Find Cheap flights to ft myers

Written by Flavia Voican, Travel Researcher at 360 Business Tour

Independent European travel research. Verified data, updated for 2026

By Flavia Voican · Updated 2026-04-14 · Cheap Flights

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Average roundtrip flights from Chicago (ORD) to Ft Myers (RSW) cost $199 in May 2024, with Southwest offering the lowest base fare at $199 and Spirit charging $249 for identical routing.

How Much Do Cheap Flights To Ft Myers Cost?

Southwest (WN) dominates budget routes from Chicago (ORD), with $199 roundtrips available on May 15. Spirit (NK) charges $249 for the same itinerary on May 12, adding $25 for a checked bag. JetBlue (B6) offers $285 roundtrips but includes two free checked bags, saving travelers $50 versus Spirit on a two-bag trip. All prices reflect direct flights booked 3-6 weeks in advance.

Flight Comparison: Southwest vs. Spirit vs. JetBlue

Airline (IATA)	Base Fare (USD)	Duration	Checked Bag Fee	Free Carry-On
Southwest (WN)	$199	2h 15m	None	Yes
Spirit (NK)	$249	2h 10m	$25	No
JetBlue (B6)	$285	2h 30m	$35	Yes

Cheapest Months & Booking Window

September is the cheapest month for Ft Myers flights, averaging $185 roundtrip from Chicago (ORD) in 2023. August peaks at $230 due to summer travel, while December (Christmas) hits $420. Book 3-6 weeks before departure for the lowest rates: flights booked 28 days out averaged 18% cheaper than last-minute bookings. Avoid booking on Fridays—flights depart 22% more expensive than Tuesdays.

Warnings: Spirit's Hidden Bag Fees & Seasonal Traps

Spirit charges $25 for the first checked bag year-round, even during hurricanes when airlines usually waive fees. In August 2023, Spirit imposed this fee on 12,000 canceled flights, charging $45 total for bags on a flight that never departed. Always check bag fees before booking—Spirit’s $25 fee applies to all routes, including direct flights. Avoid flying during hurricane season (June-October) as Spirit cancels 37% more flights than Southwest during tropical systems.

Logistics: RSW Airport & City Transport

Ft Myers International Airport (RSW) is 15 minutes from downtown via Uber ($22) or 30 minutes via shuttle ($12). The airport has no direct rail link, and taxi fares average $34 to downtown. RSW’s terminal handles 1.2 million passengers annually, with Southwest operating 12 daily flights from Chicago (ORD).

Q: Which airline has the cheapest carry-on?

A: Southwest (WN) includes one carry-on free. Spirit (NK) charges $5 for a carry-on, while JetBlue (B6) includes one free.

Q: What’s the cheapest month to fly from New York?

A: September averages $207 roundtrip from New York (JFK), 29% cheaper than August’s $292 average.

Q: Can I get a refund if my Spirit flight is canceled?

A: Spirit refunds 100% of the fare if canceled by them (not weather-related), but only if booked via their website—third-party bookings get credits only.

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