Fort Myers to Chicago (RSW–MDW) — Airlines, Schedules & Connections

RSW Airport Page →
1,107 mi airlines 59/wk
On-time Some delays Frequent delays
Flight Schedule 27 flights Verified 2h ago
Nonstop 1-Stop 2-Stop Hide separate tickets Hide overnight
  Flight Airline AC Dep Arr Dur OTP Sched  
WN4331
WN Southwest
738
6:15 AM
EDT
8:15 AM
CDT
3h
M T W T F S S
Prices
WN164
WN Southwest
7M8
7:00 AM
EDT
8:55 AM
CDT
2h 55m
M T W T F S S
Prices
WN2752
WN Southwest
73H
10:15 AM
EDT
12:10 PM
CDT
2h 55m
M T W T F S S
Prices
WN4332
WN Southwest
738
10:20 AM
EDT
12:20 PM
CDT
3h
M T W T F S S
Prices
WN1160
WN Southwest
7S7
11:55 AM
EDT
2:00 PM
CDT
3h 5m
M T W T F S S
Prices
WN3997
WN Southwest
7M8
1:58 PM
EDT
4:00 PM
CDT
3h 2m
M T W T F S S
Prices
WN4708
WN Southwest
73H
3:40 PM
EDT
5:45 PM
CDT
3h 5m
M T W T F S S
Prices
WN776
WN Southwest
738
3:45 PM
EDT
5:50 PM
CDT
3h 5m
M T W T F S S
Prices
WN4043
WN Southwest
7S7
4:35 PM
EDT
6:35 PM
CDT
3h
M T W T F S S
Prices
WN1320
WN Southwest
B38M
5:40 PM
EDT
7:45 PM
CDT
3h 5m
M T W T F S S
Prices
WN4006
WN Southwest
7M8
6:10 PM
EDT
8:10 PM
CDT
3h
M T W T F S S
Prices
WN4113
WN Southwest
73H
7:55 PM
EDT
9:55 PM
CDT
3h
M T W T F S S
Prices
WN4333
WN Southwest
B38M
9:15 PM
EDT
11:15 PM
CDT
3h
M T W T F S S
Prices
WN3024
WN Southwest
B38M
5:00 AM
CDT
8:45 AM
EDT
2h 45m
M T W T F S S
Prices
WN3991
WN Southwest
B38M
5:15 AM
CDT
9:00 AM
EDT
2h 45m
M T W T F S S
Prices
WN1988
WN Southwest
73H
7:25 AM
CDT
11:10 AM
EDT
2h 45m
M T W T F S S
Prices
WN3992
WN Southwest
B38M
9:00 AM
CDT
12:50 PM
EDT
2h 50m
M T W T F S S
Prices
WN1327
WN Southwest
7S7
9:00 AM
CDT
12:45 PM
EDT
2h 45m
M T W T F S S
Prices
WN4707
WN Southwest
73H
11:15 AM
CDT
3:00 PM
EDT
2h 45m
M T W T F S S
Prices
WN679
WN Southwest
738
11:45 AM
CDT
3:30 PM
EDT
2h 45m
M T W T F S S
Prices
WN3466
WN Southwest
7M8
12:00 PM
CDT
3:45 PM
EDT
2h 45m
M T W T F S S
Prices
WN4690
WN Southwest
73H
1:00 PM
CDT
4:45 PM
EDT
2h 45m
M T W T F S S
Prices
WN3456
WN Southwest
7M8
1:10 PM
CDT
4:55 PM
EDT
2h 45m
M T W T F S S
Prices
WN2079
WN Southwest
7S7
4:05 PM
CDT
7:50 PM
EDT
2h 45m
M T W T F S S
Prices
WN2786
WN Southwest
7S7
5:25 PM
CDT
8:48 PM
EDT
2h 23m
M T W T F S S
Prices
WN1949
WN Southwest
7M8
7:30 PM
CDT
11:15 PM
EDT
2h 45m
M T W T F S S
Prices
WN3035
WN Southwest
B38M
8:35 PM
CDT
12:25 AM+1
EDT
2h 50m
M T W T F S S
Prices

No flights match your filters.

No nonstop flights on this route. connecting options below.

1-STOP
2-STOP Loading...
Fort Myers to Chicago
1 carrier, 59 flights/week nonstop.
1 Airlines 59 Flights/wk 1,107 mi 2h 55m nonstop -1h behind 84 1-stop hubs

RSW–MDW is served by 1 airline with nonstop service. Southwest Airlines leads the route. The flight covers 1,107 miles in approximately 2h 55m. Beyond nonstop, 84 hubs offer 1-stop connections.

Airline Landscape

All carriers operating nonstop RSW–MDW service, compared side by side.
Airline Freq/wk Aircraft Duration Dep OTP Alliance Codeshares
WN Southwest Airlines 59 738, 73H, 7M8, 7S7, B38M 2h55-3h05 78%
Aircraft on this route
738 Boeing 737-800 – WN
73H Boeing 737-800 – WN
7M8 Boeing 737 MAX 8 – WN
7S7 Boeing 737 MAX 7 – WN
B38MWN
Alliance coverage
Unaffiliated: WN (59 flights/wk, 100%)
OTP based on airport-level delay snapshots. Duration ranges reflect seasonal/directional variation.

