Chicago, IL, USA to Naples, FL, USA from $93: 11 ways by bus, train, flight or car

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How to Get from Chicago to Naples: Cheapest, Fastest and Best Way

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$93 by busBest price

2149 kmDistance

21h 51m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Naples with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

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Traveling From Chicago to Naples

The journey from Chicago to Naples presents a fascinating contrast between the vibrant urban energy of the Windy City and the tranquil, sun-soaked shores of Naples.

Best Neighbourhoods in Naples

Naples boasts charming neighborhoods, each offering distinct experiences for visitors.

Old Naples

• Historic architecture and upscale boutiques

• Less than a mile from the beach

Pelican Bay

• Exclusive waterfront properties and luxury amenities

• Scenic parks and nature trails to explore

Vanderbilt Beach

• Gorgeous white sand beaches and lively atmosphere

• Close to dining, shopping, and entertainment options

Best Times To Visit Naples's Attractions

Timing your visit to Naples's attractions can elevate your experience significantly.

Naples Pier

Early morning offers stunning sunrise views and fewer crowds.

Naples Botanical Garden

Visit on weekday mornings for peaceful strolls and blossoming plants.

Fifth Avenue South

Late afternoon is ideal for shopping and enjoying vibrant dining options.

Naples Weather: What to Expect Year-Round

Naples enjoys a tropical climate with warm temperatures year-round, making it a desirable destination for sun-seekers. The best times to visit are typically from December to April when the weather is pleasantly mild, enhancing your outdoor experiences.

Dining Recommendation in Naples

For a taste of Naples, try the fresh catch of the day at The Dock, a waterfront restaurant that embodies the coastal charm and flavors of Southwest Florida. This experience diverges from Chicago's hearty fare, offering a lighter, more vibrant meal accented by fresh local ingredients and stunning views of the Gulf.

Chicago - Naples operators

Explore transport companies operating between Chicago and Naples, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane Show flights

Website

southwest.com

Plane from Chicago Midway (MDW) to Ft. Myers (RSW)

Average Duration

2h 49m

Estimated price

$180-930

Plane from Chicago Midway (MDW) to Ft. Myers (RSW) via Nashville

Average Duration

4h 53m

Estimated price

$180-930

Plane from Chicago Midway (MDW) to Ft. Myers (RSW) via Atlanta

Average Duration

Estimated price

$180-930

Plane from Chicago Midway (MDW) to Ft. Myers (RSW) via Columbus

Average Duration

5h 50m

Estimated price

$180-930

Website

delta.com

Plane from Chicago Midway (MDW) to Ft. Myers (RSW) via Atlanta

Average Duration

5h 12m

Estimated price

$937-935

Plane from Chicago O'Hare (ORD) to Ft. Myers (RSW) via Atlanta

Average Duration

4h 36m

Estimated price

$1531-1533

Website

united.com

Plane from Chicago O'Hare (ORD) to Ft. Myers (RSW)

Average Duration

3h 2m

Estimated price

$240-1537

Bus Show bus routes

Website

palmlandlines.com

Bus from Chicago IL to West Palm Beach FL

Average Duration

27h 20m

Estimated price

$1778-7107

Contact phone

+1 214-849-8100

Website

greyhound.com

Bus from Chicago Bus Station to Atlanta Bus Station

Average Duration

16h 10m

Estimated price

$1778-160

Bus from West Palm Beach Bus Station to Fort Myers Bus Stop

Average Duration

Estimated price

$7100-7108

Bus from Sarasota Cattlemen Transfer Center to Fort Myers Bus Stop

Average Duration

1h 15m

Estimated price

$2407-1772

Bus from Atlanta Bus Station to Orlando

Average Duration

Estimated price

$17775-2403

Bus from Chicago Bus Station to West Palm Beach FL

Average Duration

27h 20m

Estimated price

$1778-7107

Train

Contact phone

+1 800-872-7245

Website

amtrak.com

Train from Chicago Union Station to Washington Union Station

Average Duration

17h 25m

Estimated price

$17770-240

Train from Chicago Union Station to Milwaukee

Average Duration

1h 29m

Estimated price

$1777-1778

all-pages.other Show other routes

Contact phone

+1-239-878-3281

Other from Fort Myers, FL to Naples

Average Duration

47m

Estimated price

$2400-2403

Chicago to Naples: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Naples offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on an exciting road trip from the vibrant city of Chicago all the way to the sunny shores of Naples covering a distance of 1336 miles. Enjoy the diverse scenery and the freedom of the open road during the approximately 21 hours and 51 minutes journey. 💸 The cost of driving from Chicago to Naples ranges between $240 to $350, offering flexibility for different budgets. Plan your trip wisely to optimize your expenses and maybe even splurge on some local delicacies along the way.

