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

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There are 10 ways to get from Chicago to Naples by plane, bus, bus (Greyhound, Flixbus), train, car, or subway

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 Fort Lauderdale–Hollywood International Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Fort Lauderdale–Hollywood International Airport (FLL)plane plane MDW - FLL
    2. Take the bus from Fort Lauderdale Airport to Naples, FLbus bus
    7h 16m
    $198–437

  2. Fly Chicago O'Hare International Airport to Sarasota–Bradenton International Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Sarasota–Bradenton International Airport (SRQ)plane plane ORD - SRQ
    2. Take the bus from Bradenton/Sarasota - Mobil Gas Station to Naples, FLbus bus
    8h 57m
    $128–466

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Gainesvillebus bus
    3. Take the bus from University of Florida - 1956 Gale Lemerand Dr to Naples, FLbus bus
    30h 15m
    $256–396

  4. Train, bus

    1. Take the train from Chicago Union Station to Tampatrain train Floridian
    2. Take the bus from University of South Florida - 3801 USF Holly Dr to Naples, FLbus bus Tallahassee
    46h 22m
    $1,059–1,614

  5. Drive  1,255.1 mi

    1. Drive from Chicago to Naplescar car 1,255.1 mi
    22h 52m
    $230–331

  6. Fly Chicago Midway International Airport to Sarasota–Bradenton International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Sarasota–Bradenton International Airport (SRQ)plane plane MDW - SRQ
    2. Take the bus from Bradenton/Sarasota - Mobil Gas Station to Naples, FLbus bus
    8h 25m
    $164–676

  7. Subway to Chicago Midway International Airport, fly to Ft. Myers, line 240 bus, line 600 bus, line 11 bus

    1. Take the subway from Adams/Wabash to Midwaysubway subway
    2. Fly from Chicago Midway International Airport (MDW) to Ft. Myers (RSW)plane plane MDW - RSW
    3. Take the bus from South Fort Myers Transfer/P&R to Coconut Point Mallbus bus
    4. Take the bus from Coconut Point Mall to Creekside Way Transfer @ Immokalee Rdbus bus
    5. Take the bus from Creekside WLinC to 3rd Ave Sbus bus
    10h

  8. Fly Chicago O'Hare International Airport to Ft. Myers, line 240 bus, line 600 bus, line 11 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Ft. Myers (RSW)plane plane ORD - RSW
    2. Take the bus from South Fort Myers Transfer/P&R to Coconut Point Mallbus bus
    3. Take the bus from Coconut Point Mall to Creekside Way Transfer @ Immokalee Rdbus bus
    4. Take the bus from Creekside WLinC to 3rd Ave Sbus bus
    10h 27m

  9. Fly Chicago Midway International Airport to Tampa, bus

    1. Fly from Chicago Midway International Airport (MDW) to Tampa (TPA)plane plane MDW - TPA
    2. Take the bus from University of South Florida - 3801 USF Holly Dr to Naples, FLbus bus
    10h 44m
    $170–498

  10. Train to General Mitchell International Airport, fly to Ft. Myers

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Ft. Myers (RSW)plane plane MKE - RSW
    11h 39m
    $223–944

Chicago Midway International Airport (MDW) to Fort Lauderdale–Hollywood International Airport (FLL) flights

Calendar24Weekly Planes
Duration3h 30mAverage Duration
Ticket$134Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Naples.ExpandLaunch map view
  • Distance: 1,287.1 mi
  • Duration: 7h 16m

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

You can take a bus from Chicago Bus Station to Naples via Atlanta Bus Station, Gainesville, Rosa Parks RTS Downtown Station, UF Health Archer Road, University of Florida - 1956 Gale Lemerand Dr, and Naples, FL in around 30h 15m.

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