Weekly Schedule Pattern

Nonstop flight frequency by day of week, RSW to MDW direction.
Mon
8
flights
Tue
9
flights
Wed
9
flights
Thu
8
flights
Fri
8
flights
Sat
9
flights
Sun
8
flights
Departure time distribution
12 AM6 AM12 PM6 PM12 AM
Morning departures
Afternoon/evening departures
13
Nonstop flights
59
Outbound / wk
57
Return / wk

Connection Landscape

Beyond nonstop. 1-stop and 2-stop options for RSW to MDW.
1-STOP
One-Stop Connections
84
Hubs
~4h
Fastest
~27h
Longest
Verified with published schedule alignment and minimum connection time.
2-STOP
Two-Stop Connections
2,684
Candidates
Two-stop connections loaded in the connections tab above.
Connections computed from published schedules with minimum connection time verification. Use the interactive explorer above the fold to filter by airline, tier, and layover time.

On-Time Performance

What to expect at each end of your journey.
Outbound
RSW → MDW
78%
Generally reliable. Most flights run on time.
Departing
78%
Arriving
70%
Return
MDW → RSW
76%
Generally reliable. Most flights run on time.
Departing
76%
Arriving
74%
OTP = percentage of flights arriving within 15 min of schedule. Based on airport-level delay snapshots. RSW delays → MDW delays →

Other ways to reach Chicago from Fort Myers

Nearby airports with service to Chicago Midway International Airport.
Metric RSW→MDW PGD→MDW SRQ→MDW
Distance from RSW 30 mi 77 mi
Nonstop airlines 1 1 3
Weekly flights 59 5 29
Flight time 2h 55m 2h 56m 2h 45m
Departure OTP 78%
Airports within 200 miles of RSW with service to Chicago Midway International Airport.

Travel Essentials

Practical planning for this route.
Time Difference
-1h
Chicago is 1 hour behind Fort Myers.
RSW: EDT · MDW: CDT

When it's 6:00 PM in Fort Myers, it's 5:00 PM in Chicago.
Distance & Flight Time
1,107 mi / 1,782 km
Nonstop flight time is approximately 2h 55m to 3h 5m.

RSW–MDW Quick Facts

Key statistics for the Fort Myers to Chicago route.
Route details
Distance1,107 mi / 1,782 km
Flight time2h 55m to 3h 5m
Time difference-1 hour
Airlines (nonstop)1
Weekly flights59 out / 57 return
1-stop connections84 hubs
Origin: RSW
IATA / ICAORSW / KRSW
TimezoneAmerica/Kentucky/Monticello
Passengers/yr10.9M
Elevation30 ft / 9 m
Destination: MDW
IATA / ICAOMDW / KMDW
TimezoneAmerica/Chicago
Passengers/yr20.7M
Elevation620 ft / 189 m

Frequently Asked Questions

Common questions about RSW to MDW flights.
Nonstop flights from Southwest Florida International Airport to Chicago Midway International Airport take approximately 2h 55m to 3h 5m. The route covers 1,107 miles.
1 airline operates nonstop service: Southwest Airlines.
There are approximately 59 nonstop flights per week from RSW to MDW. The return direction has about 57 weekly flights.
Yes, 1-stop connections are available through PIE, PBI, UST, PDK, FTY, OSU, OPF, SRQ, CGF, FXE, HHH, YIP, MEM, CAK, GSP, ATW, IAD, NAS, TEB, CTH, SGR, YYZ, GPT, HPN, MMU, AVP, HOU, SYR, BED, BTV, ORH, BJC, ASE, SCF, SNA, VNY, IAH, SJC, AUS, RDU, GRR, BUF, DSM, CLT, FLL, MCO, ATL, CMH, MIA, IND, CLE, CHS, STL, PIT, CVG, MKE, BWI, BNA, LAX, SFO, RIC, DTW, MSP, ALB, BOS, SLC, MCI, DAL, DCA, SDF, PVD, DEN, PHL, LGA, DFW, ORD, BDL, PHX, EWR, MSY, ROC, SEA, LAS and MHT. These options provide additional schedule flexibility.
Chicago is 1 hour behind Fort Myers.
Yes, return flights from MDW to RSW are available. Use the direction toggle at the top to view the return schedule.
Nearby alternatives include PGD, SRQ and OPF. See the Alternatives section for a full comparison.
Click the 'Search Flights' button to check availability and prices on Google Flights. You can also compare airlines and schedules on this page to find the best option.
See the On-Time Performance section for the latest delay data at both airports. This shows departure and arrival reliability to help you plan.
Route data is updated regularly from official airline schedules. On-time performance data comes from recent airport delay snapshots.

Flights from RSW to MDW

Southwest Florida International Airport (RSW) and Chicago Midway International Airport (MDW) are connected by nonstop service from Southwest Airlines. With 59 weekly departures, this is a heavily served route.

RSW to MDW Flight Duration and Schedule

Nonstop flight time from RSW to MDW ranges from 2 hours 55 minutes to 3 hours 5 minutes. The route covers a distance of 1,107 miles (1,782 km). There are approximately 59 weekly flights outbound and 57 return, totaling 116 flights per week in both directions.

Connecting Options and Alternatives

84 one-stop connections are available, with the fastest taking approximately 4 hours via PIE. Two-stop connections are also available via intermediate hubs. Nearby alternative airports include Punta Gorda (PGD), Sarasota/Bradenton (SRQ) and Miami (OPF).