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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 Naplesbus bus
    7h 17m
    $180–732

  2. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to University of South Floridabus bus
    3. Take the bus from Tampa USF to Naplesbus bus
    27h 21m
    $247–443

  3. Train, bus

    1. Take the train from Chicago Union Station to Tampatrain train
    2. Take the bus from Tampa to Fort Myers Amtrak Bus Stopbus bus
    3. Take the bus from Fort Myers to Naplesbus bus
    47h 6m
    $661–1,281

  4. Drive 1,257.9 mi

    1. Drive from Chicago to Naplescar car 1,257.9 mi
    22h 59m
    $230–332

  5. Fly Chicago O'Hare International Airport to Miami International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Miami International Airport (MIA)plane plane ORD - MIA
    2. Take the bus from Miami Airport to Naplesbus bus
    8h 19m
    $214–842

  6. 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 Tampa Airport to Naplesbus bus
    8h 16m
    $184–712

  7. Fly Chicago Midway International Airport to Miami International Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Miami International Airport (MIA)plane plane MDW - MIA
    2. Take the bus from Miami Airport to Naplesbus bus
    8h 1m
    $184–692

  8. 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 49m
    $224–891

  9. 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

  10. 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 24m

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

Calendar23Weekly Planes
Duration3h 35mAverage Duration
Ticket$139Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Naples.ExpandLaunch map view
  • Distance: 1,287.5 mi
  • Duration: 7h 17m

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, Tampa USF, and Naples in around 27h 21m.

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