ORD → RSW

Find and Compare the Cheapest Ways to Fly from Chicago to Fort Myers

Compare one-way, round-trip and flight + hotel packages from Chicago to Fort Myers, a nonstop flight of about 2h 45m, with fares from around 180. Nonstop fares seen from United.

Chicago to Fort Myers flight facts

Chicago to Fort Myers is a domestic route covering about 1,121 miles, arriving at Southwest Florida International Airport (RSW) in United States. Peak travel season in Fort Myers runs February–April (sunny and comfortable), while June–September is usually the quietest and best-value time to visit. Nonstop fares we've tracked on this route come from United.

Key facts for flights from Chicago to Fort Myers
Departing fromO'Hare International Airport (ORD)
Arriving atSouthwest Florida International Airport (RSW)
Distance1,121 miles (1,806 km)
Nonstop flight timeAbout 2h 45m
Nonstop airlines seenUnited
Round-trip fares from$180 (estimate)
Cheapest monthsFebruary, October, April
Peak season in Fort MyersFebruary–April
Cheapest hotel months in Fort MyersJune–September
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit Fort Myers

  • Peak season

    February–April

    Sunny and comfortable

  • Shoulder season

    November–January & May

    Mild to warm

  • Off-peak season

    June–September

    Hot, humid, afternoon storms

Estimated round-trip fares by month, Chicago to Fort Myers

Estimated lowest round-trip fare per month
MonthFares from
January$205
February$180
March$215
April$190
May$225
June$250
July$245
August$225
September$200
October$185
November$220
December$280

Flying from Chicago to Fort Myers

Airlines Flying this Route

Nonstop fares we've tracked on this route come from United. Ducoffs.com compares full-service and low-cost airlines flying between Chicago and Fort Myers in a single search, including nonstop and one-stop options, so you can weigh price against total travel time.

Best Time to Book Flights from Chicago to Fort Myers

Fares on this route tend to be lowest in February, October, and April. For the best selection, book about 1 to 3 months before departure and stay flexible by a day or two.

Average Travel Duration

Chicago and Fort Myers are about 1,121 miles apart. A nonstop flight takes roughly 2h 45m; connecting itineraries usually add 2 to 5 hours.

Chicago to Fort Myers flight questions

How can I find the absolute cheapest flight from Chicago to Fort Myers?

The best way to secure budget rates is by comparing multiple airlines simultaneously and checking flexible dates. Ducoffs.com scans available partner networks to bring you real-time pricing options.

What is the cheapest month to fly from Chicago to Fort Myers?

Based on typical seasonal demand, February, October, and April tend to offer the lowest fares on this route, with estimated round-trip prices starting around $180. Live prices change daily, so run a search for your exact dates.

How long is the flight from Chicago to Fort Myers?

Chicago and Fort Myers are about 1,121 miles apart. A nonstop flight takes roughly 2h 45m, while connecting itineraries usually add 2 to 5 hours depending on the layover.

Which airlines fly nonstop from Chicago to Fort Myers?

Recent nonstop fares we've tracked on this route come from United. Schedules change by season, so your live search shows every airline flying your dates.

When are hotels cheapest in Fort Myers?

Hotel rates in Fort Myers are usually lowest in June–September, when demand is quieter, and highest during peak season (February–April). Booking your flight and hotel together can save up to 30%.

Which airport do I fly into for Fort Myers?

This route arrives at Southwest Florida International Airport (RSW). Your search results also show nearby airports when they offer a cheaper or faster option.

How far in advance should I book a flight to Fort Myers?

For this route, booking about 1 to 3 months before departure usually gives the best balance of price and seat selection. Mid-week departures are often cheaper than weekend flights.

Is it cheaper to bundle flights and hotels together?

Yes. Bundling your travel components can save you up to 30% compared to booking flights and hotels separately, as airlines and properties offer exclusive package discounts.