Average price

$240 - $350

🛫 Experience a smooth and efficient journey from Chicago to Naples by taking a quick 2 hour and 45-minute direct flight from Chicago Midway Airport to Ft. Myers Airport. Delta and Southwest Airlines are the two main carriers providing this convenient route.

Departure Point

Chicago Midway Airport

Arrival Point

Ft. Myers Airport

🚌 Despite there being no direct bus from Chicago to Naples, passengers can embark on a scenic journey that spans approximately 36 hours and 32 minutes with transfers along the way. Services depart from Chicago IL and arrive at US 41 and 3rd Ave S in Naples 💸 The cost of a bus ticket between Naples and Chicago ranges from $93 to $153, making it a cost-effective option for travelers seeking a long-distance journey by road. Despite the duration and transfers, the route offers a unique perspective of the diverse landscapes as you make your way from the bustling city of Chicago to the sunny shores of Naples.

Departure Point

Chicago IL station

Arrival Point

Fort Myers Bus Stop station

Frequently asked questions

Find out more about the route from Chicago to Naples.

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The distance between Chicago and Naples is approximately 1143 miles. The typical travel time from Chicago to Naples can vary depending on the mode of transportation chosen. By flying from Chicago Midway airport to Sarasota/Bradenton and then driving, the travel time is around 6 hours and 5 minutes. If driving directly, it takes approximately 21 hours and 51 minutes to reach Chicago from Naples, while taking a bus can take around 36 hours and 36 minutes.

The most cost-effective option for traveling from Chicago to Naples is by taking a bus or night bus, which typically costs between $90 and $160. However, this option also takes the longest, with a travel time of approximately 36 hours and 36 minutes. If time is a priority, the fastest way to reach Naples from Chicago is by flying and then driving. This option takes about 6 hours and 5 minutes and can cost between $160 and $700.

The prices for traveling by bus from Chicago to Naples range from $93 to $153. These prices may vary based on factors such as the time of travel, the bus company, and any additional amenities or services offered. It is advisable to check with different bus providers and compare prices to find the best deal for your journey.

To travel from Chicago to Naples without using public transportation, the best option is to drive. The road distance between the two cities is 1336 miles, and it takes around 21 hours and 51 minutes to reach Naples by car. The cost of driving from Chicago to Naples can range from $240 to $350, depending on factors such as fuel prices and vehicle efficiency.

To travel from Chicago to Naples without a car, the best option is to take a bus. The journey takes approximately 36 hours and 36 minutes and costs between $90 and $160. There are both regular bus services and night buses available for this route. It's recommended to check bus schedules and fares in advance to plan your trip accordingly.

There is no direct bus link between Chicago and Naples. However, there are bus services available with transfers. The journey typically takes approximately 36 hours and 36 minutes, including transfers. The bus services are operated by Palmland Bus Lines and Greyhound USA.

The flight duration from Chicago Midway Airport to Sarasota/Bradenton Airport is typically around 2 hours and 30 minutes. This is the quickest way to travel between the two cities. As for the cost, it varies depending on factors such as the airline, time of booking, and availability of seats. On average, the flight ticket prices can range from $100 to $400 one way.

There are plenty of options for accommodation near Naples. With over 1024 hotels to choose from, visitors are spoiled for choice. Prices for hotels in Naples start at $84 per night, making it accessible for different budgets. Whether you're looking for luxury resorts or budget-friendly options, there are accommodations to suit all needs and preferences in the area.

Chicago, IL, USA to Naples, FL, USA from $93: 11 ways by bus, train, flight or car

How to Get from Chicago to Naples: Cheapest, Fastest and Best Way

Compare Train, Bus, Flight, and Driving Options

See more options

Traveling From Chicago to Naples

Best Neighbourhoods in Naples

Best Times To Visit Naples's Attractions

Naples Weather: What to Expect Year-Round

Dining Recommendation in Naples

Chicago - Naples operators

Chicago to Naples: Overview of Bus, Train, Flight, and Car Trips

Frequently asked questions

Trips from Chicago

Trips to Naples

Popular routes