- Must visit
Edison and Ford Winter Estates
Historic riverfront estate museum with Thomas Edison and Henry Ford homes, gardens, and a large inventions museum. One of Fort Myers' signature cultural attractions.
Flights from Chicago, IL to Fort Myers, FL depart on average 54 times per day, taking around 2h 54m. Cheap flight tickets for this journey start at $88 (€72) if you book in advance.
There are 9 flights per day. The earliest flight runs at 00:10, the last at 21:55. The fastest flight covers the 1102 miles (1774 km) distance in 2h 47m. December is the cheapest month to fly.
Distance 1102 miles (1774 km) |
Average flight duration 2h 54m |
Cheapest ticket price $88 (€72) |
Flights per day 54 |
Direct flights 9 |
Fastest flight 2h 47m |
First flight 12:10 AM |
Last flight 9:55 PM |
Cheapest Month Dec |
Cheapest Day Thu |
High Season Jan - Mar |
Low Season Jul - Sep |
Busiest Day Thu |
Least Busy Day Thu |
Best time to book 28 days |
Cheapest price
$88
Average price
$195
Fastest journey
2 h 47 m
Average duration
2 h 54 m
Flights per day
4
Distance
1774 km
The best way to find a cheap flight ticket from Chicago, IL to Fort Myers, FL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Fort Myers, FL will cost around $195 if you buy it on the day, but the cheapest tickets can be found for only $88.
Of the 4 flights that leave Chicago, IL for Fort Myers, FL onSat, Jun 27, 4 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Jun 27 the direct flights cover the 1774 km distance in an average of 2 h 54 m but if you time it right, some flights will get you there in just 2 h 47 m .
On Sat, Jun 27 the longest flights will take 3 h 6 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.








Omio recommends booking the flight as it is the most popular option from Chicago, IL to Fort Myers, FL among Omio's users. If you are prioritising price take the flight with prices starting from $88. For those with little time consider booking a flight which can get you there in 2h 54m. The ticket price range depends on the travel mode: a flight costs an average of $88, and a train costs an average of $173.
Distance: 1102 miles (1774 km)
Most popular Flight | Train | Bus | Driving |
|---|---|---|---|
$223 Average price Cheapest | $357 Average price | $262 Average price | $266 Average price (fuel + tolls) |
5h 54m Average total duration Fastest 2h 54m Onboard + 3h 0m Additional time* | 44h 35m Average total duration 44h 5m Onboard + 30m Additional time* | 29h 30m Average total duration 29h 0m Onboard + 30m Additional time* | 19h 12m Average total duration (door-to-door) |
![]() Most popular airline | ![]() Most popular train company | ![]() Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Fort Myers, FL:
A flight is $38 (€31) less than a bus for this route with tickets for a bus from Chicago, IL to Fort Myers, FL costing on average $262 (€214).
A flight is $134 (€110) less than a train for this route with tickets for a train from Chicago, IL to Fort Myers, FL costing on average $357 (€292).
Other travel options to Fort Myers, FL take longer:
Bus takes on average 29h 0m.
Train takes on average 44h 5m.
The table below shows live departures for Chicago, IL to Fort Myers, FL flights for today, Saturday, June 20. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
UA5518 · UA1100 | 3:50 PM O'Hare International Airport | 19h07 | 11:57 AM Southwest Florida International Airport | 1 transfer | |
UA2437 · UA1406 | 3:53 PM O'Hare International Airport | 18h00 | 10:53 AM Southwest Florida International Airport | 1 transfer | |
UA2618 | 4:26 PM O'Hare International Airport | 3h08 | 8:34 PM Southwest Florida International Airport | 0 transfersDirect | |
B6406 · B61529 | 5:22 PM O'Hare International Airport | 17h15 | 11:37 AM Southwest Florida International Airport | 1 transfer | |
UA2652 · UA1100 | 5:50 PM O'Hare International Airport | 17h07 | 11:57 AM Southwest Florida International Airport | 1 transfer | |
UA2202 · UA1406 | 6:12 PM O'Hare International Airport | 15h41 | 10:53 AM Southwest Florida International Airport | 1 transfer | |
| Sunday, June 21 | |||||
![]() | 12:42 AM Chicago, IL | 2h48 | 3:30 AM Fort Myers, FL | 0 transfersDirect | |
| Saturday, June 20 | |||||
UA2813 · UA1361 | 8:09 PM O'Hare International Airport | 18h43 | 3:52 PM Southwest Florida International Airport | 1 transfer | |
UA457 · UA1100 | 9:29 PM O'Hare International Airport | 13h28 | 11:57 AM Southwest Florida International Airport | 1 transfer | |
| Sunday, June 21 | |||||
![]() | 11:50 AM Chicago, IL | 2h47 | 2:37 PM Fort Myers, FL | 0 transfersDirect | |
![]() | 1:20 PM Chicago, IL | 2h56 | 4:16 PM Fort Myers, FL | 0 transfersDirect | |
![]() | 6:55 PM Chicago, IL | 3h06 | 10:01 PM Fort Myers, FL | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
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 Fort Myers — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Fort Myers trip today.
Historic riverfront estate museum with Thomas Edison and Henry Ford homes, gardens, and a large inventions museum. One of Fort Myers' signature cultural attractions.
Family-friendly science and local history museum with interactive exhibits, aquariums, and hands-on learning. Popular for visitors with children.
Downtown visual and performing arts venue hosting exhibitions, events, and community programming in a restored historic federal building.
The city's most popular walkable historic area, with brick streets, murals, shops, galleries, and nightlife. The top area to explore on foot.
Seasonal waterfront park famous for winter manatee viewing, boardwalks, and kayak access. Widely shared on social media during cooler months.
Popular nature preserve with a scenic boardwalk through wetlands, wildlife spotting, and strong appeal among photographers and nature lovers.
A Southwest Florida seasonal specialty, usually served chilled with mustard sauce. They are prized for sweet, firm meat and are strongly associated with Gulf Coast seafood culture.
A classic Florida coastal dish made with fresh local grouper, often grilled, blackened, or fried on a bun. It is a staple at waterfront restaurants around Fort Myers.
Fritters made with chopped conch in a seasoned batter, reflecting Caribbean and old Florida influences common in Southwest Florida seafood menus.
An established downtown fine-dining restaurant known for Southern-influenced cuisine, steaks, and seafood served in historic house-style rooms with a romantic atmosphere.
A popular Florida casual restaurant known for seafood, Yucatan-style flavors, and rum drinks in a lively, polished setting.
A casual, well-known seafood restaurant near the water, valued for fresh Gulf seafood and an old-Florida fish-house feel.
Moderate by U.S. standards. Casual dining is affordable, but beach areas, hotels, and seasonal travel can raise costs noticeably.
Tip 18-20% in restaurants; 20%+ for excellent service. Bartenders: USD 1-2 per drink. Taxis/rideshares: 10-15%. Hotel staff: USD 2-5. Not usually needed for fast food.
Find answers to the most common questions about traveling from Chicago, IL to Fort Myers, FL 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 Fort Myers, FL, this guide helps you travel smarter and with confidence.

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