Cheap Flights from Chicago to Fort Myers
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RatePunk searches hundreds of travel sites at once for deals on flights to Fort Myers
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
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Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)
Today’s best flight deals from Chicago to Fort Myers
Explore current cheapest deals departing from Chicago to Fort Myers
Round trip
Sort by: Cheapest
September 2 - September 9
MDW - Fort Myers
$162
$190
Round trip
November 11 - November 18
ORD - Fort Myers
$212
$190
Round trip
August 20 - August 25
MDW - Fort Myers
$193
$210
Round trip
September 16 - September 21
ORD - Fort Myers
$193
$210
Round trip
October 17 - October 20
ORD - Fort Myers
$185
$210
Round trip
October 17 - October 21
ORD - Fort Myers
$185
$210
Round trip
August 15 - August 24
MDW - Fort Myers
$180
$230
Round trip
August 27 - August 31
MDW - Fort Myers
$192
$230
Round trip
September 19 - September 26
MDW - Fort Myers
$172
$230
Round trip
October 17 - October 24
ORD - Fort Myers
$180
$230
Round trip
Unlock all 500+ flight deals to Fort Myers and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to Fort Myers
How much is a round trip from Chicago to Fort Myers
Regular price: $128 - $324
Prices for flights from Chicago to Fort Myers are currently within the regular range.
The regular price range for this route is between $128 and $324. The current lowest deal is $190 with Southwest Airlines, for travel from September 2 to September 9.
now $190
Low $128
High $324
The cheapest time to fly from Chicago to Fort Myers
The cheapest month to fly from Chicago to Fort Myers is April, with a median price of $131. The most expensive month is March, with a median price of $1421. Prices are generally lower from January to November.
April
Flights from $131
March
Flights from $1,421
Direct flights from Chicago to Fort Myers
American Airlines
Last-minute flights going from Chicago to Fort Myers
Wed, Jul 1
ORD - Fort Myers
Chicago (ORD) - Fort Myers (RSW)
Deutsche Luft Hansa
$509
$362
One-way
Tue, Jul 7
ORD - Fort Myers
Chicago (ORD) - Fort Myers (RSW)
United Airlines
$359
$257
One-way
Tue, Jul 7
MDW - Fort Myers
Chicago (MDW) - Fort Myers (RSW)
$373
$257
One-way
Tue, Jul 7
MDW - Fort Myers
Chicago (MDW) - Fort Myers (RSW)
$366
$257
One-way
Wed, Jul 8
MDW - Fort Myers
Chicago (MDW) - Fort Myers (RSW)
$373
$277
One-way
Tue, Jul 14
ORD - Fort Myers
Chicago (ORD) - Fort Myers (RSW)
American Airlines
$356
$257
One-way
Biggest price drops on these dates for flights from Chicago to Fort Myers
Dec 24 - Dec 30
$853 → $314
63%
Dec 22 - Dec 29
$852 → $334
61%
Dec 21 - Dec 28
$852 → $336
61%
Dec 22 - Dec 26
$860 → $344
60%
Popular Airports to fly from Chicago to Fort Myers
Chicago - Fort Myers route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares from Chicago to Fort Myers are above the typical level, with a median price of $407.
📅 Best time to fly
April is historically the cheapest month to fly.
Historically, April is the cheapest month to fly from Chicago to Fort Myers, with a median price of $131.
⏱️ Flight duration
The typical flight duration is 6h 51m.
Flights from Chicago to Fort Myers typically take 6 hours and 51 minutes.
✈️ Airlines & availability
Deals are frequent for this route.
Deals for flights from Chicago to Fort Myers are frequent, with approximately 0.8 deals per day.
🏆 Airline highlight
American Airlines offers direct flights.
American Airlines offers direct flights from Chicago to Fort Myers.
🎯 Booking tip
Consider booking in April, May, or July.
Historically, April, May, and July have offered the lowest median prices for this route.
Chicago main airports to depart from
Chicago Midway International (MDW)
Consider Chicago Midway International for flights from Chicago to Fort Myers, offering competitive prices.
