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

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

Cheap Flights from MDW to RSW starting at $90 One Way, $197 Round Trip

Prices starting at $197 for return flights and $90 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.

Mon, May 19 - Sat, May 24
MDW
Chicago
RSW
Fort Myers
$197 Roundtrip, found 8 hours ago
$197
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Mon, May 19 from Chicago to Fort Myers, returning Sat, May 24, priced at $197 found 8 hours ago
Tue, Jul 1 - Fri, Jul 4
MDW
Chicago
RSW
Fort Myers
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 1 from Chicago to Fort Myers, returning Fri, Jul 4, priced at $198 found 1 day ago
Sat, May 17 - Sat, May 24
MDW
Chicago
RSW
Fort Myers
$208 Roundtrip, found 2 days ago
$208
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, May 17 from Chicago to Fort Myers, returning Sat, May 24, priced at $208 found 2 days ago
Tue, May 20 - Sun, May 25
MDW
Chicago
RSW
Fort Myers
$215 Roundtrip, found 8 hours ago
$215
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Tue, May 20 from Chicago to Fort Myers, returning Sun, May 25, priced at $215 found 8 hours ago
Wed, May 28 - Tue, Jun 3
MDW
Chicago
RSW
Fort Myers
$217 Roundtrip, found 17 hours ago
$217
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, May 28 from Chicago to Fort Myers, returning Tue, Jun 3, priced at $217 found 17 hours 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
The price is $137 per night from Apr 26 to Apr 27
$137
includes taxes & fees
$123 per night
Apr 26 - Apr 27
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 ...
9.4/10 Exceptional! (869 reviews)
"There is no one else I’d rather interact with at 10:30pm checkin and 4am checkout than Allison. She was delightful."

Reviewed on Apr 20, 2025

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
The price is $95 per night from Apr 27 to Apr 28
$95
includes taxes & fees
$85 per night
Apr 27 - Apr 28
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 ...
"The young man who greeted us was very friendly and efficient. It was nice to receive a cold drink and some popcorn upon arrival. We didn’t get the cookie though because we got in too late after we went out to meet friends. I wish he would’ve given us a cookie for before bedtime!. we didn’t get the ..."

Reviewed on Apr 21, 2025

Days Inn & Suites by Wyndham Fort Myers Near JetBlue Park
Comfort Inn & Suites Airport
Comfort Inn & Suites Airport
2.5 out of 5
Fort Myers
The price is $89 per night from Apr 27 to Apr 28
$89
includes taxes & fees
$80 per night
Apr 27 - Apr 28
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 ...
8.6/10 Excellent! (1,016 reviews)
"Great location but property needs some TLC which there was evidence that this may be happening. It served our purpose since we were mostly in and out and did not stay on property that much."

Reviewed on Apr 17, 2025

Comfort Inn & Suites 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

Hyatt Place Fort Myers/at The Forum
Hyatt Place Fort Myers/at The Forum
3 out of 5
2600 Champion Ring Rd, Fort Myers, FL
The price is $115 per night from May 18 to May 19
$115
includes taxes & fees
$103 per night
May 18 - May 19
Stay at this 3-star business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,002 reviews)
"Good for traveling stay."

Reviewed on Apr 17, 2025

Hyatt Place Fort Myers/at The Forum
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
The price is $137 per night from Apr 26 to Apr 27
$137
includes taxes & fees
$123 per night
Apr 26 - Apr 27
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 ...
9.4/10 Exceptional! (869 reviews)
"There is no one else I’d rather interact with at 10:30pm checkin and 4am checkout than Allison. She was delightful."

Reviewed on Apr 20, 2025

Holiday Inn Express & Suites Fort Myers Airport by IHG
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
2.5 out of 5
20091 Summerlin Road, Fort Myers, FL
The price is $120 per night from May 4 to May 5
$120
includes taxes & fees
$108 per night
May 4 - May 5
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 pool in ...
7.4/10 Good! (1,007 reviews)
"Amazing all the way around!"

Reviewed on Apr 21, 2025

La Quinta Inn & Suites by Wyndham Ft. Myers-Sanibel Gateway
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
The price is $149 per night from May 12 to May 13
$149
includes taxes & fees
$134 per night
May 12 - May 13
Stay at this 4-star business-friendly hotel in Fort Myers. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
9/10 Wonderful! (975 reviews)
"Nice place to stay for the area."

Reviewed on Apr 11, 2025

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
The price is $77 per night from Apr 27 to Apr 28
$77
includes taxes & fees
$69 per night
Apr 27 - Apr 28
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 ...
7.2/10 Good! (1,000 reviews)
"Staff above and beyond"

Reviewed on Apr 17, 2025

Travelodge by Wyndham Fort Myers Airport
Baymont by Wyndham Fort Myers Airport
Baymont by Wyndham Fort Myers Airport
2.5 out of 5
9401 Marketplace Road, Fort Myers, FL
The price is $79 per night from May 1 to May 2
$79
includes taxes & fees
$71 per night
May 1 - May 2
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. ...
6/10 (1,002 reviews)
"Great greeting and feel like home"

Reviewed on Apr 7, 2025

Baymont by Wyndham 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.

