
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $125 (Kiwi.com) |
One-way from | $53 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $341 |
Fly from
Fly to
Route
Depart
Return
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 5/9
1:55 pm-9:40 pm
2 stops6h 45m
Fort Myers SW Florida Intl
Sat 5/16
10:00 am-12:10 pm
Nonstop3h 10m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Mon 4/27
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Mon 5/11
6:20 am-2:55 pm
2 stops9h 35m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Wed 4/15
3:00 pm-8:35 pm
1 stop4h 35m
Fort Myers SW Florida Intl
Sat 4/18
5:55 pm-10:35 pm
1 stop5h 40m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Sat 5/2
3:40 pm-7:25 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Mon 5/4
9:30 am-2:55 pm
1 stop6h 25m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Fri 4/17
5:53 pm-12:48 am
1 stop5h 55m
Fort Myers SW Florida Intl
Wed 4/22
1:46 pm-8:16 pm
1 stop7h 30m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Fri 5/1
10:30 am-2:25 pm
Nonstop2h 55m
Fort Myers SW Florida Intl
Mon 5/11
3:15 pm-5:30 pm
Nonstop3h 15m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Fri 5/1
6:55 pm-10:40 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Mon 5/4
7:50 pm-11:30 pm
1 stop4h 40m
ChicagoFort Myers
MDW - RSW
MDWRSW
Chicago Midway
Sun 4/26
1:00 pm-4:45 pm
Nonstop2h 45m
Fort Myers SW Florida Intl
Sat 5/2
6:00 am-7:55 am
Nonstop2h 55m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Sat 6/6
3:47 pm-11:12 pm
1 stop6h 25m
Fort Myers SW Florida Intl
Sat 6/13
8:30 am-2:14 pm
1 stop6h 44m
ChicagoFort Myers
ORD - RSW
ORDRSW
Chicago O'Hare Intl
Fri 5/8
2:40 pm-9:50 pm
2 stops6h 10m
Fort Myers SW Florida Intl
Sun 5/10
5:15 am-3:00 pm
1 stop10h 45m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
The best time to book flights from Chicago to Fort Myers is 87 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, March is the cheapest month in which you can book a flight from Chicago to Fort Myers (average of $37). Flying from Chicago to Fort Myers in November is currently the most expensive (average of $133). 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 in the morning.
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 Sunday (35 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (19 on average).
About 18% 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.
Tuesday 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 13% of flights being delayed.
Boarding
Food
Crew
Entertainment
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Food
Crew
Entertainment
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Food
Crew
Entertainment
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Food
Crew
Entertainment
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Food
Crew
Entertainment
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
Boarding
Food
Crew
Entertainment
Comfort
Overall
Reviews
Scott,Feb 2026
HOU - FLL
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$174 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$66 | Average$182 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$130 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$143 | Average$230 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$278 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$159 | Average$312 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$171 | Average$351 | FlexibilityNo cancel fee | On-time63% |