📍 ~15 km from Chicago city center (reachable by car or train)
💸 Flights from ~$190
Chicago Rockford International (RFD)
Chicago Rockford International is an alternative departure airport for your trip to Fort Myers.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$351
O Hare International (ORD)
O Hare International is a major airport option for flights from Chicago to Fort Myers.
📍 ~25 km from Chicago city center (reachable by car or train)
💸 Flights from ~$190
Fort Myers main airports to arrive at
Southwest Florida International (RSW)
Southwest Florida International Airport is a convenient arrival option for flights to Fort Myers.
📍 ~15 km from Fort Myers (reachable by car)
💸 Flights from ~$190
Airports nearby Fort Myers used as alternative
Southwest Florida International (RSW)
RSW is the primary commercial airport for the Fort Myers area, offering full-service major carrier support.
📍 ~15 km from Fort Myers (reachable by car)
💸 Flights from ~$190
Punta Gorda (PGD)
PGD is very close to Fort Myers and excellent for low-cost carrier options with faster security.
📍 ~33 km from Fort Myers (reachable by car)
💸 Flights from ~$102
Sarasota–Bradenton International (SRQ)
SRQ offers a growing selection of domestic routes and is less crowded than major hubs.
📍 ~107 km from Fort Myers (reachable by car)
💸 Flights from ~$102
Tampa International (TPA)
TPA is a major hub with extensive connections and competitive pricing, despite the drive.
📍 ~190 km from Fort Myers (reachable by car)
💸 Flights from ~$96
Fort Lauderdale–Hollywood International (FLL)
FLL is a major low-cost carrier hub, often cheaper for long-haul flights, with direct highway access.
📍 ~180 km from Fort Myers (reachable by car)
💸 Flights from ~$61
Business & First Class Flight Deals to Fort Myers
Discover luxury on the budget with premium cabin class on flights from Chicago to Fort Myers.
Elite
Best Elite deals to Fort Myers
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Aug 13
Fort Myers, United States
85% AI deal score
$1,602
$809
Save $793
From ORD
Elite
Aug 12
Fort Myers, United States
85% AI deal score
$1,315
$631
Save $684
From ORD
Elite
Aug 05
Fort Myers, United States
84% AI deal score
$1,270
$619
Save $651
From ORD
Elite
Aug 12
Fort Myers, United States
84% AI deal score
$1,296
$631
Save $665
From ORD
Elite
Aug 24
Fort Myers, United States
84% AI deal score
$1,298
$631
Save $667
From ORD
Elite
Aug 04
Fort Myers, United States
84% AI deal score
$1,278
$631
Save $647
From ORD
Elite
Oct 14
Fort Myers, United States
82% AI deal score
$1,263
$797
Save $466
From ORD
Elite
Aug 18
Fort Myers, United States
82% AI deal score
$1,289
$797
Save $492
From ORD
Elite
Jul 28
Fort Myers, United States
82% AI deal score
$1,196
$797
Save $399
From ORD
Elite
Oct 20
Fort Myers, United States
82% AI deal score
$1,273
$807
Save $466
From ORD
Elite
Sep 16
Fort Myers, United States
81% AI deal score
$1,204
$797
Save $407
From ORD
Elite
Sep 29
Fort Myers, United States
81% AI deal score
$1,216
$797
Save $419
From ORD
Elite
Oct 03
Fort Myers, United States
81% AI deal score
$1,238
$821
Save $417
From ORD
Elite
Sep 01
Fort Myers, United States
80% AI deal score
$1,206
$816
Save $390
From ORD
Elite
Sep 24
Fort Myers, United States
80% AI deal score
$1,216
$821
Save $395
