Cheap flights from MDW to RSW (Midway Intl. to Southwest Florida Intl.)

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Cheap Flights from MDW to RSW starting at $129 One Way, $257 Round Trip

Prices starting at $257 for return flights and $129 for one-way flights to Southwest Florida Intl. were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Dec 5 - Sat, Dec 12
MDW
Chicago
RSW
Fort Myers
$257 Roundtrip, just found
$257
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Dec 5 from Chicago to Fort Myers, returning Sat, Dec 12, priced at $257 just found
Sat, Jul 25 - Tue, Jul 28
MDW
Chicago
RSW
Fort Myers
$263 Roundtrip, found 17 hours ago
$263
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Sat, Jul 25 from Chicago to Fort Myers, returning Tue, Jul 28, priced at $263 found 17 hours ago
Wed, Jul 22 - Sat, Jul 25
MDW
Chicago
RSW
Fort Myers
$267 Roundtrip, just found
$267
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Jul 22 from Chicago to Fort Myers, returning Sat, Jul 25, priced at $267 just found
Wed, Sep 9 - Mon, Sep 14
MDW
Chicago
RSW
Fort Myers
$269 Roundtrip, found 6 hours ago
$269
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Sep 9 from Chicago to Fort Myers, returning Mon, Sep 14, priced at $269 found 6 hours ago
Sat, Oct 3 - Tue, Oct 6
MDW
Chicago
RSW
Fort Myers
$272 Roundtrip, found 1 day ago
$272
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Oct 3 from Chicago to Fort Myers, returning Tue, Oct 6, priced at $272 found 1 day ago

Hotel Ideas near Southwest Florida Intl.

Airport Hotels near Southwest Florida Intl.

Holiday Inn Express & Suites Fort Myers Airport by IHG

Holiday Inn Express & Suites Fort Myers Airport by IHG

2.5 out of 5
14567 GLOBAL PARKWAY Fort Myers FL
$75 nightly
The price is $84 total per night from Jul 4 to Jul 5
$84 total
Jul 4 - Jul 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,105 reviews)
"I have stayed at this hotel many times over the past 2 years because of it's cleanliness,however this time my room was clean as always but the bathroom and tiled area smelled like it was mopped with a dirty mop. I was very disappointed and will have second thoughts of staying again."

Reviewed on Jun 22, 2026

Holiday Inn Express & Suites Fort Myers Airport by IHG
Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park

2 out of 5
10150 Daniels Pkwy Fort Myers FL
$69 nightly
The price is $77 total per night from Jun 24 to Jun 25
$77 total
Jun 24 - Jun 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
8/10 Very Good! (1,695 reviews)
"This is my second time staying at this hotel. I have had no problem with it. Its is quiet and kept well."

Reviewed on Jun 22, 2026

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park
Comfort Inn & Suites Fort Myers Airport

Comfort Inn & Suites Fort Myers Airport

2.5 out of 5
Fort Myers FL
$75 nightly
The price is $83 total per night from Jun 30 to Jul 1
$83 total
Jun 30 - Jul 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,144 reviews)
"The free breakfast was great, the property was quiet and the airport transfer was extremely helpful."

Reviewed on Jun 22, 2026

Comfort Inn & Suites Fort Myers Airport
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels In Fort Myers

Baymont by Wyndham Fort Myers Central

Baymont by Wyndham Fort Myers Central

2.5 out of 5
4850 S Cleveland Ave Fort Myers FL
$64 nightly
The price is $71 total per night from Jun 26 to Jun 27
$71 total
Jun 26 - Jun 27
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.8/10 (1,130 reviews)
"I enjoyed my stay I have no complaints"

Reviewed on Jun 22, 2026

Baymont by Wyndham Fort Myers Central
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
$239 nightly
The price is $266 total per night from Jul 6 to Jul 7
$266 total
Jul 6 - Jul 7
Total with taxes and fees
Book a stay at this spa resort in Fort Myers. Enjoy 3 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...
Marriott Sanibel Harbour Resort & Spa
Hilton Garden Inn Ft Myers

Hilton Garden Inn Ft Myers

3 out of 5
12600 University Dr Fort Myers FL
$95 nightly
The price is $106 total per night from Jul 5 to Jul 6
$106 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.8/10 Excellent! (1,006 reviews)
"Had a great experience. Will stay again."

