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Cheap Flights from Fort Myers Southwest Florida Reg to Chicago Midway

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Compare Fort Myers Southwest Florida Reg to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

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Flight deals from Fort Myers Southwest Florida Reg to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Fort Myers Southwest Florida Reg to Chicago Midway? Find the lowest prices on one-way and return tickets right here.
Chicago.125 € per passenger.Departing Tue, 5 Aug, returning Thu, 7 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Tue, 5 Aug, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 7 Aug, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 125 €, select.
Chicago.139 € per passenger.Departing Thu, 31 Jul, returning Mon, 4 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Thu, 31 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 4 Aug, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 139 €, select.
Chicago.140 € per passenger.Departing Fri, 11 Jul, returning Sun, 13 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Fri, 11 Jul, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 13 Jul, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 140 €, select.
Chicago.172 € per passenger.Departing Tue, 9 Sep, returning Tue, 16 Sep.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Fort Myers Southwest Florida Reg on Tue, 9 Sep, arriving in Chicago Midway.Inbound indirect flight with Southwest Airlines, departs from Chicago Midway on Tue, 16 Sep, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 172 €, select.
Chicago.180 € per passenger.Departing Wed, 18 Jun, returning Wed, 25 Jun.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Wed, 18 Jun, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 25 Jun, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 180 €, select.
Chicago.185 € per passenger.Departing Fri, 3 Oct, returning Sun, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Fri, 3 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 5 Oct, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 185 €, select.
Chicago.189 € per passenger.Departing Thu, 6 Nov, returning Sun, 9 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Fort Myers Southwest Florida Reg on Thu, 6 Nov, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 9 Nov, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 189 €, select.
Chicago.219 € per passenger.Departing Fri, 31 Oct, returning Sun, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Fort Myers Southwest Florida Reg on Fri, 31 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 2 Nov, arriving in Fort Myers Southwest Florida Reg.Price includes taxes and charges.From 219 €, select.

Find the cheapest month to fly from Fort Myers Southwest Florida Reg to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Fort Myers Southwest Florida Reg to Chicago Midway flights are currently cheapest in August.
Jun
from 180 €
Jul
from 140 €
Aug
from 125 €
Sep
from 172 €
Oct
from 185 €
Nov
from 189 €
Dec
Find prices
Jan
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Feb
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Mar
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Apr
from 401 €
May
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Direct flights from Fort Myers Southwest Florida Reg to Chicago Midway

Fort Myers Southwest Florida Reg to Chicago Midway: Alternative routes

Compare routes from Fort Myers Southwest Florida Reg to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Fort Myers to Chicago: Flight information

The things to know before you go.
Cheapest flight found125 €
Cheapest month to flyAugust
Average flight time2 hrs, 56 mins
Most popular airlineSouthwest Airlines
Average flights per week18

Finding cheap flights from Fort Myers Southwest Florida Reg to Chicago Midway: Frequently asked questions

The best price we found for a return flight from Fort Myers Southwest Florida Reg to Chicago Midway is 125 €. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 56 minutes is the average flight time from Fort Myers Southwest Florida Reg to Chicago Midway.
Southwest Airlines flies direct from Fort Myers Southwest Florida Reg to Chicago Midway.
As of June 2025, there are 18 flights per week flying from Fort Myers Southwest Florida Reg to Chicago Midway.
The cheapest month to fly from Fort Myers Southwest Florida Reg to Chicago Midway is usually June 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Fort Myers Southwest Florida Reg Airport to Chicago Midway Airport on Tuesday, 5 August 2025.
Yes – the average flight time is 2 hours and 56 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Southwest Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Southwest Florida International Airport (RSW) to Chicago Midway International Airport (MDW): what you need to know

  • Book a direct flight from Southwest Florida International Airport to Chicago Midway International Airport and you'll be travelling for an average of 2 hours 55 minutes.

  • The timezone in Chicago is UTC-5, which is one hour behind Fort Myers.

