Fort Myers to Chicago (RSW–ORD) — Airlines, Schedules & Connections
No flights match your filters.
No scheduled airline flights on this route — it's flown by charter / private operators (). No nonstop flights on this route. connecting options below.
Most recently operated nonstop flights — the month shown is when each was last scheduled. Most destinations remain reachable with a connection.
No discontinued nonstop flights on record for this route.
RSW–ORD is served by 5 airlines with nonstop service. United Airlines, American Airlines and Southwest Airlines lead the route. The flight covers 1,123 miles in approximately 3h 22m. Beyond nonstop, 1-stop connecting options are also available.
Airline Landscape
| Airline | Freq/wk | Aircraft | Duration | Dep OTP | Alliance | Codeshares |
|---|---|---|---|---|---|---|
| UA United Airlines Also: AC, LX, NZ | 29 | 32Q, B39M | 3h04-3h25 | Star Alliance | AC, LX, NZ | |
| AA American Airlines Also: AS, AY, QR | 26 | 738 | 3h18-3h31 | Oneworld | AS, AY, QR | |
| WN Southwest Airlines | 5 | – | – | – | – | |
| F9 Frontier | 0 | – | – | – | – | |
| NK Spirit Airlines | 0 | – | – | – | – |
Weekly Schedule Pattern
Connection Landscape
On-Time Performance
Other ways to reach Chicago from Fort Myers
| Metric | RSW→ORD | PGD→ORD | SRQ→ORD |
|---|---|---|---|
| Distance from RSW | – | 30 mi | 77 mi |
| Nonstop airlines | 5 | 1 | 8 |
| Weekly flights | 135 | – | 31 |
| Flight time | 3h 22m | 2h 44m | 3h 13m |
| Departure OTP | 100% | – | – |
Travel Essentials
RSW: EDT · ORD: CDT
When it's 6:00 PM in Fort Myers, it's 5:00 PM in Chicago.
CTA Blue Line runs 24/7 from O'Hare to downtown Chicago (45 min, $5). Taxis use a flat-rate zone system; downtown is around $40–45 plus tip. Ride-shares are typically $30–50.The Airport Transit System (ATS) connects all terminals and parking. Metra commuter rail does not serve O'Hare directly; transfer downtown via Blue Line.
Continental climate with four distinct seasons. Summers are warm and humid (25–32°C) with afternoon thunderstorms. Winters are cold (−10 to −2°C) with heavy snowfall that regularly delays flights December through March.
Spring and fall are mild but unpredictable. Pack layers. Lake Michigan moderates temperatures near the lakefront, but O'Hare sits inland and runs colder.
RSW–ORD Quick Facts
Frequently Asked Questions
Fort Myers to Chicago O'Hare: Southwest Florida's Midwest Lifeline
RSW-ORD is one of Southwest Florida Regional Airport's most important cold-weather routes. Chicago's large population of seasonal Florida travelers drives heavy inbound traffic to Fort Myers from November through April, when Southwest Florida beaches, golf courses, and retirement communities see peak occupancy. American and United are the primary nonstop carriers, operating mainline Boeing 737s on two to four daily departures at peak. Block time is two hours 30 minutes northbound. Southwest Florida Regional (RSW) serves Fort Myers, Cape Coral, Naples, and the broader Lee and Collier county market; it is the busiest commercial airport between Tampa and Miami on Florida's Gulf Coast.
Seasonal and Connectivity Context
The RSW-ORD nonstop schedule contracts noticeably in summer, when some airlines reduce to single daily departures or suspend the route temporarily. Passengers traveling RSW-ORD in June through August should confirm nonstop availability before booking, as the alternative involves a connection through Charlotte, Miami, or Atlanta. O'Hare's position as both a United and American hub means RSW passengers connecting onward to the Midwest, Pacific, or international destinations have broad carrier options. Fort Myers has seen above-average population growth in the 2020s following remote-work migration patterns from the upper Midwest, which has modestly lifted year-round baseline demand beyond the traditional seasonal spike.