bus (Greyhound, Flixbus), train (Amtrak), car, or train

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 Tampa (TPA)plane plane MDW - TPA
    6h 17m
    $138–410
  2. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus Greyhound US0100
    2. Take the bus from Atlanta Bus Station to Tampa Bus Stationbus bus FlixBus N2467
    28h
    $179–319
  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    41h 11m
    $591–1,206
  4. Drive 1,121.2 mi

    1. Drive from Chicago to Oldsmarcar car 1,121.2 mi
    20h 19m
    $205–296
  5. Fly from Chicago O'Hare International Airport

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    6h 46m
    $168–560
  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 Tampa (TPA)plane plane MKE - TPA
    7h 56m
    $173–773

Chicago to Oldsmar by bus

Calendar7Weekly Buses
Duration28hAverage Duration
Ticket$179Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Oldsmar, FL, USA?

Southwest Airlines and Delta fly from Chicago Midway International Airport (MDW) to Tampa (TPA) every 4 hours. Alternatively, you can take a bus from Chicago Bus Station to Tampa Rd & Commerce Blvd via Atlanta Bus Station, Marion Transit Center, and North West Transfer Center Tampa in around 28h.

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