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How to get fromBrooksville to Chicagoby shuttle, plane, taxi, bus, train, or car

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There are 8 ways to get from Brooksville to Chicago by shuttle, plane, taxi, 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. Shuttle to Tampa, fly to Chicago Midway International Airport

    best
    1. Take a shuttle bus from Brooksville Wawa to Tampa International Airport - Red Terminalshuttle bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    5h 45m
    $154–532

  2. Taxi, bus

    1. Take the taxi from Brooksville to Ocala, FLtaxi taxi
    2. Take the bus from Ocala, FL to University of Florida - 1956 Gale Lemerand Drbus bus
    3. Take the bus from Gainesville to Atlanta Bus Stationbus bus
    4. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    27h 39m
    $338–529

  3. Taxi, bus, train

    1. Take the taxi from Brooksville to Wildwood Amtrak Stationtaxi taxi
    2. Take the bus from Wildwood Amtrak Station to Jacksonvillebus bus
    3. Take the train from Jacksonville to Chicago Union Stationtrain train
    41h 3m
    $643–1,285

  4. Drive 1,076.6 mi

    1. Drive from Brooksville to Chicagocar car 1,076.6 mi
    19h 33m
    $197–284

  5. Shuttle to Tampa, fly to Chicago O'Hare International Airport

    1. Take a shuttle bus from Brooksville Wawa to Tampa International Airport - Red Terminalshuttle bus
    2. Fly from Tampa (TPA) to Chicago O'Hare International Airport (ORD)plane plane TPA - ORD
    6h 17m
    $219–632

  6. Taxi, shuttle to Orlando, fly to Chicago Midway International Airport

    1. Take the taxi from Brooksville to Sleep Inn and Suites Wildwood-The Villagestaxi taxi
    2. Take a shuttle bus from Sleep Inn and Suites Wildwood-The Villages to Orlando Airportshuttle bus
    3. Fly from Orlando (MCO) to Chicago Midway International Airport (MDW)plane plane MCO - MDW
    6h 22m
    $351–661

  7. Taxi, shuttle to Orlando, fly to Chicago O'Hare International Airport

    1. Take the taxi from Brooksville to Sleep Inn and Suites Wildwood-The Villagestaxi taxi
    2. Take a shuttle bus from Sleep Inn and Suites Wildwood-The Villages to Orlando Airportshuttle bus
    3. Fly from Orlando (MCO) to Chicago O'Hare International Airport (ORD)plane plane MCO - ORD
    6h 45m
    $221–771

  8. Bus to Sarasota–Bradenton International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Dade City to Bradentonbus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    8h 34m
    $224–734

Tampa (TPA) to Chicago Midway International Airport (MDW) flights

Calendar41Weekly Planes
Duration4hAverage Duration
Ticket$97Cheapest Price
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Questions & Answers

Map of how to get from Brooksville to Chicago.ExpandLaunch map view
  • Distance: 1,078 mi
  • Duration: 5h 45m

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

There is no direct connection from Brooksville to Chicago. However, you can take the taxi to Brooksville Wawa, take the shuttle to Tampa International Airport - Red Terminal, walk to Tampa (TPA) airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take the taxi to Ocala, FL, take the bus to University of Florida - 1956 Gale Lemerand Dr, walk to Reitz Union, take the line 46 bus to Rosa Parks RTS Downtown Station, walk to Gainesville, take the bus to Atlanta Bus Station, then take the bus to Chicago Bus Station.

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