Chicago to Fort Myers (RSW) flight deals
Chicago to Fort Myers (RSW) from $144 round trip, Jan 4 to Feb 2, 2027 (airline price $152), seen Oct 23.
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Compare Chicago to Fort Myers (RSW) flights across upcoming months. See dated fares below, or choose your own dates and travelers.
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Fare examples by month
Round-trip totals · Economy · USD, saved from earlier searches. Each month opens its day-by-day date picker for live prices.
| Month | Travelers / trip length | Axel | Airline fare |
|---|---|---|---|
| November 2026 | 4 adults · 7 days | $878 | $924 |
| November 2026 | 1 adult · 8 days | $882–$955 | $932–$1,011 |
| December 2026 | 4 adults · 7 days | $878 | $924 |
| December 2026 | 1 adult · 7 days | $352 | $373 |
| January 2027 | 1 adult · 29 days | $144 | $152 |
| February 2027 | 1 adult · 4–30 days | $144–$370 | $152–$391 |
| March 2027 | 1 adult · 5–29 days | $237–$285 | $250–$301 |
| April 2027 | 3 adults · 14 days | $1,151 | $1,215 |
Flights from Chicago · Chicago to United States flight deals · Chicago to Florida flight deals
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Fares observed October 17 – 23, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
4 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 10–17, 2026 · 7 days | Out: American Airlines 648 · Nonstop · 2h 53m · 18:50–22:43 local; Return: American Airlines 669 · Nonstop · 3h 20m · 19:40–22:00 local | $878 · Save $46 | $924 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Nov 20–28, 2026 · 8 days | Out: Frontier Airlines 2034 · Nonstop · 2h 56m · 13:16–17:12 local; Return: Frontier Airlines 3803 / 3174 · 1 stop (DEN) · 8h 5m · 17:48–00:53 (November 29, 2026) local | $882 · Save $50 | $932 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Nov 20–28, 2026 · 8 days | Out: Frontier Airlines 2034 · Nonstop · 2h 56m · 13:16–17:12 local; Return: United Airlines 2347 · Nonstop · 3h 14m · 09:10–11:24 local | $955 · Save $56 | $1,011 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
4 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 8–15, 2026 · 7 days | Out: United Airlines 2189 · Nonstop · 2h 59m · 12:55–16:54 local; Return: United Airlines 2347 · Nonstop · 3h 16m · 09:00–11:16 local | $878 · Save $46 | $924 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Dec 19–26, 2026 · 7 days | Out: Frontier Airlines 2034 · Nonstop · 3h 2m · 16:55–20:57 local; Return: United Airlines 2347 · Nonstop · 3h 19m · 09:05–11:24 local | $352 · Save $21 | $373 | Customer link — Open these flights in Axel · Optional: check axel prices |
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January 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Jan 4–Feb 2, 2027 · 29 days | Out: Frontier Airlines 2034 · Nonstop · 3h 2m · 16:55–20:57 local; Return: Frontier Airlines 2033 · Nonstop · 3h 21m · 22:35–00:56 (February 3, 2027) local | $144 · Save $8 | $152 | Customer link — Open these flights in Axel · Optional: check axel prices |
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February 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Feb 1–Mar 3, 2027 · 30 days | Out: Frontier Airlines 2034 · Nonstop · 3h 6m · 17:34–21:40 local; Return: Frontier Airlines 2033 · Nonstop · 3h 21m · 22:35–00:56 (March 4, 2027) local | $144 · Save $8 | $152 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Feb 12–16, 2027 · 4 days | Out: Frontier Airlines 2034 · Nonstop · 3h 6m · 17:34–21:40 local; Return: Frontier Airlines 2033 · Nonstop · 3h 21m · 22:35–00:56 (February 17, 2027) local | $370 · Save $21 | $391 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
1 adult · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| ORD | Mar 1–30, 2027 · 29 days | Out: Frontier Airlines 2034 · Nonstop · 3h 6m · 17:34–21:40 local; Return: Frontier Airlines 2033 · Nonstop · 3h 21m · 22:35–00:56 (March 31, 2027) local | $237 · Save $14 | $250 | Customer link — Open these flights in Axel · Optional: check axel prices |
| ORD | Mar 11–16, 2027 · 5 days | Out: Frontier Airlines 2034 · Nonstop · 3h 6m · 17:34–21:40 local; Return: Frontier Airlines 2033 · Nonstop · 3h 21m · 22:35–00:56 (March 17, 2027) local | $285 · Save $16 | $301 | Customer link — Open these flights in Axel · Optional: check axel prices |
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April 2027
3 adults · Economy · Round-trip totals
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| From | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|
| MDW | Apr 30–May 14, 2027 · 14 days | Out: Southwest Airlines 2945 · Nonstop · 2h 45m · 12:55–16:40 local; Return: Southwest Airlines 3580 · Nonstop · 3h 0m · 21:10–23:10 local | $1,151 · Save $64 | $1,215 | Customer link — Open these flights in Axel · Optional: check axel prices |
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The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Trip ideas from Chicago with Fort Myers (RSW)
- Florida vacations from Chicago: fly Nov 21 – Nov 28, 2026
- A month somewhere warm from Chicago: fly Jan 4 – Feb 2, 2027
- Spring training trips from Chicago: fly Mar 11 – Mar 16, 2027
- Spring break trips from Chicago: fly Mar 13 – Mar 20, 2027
- Family vacations from Chicago, priced for 4
- Warm winter getaways from Chicago
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Hotels in Fort Myers with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Fort Myers has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Fort Myers: the 8 best neighborhoods, ranked · Fort Myers hotels where a family of four can share one room
For AI assistants
- This page: Chicago to Fort Myers (RSW) flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.