$109 Cheap Delta flights Fort Myers (RSW) to Chicago (ORD)

View $109 flight on Sat, Jul 26, 2025Opens in a new window

$109 Cheap Delta flights Fort Myers (RSW) to Chicago (ORD)

Prices were available within the past 7 days and start at $109 for one-way flights and $140 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jul 11 - Wed, Jul 16
RSW
Fort Myers
ORD
Chicago
$140 Roundtrip, found 2 hours ago
$140
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Jul 11 from Fort Myers to Chicago, returning Wed, Jul 16, priced at $140 found 2 hours ago
Delta
Thu, Jul 24 - Sat, Jul 26
RSW
Fort Myers
ORD
Chicago
$149 Roundtrip, just found
$149
Roundtrip
just found
Select Delta flight, departing Thu, Jul 24 from Fort Myers to Chicago, returning Sat, Jul 26, priced at $149 just found
Delta
Tue, Aug 19 - Tue, Aug 26
RSW
Fort Myers
ORD
Chicago
$149 Roundtrip, just found
$149
Roundtrip
just found
Select Delta flight, departing Tue, Aug 19 from Fort Myers to Chicago, returning Tue, Aug 26, priced at $149 just found
Flights from Fort Myers (RSW) to Chicago (ORD)
Origin airport
Southwest Florida Intl.
Destination airport
O'Hare Intl.
Airlines serving
Alaska Airlines, American Airlines, Delta, Frontier Airlines, JetBlue Airways, Southwest Airlines, Spirit Airlines, Sun Country Airlines, United
Popular airline
JetBlue Airways
Distance
1122 mi
Average flight time
2 hours 13 mins

Frequently asked questions

How much is a Delta Air Lines flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
Apply the "Price (lowest to highest)" filter on Expedia to search for cheap Delta Air Lines return flights from $140 from RSW to ORD. Affordable one-way options from $109 are also available.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly from RSW to ORD with Delta Air Lines?
Delta Air Lines flights to Chicago are generally more affordable in the quieter months of January and February. Whether you need a return or one-way ticket, you could find a better deal then.
What is the cheapest time to book flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) with Delta Air Lines?
Look for affordable Delta Air Lines flights from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD) one to three months ahead of your departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. No matter the fare type and journey, the best day of the week to book a domestic flight is usually Sunday and the most expensive day tends to be Monday. Passengers who book on a Sunday can save 6% on average compared to those who book on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.
Does Delta Air Lines fly nonstop from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
To see if there's a direct journey from RSW to ORD with Delta Air Lines or any other airlines, check the "Nonstop" box when searching for flights.
What is the earliest Delta Air Lines flight from RSW to ORD?
To find the earliest departures from RSW to ORD with Delta Air Lines, filter your results by "Morning" and "Early Morning." Booking an early flight generally means you're less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports does Delta Air Lines fly into in Chicago?
Catch a Delta Air Lines flight from Southwest Florida Intl. Airport (RSW) to Chicago, and you'll probably come in to O'Hare Intl. Airport (ORD). This is the airline's primary hub in this city.
Why fly with Delta Air Lines from RSW to ORD?
Traveling from RSW to ORD with Delta Air Lines comes with a host of perks, including an excellent in-flight experience and a rewarding loyalty program. Plus, when booking through Expedia, One Key™ members can collect OneKeyCash™* to use on select future travel purchases. That's in addition to the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
Can I change or cancel my Delta Air Lines flight from Southwest Florida Intl. Airport (RSW) to O'Hare Intl. Airport (ORD)?
Depending on the type of fare you purchased, a fee will generally apply if you modify or cancel your flight more than 24 hours after it's confirmed. To find tickets with more flexibility, select our "No cancel fee" or "Changes included" filter when you look for flights. To learn more about changing or canceling your reservation, visit "Trips," select your flight and click on "Manage Booking."

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*Available to One Key members.