- Must visit
Art Institute Of Chicago
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Flights from Fort Myers, FL to Chicago, IL depart on average 55 times per day, taking around 3h 10m. Cheap flight tickets for this journey start at $104 (€85) if you book in advance.
There are 9 flights per day. The earliest flight runs at 00:10, the last at 22:34. The fastest flight covers the 1102 miles (1774 km) distance in 3h 5m. June is the cheapest month to fly.
Distance 1102 miles (1774 km) |
Average flight duration 3h 10m |
Cheapest ticket price $104 (€85) |
Flights per day 55 |
Direct flights 9 |
Fastest flight 3h 5m |
First flight 12:10 AM |
Last flight 10:34 PM |
Cheapest Month Jun |
Cheapest Day Fri |
High Season Jan - Mar |
Low Season Jul - Sep |
Best time to book 70 days |
Omio recommends booking the flight as it is the most popular option from Fort Myers, FL to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from $104. For those with little time consider booking a flight which can get you there in 3h 10m. The ticket price range depends on the travel mode: a flight costs an average of $104, and a train costs an average of $234.
Distance: 1102 miles (1774 km)
Most popular Flight | Train | Bus | Driving |
|---|---|---|---|
$225 Average price Cheapest | $403 Average price | $289 Average price | $248 Average price (fuel + tolls) |
6h 10m Average total duration Fastest 3h 10m Onboard + 3h 0m Additional time* | 46h 45m Average total duration 46h 15m Onboard + 30m Additional time* | 34h 29m Average total duration 33h 59m Onboard + 30m Additional time* | 18h 47m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Fort Myers, FL to Chicago, IL:
A flight is $64 (€52) less than a bus for this route with tickets for a bus from Fort Myers, FL to Chicago, IL costing on average $289 (€237).
A flight is $178 (€146) less than a train for this route with tickets for a train from Fort Myers, FL to Chicago, IL costing on average $403 (€330).
Other travel options to Chicago, IL take longer:
Bus takes on average 33h 59m.
Train takes on average 46h 15m.
Compare bus, train, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
One of the premier art museums in the US, known for Impressionist masterpieces, modern works, and the iconic bronze lions at its entrance.
Major natural history museum famous for Sue the T. rex, ancient cultures, and extensive science collections that appeal to both adults and children.
Large hands-on science museum in Hyde Park featuring a submarine, space exhibits, engineering displays, and immersive family-friendly experiences.
The city’s signature public space, home to Cloud Gate, gardens, events, and major skyline views that define modern Chicago.
Famous stretch of Michigan Avenue lined with historic buildings, shops, hotels, and frequent first-time visitor photo stops.
Highly popular waterfront promenade with architecture views, bridges, and one of the best urban walks in the city.
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
Moderate for a major U.S. city: casual food is manageable, but hotels, attractions, and downtown dining can be pricey.
Tip 18-20% in restaurants; 20%+ for great service. Tip bartenders USD 1-2 per drink, taxis about 10-15%, and hotel staff a few dollars.
Find answers to the most common questions about traveling from Fort Myers, FL to Chicago, IL by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

Most Fort Myers, FL to Chicago, IL flights use the Southwest Florida International Airport to O'Hare International Airport airport pair. Use this guide to compare Fort Myers, FL and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Here are some other resources that might have the information you need