Cheap flights from Fort Myers to Chicago from $128 RSW → ORD
Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD)
The cheapest return found recently is $297 with Frontier Airlines, 30 Dec – 31 Dec, found 5 days ago. The cheapest one-way found recently is $128 with Frontier Airlines, 19 Dec, found 2 days ago.
- Cheapest one-way found recently
- $128, Frontier Airlines, found 2 days ago
- Cheapest return found recently
- $297, 30 Dec to 31 Dec
- Airlines with nonstop flights
- Frontier Airlines
- Shortest nonstop flight found
- 3 h 21 min
Return
Not enough comparable prices yet for a usual return price.
Cheapest return found recently
$297
30 Dec – 31 Dec · Frontier Airlines
Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD)
Leaves 9:57 p.m. · Return leaves 7:00 a.m. · 11 h 47 min of travel, both ways together
out nonstop, back 1 stop
found 5 days ago
Cheapest nonstop return
None seen yet.
Found recently, and the cheapest we hold
$297 30 Dec – 31 Decfound 5 days agoSee prices for these dates
It is also the cheapest return we hold, of any age.
What have prices looked like?
Over 14 days, 29 Oct to 11 Nov, the cheapest return we saw each day was $256 to $297.
At $297, the cheapest return found recently is at the high end of that range.
14 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?
Not enough comparable prices yet: we hold return fares on 1 departure date and need at least 3 to say what is usual.
Could nearby dates be cheaper?
We hold no other 1-night return fares leaving within 3 days of 30 Dec to compare.
Every date we hold
1 fares on 1 departure dates
See every date as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 30 Dec – 31 Dec | $297 | Frontier Airlines | Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD) | out nonstop, back 1 stop | found 5 days ago | See prices for these dates |
Airlines on the cheapest dates: Frontier Airlines.
One-way
The cheapest one-way fare on each of 3 departure dates is usually $120 to $134.
Cheapest one-way found recently
$128
19 Dec · Frontier Airlines
Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD)
Leaves 9:57 p.m. · 3 h 21 min trip
nonstop
found 2 days ago
Cheapest nonstop one-way
$128
19 Dec · Frontier Airlines
Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD)
Leaves 9:57 p.m. · 3 h 21 min trip
nonstop
found 2 days ago
Found recently, and the cheapest we hold
$128 19 Decfound 2 days agoOpen this trip
$111 4 Decfound 5 days agoOpen this trip
What have prices looked like?
Over 31 days, 11 Oct to 11 Nov, the cheapest one-way we saw each day was $94 to $137.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 3 departure dates from 4 Dec to 19 Dec, 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?
We hold no other one-way fares leaving within 3 days of 19 Dec to compare.
Every date we hold
3 fares on 3 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 4 Dec | $111 | Frontier Airlines | Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 7 Dec | $139 | Frontier Airlines | Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD) | nonstop | found 5 days ago | Open this trip |
| 19 Dec | $128 | Frontier Airlines | Southwest Florida International Airport (RSW) → O'Hare International Airport (ORD) | nonstop | found 2 days ago | Open this trip |
Airlines on the cheapest dates: Frontier Airlines.
Premium cabin fares from Fort Myers to Chicago
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 30 Dec – 31 Dec in another cabin: Premium economy · Business · First
Today's prices for 19 Dec in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Fort Myers to Chicago?
Return
Not enough history yet: in 14 days of return prices, 29 Oct to 11 Nov, fewer than 3 booking ranges had prices on 7 days or more.
One-way
The cheapest fares were 30 to 59 days before departure.
From the cheapest one-way each day between 11 Oct and 11 Nov (31 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 |
|---|---|---|---|---|
| 14–29 days | $111 | $94 | +3% | 15 |
| 30–59 days | $108 | $94 | Cheapest seen | 20 |
| 60–89 days | $137 | $109 | +27% | 16 |
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
Sarasota → Chicago
101 km from Fort Myers
$192
$105 less than flying from Fort Myers
29 Dec – 3 Jan 2027 · SRQ → RFD · out nonstop, back nonstop
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 30 Dec – 31 Dec. A live search on this page shows what those dates cost now, for one adult in economy.
Questions about this trip
How much is a return flight from Fort Myers to Chicago?
The cheapest return found recently is $297 with Frontier Airlines, 30 Dec to 31 Dec, found 5 days ago.
How much is a one-way flight from Fort Myers to Chicago?
The cheapest one-way found recently is $128 with Frontier Airlines, 19 Dec, found 2 days ago. The cheapest one-way we hold, of any age, is $111 with Frontier Airlines, 4 Dec, found 5 days ago. The cheapest one-way fare on each of 3 departure dates is usually $120 to $134.
How far ahead should I book a flight from Fort Myers to Chicago?
In 31 days of prices between 11 Oct and 11 Nov, one-way fares were cheapest 30 to 59 days before departure.
Is there a direct flight from Fort Myers to Chicago?
Yes, the cheapest nonstop one-way found recently is $128 with Frontier Airlines, 19 Dec, found 2 days ago.
How long is the flight from Fort Myers to Chicago?
The cheapest nonstop one-way found recently, with Frontier Airlines on 19 Dec, takes 3 h 21 min from Southwest Florida International Airport (RSW) to O'Hare International Airport (ORD).
Which airlines have the cheapest flights from Fort Myers to Chicago?
Between 4 Dec and 19 Dec, Frontier Airlines has the cheapest one-way on all 3 departure dates we hold.
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