Cheap flights from MDW to RSW (Midway Intl. to Southwest Florida Intl.)
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Cheap Flights from MDW to RSW starting at $142 One Way, $294 Round Trip
Prices starting at $294 for return flights and $142 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
$294 Roundtrip, found 3 hours ago
$294
Roundtrip
found 3 hours ago
MDW
Chicago
RSW
Fort Myers
$300 Roundtrip, found 3 hours ago
$300
Roundtrip
found 3 hours ago
MDW
Chicago
RSW
Fort Myers
$304 Roundtrip, found 3 hours ago
$304
Roundtrip
found 3 hours ago
MDW
Chicago
RSW
Fort Myers
$305 Roundtrip, found 5 hours ago
$305
Roundtrip
found 5 hours ago
MDW
Chicago
RSW
Fort Myers
$309 Roundtrip, found 3 hours ago
$309
Roundtrip
found 3 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
$91 nightly
The price is $101 total per night from Sep 4 to Sep 5
$101 total
Sep 4 - Sep 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 ...
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 Aug 9 to Aug 10
$77 total
Aug 9 - Aug 10
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 ...
8.2/10 Very Good! (1,756 reviews)
"Perfect"
Reviewed on Aug 6, 2026
Comfort Inn & Suites Fort Myers Airport
Fort Myers FL
$68 nightly
The price is $76 total per night from Aug 23 to Aug 24
$76 total
Aug 23 - Aug 24
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! (1,145 reviews)
"This hotel is convenient if you need to stay close to the airport. The staff were helpful. However, the rooms could use some maintenance, especially the bathroom, which is showing signs of wear and would benefit from some updates. Overall, it was an acceptable stay for a short visit, mainly because ..."
Reviewed on Aug 4, 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
Baymont by Wyndham Fort Myers Central
4850 S Cleveland Ave Fort Myers FL
$63 nightly
The price is $70 total per night from Aug 13 to Aug 14
$70 total
Aug 13 - Aug 14
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 ...
Marriott Sanibel Harbour Resort & Spa
17260 Harbour Pointe Dr Fort Myers FL
$223 nightly
The price is $248 total per night from Aug 23 to Aug 24
$248 total
Aug 23 - Aug 24
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 ...
Hilton Garden Inn Ft Myers
12600 University Dr Fort Myers FL
$95 nightly
The price is $106 total per night from Aug 9 to Aug 10
$106 total
Aug 9 - Aug 10
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 ...
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
$130 nightly
The price is $145 total per night from Sep 6 to Sep 7
$145 total
Sep 6 - Sep 7
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)
"Breakfast, room size, staff, cleanliness and comfy beds,"
Reviewed on Aug 4, 2026
Travelodge by Wyndham Fort Myers Airport
13661 Indian Paint Lane Fort Myers FL
$55 nightly
The price is $61 total per night from Sep 6 to Sep 7
$61 total
Sep 6 - Sep 7
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 ...
Baymont Inn & Suites by Wyndham Fort Myers I-75
9401 Marketplace Road Fort Myers FL
$58 nightly
The price is $64 total per night from Aug 14 to Aug 15
$64 total
Aug 14 - Aug 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. ...
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 Aug 9 to Aug 10
$77 total
Aug 9 - Aug 10
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 ...
8.2/10 Very Good! (1,756 reviews)
"Perfect"
Reviewed on Aug 6, 2026
Travelodge by Wyndham Fort Myers North
13353 N Cleveland Ave North Fort Myers FL
$48 nightly
The price is $54 total per night from Aug 15 to Aug 16
$54 total
Aug 15 - Aug 16
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 Edison and Ford Winter Estates and Caloosa ...
Baymont Inn & Suites by Wyndham Fort Myers I-75
9401 Marketplace Road Fort Myers FL
$58 nightly
The price is $64 total per night from Aug 14 to Aug 15
$64 total
Aug 14 - Aug 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. ...
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
$248 nightly
The price is $276 total per night from Aug 17 to Aug 18
$276 total
Aug 17 - Aug 18
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! (1,421 reviews)
"Out standing breakfast included! Bongos has great food! Pools open late even in the dark. Beautiful beaches! Free bicycle rentals! Free kayaking! Staff super friendly !"
Reviewed on Aug 7, 2026
Sundial Beach Resort & Spa
1451 Middle Gulf Drive Sanibel FL
$448 nightly
The price is $500 total per night from Aug 9 to Aug 10
$500 total
Aug 9 - Aug 10
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! (2,683 reviews)
"We will be coming back for sure!! We had an awful time getting down there because of our flights. The staff there felt so bad for us they upgraded our room, which honestly was just an added bonus that put our stay over the top. If that had not of happened, and we had our room that I had originally ..."
Reviewed on Aug 7, 2026
South Seas
5400 South Seas Plantation Rd Captiva FL
$367 nightly
The price is $409 total per night from Sep 7 to Sep 8
$409 total
Sep 7 - Sep 8
Total with taxes and fees
Book a stay at this beach resort in Captiva. Enjoy 6 outdoor pools, 5 restaurants, and a private beach. Popular attractions Bowman's Beach and Jungle Drums are ...
8.4/10 Very Good! (1,004 reviews)
"Beautiful property with excellent amenities—we really enjoyed our stay. One suggestion would be to provide daily housekeeping instead of every other day. Also, while construction is ongoing, it would be appreciated if guests could be assigned rooms farther away from the construction area whenever ..."
Reviewed on Aug 2, 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
- Flights From Other Airports
- 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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