Naples, FL, USA to Chicago, IL, USA from $90: 9 ways by bus, train, flight or car

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

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$90 by busBest price

1840 kmDistance

5h 32m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Naples to Chicago 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 Naples to Chicago

The journey from Naples to Chicago brings you from sunny coastal relaxation to the vibrant hustle and architectural wonders of the Windy City.

Best Neighbourhoods in Chicago

Chicago boasts diverse neighborhoods, each offering distinct vibes and experiences.

Wicker Park

• Trendy shops and art galleries abound.

• Lively nightlife with eclectic bars.

The Loop

• Iconic architecture and skyscrapers dominate the skyline.

• Home to major theaters and museums.

Lincoln Park

• Beautiful parks and gardens for outdoor enthusiasts.

• Rich dining scene featuring diverse cuisines.

Best Times To Visit Chicago's Attractions

Timing can elevate your experience at Chicago's iconic spots. Here are some recommendations to help you enjoy them to the fullest.

Millennium Park

Visit early morning or during weekdays to enjoy the gardens and art installations without crowds.

The Art Institute of Chicago

Explore on weekday afternoons for a quieter atmosphere to appreciate the masterpieces.

Navy Pier

Go during the off-peak hours of late afternoon or early evening for fewer tourists.

Chicago Weather: What to Expect Year-Round

Chicago experiences a mix of seasonal climates, with cold winters and warm summers; visiting during late spring or early fall often brings pleasantly mild temperatures. Understanding the weather patterns helps you prepare for your adventures and maximize your enjoyment of the city's outdoor offerings.

Culinary Delights in Chicago

Don’t miss the opportunity to savor deep-dish pizza at Giordano's, a hearty departure from the thin crusts of Naples; the combination of a buttery crust layered with gooey cheese and rich tomato sauce creates a comforting experience that embodies Chicago’s culinary identity. The lively atmosphere and local ingredients give this dining experience a distinctive charm, setting it apart from the flavors of your hometown.

Naples - Chicago operators

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

Bus Show bus routes

Contact phone

+1 214-849-8100

Website

https://www.greyhound.com/

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

Average Duration

2h 50m

Estimated price

$909-1100

Bus from Fort Myers Bus Stop to Sarasota Cattlemen Transfer Center

Average Duration

1h 15m

Estimated price

$1103-1565

Bus from Fort Myers Bus Stop to Tampa Bus Station

Average Duration

2h 25m

Estimated price

$11024-1100

Bus from West Palm Beach FL to Chicago IL

Average Duration

27h 20m

Estimated price

$4963-906

Contact phone

+1 239-533-2111

Website

https://leegov.com/

Bus from Creekside Transfer Center - Creekside Way @ Immokalee Rd to Coconut Pt. Mall - PLAZA DEL LAGO @ MEDITERRANEAN

Average Duration

35m

Estimated price

$1102-907

Bus from Coconut Pt. Mall - PLAZA DEL LAGO @ MEDITERRANEAN to South Fort Myers Transfer/P&R Arrival

Average Duration

37m

Estimated price

$1102-907

Bus from Coconut Pt. Mall - PLAZA DEL LAGO @ MEDITERRANEAN to Rosa Parks Transportation Ctr

Average Duration

1h 15m

Estimated price

$1102-907

Plane Show flights

Website

https://www.allegiantair.com/

Plane from Punta Gorda Airport to South Bend Airport

Average Duration

2h 46m

Estimated price

$901-904

Website

https://www.southwest.com/

Plane from Fort Myers (RSW) to Chicago Midway (MDW)

Average Duration

Estimated price

$2824-2825

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

Average Duration

3h 15m

Estimated price

$2827-2828

Train

Contact phone

+1 800-872-7245

Website

https://www.amtrak.com/home.html

Train from Milwaukee to Chicago Union Station

Average Duration

1h 29m

Estimated price

$907-4963

Train from Tampa to Washington Union Station

Average Duration

21h 44m

Estimated price

$1565-904

Train from Washington Union Station to Chicago Union Station

Average Duration

17h 40m

Estimated price

$9070-240

Taxi

Contact phone

+1 239-352-3333

Website

https://naplesfltaxi.com/

Taxi from Naples to Punta Gorda

Average Duration

1h 8m

Estimated price

$901-110270

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

Traveling between Naples and Chicago 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 a scenic road trip from Naples to Chicago, covering a distance of 1337 miles. The journey offers a mix of coastal views, charming towns, and sprawling countryside landscapes. 💸 Budget-conscious travelers can expect to spend between $240 to $350 on gas, tolls, and potential overnight stays along the route. Plan your stops wisely to make the most of your travel budget without compromising on comfort. 🏙️ Arrive in dynamic Chicago after approximately 21 hours and 53 minutes of driving, ready to explore iconic sights like Millennium Park, Navy Pier, and the vibrant neighborhoods that give the city its distinctive character.

