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

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There are 7 ways to get from Chicago to Oldsmar by plane, bus (Greyhound, Flixbus), train (Amtrak), car, train, subway, or bus

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 Chicago Midway International Airport to Tampa

    best
    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    6h 17m
    $108–410

  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
    $167–309

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    41h 11m
    $527–1,117

  4. Drive 1,119.7 mi

    1. Drive from Chicago to Oldsmarcar car 1,119.7 mi
    20h 19m
    $205–296

  5. Fly Chicago O'Hare International Airport to Tampa

    1. Fly from Chicago O'Hare International Airport (ORD) to Tampa (TPA)plane plane ORD - TPA
    6h 47m
    $158–560

  6. Train to General Mitchell International Airport, fly to Tampa

    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
    $680–1,169

  7. Subway to Chicago Midway International Airport, fly to Sarasota–Bradenton International Airport, line 203 bus, line 18 bus, line 62 bus, line 78 bus

    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    3. Take the bus from Downtown Station to Psta Grand Central Stationbus bus
    4. Take the bus from Grand Central Station - C to Tyrone Square Mall Shelter - Bbus bus
    5. Take the bus from Tyrone Square Mall Shelter - C to Main St + Pine Tree Lnbus bus
    6. Take the bus from Main St + Pine Tree Ln to Tampa Rd + Pinckney Stbus bus
    9h 50m
    $194–924

Chicago to Oldsmar by bus

Calendar7Weekly Buses
Duration28hAverage Duration
Ticket$167Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Oldsmar.ExpandLaunch map view
  • Distance: 1,026.9 mi
  • Duration: 6h 17m

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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