Reviewed on Jun 22, 2026

Hilton Garden Inn Ft Myers
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fort Myers Hotels With Airport Transportation

Crowne Plaza Ft. Myers Gulf Coast by IHG

Crowne Plaza Ft. Myers Gulf Coast by IHG

4 out of 5
9931 Interstate Commerce Dr Fort Myers FL
$134 nightly
The price is $149 total per night from Jul 22 to Jul 23
$149 total
Jul 22 - Jul 23
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
9.2/10 Wonderful! (1,001 reviews)
"Front desk not welcoming and attitude was stiff. Half the time not there, oblivious or non approachable. Garbage basket in room had trash in it and candy wrapper under chair in room. Certainly not thorough. No hair dryer in room and no exhaust fan in bathroom."

Reviewed on Jun 15, 2026

Crowne Plaza Ft. Myers Gulf Coast by IHG
Travelodge by Wyndham Fort Myers Airport

Travelodge by Wyndham Fort Myers Airport

2 out of 5
13661 Indian Paint Lane Fort Myers FL
$58 nightly
The price is $64 total per night from Jun 24 to Jun 25
$64 total
Jun 24 - Jun 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
7.6/10 Good! (1,002 reviews)
"Proximity to the airport and rate"

Reviewed on May 31, 2026

Travelodge by Wyndham Fort Myers Airport
Baymont Inn & Suites by Wyndham Fort Myers I-75

Baymont Inn & Suites by Wyndham Fort Myers I-75

2.5 out of 5
9401 Marketplace Road Fort Myers FL
$65 nightly
The price is $72 total per night from Jul 20 to Jul 21
$72 total
Jul 20 - Jul 21
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.2/10 (1,000 reviews)
"Very old property. Rooms were basically clean, but in desperate need of some updating. The bathrooms have a tub with a shower in it, but with no safety features such as nonslip strips on the floor or a safety bar to grasp onto as you’re getting in and out. The two ladies who took care of the breakfast ..."

Reviewed on Jun 6, 2026

Baymont Inn & Suites by Wyndham Fort Myers I-75
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Low Priced Fort Myers Hotels

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park

2 out of 5
10150 Daniels Pkwy Fort Myers FL
$69 nightly
The price is $77 total per night from Jun 24 to Jun 25
$77 total
Jun 24 - Jun 25
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the clean rooms ...
8/10 Very Good! (1,695 reviews)
"This is my second time staying at this hotel. I have had no problem with it. Its is quiet and kept well."

Reviewed on Jun 22, 2026

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park
Travelodge by Wyndham Fort Myers North

Travelodge by Wyndham Fort Myers North

2 out of 5
13353 N Cleveland Ave North Fort Myers FL
$50 nightly
The price is $56 total per night from Jul 3 to Jul 4
$56 total
Jul 3 - Jul 4
Total with taxes and fees
Stay at this hotel in North Fort Myers. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Art of the Olympians Museum and Caloosa ...
6.2/10 (1,004 reviews)
"pool not open"

Reviewed on Jun 9, 2026

Travelodge by Wyndham Fort Myers North
Baymont Inn & Suites by Wyndham Fort Myers I-75

Baymont Inn & Suites by Wyndham Fort Myers I-75

2.5 out of 5
9401 Marketplace Road Fort Myers FL
$65 nightly
The price is $72 total per night from Jul 20 to Jul 21
$72 total
Jul 20 - Jul 21
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.2/10 (1,000 reviews)
"Very old property. Rooms were basically clean, but in desperate need of some updating. The bathrooms have a tub with a shower in it, but with no safety features such as nonslip strips on the floor or a safety bar to grasp onto as you’re getting in and out. The two ladies who took care of the breakfast ..."

