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

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There are 10 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
    7h 3m
    $138–456

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

    cheapest
    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
    7h 31m
    $128–356

  3. Taxi, bus

    1. Take the taxi from Brooksville to Wiregrass Park n Ridetaxi taxi
    2. Take the bus from Tampa Bus Station to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    29h 17m
    $264–416

  4. Taxi, train

    1. Take the taxi from Brooksville to Tampataxi taxi
    2. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    41h 55m
    $1,073–1,746

  5. Drive  1,075.1 mi

    1. Drive from Brooksville to Chicagocar car 1,075.1 mi
    19h 33m
    $197–284

  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 27m
    $341–631

  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 49m
    $246–571

  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 23m
    $199–604

  9. Bus to Sarasota–Bradenton International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Dade City to Bradentonbus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD)plane plane SRQ - ORD
    8h 55m
    $174–494

  10. Taxi, shuttle to Orlando, fly to General Mitchell International Airport, train

    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 General Mitchell International Airport (MKE)plane plane MCO - MKE
    4. Take the train from Milwaukee to Chicago Union Stationtrain train
    8h 46m
    $606–1,355

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

Calendar45Weekly Planes
Duration3hAverage Duration
Ticket$92Cheapest Price
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Comparing Your Travel Options

Map of how to get from Brooksville to Chicago.ExpandLaunch map view
  • Distance: 1,082 mi
  • Duration: 7h 3m

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 bus to Walmart at Cortez Blvd/SR50, walk 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 Wiregrass Park n Ride, take the line 275 bus to Marion Transit Center, take the bus to Atlanta Bus Station, then take the bus to Chicago Bus Station.

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