Cheap Flights From Southwest Florida Intl. (RSW) To Midway Intl. (MDW)

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Cheapest Flights from Fort Myers (RSW) to Chicago (MDW)

The cheapest flights to Midway Intl. found within the past 7 days were CA $343 round trip and CA $204 one way. Prices and availability subject to change. Additional terms may apply.

Sat, Feb 7 - Mon, Feb 16
RSW
Fort Myers
MDW
Chicago
CA $343 Roundtrip, found 6 days ago
CA $343
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Feb 7 from Fort Myers to Chicago, returning Mon, Feb 16, priced at CA $343 found 6 days ago
Fri, Feb 6 - Mon, Feb 16
RSW
Fort Myers
MDW
Chicago
CA $350 Roundtrip, found 6 days ago
CA $350
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Feb 6 from Fort Myers to Chicago, returning Mon, Feb 16, priced at CA $350 found 6 days ago
Wed, Feb 4 - Mon, Feb 16
RSW
Fort Myers
MDW
Chicago
CA $391 Roundtrip, found 6 days ago
CA $391
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Feb 4 from Fort Myers to Chicago, returning Mon, Feb 16, priced at CA $391 found 6 days ago
Tue, Feb 3 - Mon, Feb 16
RSW
Fort Myers
MDW
Chicago
CA $401 Roundtrip, found 6 days ago
CA $401
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Feb 3 from Fort Myers to Chicago, returning Mon, Feb 16, priced at CA $401 found 6 days ago
Thu, Feb 5 - Mon, Feb 16
RSW
Fort Myers
MDW
Chicago
CA $429 Roundtrip, found 6 days ago
CA $429
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Feb 5 from Fort Myers to Chicago, returning Mon, Feb 16, priced at CA $429 found 6 days ago
Sat, Feb 7 - Fri, Feb 13
RSW
Fort Myers
MDW
Chicago
CA $654 Roundtrip, found 6 days ago
CA $654
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Feb 7 from Fort Myers to Chicago, returning Fri, Feb 13, priced at CA $654 found 6 days ago
Fri, Feb 6 - Fri, Feb 13
RSW
Fort Myers
MDW
Chicago
CA $662 Roundtrip, found 6 days ago
CA $662
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Feb 6 from Fort Myers to Chicago, returning Fri, Feb 13, priced at CA $662 found 6 days ago
Wed, Feb 4 - Fri, Feb 13
RSW
Fort Myers
MDW
Chicago
CA $702 Roundtrip, found 6 days ago
CA $702
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Feb 4 from Fort Myers to Chicago, returning Fri, Feb 13, priced at CA $702 found 6 days ago
Tue, Feb 3 - Fri, Feb 13
RSW
Fort Myers
MDW
Chicago
CA $717 Roundtrip, found 6 days ago
CA $717
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Feb 3 from Fort Myers to Chicago, returning Fri, Feb 13, priced at CA $717 found 6 days ago
Fri, Feb 6 - Fri, Feb 13
RSW
Fort Myers
MDW
Chicago
CA $731 Roundtrip, found 6 days ago
CA $731
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Feb 6 from Fort Myers to Chicago, returning Fri, Feb 13, priced at CA $731 found 6 days ago
Thu, Feb 5 - Fri, Feb 13
RSW
Fort Myers
MDW
Chicago
CA $745 Roundtrip, found 6 days ago
CA $745
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Feb 5 from Fort Myers to Chicago, returning Fri, Feb 13, priced at CA $745 found 6 days ago

Frequently asked questions

Are there direct flights from RSW to Midway Airport?
If you want to fly directly from Southwest Florida Intl. Airport to Midway Airport, look into Southwest Airlines. This is the airline for you if you prefer to reach your destination with minimum fuss.
What airlines fly from Southwest Florida Intl. Airport to Midway Intl. Airport (MDW)?
With Southwest Airlines, you won't have to bother with lengthy layovers or standing around waiting to catch your next flight. This airline company will take you straight from RSW to Chicago Airport on one of the 117 flights offered on this route each month.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Fort Myers (RSW)

Travelers at RSW love to visit these top cities. Roam to the top destinations from Fort Myers (RSW) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (MDW)

Travelers at MDW love to visit these top cities. Roam to the top destinations from Chicago(MDW) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.