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

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There are 10 ways to get from Chicago Union Station 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 26m
    $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 University of South Florida - 3801 USF Holly Dr to Naples, FLbus bus
    29h 40m
    $241–437

  3. 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 45m
    $639–1,297

  4. Drive 1,258.8 mi

    1. Drive from Chicago Union Station to Naplescar car 1,258.8 mi
    23h
    $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 Naples, FLbus bus
    8h 23m
    $214–847

  6. 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 Naples, FLbus bus
    8h 6m
    $184–697

  7. 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
    9h 4m
    $214–891

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

    1. Take the subway from Quincy 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 15m

  9. 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 37m

  10. 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
    11h 25m
    $198–522

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

Calendar23Weekly Planes
Duration3h 35mAverage Duration
Ticket$134Cheapest Price
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Questions & Answers

Map of how to get from Chicago Union Station to Naples.ExpandLaunch map view
  • Distance: 1,288.8 mi
  • Duration: 7h 26m

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

You can take a vehicle from Chicago Union Station to Naples via Chicago Bus Station, Atlanta Bus Station, University of South Florida - 3801 USF Holly Dr, and Naples, FL in around 29h 40m.

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