Average price

$240 - $350

🛫 Experience a seamless journey from Naples to Chicago by taking a quick direct flight from Punta Gorda Airport to South Bend Airport. In just 2 hours and 46 minutes, Allegiant Air can efficiently transport you to your destination.

Departure Point

Punta Gorda Airport

Arrival Point

South Bend Airport

🚌 Although there is no direct bus from Naples to Chicago travelers can take a route with transfers. The journey involves stops at Creekside Transfer Center, Coconut Pt. Mall, Fort Myers, and West Palm Beach, lasting approximately 35 hours and 58 minutes. 💲 The prices for Naples to Chicago bus tickets range from $90 to $156, offering affordable travel options for those looking to explore the route by bus. Despite the duration of the journey, the scenic views and comfortable travel experience can make the trip memorable and enjoyable.

Departure Point

Fort Myers Bus Stop station

Arrival Point

Chicago IL station

Frequently asked questions

Find out more about the route from Naples to Chicago.

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The distance between Naples and Chicago is approximately 1143 miles. By car, it takes around 21 hours and 53 minutes to travel from Chicago to Naples. If you choose to fly, you can take a drive to Sarasota/Bradenton and then catch a flight to Chicago Midway, which would take about 5 hours and 24 minutes. Another option is to take a bus, which would take approximately 35 hours and 58 minutes to reach Chicago from Naples.

The most cost-effective way to travel from Naples to Chicago is by taking a bus. While it may take longer at approximately 35 hours and 58 minutes, the cost ranges from $90 to $160. For a more time-efficient option, driving to Sarasota/Bradenton and then flying to Chicago Midway is the quickest way, taking approximately 5 hours and 24 minutes and costing between $160 and $700. Depending on one's preferences and budget, both options provide different trade-offs in terms of time and cost.

The prices of a bus ticket between Naples and Chicago vary from $90 to $156, depending on the bus company and the specific travel dates. These prices are subject to change and may also be influenced by factors such as the level of demand and any promotional offers. It is recommended to check with the bus companies directly or use online travel booking platforms to get the most accurate and up-to-date prices.

To travel from Naples to Chicago without using public transportation, you can drive the distance of 1337 miles. The journey takes approximately 21 hours and 53 minutes, depending on traffic and breaks. Renting a car or using your own vehicle would be a convenient and flexible option. The cost to get from Naples to Chicago by car typically ranges from $240 to $350, considering gas expenses and any tolls along the way.

To travel from Naples to Chicago without a car, the best option is to take a bus. The journey takes approximately 35 hours and 58 minutes, and the cost ranges from $90 to $160. There are several bus companies that offer this route, providing a convenient and affordable transportation option for travelers.

There is no direct bus link between Naples and Chicago. However, there are bus services that can take you from Naples to Chicago with transfers. The journey, including transfers, takes approximately 35 hours and 58 minutes. The bus services are operated by Greyhound USA and Palmland Bus Lines.

The flight from Naples to Chicago typically takes around 2 hours and 40 minutes. The quickest route is a direct flight from Sarasota/Bradenton Airport to Chicago Midway Airport. As for the cost, it can vary depending on the airline, time of year, and how far in advance you book. However, on average, tickets for this route can range from $150 to $400.

There are plenty of options for accommodation in Chicago, with over 1116 hotels to choose from. Prices start at $58 per night, providing a range of affordable choices. Whether you prefer luxury hotels, budget-friendly options, or something in between, you'll find a variety of accommodations to suit your preferences and budget in Chicago.

Naples, FL, USA to Chicago, IL, USA from $90: 9 ways by bus, train, flight or car

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

Compare Train, Bus, Flight, and Driving Options

See more options

Traveling From Naples to Chicago

Best Neighbourhoods in Chicago

Best Times To Visit Chicago's Attractions

Chicago Weather: What to Expect Year-Round

Culinary Delights in Chicago

Naples - Chicago operators

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

Frequently asked questions

Trips from Naples

Trips to Chicago

Popular routes