  • Choose from 15 weekly Southwest Florida International Airport to Chicago Midway International Airport flights. The 05:25 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the last service of the day at 21:50.

  • To ensure you get on your RSW to MDW flight, leave plenty of time to check in and find your gate. Turning up two hours ahead of international departures and one hour before domestic flights is the standard rule.

  • You can expect bigger queues during popular months like October. Arriving up to four hours ahead of international flights and two hours for domestic departures is a good idea.

  • Jetting into Chicago (and then discovering more of United States!) is a snap with Southwest Airlines. This popular carrier has direct flights from Southwest Florida International Airport to Chicago Midway International Airport.

  • Southwest Airlines tops the list for bookings on this route.

  • The most punctual carrier offering RSW to MDW flights is Southwest Airlines. Its services land as planned 77.05% of the time.

  • If you want to add a stop to your trip, just deselect 'Direct flights only' when searching for your ticket from Southwest Florida International Airport to Chicago Midway International Airport. These are the most popular stopovers between RSW and MDW:

    • Hartsfield-Jackson Atlanta International Airport

    • Detroit Metropolitan Wayne County Airport

    • Cleveland Hopkins International Airport

How to find the cheapest flights from Southwest Florida International Airport (RSW) to Chicago Midway International Airport (MDW)

  • Currently, 63 € is the lowest price we've found for a one-way Southwest Florida International Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is 125 €. Keep in mind that fares may change due to demand when booking.

  • Get cheap tickets from RSW to MDW by booking at least six months ahead. According to our research, that's the sweet spot for picking up a bargain.

  • The cheapest month for flights from Southwest Florida International Airport to Chicago Midway International Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have flexible dates.

  • Stay on top of deals for cheap flights from RSW to MDW by creating a Price Alert. We'll send you an email or notification through the app when a lower fare becomes available.

  • Discover the perfect flight for you with the help of the filters. To see the 'Cheapest,' 'Fastest' or 'Best' flights from Southwest Florida International Airport to Chicago Midway International Airport, use the 'Sort by' function. You can also filter results by airline, departure and arrival times, and journey duration.

Handy information about Southwest Florida International Airport (RSW)

  • RSW is located at 11000 Terminal Access Road.

  • When it comes to Southwest Florida International Airport's on-time performance, data shows 77.32% of flights arrive within the expected timeframe.

  • Southwest Florida International Airport is about 23 kilometres from central Fort Myers. If you're driving, ride-sharing or catching a cab from the centre, it'll take 25 minutes or so to arrive, depending on the traffic.

  • Searching for a convenient hotel near RSW? If you're boarding an early flight from Southwest Florida International Airport to Chicago Midway International Airport, these stays will put you moments from check-in:

Arriving at Chicago Midway International Airport (MDW)

  • The last thing you need is a lengthy trip to your hotel if you're getting in late on a Southwest Florida International Airport to Chicago Midway International Airport flight. Check in to one of these accommodation options near MDW instead:

  • Begin your adventure by picking up a Chicago Midway International Airport rental car. Grab a set of wheels from Dollar, Hertz or Budget to explore Chicago and beyond.

  • To get the lowest price, book your ride from Chicago Midway International Airport around four weeks before you travel.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • You'll find MDW at 5700 South Cicero.

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 20 minutes to reach the centre driving.

  • Travelling on public transport takes about 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

  • July is the most popular month for flights from Southwest Florida International Airport to Chicago Midway International Airport. For smaller crowds, visit Chicago in May.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC (59ºF) and 29ºC (84ºF). Lock in your flights from Southwest Florida International Airport to Chicago Midway International Airport in this month if this is the kind of weather you like.

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from RSW to MDW sometime then if you want to travel when it's cooler.

Explore more of United States

  • You've visited Chicago, now it's time to explore other corners of United States. Journey about 451 kilometres south-east to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Ohio Statehouse and German Village, you've got a jam-packed schedule ahead.

  • Indianapolis is another essential stop in United States and is around 257 kilometres south-east of Chicago. No journey is complete without visiting The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from Fort Myers to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.