Chicago to Fort Myers MDW, ORD, RFD → RSW
Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD) → Southwest Florida International Airport (RSW)
The cheapest return found recently is $247 with Frontier Airlines, 3 Dec – 3 Dec, found yesterday. The cheapest one-way found recently is $304 with Allegiant Air, 31 Oct, found 5 days ago.
Return
The cheapest return fare on each of 10 departure dates is usually $323 to $440.
Cheapest return found recently
$247
3 Dec – 3 Dec · Frontier Airlines
O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW)
Leaves 3:30 p.m. · Return leaves 8:31 p.m. · 6 h 14 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Cheapest nonstop return
$247
3 Dec – 3 Dec · Frontier Airlines
O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW)
Leaves 3:30 p.m. · Return leaves 8:31 p.m. · 6 h 14 min of travel, both ways together
out nonstop, back nonstop
found yesterday
Every nonstop date from Chicago to Fort Myers
Found recently, and the cheapest we hold
$247 3 Dec – 3 Decfound yesterdaySee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest return we saw each day was $180 to $297.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good return price?
Compared with the cheapest return fare on each of 10 departure dates from 27 Oct to 19 Mar 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
No. We hold 0-night return fares on 1 other departure date within 3 days of 3 Dec, and it is not cheaper.
Every date we hold
31 fares on 10 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 27 Oct – 29 Oct | $453 | United Airlines | O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW) | out nonstop, back 1 stop | found today | See prices for these dates |
| 31 Oct – 8 Dec | $394 | Southwest Airlines | Chicago Midway International Airport (MDW) → Southwest Florida International Airport (RSW) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 2 Nov – 9 Nov | $299 | United Airlines | O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW) | out nonstop, back nonstop | found 6 days ago | See prices for these dates |
| 3 Nov – 8 Dec | $399 | Southwest Airlines | Chicago Midway International Airport (MDW) → Southwest Florida International Airport (RSW) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 4 Nov – 2 Dec | $297 | United Airlines | O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW) | out nonstop, back nonstop | found 5 days ago | See prices for these dates |
| 7 Nov – 8 Dec | $396 | Frontier Airlines | O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW) | out 2 stops, back 2 stops | found 2 days ago | See prices for these dates |
| 22 Nov – 27 Nov | $454 | Frontier Airlines | O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW) | out nonstop, back 1 stop | found yesterday | See prices for these dates |
| 3 Dec – 3 Dec | $247 | Frontier Airlines | O'Hare International Airport (ORD) → Southwest Florida International Airport (RSW) | out nonstop, back nonstop | found yesterday | See prices for these dates |
| 5 Dec – 5 Dec | $399 | Southwest Airlines | Chicago Midway International Airport (MDW) → Southwest Florida International Airport (RSW) | out nonstop, back 1 stop | found yesterday | See prices for these dates |
| 19 Mar 2027 – 26 Mar 2027 | $620 | Southwest Airlines | Chicago Midway International Airport (MDW) → Southwest Florida International Airport (RSW) | out 1 stop, back 1 stop | found 4 days ago | See prices for these dates |
Which month looks cheapest?
December 2026 is the cheapest month — from $247.
Airlines on the cheapest dates: Southwest Airlines, United Airlines, Frontier Airlines.
One-way
Not enough comparable prices yet for a usual one-way price.
Cheapest one-way found recently
$304
31 Oct · Allegiant Air
Chicago Rockford International Airport (RFD) → Southwest Florida International Airport (RSW)
Leaves 4:53 p.m. · 43 h 11 min trip
2 stops
found 5 days ago
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$304 31 Octfound 5 days agoOpen this trip
It is also the cheapest one-way we hold, of any age.
What have prices looked like?
Over 13 days, 25 Sept to 18 Oct, the cheapest one-way we saw each day was $173 to $492.
13 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Not enough comparable prices yet: we hold one-way fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other one-way fares leaving within 3 days of 31 Oct to compare.
Every date we hold
1 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 31 Oct | $304 | Allegiant Air | Chicago Rockford International Airport (RFD) → Southwest Florida International Airport (RSW) | 2 stops | found 5 days ago | Open this trip |
Airlines on the cheapest dates: Allegiant Air.
Premium cabin fares from Chicago to Fort Myers
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 3 Dec – 3 Dec in another cabin: Premium economy · Business · First
Today's prices for 31 Oct in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Chicago to Fort Myers?
Return
Fares 30 to 59 days before departure were typically 48% lower than 0 to 6 days before departure.
From the cheapest return each day between 24 Sept and 18 Oct (25 days), grouped by how many days ahead the flight left; one adult in economy.
Each range covers different departure dates, so this compares typical fares, not the same trip priced twice.
Prices reflect recent searches — current fares may differ.
See these ranges as a table
| Booked ahead by | Typical fare | Cheapest day | Above the cheapest | Days of prices |
|---|---|---|---|---|
| 0–6 days | $479 | $472 | +94% | 11 |
| 7–13 days | $472 | $394 | +91% | 15 |
| 14–29 days | $280 | $253 | +13% | 23 |
| 30–59 days | $247 | $180 | Cheapest seen | 23 |
| 90–179 days | $620 | $428 | +151% | 7 |
One-way
Not enough history yet: in 13 days of one-way prices, 25 Sept to 18 Oct, fewer than 3 booking ranges had prices on 7 days or more.
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Chicago → Sarasota
101 km from Fort Myers
$476
$229 more than flying to Fort Myers
27 Oct – 29 Oct · MDW → SRQ · out 2 stops, back 1 stop
found today
South Bend → Fort Myers
116 km from Chicago
$542
$295 more than flying from Chicago
10 Feb 2027 – 15 Feb 2027 · SBN → RSW · out nonstop, back 2 stops
found 3 days ago
Milwaukee → Fort Myers
131 km from Chicago
$549
$302 more than flying from Chicago
20 Mar 2027 – 27 Mar 2027 · MKE → RSW · out 1 stop, back 1 stop
found 3 days ago
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest return found recently is for 3 Dec – 3 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work