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RSW → ORD

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

Compare one-way, round-trip and flight + hotel packages from Fort Myers to Chicago, a nonstop flight of about 2h 45m, with fares from around 175.

Search Live Rates for Fort Myers to Chicago

Fort Myers to Chicago flight facts

Fort Myers to Chicago is a domestic route covering about 1,121 miles, arriving at O'Hare International Airport (ORD) in United States. Peak travel season in Chicago runs June–August (warm, lakefront festivals), while November–April is usually the quietest and best-value time to visit.

Key facts for flights from Fort Myers to Chicago
Departing fromSouthwest Florida International Airport (RSW)
Arriving atO'Hare International Airport (ORD)
Distance1,121 miles (1,806 km)
Nonstop flight timeAbout 2h 45m
Round-trip fares from$175 (estimate)
Cheapest monthsFebruary, September, April
Peak season in ChicagoJune–August
Cheapest hotel months in ChicagoNovember–April
Best time to book1 to 3 months ahead
Route info updatedOctober 16, 2026

When to visit Chicago

  • Peak season

    June–August

    Warm, lakefront festivals

  • Shoulder season

    May & September–October

    Mild and comfortable

  • Off-peak season

    November–April

    Cold, windy and snowy

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

Estimated lowest round-trip fare per month
MonthFares from
January$205
February$175
March$235
April$200
May$205
June$235
July$260
August$230
September$180
October$210
November$205
December$255

Flying from Fort Myers to Chicago

Airlines Flying this Route

Ducoffs.com compares full-service and low-cost airlines flying between Fort Myers and Chicago 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 Fort Myers to Chicago

Fares on this route tend to be lowest in February, September, 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

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

Fort Myers to Chicago flight questions

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

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 Fort Myers to Chicago?

Based on typical seasonal demand, February, September, and April tend to offer the lowest fares on this route, with estimated round-trip prices starting around $175. Live prices change daily, so run a search for your exact dates.

How long is the flight from Fort Myers to Chicago?

Fort Myers and Chicago 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.

When are hotels cheapest in Chicago?

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

Which airport do I fly into for Chicago?

This route arrives at O'Hare International Airport (ORD). 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 Chicago?

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.

Travel guides for this trip

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