
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (American Airlines) |
One-way from | $109 (Frontier) |
Popular in | December |
Cheapest in | August |
Average price | $326 |
Fly from
Fly to
Route
Depart
Return
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Tue 7/21
7:05 am-11:14 am
Nonstop3h 09m
Fort Myers SW Florida Intl
Tue 7/28
4:39 pm-7:00 pm
Nonstop3h 21m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Tue 6/9
7:30 am-3:52 pm
1 stop7h 22m
Fort Myers SW Florida Intl
Tue 6/16
4:39 pm-7:00 pm
Nonstop3h 21m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Thu 6/25
2:50 pm-6:40 pm
Nonstop2h 50m
Fort Myers SW Florida Intl
Mon 7/6
4:45 pm-8:40 pm
1 stop4h 55m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 6/2
4:05 pm-7:50 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Tue 6/9
6:10 am-12:15 pm
2 stops7h 05m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Sat 7/4
9:15 am-1:00 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Tue 7/21
11:25 am-7:05 pm
2 stops8h 40m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Tue 6/30
7:01 am-1:12 pm
1 stop5h 11m
Fort Myers SW Florida Intl
Thu 7/9
7:00 am-3:05 pm
1 stop9h 05m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Mon 6/29
9:48 am-4:39 pm
1 stop5h 51m
Fort Myers SW Florida Intl
Sat 7/4
8:30 am-2:14 pm
1 stop6h 44m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Mon 6/29
4:25 pm-11:10 pm
1 stop5h 45m
Fort Myers SW Florida Intl
Sat 7/4
6:34 pm-10:17 pm
1 stop4h 43m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Thu 6/25
11:05 am-6:51 pm
1 stop6h 46m
Fort Myers SW Florida Intl
Mon 6/29
10:30 am-3:40 pm
1 stop6h 10m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Tue 6/9
11:25 am-9:10 pm
2 stops8h 45m
Fort Myers SW Florida Intl
Tue 6/16
1:05 pm-5:55 pm
1 stop5h 50m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Fort Myers is 86 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
Currently, September is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $40). Flying from Chicago to Fort Myers in June is currently the most expensive (average of $483). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
A simple way to save on the total cost of your ticket is to fly from Chicago to Fort Myers in the evening. If you’re flexible enough to do this you can expect to save up to 7% on your trip compared to booking a flight at noon.
Travelers seeking maximum savings on their Chicago to Fort Myers flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
The most flights from CHI to RSW are scheduled on a Friday (25 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (13 on average).
About 20% of weekly flights between Chicago and Fort Myers have experienced delays in the past year, with the average delay time being 148 minutes.
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
Thursday tends to have the lowest number of delays on this route, whereas Sunday has historically faced a higher average of delays compared to other days of the week.
Over the last year, United Airlines have had the lowest number of delays on this route, with just 15% of flights being delayed.
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Scott,Feb 2026
HOU - FLL
Comfort
Entertainment
Food
Overall
Boarding
Crew
Reviews
Scott,Feb 2026
HOU - FLL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$187 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$66 | Average$181 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$388 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$157 | Average$290 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$160 | Average$319 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$171 | Average$361 | FlexibilityNo cancel fee | On-time63% |