Best Flights starting from $193
from$193economy
Chicago (MDW)
Sat, May 2
Roundtrip
Fort Myers (RSW)
Wed, May 6
from$193economy
Chicago (MDW)
Sat, May 9
Roundtrip
Fort Myers (RSW)
Wed, May 13
from$209economy
Chicago (MDW)
Wed, May 27
Roundtrip
Fort Myers (RSW)
Mon, Jun 1
from$221economy
Chicago (MDW)
Tue, May 26
Roundtrip
Fort Myers (RSW)
Mon, Jun 1
from$234economy
Chicago (MDW)
Thu, May 28
Roundtrip
Fort Myers (RSW)
Wed, Jun 3
from$237economy
Chicago (MDW)
Sat, May 2
Roundtrip
Fort Myers (RSW)
Thu, May 7
from$258economy
Chicago (MDW)
Tue, May 19
Roundtrip
Fort Myers (RSW)
Sat, May 23
from$267economy
Chicago (MDW)
Fri, May 29
Roundtrip
Fort Myers (RSW)
Thu, Jun 4
from$282economy
Chicago (MDW)
Mon, May 4
Roundtrip
Fort Myers (RSW)
Sat, May 9
from$289economy
Chicago (MDW)
Sun, May 24
Roundtrip
Fort Myers (RSW)
Sat, May 30
from$292economy
Chicago (MDW)
Sat, May 30
Roundtrip
Fort Myers (RSW)
Fri, Jun 5
from$326economy
Chicago (MDW)
Mon, May 25
Roundtrip
Fort Myers (RSW)
Sun, May 31
Fields updated — click View Prices to search ↑
Other Options for This Route
Other Destinations
Chicago (MDW) to Miami (MIA) in May from $80
From $80
Chicago (MDW) to Washington, D.C. (DCA) in May from $104
From $104
Chicago (MDW) to Pensacola (PNS) in May from $136
From $136
Chicago (MDW) to Dallas (DAL) in May from $160
From $160
Chicago (MDW) to New York (Any) in May from $177
From $177
Chicago (MDW) to Detroit (DTW) in May from $191
From $191
Flights from Other Cities
Hartford (BDL) to Fort Myers (RSW) in May from $74
From $74
Philadelphia (Any) to Fort Myers (RSW) in May from $74
From $74
Atlantic City (ACY) to Fort Myers (RSW) in May from $81
From $81
Cleveland (CLE) to Fort Myers (RSW) in May from $88
From $88
Boston (BOS) to Fort Myers (RSW) in May from $109
From $109
Hartford (BDL) to Fort Myers (RSW) in May from $143
From $143
✈️ Flight Guide: Chicago (MDW) → Fort Myers (RSW)
Complete travel information for your May journey
Departing from Chicago (MDW) FAQs
For departures from Southwest Florida International Airport (RSW) in June, book 6–10 weeks ahead and target mid-week travel (Tuesdays or Wednesdays) for the cheapest economy fares. June is early summer demand rising, so comparing fares across multiple carriers and setting price alerts will help you capture fare sales and last-minute deals.
Yes. Southwest Florida International Airport (RSW) offers seasonal and year-round direct economy flights to hubs like Atlanta (ATL), New York area airports, and Chicago depending on the carrier. For the cheapest options, compare nonstop vs one-stop fares and watch for low-cost carrier sales during off-peak months such as September and early December.
Major low-cost and legacy carriers operating departures at Southwest Florida International Airport (RSW) include Southwest Airlines, Spirit Airlines, JetBlue, American Airlines, and Delta. Budget carriers frequently offer discounted economy seats and flash sales—sign up for airline newsletters and follow RSW fare alerts to secure the cheapest economy travel.
During December holiday peaks at Southwest Florida International Airport (RSW), expect check-in and TSA security wait times to average 45–90 minutes depending on the hour and day. To avoid delays for economy travelers, arrive 2–2.5 hours before domestic departures and consider TSA PreCheck for faster screening.
Yes. Connecting through major hubs such as Atlanta (ATL), Charlotte (CLT), or Dallas (DFW) can produce significant savings on long-haul economy travel from Southwest Florida International Airport (RSW). Use multi-airline searches, flexible date calendars, and mixed-airline itineraries to find the lowest total fares.
To save on baggage and seat fees for RSW departures, travel with carry-on only if possible, pre-purchase checked bags online, and book basic economy only when you can travel light. Consider loyalty program status or credit cards that include free checked bags and priority boarding for economy travelers.
Arriving at Fort Myers (RSW) FAQs
Cheapest Economy Fare (ECON) usually includes a basic seat, one small personal item, and standard boarding with limited or no free checked baggage. Fare rules vary by carrier—always review baggage and change fee policies before booking to avoid surprise costs upon arrival.
Economy travelers targeting the Cheapest Economy Fare (ECON) can often reach major hubs like New York City, Orlando, Atlanta, Chicago, Dallas, and Los Angeles most affordably by choosing flexible dates and one-stop itineraries. Using nearby airports and traveling mid-week improves access to lower-priced economy arrivals.
In September, demand softens after summer, making it one of the best months to monitor for Cheapest Economy Fare (ECON) arrivals. Use flexible-date searches, set price alerts, and compare nearby arrival airports to capture the lowest prices.
Most Cheapest Economy Fare (ECON) tickets are non-refundable and have costly change fees, though policies vary and some carriers now offer fee waivers or paid flexibility add-ons. Always check the fare class rules before booking and consider travel insurance for added protection.
Cheapest Economy Fare (ECON) often assigns seats at check-in or uses open seating; priority or advance seat selection may require an extra fee. For early boarding or specific seats, purchase seat assignments during booking or check for upgrades at check-in.
After arriving with a Cheapest Economy Fare (ECON), plan ground transfers in advance—use shuttle services, shared rides, or public transit to reach major nearby cities like Orlando or Atlanta affordably. Factor in local transit costs when comparing fares to different arrival airports to ensure overall savings.
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Best Time to Fly — When to Book Cheap Economy Flights from RSW
Find the best time to book cheap flights from Southwest Florida International Airport (RSW) — set alerts and compare flexible dates now.
Direct vs Connecting Flights — Balancing Cheap Economy (ECON) vs Convenience from RSW
Direct (nonstop) flights from Southwest Florida International Airport (RSW) offer faster travel and lower missed-connection risk but often cost more than connecting itineraries. Connecting flights via hubs like Atlanta (ATL), Charlotte (CLT), or Dallas/Fort Worth (DFW) can reduce the cheapest economy fare significantly.
Compare nonstop and one-stop options for your RSW departure to get the cheapest economy fare that balances price and convenience.
Flight Time & Schedules — Typical Durations from Southwest Florida International Airport (RSW)
Typical Flight Durations
Check current RSW schedules and compare typical flight times to book the cheapest economy option that fits your itinerary.