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Data updated: 2026-10-28 13:15:59

Chicago (MDW) to Fort Myers (RSW) Flights

Compare flights from Chicago to Fort Myers, explore popular airlines, airports, and travel tips.
Get the latest collected flight schedules, prices, and route information all in one place.
MDW········· ·········RSW
Chicago Midway International AirportSouthwest Florida International Airport
Distance
1,105 miles
Flight time
2h 45m
Time difference
RSW is 1h ahead
Departure date
Return date

Flights from Chicago to Fort Myers

All times are shown in local time. Prices are for one-way, per adult, including taxes and fees.

Transfers
Airlines
Airline allianceAirlines
Departure / arrival
Departure time (local time)Arrival time (local time)
Airport
Departure airports
Arrival airports
Collected nonstop flight records from MDW to RSW on 2026-10-29
05:05MDWCDT UTC−52h 40m
····· ✈ ·····
Nonstop
08:45RSWEDT UTC−4$227.00One-way
Flight details
12:50MDWCDT UTC−52h 45m
····· ✈ ·····
Nonstop
16:35RSWEDT UTC−4$283.00One-way
Flight details
18:50MDWCDT UTC−52h 50m
····· ✈ ·····
Nonstop
22:40RSWEDT UTC−4$283.00One-way
Flight details

Flight route map

Chicago (MDW) to Fort Myers (RSW) Non-stop flight routes illustrated on a map.

Flights from Chicago (MDW), Illinois, to Fort Myers (RSW), Florida, are shown on the map. Based on recorded flight history, the distance is approximately 1,105 miles.

Departure
Chicago Midway International Airport · Illinois, United States · 41° 47' 10" N 87° 45' 09" W
Flight route
1,105 miles · 2h 45m
Direction
160.20° (SSE)
Geographic midpoint
The geographic midpoint is at latitude 34.19655, longitude -84.47982, approximately 553.71 miles from both airports.
Great-circle distance
1,107.4 miles
Driving route
1,252 miles · 25 hr 12 min
Time difference
RSW is 1h ahead
Destination
Southwest Florida International Airport · Florida, United States · 26° 32' 05" N 81° 45' 10" W
Distance and time are approximate; flight schedules and local times may change.

Route information

Distance
1,105 miles
Average flight time
2h 45m
Time difference
RSW is 1h ahead
Route direction
The initial bearing on the course from Chicago to Fort Myers is 160.20°, and the compass direction is SSE.

Airport information

Chicago Midway International Airport

Chicago Midway International Airport
Chicago, Illinois, United States
41° 47' 10" N, 87° 45' 09" W
Elevation: 620 ft (189 m)
Time zone: CDT UTC−5
View airport details

What's the weather like in Chicago and Fort Myers?

Temperature unit:

MDW · Chicago

53°FSunnyFeels like 51°F
Humidity
85%
Wind
4 mph
Precipitation
0 mm

RSW · Fort Myers

79°FOvercastFeels like 82°F
Humidity
78%
Wind
16 mph
Precipitation
0 mm
Wed, Oct 2882°F | 72°FOvercast
Thu, Oct 2986°F | 71°FLight drizzle
Fri, Oct 3088°F | 72°FOvercast
Sat, Oct 3187°F | 72°FLight drizzle
Sun, Nov 188°F | 73°FModerate drizzle

Popular airlines from Chicago to Fort Myers

Popular airports near Chicago

Popular airports near Fort Myers

Everything you need to know for your flight from Chicago to Fort Myers

Which departure days are usually cheaper?

If you have flexibility with your travel dates, Tuesday and Wednesday departures are consistently your best bet for finding the lowest airfares. Across global flight routes, flying midweek can easily save you 10% to 20% compared to weekend departures, mainly because you avoid both Monday business trips and Friday weekend getaways. On the flip side, Fridays and Sundays tend to be the most expensive days of the week as leisure travelers head out and return. Another insider tip: opting for early morning flights (before 7:00 AM) or overnight red-eyes often unlocks additional savings while helping you breeze through airport security lines.

How far in advance do fares usually reach their lowest point?

There is no fixed booking window that guarantees the lowest fare for United States to United States (US-US). Once your plans are clearer, compare prices for your intended dates and nearby alternatives, using the same cabin, baggage and change conditions. Choose a fare that fits your budget and flexibility; waiting can result in either lower prices or fewer suitable options.

Which travel month has the lowest reference fare, and by how much?

In average round-trip fares grouped by travel month over the past 12 months, Jan is lowest at USD 278. Compared with the selected date's calendar month average of USD 295, the difference is USD 17. This is not a quote for a specific date or nonstop flight.

Should I book now or wait for a lower fare?

If you can change departure dates, the price calendar shows a reference fare of USD 127 on 2026-11-17, USD 100 below the selected date. Prices for different departure dates cannot predict whether the same flight will get cheaper later; check the latest price and availability before booking.

How much could changing the departure date by a few days save?

Among available departure dates within three days of the selected date, the same-currency reference nonstop fare of USD 227 on 2026-10-29 is tied for the lowest. Fares on different dates may not be for the same cabin or fare product; check the latest price and availability before booking.