Cheap Flight Tickets from Fort Myers (RSW) to Chicago (ORD), Starting at $181

Good to Know: Cheapest and Fastest RSW - ORD Flights

Useful information for finding best airline tickets from Southwest Florida International to Chicago O'Hare International on your next trip.

Cheapest Round Trip Flight

$237

DL Delta Airlines • 1 stop • 10h 41m

Sep 20 – Sep 27

The cheapest round trip flight from Fort Myers to Chicago (RSW-ORD-RSW) is currently $237

🔍 Search Flights

Cheapest One way Flight

$181

DL Delta Airlines • 1 stop • 9h 14m

Sep 20

The cheapest one way flight from Fort Myers to Chicago (RSW-ORD) is currently $181

🔍 Search Flights

Cheapest Direct Flight

$4895

AS Alaska Airlines • nonstop • 5h 19m

Sep 20

The cheapest nonstop flight from Fort Myers to Chicago (RSW-ORD) is currently $4895

🔍 Search Flights

Fastest Flight

5h 19m

The fastest nonstop flight from Fort Myers to Chicago (RSW-ORD) takes 5h 19m

Top Airlines Flying from Fort Myers to Chicago

Delta Airline, DL

Delta Airlines

Sun Country Airlines (SY)

Sun Country Airlines

Alaska Airlines -AS

Alaska Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

Latest Flight Deals from Fort Myers (RSW) to Chicago (ORD)

Compare and book low fare round-trip air tickets from Fort Myers to Chicago. Ideal for travelers with confirmed return itineraries.

Sep 20 - Sep 27, Economy
DL
Fort Myers → Chicago
10h 41m
7:00 AM - 12:41 PM • 1 stop
DL
Fort Myers → Chicago
10h 41m
6:40 AM - 2:21 PM • 1 stop
$237
Delta Airlines
Sep 20 - Sep 27, Economy
DL
Fort Myers → Chicago
9h 9m
5:30 AM - 10:19 AM • 1 stop
DL
Fort Myers → Chicago
10h 41m
6:40 AM - 2:21 PM • 1 stop
$237
Delta Airlines
Sep 20 - Sep 27, Economy
DL
Fort Myers → Chicago
8h 51m
8:10 AM - 12:41 PM • 1 stop
DL
Fort Myers → Chicago
10h 41m
6:40 AM - 2:21 PM • 1 stop
$237
Delta Airlines
Sep 20 - Sep 27, Economy
DL
Fort Myers → Chicago
13h 49m
7:00 AM - 2:29 PM • 1 stop
DL
Fort Myers → Chicago
10h 41m
6:40 AM - 2:21 PM • 1 stop
$313
Delta Airlines
Sep 20 - Sep 27, Economy
DL
Fort Myers → Chicago
14h 4m
1:12 PM - 8:56 PM • 1 stop
DL
Fort Myers → Chicago
10h 41m
6:40 AM - 2:21 PM • 1 stop
$346
Delta Airlines
Sep 20 - Sep 27, Economy
DL
Fort Myers → Chicago
10h 33m
1:12 PM - 6:45 PM • 1 stop
DL
Fort Myers → Chicago
7h 6m
6:40 AM - 12:06 PM • 1 stop
$390
Delta Airlines

Fly from Fort Myers to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Fort Myers to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on Fort Myers to Chicago Flights

What are the airports in Fort Myers?
RSW
What’s the most popular airline flying from RSW to ORD?
The most popular airline flying from Fort Myers to Chicago are
Can I fly from RSW to ORD non-stop?
Yes, you can fly RSW to ORD non-stop on
Which airlines fly nonstop between Fort Myers and Chicago?
The non-stop flights between Fort Myers and Chicago are .
What’s the earliest departure time from RSW to ORD Airport?
The earliest flight leaves RSW at 5:30 am and lands in ORD - Chicago O'Hare International
What are the airports in Chicago?
MDW,ORD
Can I make changes to my Fort Myers to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from RSW to ORD?
Read the fare rules of the Fort Myers to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Fort Myers and Chicago?
operate flights between Fort Myers and Chicago
How long does a flight from Fort Myers to Chicago take?
It takes approximately 3 hour to fly non-stop from RSW to ORD, which is 1120.28 miles by air.
Which airlines provide the cheapest flights from Fort Myers (RSW) to Chicago (ORD) ?
In the past couple of days, the cheapest tickets to ORD from RSW were found on DL : USD 187
Do I need a passport to fly between RSW and ORD?
No
What’s the latest departure time from RSW to ORD ?
The last flight leaves RSW at 7:12 pm

Fort Myers (RSW) to Chicago (ORD): Airport Information

Origin Airport Southwest Florida International , Fort Myers, US
Destination Airport Chicago O'Hare International , Chicago, US
Distance 1120 miles

More Flight Options for Fort Myers (RSW) and Chicago (ORD)

Why Fareleaders for RSW to ORD Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on Fort Myers to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on RSW to ORD flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of Fort Myers to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the Fort Myers (RSW) to Chicago (ORD)
Terms and Conditions*