Reviewed on Jun 6, 2026

Baymont Inn & Suites by Wyndham Fort Myers I-75
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Family Friendly Hotels in Fort Myers

Pink Shell Beach Resort and Marina

Pink Shell Beach Resort and Marina

4 out of 5
275 Estero Blvd Fort Myers Beach FL
$269 nightly
The price is $300 total per night from Jul 19 to Jul 20
$300 total
Jul 19 - Jul 20
Total with taxes and fees
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and a full-service spa. Our guests praise the breakfast and the ...
9.4/10 Exceptional! (1,393 reviews)
"From check in to check out this place was a dream. Gorgeous view from balcony of the gulf, rooms were well appointed and the beds were super cozy with upgraded bedding. Robes in the room were an added bonus. From the beach to the pool and back again. Breakfast was free and had wait staff ensuring ..."

Reviewed on Jun 19, 2026

Pink Shell Beach Resort and Marina
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

5 out of 5
1451 Middle Gulf Drive Sanibel FL
$478 nightly
The price is $533 total per night from Jul 5 to Jul 6
$533 total
Jul 5 - Jul 6
Total with taxes and fees
Book a stay at this luxury aparthotel in Sanibel. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the property condition in our reviews. ...
8.6/10 Excellent! (2,660 reviews)
"Very clean rooms. The kitchen was fully stocked with everything we needed to cook/bake anything. Beautiful views. One downside was the earlier closing hours (7PM for restaurants/services/market/beach chairs). When we visited mid-June, the sunset was not until after 8:30."

Reviewed on Jun 22, 2026

Sundial Beach Resort & Spa
South Seas

South Seas

3.5 out of 5
5400 South Seas Plantation Rd Captiva FL
Book a stay at this beach resort in Captiva. Enjoy 3 outdoor pools, 5 restaurants, and a private beach. Popular attractions Captiva Beach and Jungle Drums are ...
8.4/10 Very Good! (1,001 reviews)
"Felt like they weren’t fully staffed. There wasn’t a lot of vibes of merriment even though they have great amenities to do so. Allison at Flippers was very nice and enjoyable. Gigi at Beach House was very sweet and we enjoyed her service but have to say we had told the restaurant that it was our ..."

Reviewed on Jun 10, 2026

Get rates
South Seas
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

MDW to RSW Route Info

Origin Airport
Destination Airport
Number Of Airlines Serving
Distance
Shortest Flight Departure Time
Shortest Flight Departure Date
MDW Address & GPS
Address:
5700 South Cicero
Chicago IL, 60638
United States
IATA Code:
MDW
Longitude:
-87.740871
Latitude:
41.788136
Time Zone:
America/Chicago
RSW Address & GPS
Address:
11000 Terminal Access Road
Fort Myers FL,
United States
IATA Code:
RSW
Longitude:
-81.755263
Latitude:
26.527887
Time Zone:
America/New_York

Frequently asked questions

Are there non-stop flights from Chicago Airport to Southwest Florida Intl. Airport?
You won't have to bother with the hassle of swapping planes or missing your connection on this route. Southwest Airlines will fly you directly from Midway Intl. Airport (MDW) to Southwest Florida Intl. Airport.
What is the shortest flight from Chicago Airport to RSW?
If conditions are good and all goes according to plan, you could be flying into Southwest Florida Intl. Airport (RSW) from Midway Airport in only 2 hours and 50 minutes. With such a quick flight time, think about bringing carry-on luggage only.
How many hours flight from MDW to Southwest Florida Intl. Airport?
The average flight time from Midway Airport to Southwest Florida Intl. Airport is just 2 hours and 52 minutes. So, throw a few things in your suitcase and book a flight. There's nothing more exciting than an impromptu getaway.
What airlines have the most flights from Chicago Airport to Southwest Florida Intl. Airport?
Whether you opt for aisle, middle or window, you'll travel to your destination easily and comfortably with Southwest Airlines. This top-rated carrier operates 108 flights from Chicago to Fort Myers each month.

Map To Nearby Hotels

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.

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