Cheap flights from MDW to RSW (Midway Intl. to Southwest Florida Intl.)
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Cheap Flights from MDW to RSW starting at $138 One Way, $295 Round Trip
Prices starting at $295 for return flights and $138 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.
MDW
Chicago
RSW
Fort Myers
$295 Roundtrip, found 2 hours ago
$295
Roundtrip
found 2 hours ago
MDW
Chicago
RSW
Fort Myers
$302 Roundtrip, found 9 hours ago
$302
Roundtrip
found 9 hours ago
MDW
Chicago
RSW
Fort Myers
$305 Roundtrip, found 2 hours ago
$305
Roundtrip
found 2 hours ago
MDW
Chicago
RSW
Fort Myers
$310 Roundtrip, found 1 day ago
$310
Roundtrip
found 1 day ago
MDW
Chicago
RSW
Fort Myers
$312 Roundtrip, found 4 hours ago
$312
Roundtrip
found 4 hours ago
Hotel Ideas near Southwest Florida Intl.
Airport Hotels near Southwest Florida Intl.
Holiday Inn Express & Suites Fort Myers Airport by IHG
14567 GLOBAL PARKWAY Fort Myers FL
$83 nightly
The price is $93 total per night from Jul 1 to Jul 2
$93 total
Jul 1 - Jul 2
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! (1,070 reviews)
"Room was clean and staff were very friendly."
Reviewed on Jun 7, 2026
Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park
10150 Daniels Pkwy Fort Myers FL
$69 nightly
The price is $77 total per night from Jun 8 to Jun 9
$77 total
Jun 8 - Jun 9
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! (1,694 reviews)
"Poor breakfast Checl-in and Chevk-out automated."
Reviewed on Jun 7, 2026
Comfort Inn & Suites Fort Myers Airport
Fort Myers FL
$77 nightly
The price is $85 total per night from Jun 28 to Jun 29
$85 total
Jun 28 - Jun 29
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! (1,131 reviews)
"Nice"
Reviewed on Jun 7, 2026
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
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
$270 nightly
The price is $301 total per night from Jun 8 to Jun 9
$301 total
Jun 8 - Jun 9
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 ...
8.6/10 Excellent! (1,013 reviews)
"Very beautiful hotel. Nice facilities and plenty of space to enjoy the environment."
Reviewed on Jun 7, 2026
Baymont by Wyndham Fort Myers Central
4850 S Cleveland Ave Fort Myers FL
$67 nightly
The price is $74 total per night from Jul 1 to Jul 2
$74 total
Jul 1 - Jul 2
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 (1,121 reviews)
"Musty and dirty."
Reviewed on Jun 7, 2026
Hilton Garden Inn Ft Myers
12600 University Dr Fort Myers FL
$95 nightly
The price is $106 total per night from Jun 14 to Jun 15
$106 total
Jun 14 - Jun 15
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! (1,015 reviews)
"Our entire state was lovely. Very relaxing. The pool area is nice. The staff was very nice and helpful with questions that we had. I would definitely come back."
Reviewed on Jun 7, 2026
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
9931 Interstate Commerce Dr Fort Myers FL
$134 nightly
The price is $149 total per night from Jul 5 to Jul 6
$149 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 and ...
9.2/10 Wonderful! (1,002 reviews)
"We had a wonderful stay. The lady at the front desk deserves special recognition: she was incredibly kind, attentive, and truly went above and beyond to make sure our family was comfortable. We were traveling with our 24‑year‑old daughter, and she made sure our rooms were very close to each other ..."
Reviewed on Jun 1, 2026
Travelodge by Wyndham Fort Myers Airport
13661 Indian Paint Lane Fort Myers FL
$59 nightly
The price is $66 total per night from Jun 10 to Jun 11
$66 total
Jun 10 - Jun 11
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! (1,000 reviews)
"Proximity to the airport and rate"
Reviewed on May 31, 2026
Baymont Inn & Suites by Wyndham Fort Myers I-75
9401 Marketplace Road Fort Myers FL
$66 nightly
The price is $73 total per night from Jun 14 to Jun 15
$73 total
Jun 14 - Jun 15
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 (1,004 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
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
10150 Daniels Pkwy Fort Myers FL
$69 nightly
The price is $77 total per night from Jun 8 to Jun 9
$77 total
Jun 8 - Jun 9
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! (1,694 reviews)
"Poor breakfast Checl-in and Chevk-out automated."
Reviewed on Jun 7, 2026
Travelodge by Wyndham Fort Myers North
13353 N Cleveland Ave North Fort Myers FL
$53 nightly
The price is $59 total per night from Jun 20 to Jun 21
$59 total
Jun 20 - Jun 21
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 Caloosa Sound Amphitheater and Centennial ...