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
The price is $95 per night from Apr 27 to Apr 28
$95
includes taxes & fees
$85 per night
Apr 27 - Apr 28
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 ...
"The young man who greeted us was very friendly and efficient. It was nice to receive a cold drink and some popcorn upon arrival. We didn’t get the cookie though because we got in too late after we went out to meet friends. I wish he would’ve given us a cookie for before bedtime!. we didn’t get the ..."

Reviewed on Apr 21, 2025

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
The price is $70 per night from May 4 to May 5
$70
includes taxes & fees
$63 per night
May 4 - May 5
Stay at this hotel in North Fort Myers. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Edison Mall and Harborside Event Center ...
5.8/10 (1,003 reviews)
"It started out not good when i got charged but the owner was very accommodating and told us that for our troubles that the next time were in town he would give us a 15% off our stay."

Reviewed on Mar 29, 2025

Travelodge by Wyndham Fort Myers North
Baymont by Wyndham Fort Myers Airport
Baymont by Wyndham Fort Myers Airport
2.5 out of 5
9401 Marketplace Road, Fort Myers, FL
The price is $79 per night from May 1 to May 2
$79
includes taxes & fees
$71 per night
May 1 - May 2
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. ...
6/10 (1,002 reviews)
"Great greeting and feel like home"

Reviewed on Apr 7, 2025

Baymont by Wyndham 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.

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
The price is $306 per night from May 12 to May 13
$306
includes taxes & fees
$274 per night
May 12 - May 13
Stay at this 4-star beach resort in Fort Myers Beach. Enjoy free breakfast, 3 outdoor pools, and 3 restaurants. Our guests praise the breakfast and the pool ...
9.2/10 Wonderful! (1,000 reviews)
"i love this place, i came back after 30 years, its even better! million dollar views"

Reviewed on Apr 18, 2025

Pink Shell Beach Resort and Marina
Sundial Beach Resort & Spa
Sundial Beach Resort & Spa
5 out of 5
1451 Middle Gulf Drive, Sanibel, FL
The price is $643 per night from Apr 27 to Apr 28
$643
includes taxes & fees
$577 per night
Apr 27 - Apr 28
Stay at this 5-star luxury condo in Sanibel. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the property condition in our reviews. ...
8.6/10 Excellent! (2,561 reviews)
"Resort was very clean. Staff were very friendly. Received $180.00 food/ service credit on arrival because some of the resort areas are under renovation because of the Hurricane last fall. My room was so nice and the bed was luxurious. Beach was beautiful!!!"

Reviewed on Mar 15, 2025

Sundial Beach Resort & Spa
South Seas Resort
South Seas Resort
3.5 out of 5
5400 South Seas Plantation Rd, Captiva, FL
Book a stay at this beach resort in Captiva. Enjoy 2 outdoor pools, 6 restaurants, and a private beach. Popular attractions Jungle Drums and McCarthy's Marina ...
8.2/10 Very Good! (1,000 reviews)
"Wonderful stay! We rented a golf cart that allowed us to travel throughout the resort, different beaches, and restaurants right outside of the resort area. Friendly staff, and clean property."

Reviewed on Mar 29, 2025

Get rates
South Seas Resort
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
Chicago
Destination Airport
Fort Myers
Number Of Airlines Serving
1
Distance
1107 mi
Shortest Flight Departure Time
6:30PM CDT
Shortest Flight Departure Date
May 1
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

Am I able to catch a flight from Chicago, IL Airport (MDW-Midway Intl.) to Fort Myers, FL Airport (RSW-Southwest Florida Intl.) now?
If you’re agonizing over travel restrictions and quarantine requirements when catching a flight from Chicago, IL Airport (MDW-Midway Intl.) to Fort Myers, FL Airport (RSW-Southwest Florida Intl.), check out the Covid-19 Travel Advisor.
Are there non-stop flights from Midway Airport to Fort Myers, FL Airport (RSW-Southwest Florida Intl.)?
The great news is Southwest Airlines flies directly from West Lawn to Edison Park Historic District, so you won’t have to worry about getting off the plane until you arrive at Fort Myers, FL Airport (RSW-Southwest Florida Intl.).
What is the shortest flight from Chicago Airport to RSW?
Air travel is one of life’s great pleasures and privileges, especially when the journey is a mere 2 hours and 45 minutes. That’s all it takes to jet from Chicago Airport to RSW.
How many hours flight from MDW to RSW?
With a general flight time of about 2 hours and 45 minutes between Chicago Airport and RSW, you’ll be having a blast in Fort Myers before you can say, “Are we there yet?”
If I am not able to travel due to COVID-19, can I cancel my flight to Fort Myers, FL Airport (RSW-Southwest Florida Intl.)?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Fort Myers, FL Airport (RSW-Southwest Florida Intl.) have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Fort Myers, FL Airport (RSW-Southwest Florida Intl.) with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Fort Myers, FL Airport (RSW-Southwest Florida Intl.) without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What airlines have the most flights from Chicago Airport to Southwest Florida Intl. Airport (RSW)?
If you’re looking for a trouble-free journey, consider reserving your ticket with Southwest Airlines. This carrier advertises 110 flights per month between West Lawn and Edison Park Historic District and is one of the top airlines servicing this route.

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.