$30 Cheap flight deals from Port Charlotte (RSW) to Chicago (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 Port Charlotte to Chicago

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.

Sat, Jan 24 - Mon, Feb 2
RSW
Southwest Florida Intl.
ORD
O'Hare Intl.
$161 Roundtrip, found 2 days ago
$161
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Jan 24 from Southwest Florida Intl. to O'Hare Intl., returning Mon, Feb 2, priced at $161 found 2 days ago
Fri, Jan 23 - Tue, Jan 27
RSW
Southwest Florida Intl.
MDW
Midway Intl.
$317 Roundtrip, found 6 days ago
$317
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Jan 23 from Southwest Florida Intl. to Midway Intl., returning Tue, Jan 27, priced at $317 found 6 days ago
Sat, Jan 24 - Mon, Jan 26
RSW
Southwest Florida Intl.
RFD
Greater Rockford
$356 Roundtrip, found 4 days ago
$356
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jan 24 from Southwest Florida Intl. to Greater Rockford, returning Mon, Jan 26, priced at $356 found 4 days ago
Fri, Jan 23 - Sun, Jan 25
SRQ
Sarasota-Bradenton Intl.
ORD
O'Hare Intl.
$702 Roundtrip, found 20 hours ago
$702
Roundtrip
found 20 hours ago
Select United flight, departing Fri, Jan 23 from Sarasota-Bradenton Intl. to O'Hare Intl., returning Sun, Jan 25, priced at $702 found 20 hours ago

Airfares from $30 One Way, $50 Round Trip from Port Charlotte to Chicago

Prices starting at $50 for return flights and $30 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, Feb 25 - Tue, Mar 3
RSW
Fort Myers
ORD
Chicago
$50 Roundtrip, found 5 days ago
$50
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Feb 25 from Fort Myers to Chicago, returning Tue, Mar 3, priced at $50 found 5 days ago
Sat, Feb 14 - Sun, Feb 15
RSW
Fort Myers
ORD
Chicago
$59 Roundtrip, found 7 hours ago
$59
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Fort Myers to Chicago, returning Sun, Feb 15, priced at $59 found 7 hours ago
Sat, Feb 14 - Sat, Feb 21
RSW
Fort Myers
MDW
Chicago
$156 Roundtrip, found 2 days ago
$156
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Fort Myers to Chicago, returning Sat, Feb 21, priced at $156 found 2 days ago
Fri, Feb 20 - Tue, Feb 24
RSW
Fort Myers
ORD
Chicago
$170 Roundtrip, found 11 hours ago
$170
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Fri, Feb 20 from Fort Myers to Chicago, returning Tue, Feb 24, priced at $170 found 11 hours ago
Fri, Feb 13 - Tue, Feb 17
RSW
Fort Myers
MDW
Chicago
$173 Roundtrip, found 6 days ago
$173
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Feb 13 from Fort Myers to Chicago, returning Tue, Feb 17, priced at $173 found 6 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Chicago Magnificent Mile
3.0-star property

Courtyard by Marriott Chicago Magnificent Mile

8.8/10 Excellent! (1,555 reviews)

Feb 26 - Mar 2

4 night stay

Fort Myers (RSW) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Coach
Price was $389, price is now $252 per person
$252
per person
found 1 day ago
Valet parking was easy and quick. The staff were all very pleasant and accommodating. The rooms were clean and the hotel overall was pleasant. Great location by restaurants and Mag Mile. Would stay again!

Reviewed on Nov 13, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 26 - Mar 2

4 night stay

Fort Myers (RSW) to Chicago (ORD)

Frontier Airlines • Coach

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Coach
Price was $564, price is now $331 per person
$331
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Mar 15 - Mar 20

5 night stay

Fort Myers (RSW) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Fort Myers (RSW)

Delta • Coach
Save 100% on your flight
Price was $1,662, price is now $979 per person
$979
per person
found 8 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Don't see what you're looking for?
See all available trips from Port Charlotte to Chicago
View all trips

More About Flying To Chicago from Port Charlotte

Route Information for Flights from Port Charlotte to Chicago

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

Port Charlotte to Chicago

The perfect trip begins with Orbitz. From booking your flights from Port Charlotte to Chicago to finding the best hotels, Orbitz has got it covered.

Stress-free Searching

With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Port Charlotte to Chicago flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.

Be One Step Ahead

Need to know what is going on at the airport before you get there? With Orbitz’s free alerts service, you can quickly find out about any booking changes, or flight from Port Charlotte to Chicago disruptions, saving you hours of wasted time. And if you are being picked up at the airport after your Port Charlotte to Chicago flights, have alerts sent straight to your contact’s mobile phone or email.

Cutting-Edge Mobile Tools

Find the best price on flights from Port Charlotte to Chicago with Orbitz’s mobile apps for iPhone and Android. Use m.orbitz.com on your mobile browser to check your gate, baggage allowance and delays, or find exclusive deals on hotels only available to mobile users.

We Work, you Rest and Play

Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Port Charlotte to Chicago flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

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.