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How to get fromNaples to Chicagoby bus, plane, bus (Flixbus, Greyhound), train, or car

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There are 10 ways to get from Naples to Chicago by bus, plane, bus (Flixbus, Greyhound), 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. Bus to Fort Lauderdale–Hollywood International Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Naples to Fort Lauderdale Airportbus bus
    2. Fly from Fort Lauderdale–Hollywood International Airport (FLL) to Chicago Midway International Airport (MDW)plane plane FLL - MDW
    6h 30m
    $150–532

  2. Bus

    1. Take the bus from Naples to Tampa USFbus bus
    2. Take the bus from University of South Florida to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    27h 29m
    $243–447

  3. Bus, train

    1. Take the bus from Naples to Tampa USFbus bus Miami–Tampa / ...
    2. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    46h 8m
    $617–1,311

  4. Drive 1,257.8 mi

    1. Drive from Naples to Chicagocar car 1,257.8 mi
    22h 52m
    $230–332

  5. Bus to Tampa, fly to Chicago Midway International Airport

    1. Take the bus from Naples to Tampa Airportbus bus
    2. Fly from Tampa (TPA) to Chicago Midway International Airport (MDW)plane plane TPA - MDW
    7h 40m
    $160–562

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

    1. Take the bus from Naples, FL to Bradenton/Sarasota - Mobil Gas Stationbus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW)plane plane SRQ - MDW
    8h 12m
    $174–691

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

    1. Take the bus from 3rd Ave S to Creekside WLinCbus bus
    2. Take the bus from Creekside Way Transfer @ Immokalee Rd to Coconut Point Mallbus bus
    3. Take the bus from Coconut Point Mall to South Fort Myers Transfer/P&Rbus bus
    4. Fly from Ft. Myers (RSW) to Chicago Midway International Airport (MDW)plane plane RSW - MDW
    9h 13m

  8. Bus to Punta Gorda Airport, fly to Chicago Midway International Airport

    1. Take the bus from Naples to Fort Myersbus bus
    2. Fly from Punta Gorda Airport (PGD) to Chicago Midway International Airport (MDW)plane plane PGD - MDW
    5h 54m
    $204–585

  9. Line 11 bus, line 600 bus, line 240 bus to Ft. Myers, fly to Chicago O'Hare International Airport

    1. Take the bus from 3rd Ave S to Creekside WLinCbus bus
    2. Take the bus from Creekside Way Transfer @ Immokalee Rd to Coconut Point Mallbus bus
    3. Take the bus from Coconut Point Mall to South Fort Myers Transfer/P&Rbus bus
    4. Fly from Ft. Myers (RSW) to Chicago O'Hare International Airport (ORD)plane plane RSW - ORD
    9h 46m

  10. Bus to Punta Gorda Airport, fly to South Bend, train

    1. Take the bus from Naples to Fort Myersbus bus
    2. Fly from Punta Gorda Airport (PGD) to South Bend (SBN)plane plane PGD - SBN
    3. Take the train from South Bend Airport to Van Buren St.train train
    7h 57m
    $270–905

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

Calendar19Weekly Planes
Duration3h 33mAverage Duration
Ticket$102Cheapest Price
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Questions & Answers

Map of how to get from Naples to Chicago.ExpandLaunch map view
  • Distance: 1,287.5 mi
  • Duration: 6h 30m

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

You can take a vehicle from Naples to Chicago Bus Station via Naples, University of South Florida, and Atlanta Bus Station in around 27h 29m.

Airlines
Train operators
Bus operators

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