$30 Cheap flight deals from Fort Myers (FMY) to Naperville (CHI)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

This Weekend's Flight Deals from Fort Myers to Naperville

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 2 - Mon, Feb 2
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$305 Roundtrip, found 10 hours ago
$305
Roundtrip
found 10 hours ago
Select Spirit Airlines flight, departing Fri, Jan 2 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Feb 2, priced at $305 found 10 hours ago
Sun, Jan 4 - Mon, Jan 5
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$922 Roundtrip, found 11 hours ago
$922
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Sun, Jan 4 from Southwest Florida Intl. to Midway Intl., returning Mon, Jan 5, priced at $922 found 11 hours ago
Fri, Jan 2 - Sun, Jan 4
RSW
Southwest Florida Intl.
RFD
Greater Rockford
$967 Roundtrip, found 17 hours ago
$967
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Fri, Jan 2 from Southwest Florida Intl. to Greater Rockford, returning Sun, Jan 4, priced at $967 found 17 hours ago

Airfares from $30 One Way, $59 Round Trip from Fort Myers to Naperville

Prices starting at $59 for return flights and $30 for one-way flights to Naperville were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Feb 19 - Sun, Feb 22
RSW
Fort Myers
ORD
Chicago
$59 Roundtrip, found 12 hours ago
$59
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Fort Myers to Chicago, returning Sun, Feb 22, priced at $59 found 12 hours ago
Sat, Jan 31 - Sat, Feb 7
RSW
Fort Myers
ORD
Chicago
$60 Roundtrip, found 1 day ago
$60
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Jan 31 from Fort Myers to Chicago, returning Sat, Feb 7, priced at $60 found 1 day ago
Thu, Feb 19 - Sun, Feb 22
RSW
Fort Myers
ORD
Chicago
$68 Roundtrip, found 12 hours ago
$68
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Thu, Feb 19 from Fort Myers to Chicago, returning Sun, Feb 22, priced at $68 found 12 hours ago
Sat, Jan 17 - Tue, Jan 20
RSW
Fort Myers
MDW
Chicago
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Fort Myers to Chicago, returning Tue, Jan 20, priced at $153 found 1 day ago
Sat, Feb 14 - Tue, Feb 17
RSW
Fort Myers
RFD
Rockford
$161 Roundtrip, found 3 days ago
$161
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Feb 14 from Fort Myers to Rockford, returning Tue, Feb 17, priced at $161 found 3 days ago

Naperville economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
4.0-star property

Palmer House a Hilton Hotel

8.4/10 Very Good! (2,059 reviews)

Feb 13 - Feb 15

2 night stay

Fort Myers (RSW) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Fort Myers (RSW)

Frontier Airlines • Coach
Price was $317, price is now $223 per person
$223
per person
found 1 day ago
Our stay was absolutely perfect. The room was clean. The staff was amazing! The decorations were festive and the pool was spotless warm and very very family friendly!!

Reviewed on Dec 29, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 13 - Feb 15

2 night stay

Fort Myers (RSW) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Fort Myers (RSW)

Frontier Airlines • Coach
Price was $387, price is now $261 per person
$261
per person
found 1 day ago
Staff is TOP NOTCH! I am in a wheelchair right now, recovering from a knee surgery, and staff could not have been more solicitous and helpful. Also, when we checked in, upon learning of my daughter‘s birthday on Christmas, the front desk representative gave us a complementary room upgrade and sent up chocolates! The room was very clean and the shower was fantastic. Not enough good words about the buffet, as long as you’re clear that it is a “breakfast“ buffet and not a “brunch“ buffet :-). I think I was expecting a sliced roast beef and an omelette bar, but it is in fact a very extensive selection of breakfast foods. The restaurant recommendation was spot on. We had a delicious dinner of fine Mediterranean/Sardinian foodat Nora’s next door and enjoyed it immensely. I have now joined the capital RIU club and plan on spending much more time at their other properties, particularly in Costa Rica, where I am moving next month. Kudos to all, and thank you for our wonderful stay!

Reviewed on Dec 28, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (2,229 reviews)

Feb 19 - Feb 22

3 night stay

Fort Myers (RSW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $414, price is now $294 per person
$294
per person
found 13 hours ago
Courteous staff, clean room, conveniently located right on the pier.

Reviewed on Nov 3, 2025

Don't see what you're looking for?
See all available trips from Fort Myers to Naperville
View all trips

More About Flying To Naperville from Fort Myers

Route Information for Flights from Fort Myers to Naperville

Origin Airport IATA Code
FMY
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Fort Myers to Naperville

Need bargain Fort Myers to Naperville flights in an instant? Find discount air tickets at Orbitz! At Orbitz, we don’t need to run sales to provide you with low prices on flights.

Find Guaranteed Low Prices wWth Cutting-Edge Mobile Tools

When you’re searching for Fort Myers to Naperville flights in a hurry, just use our mobile app. Once you’ve booked your air ticket, you can rely on our app to provide you with further details on your trip and to help you to find exclusive offers on hotels we know you’ll love to stay in.

Accumulate Miles and Enjoy Greater Discounts

If you are part of a frequent flyer program, you can also earn miles and points with the qualifying flights you book with Orbitz. Enjoy great deals on your Fort Myers to Naperville flights and get points and miles in return.

Stay Informed With Personalized Flight Alerts

Orbitz is the top source for low cost flights from Fort Myers to Naperville. We pride ourselves on not only offering you value for money but providing you with personal travel care. This is why we send you flight alerts about your travel plans at no added cost when you provide us with your email address or phone number.

See Significant Savings That Fit Your Schedule

We make it as easy as possible for you to book great deals on flights from Fort Myers to Naperville. You won’t be forced to compromise on your schedule—you can pick Fort Myers to Naperville flights that suit your needs.

More Destinations

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.