$32 Cheap flight deals from Chicago (CHI) to Port Charlotte (RSW)

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This Weekend's Flight Deals from Chicago to Port Charlotte

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, Jul 18 - Mon, Jul 21
ORD
O'Hare Intl.
RSW
Southwest Florida Intl.
$256 Roundtrip, just found
$256
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Southwest Florida Intl., returning Mon, Jul 21, priced at $256 just found
Sat, Jul 19 - Sun, Jul 27
MDW
Midway Intl.
RSW
Southwest Florida Intl.
$336 Roundtrip, found 4 days ago
$336
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Jul 19 from Midway Intl. to Southwest Florida Intl., returning Sun, Jul 27, priced at $336 found 4 days ago
Sat, Jul 19 - Thu, Jul 24
MDW
Midway Intl.
SRQ
Sarasota-Bradenton Intl.
$465 Roundtrip, found 4 days ago
$465
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Jul 19 from Midway Intl. to Sarasota-Bradenton Intl., returning Thu, Jul 24, priced at $465 found 4 days ago
Sat, Jul 19 - Thu, Jul 24
ORD
O'Hare Intl.
SRQ
Sarasota-Bradenton Intl.
$473 Roundtrip, found 4 days ago
$473
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jul 19 from O'Hare Intl. to Sarasota-Bradenton Intl., returning Thu, Jul 24, priced at $473 found 4 days ago

Airfares from $32 One Way, $80 Round Trip from Chicago to Port Charlotte

Prices starting at $80 for return flights and $32 for one-way flights to Port Charlotte 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, Aug 6 - Sun, Aug 10
ORD
Chicago
RSW
Fort Myers
$80 Roundtrip, found 1 hour ago
$80
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Aug 6 from Chicago to Fort Myers, returning Sun, Aug 10, priced at $80 found 1 hour ago
Sat, Oct 25 - Sat, Nov 1
ORD
Chicago
RSW
Fort Myers
$93 Roundtrip, found 5 days ago
$93
Roundtrip
found 5 days ago
Select United flight, departing Sat, Oct 25 from Chicago to Fort Myers, returning Sat, Nov 1, priced at $93 found 5 days ago
Wed, Aug 20 - Wed, Aug 27
MDW
Chicago
RSW
Fort Myers
$94 Roundtrip, found 2 days ago
$94
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Fort Myers, returning Wed, Aug 27, priced at $94 found 2 days ago
Wed, Aug 27 - Thu, Aug 28
ORD
Chicago
RSW
Fort Myers
$95 Roundtrip, found 5 days ago
$95
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Aug 27 from Chicago to Fort Myers, returning Thu, Aug 28, priced at $95 found 5 days ago
Wed, Aug 27 - Tue, Sep 2
ORD
Chicago
SRQ
Sarasota
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select United flight, departing Wed, Aug 27 from Chicago to Sarasota, returning Tue, Sep 2, priced at $135 found 4 days ago

Port Charlotte economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Fort Myers/at The Forum
3.0-star property

Hyatt Place Fort Myers/at The Forum

8.2/10 Very Good! (1,001 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
The staff was very friendly and helpful. The rooms as well as main spaces were clean. The complimentary breakfast was good. My overall experience was great. I’d highly recommend staying here

Reviewed on Jun 22, 2025

Inn on Fifth
4.0-star property

Inn on Fifth

9.4/10 Exceptional! (1,000 reviews)

Aug 19 - Aug 26

7 night stay

Chicago (ORD) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
per person
found 1 day ago
The location is a 10 but this isn’t a 5-star property. I’ve stayed at this hotel the past 5 years, always for 5 nights between Christmas and New Years. The value for the price is terrible. The hair dryers in the room are trash, the TV in our room flickered on and off during our entire stay in 2024, the rooms are clean but not immaculate, the elevator takes forever to move between floors. Overall this hotel could use a major refresh and I will be finding a different hotel to stay at in Dec 2025.

Reviewed on Jan 2, 2025

Lani Kai Beachfront Resort
3.5-star property

Lani Kai Beachfront Resort

8.6/10 Excellent! (1,020 reviews)

Aug 29 - Sep 1

3 night stay

Chicago (CHI) to Fort Myers (RSW)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Very terrific staff & met one of the grand daughters who worked in the gift shop on our day of departure, she was so sweet, my daughter & I thoroughly enjoyed ourself.

Reviewed on Jul 8, 2025

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Port Charlotte first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Alba, Tapestry Collection by Hilton
4.0-star property

Hotel Alba, Tapestry Collection by Hilton

8.8/10 Excellent! (1,978 reviews)

Aug 28 - Sep 1

4 night stay

Chicago (CHI) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Chicago (CHI)

United • Non-stop • FirstClass
per person
found 1 day ago
We absolutely loved our stay here it was super clean, house keeping comes to your room every day and will clean if you want. A lot of the staff will get off work and come hang out at the pool and will also give advice on where to go in the area. The drinks at the pool side bar was amazing and Brian the bar tender is such a vibe and a lovely person. I will definitely be coming back again I really enjoyed myself. The only downside is the elevator being broken but they made the best out of what they had and have an attendant which I loved it made me feel 10x safer getting on and off the elevator! Definitely would recommend anyone checking them out!

Reviewed on Jun 16, 2025

The Westin Tampa Bay
4.0-star property

The Westin Tampa Bay

8.2/10 Very Good! (1,010 reviews)

Aug 28 - Sep 1

4 night stay

Chicago (CHI) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Chicago (CHI)

United • Non-stop • FirstClass
per person
found 1 day ago
This property has a great location. The staff was friendly and helpful. The hotel is nice but the air in our room barely worked, maintenance was very nice but our room never really cooled off. Also, be advised that if your room is on the 7th floor, so are the banquet rooms and it noisy. I would go back to this property but I refuse to stay on the 7th floor.

Reviewed on Jun 23, 2025

Hilton Garden Inn Tampa Airport Westshore
3.0-star property

Hilton Garden Inn Tampa Airport Westshore

9/10 Wonderful! (1,732 reviews)

Aug 28 - Sep 1

4 night stay

Chicago (CHI) to Sarasota (SRQ)

Delta • Non-stop • FirstClass

Sarasota (SRQ) to Chicago (CHI)

United • Non-stop • FirstClass
per person
found 1 day ago
For a hotel next to an airport, air traffic did not disrupt sleeping. The rooms are spacious, plenty of room to work and eat in.

Reviewed on Jul 8, 2025

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More About Flying To Port Charlotte from Chicago

Route Information for Flights from Chicago to Port Charlotte

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

Chicago to Port Charlotte

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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.