Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 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 Sarasota–Bradenton International Airport, fly to Chicago Midway International Airport

    best
    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
    7h 57m
    $144–526

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

    cheapest
    1. Take the bus from Naples, FL to Bradenton/Sarasota - Mobil Gas Stationbus bus
    2. Fly from Sarasota–Bradenton International Airport (SRQ) to Chicago O'Hare International Airport (ORD)plane plane SRQ - ORD
    8h 29m
    $124–436

  3. Bus

    1. Take the bus from Naples, FL to University of Florida - 1956 Gale Lemerand Drbus bus
    2. Take the bus from Gainesville to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    31h 36m
    $255–399

  4. Bus, train

    1. Take the bus from Naples, FL to University of South Florida - 3801 USF Holly Drbus bus Miami
    2. Take the train from Tampa to Chicago Union Stationtrain train Floridian
    46h 41m
    $1,017–1,691

  5. Drive  1,256.4 mi

    1. Drive from Naples to Chicagocar car 1,256.4 mi
    22h 52m
    $230–332

  6. 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 18m

  7. Bus, bus to Fort Lauderdale–Hollywood International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Naples, FL to Miami Airportbus bus
    2. Take the bus from Miami Airport to Fort Lauderdale Airportbus bus
    3. Fly from Fort Lauderdale–Hollywood International Airport (FLL) to Chicago Midway International Airport (MDW)plane plane FLL - MDW
    8h 34m
    $208–451

  8. 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 43m

Sarasota–Bradenton International Airport (SRQ) to Chicago Midway International Airport (MDW) flights

Calendar29Weekly Planes
Duration4h 7mAverage Duration
Ticket$93Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Naples to Chicago.ExpandLaunch map view
  • Distance: 1,183.7 mi
  • Duration: 7h 57m

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, FL, University of Florida - 1956 Gale Lemerand Dr, Reitz Union, Rosa Parks RTS Downtown Station, Gainesville, and Atlanta Bus Station in around 31h 36m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

Booking & Getting There