6.2/10 (1,003 reviews)
"Horrible DONT DO IT , spend extra"
Reviewed on May 31, 2026
Baymont Inn & Suites by Wyndham Fort Myers I-75
9401 Marketplace Road Fort Myers FL
$66 nightly
The price is $73 total per night from Jun 14 to Jun 15
$73 total
Jun 14 - Jun 15
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 (1,004 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
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
275 Estero Blvd Fort Myers Beach FL
$274 nightly
The price is $305 total per night from Jun 16 to Jun 17
$305 total
Jun 16 - Jun 17
Total with taxes and fees
Book a stay at this beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
9.4/10 Exceptional! (1,393 reviews)
"No se los recomiendo muy aburrido mala atención todo súper caro no hay diversión para los niños"
Reviewed on Jun 7, 2026
Sundial Beach Resort & Spa
1451 Middle Gulf Drive Sanibel FL
$498 nightly
The price is $555 total per night from Jun 8 to Jun 9
$555 total
Jun 8 - Jun 9
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! (2,654 reviews)
"I stayed at this property with my husband for almost a week. Super quick walk to the beach from our room and the hotel provides chairs and umbrellas. Our favorite amenity was the bikes that they let you check out. We rode the bikes all over the Island and it was wonderful. The staff refreshed our ..."
Reviewed on Jun 1, 2026
South Seas
5400 South Seas Plantation Rd Captiva FL
$600 nightly
The price is $669 total per night from Jun 9 to Jun 10
$669 total
Jun 9 - Jun 10
Total with taxes and fees
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! (1,003 reviews)
"We recently stayed at this resort and overall had a pleasant experience. The beachfront location is beautiful, and the water park was definitely one of the highlights of our trip. The staff throughout the resort were friendly, helpful, and always willing to assist when needed. That said, there were ..."
Reviewed on May 31, 2026
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 | |
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Destination Airport | |
Number Of Airlines Serving | |
Distance | |
Shortest Flight Departure Time | |
Shortest Flight Departure Date |
- Airport Locations
- More Popular Flights
- Top Trending
- Flights from Other Cities
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- Great Travel Ideas
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
Other Flights from Midway Intl. Airport (MDW)
Other Flights to Southwest Florida Intl. Airport (RSW)
- O'Hare Intl. Airport (ORD)
- Chicago Executive Airport (PWK)
- Dupage Airport (DPA)
- Kenosha Regional Airport (ENW)
- South Bend Intl. Airport (SBN)
- Greater Rockford Airport (RFD)
- General Mitchell Intl. Airport (MKE)
- Waukesha County Airport (UES)
- Goshen Municipal Airport (GSH)
- Purdue University Airport (LAF)
Top Trending
Flights
- Ronald Reagan Washington National (DCA) To Orlando Intl. (MCO)
- Logan Intl. (BOS) To Orlando Intl. (MCO)
- Bradley Intl. (BDL) To Orlando Intl. (MCO)
- LaGuardia (LGA) To Miami Intl. (MIA)
- LaGuardia (LGA) To Fort Lauderdale - Hollywood Intl. (FLL)
- Orlando Intl. (MCO) To Los Angeles Intl. (LAX)
- Detroit Metropolitan Wayne County (DTW) To Orlando Intl. (MCO)
- Ronald Reagan Washington National (DCA) To Miami Intl. (MIA)
- Orlando Intl. (MCO) To LaGuardia (LGA)
- Baltimore Washington Intl. Thurgood Marshall (BWI) To Miami Intl. (MIA)
- John F. Kennedy Intl. (JFK) To Fort Lauderdale - Hollywood Intl. (FLL)
- Los Angeles Intl. (LAX) To Orlando Intl. (MCO)
- Newark Liberty Intl. Airport (EWR) To Orlando Intl. (MCO)
- Hartsfield-Jackson Atlanta Intl. (ATL) To Orlando Intl. (MCO)
- LaGuardia (LGA) To Orlando Intl. (MCO)
- Minneapolis - St. Paul Intl. (MSP) To Orlando Intl. (MCO)
- Baltimore Washington Intl. Thurgood Marshall (BWI) To Fort Lauderdale - Hollywood Intl. (FLL)
- Orlando Intl. (MCO) To John F. Kennedy Intl. (JFK)
- Orlando Intl. (MCO) To Newark Liberty Intl. Airport (EWR)
- O'Hare Intl. (ORD) To Orlando Intl. (MCO)
- Orlando Intl. (MCO) To Luis Munoz Marin Intl. (SJU)
- Detroit Metropolitan Wayne County (DTW) To Miami Intl. (MIA)
- Philadelphia Intl. (PHL) To Orlando Intl. (MCO)
- Baltimore Washington Intl. Thurgood Marshall (BWI) To Orlando Intl. (MCO)
- John F. Kennedy Intl. (JFK) To Orlando Intl. (MCO)
- John F. Kennedy Intl. (JFK) To Miami Intl. (MIA)
- Fort Lauderdale - Hollywood Intl. (FLL) To John F. Kennedy Intl. (JFK)
- Ronald Reagan Washington National (DCA) To Fort Lauderdale - Hollywood Intl. (FLL)
- Raleigh - Durham Intl. (RDU) To Orlando Intl. (MCO)
- John F. Kennedy Intl. (JFK) To Tampa Intl. (TPA)
Frequently asked questions
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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