From ORD
Elite
Oct 06
Fort Myers, United States
78% AI deal score
$929
$619
Save $310
From ORD
Elite
Aug 01
Fort Myers, United States
77% AI deal score
$1,048
$818
Save $230
From ORD
Elite
Sep 08
Fort Myers, United States
77% AI deal score
$900
$631
Save $269
From ORD
Elite
Jul 07
Fort Myers, United States
72% AI deal score
$955
$787
Save $168
From ORD
Elite
Jul 21
Fort Myers, United States
72% AI deal score
$920
$787
Save $133
From ORD
Elite
Aug 15
Fort Myers, United States
72% AI deal score
$1,007
$811
Save $196
From ORD
Elite
Aug 10
Fort Myers, United States
72% AI deal score
$1,007
$811
Save $196
From ORD
Elite
Jul 01
Fort Myers, United States
72% AI deal score
$1,005
$833
Save $172
From ORD
Elite
Jul 16
Fort Myers, United States
72% AI deal score
$1,087
$856
Save $231
From ORD
Elite
Jul 07
Fort Myers, United States
72% AI deal score
$1,091
$858
Save $233
From ORD
Elite
Jun 27
Fort Myers, United States
72% AI deal score
$1,120
$904
Save $216
From ORD
Elite
Sep 22
Fort Myers, United States
72% AI deal score
$857
$619
Save $238
From ORD
Elite
Sep 01
Fort Myers, United States
72% AI deal score
$855
$619
Save $236
From ORD
Elite
Jul 21
Fort Myers, United States
72% AI deal score
$763
$619
Save $144
From ORD
Elite
Jul 08
Fort Myers, United States
72% AI deal score
$748
$619
Save $129
From ORD
Elite
Jul 07
Fort Myers, United States
72% AI deal score
$745
$619
Save $126
From ORD
Elite
Jul 14
Fort Myers, United States
72% AI deal score
$761
$619
Save $142
From ORD
Elite
Jul 29
Fort Myers, United States
72% AI deal score
$765
$619
Save $146
From ORD
Elite
Sep 05
Fort Myers, United States
72% AI deal score
$872
$631
Save $241
From ORD
Elite
Sep 19
Fort Myers, United States
72% AI deal score
$880
$631
Save $249
From ORD
Elite
Sep 01
Fort Myers, United States
72% AI deal score
$871
$631
Save $240
From ORD
Elite
Sep 24
Fort Myers, United States
72% AI deal score
$881
$643
Save $238
From ORD
Elite
Aug 26
Fort Myers, United States
71% AI deal score
$948
$787
Save $161
From ORD
Elite
Jul 29
Fort Myers, United States
71% AI deal score
$899
$787
Save $112
From ORD
Elite
Aug 22
Fort Myers, United States
71% AI deal score
$946
$811
Save $135
From ORD
Elite
Aug 29
Fort Myers, United States
71% AI deal score
$952
$811
Save $141
From ORD
Elite
Jul 08
Fort Myers, United States
71% AI deal score
$1,091
$903
Save $188
From ORD
Elite
Jul 03
Fort Myers, United States
71% AI deal score
$1,088
$906
Save $182
From ORD
Elite
Sep 23
Fort Myers, United States
71% AI deal score
$880
$669
Save $211
From ORD
Elite
Sep 24
Fort Myers, United States
71% AI deal score
$892
$681
Save $211
From ORD
Elite
Sep 09
Fort Myers, United States
70% AI deal score
$912
$787
Save $125
From ORD
Elite
Sep 02
Fort Myers, United States
70% AI deal score
$910
$787
Save $123
From ORD
Elite
Sep 08
Fort Myers, United States
70% AI deal score
$912
$787
Save $125
From ORD
Elite
Jul 20
Fort Myers, United States
70% AI deal score
$920
$825
Save $95
From ORD
Elite
Aug 24
Fort Myers, United States
70% AI deal score
$958
$849
Save $109
From ORD
Elite
Jul 25
Fort Myers, United States
69% AI deal score
$899
$825
Save $74
From ORD
Elite
Jul 18
Fort Myers, United States
68% AI deal score
$920
$877
Save $43
From ORD
Elite
Jul 04
Fort Myers, United States
68% AI deal score
$974
$904
Save $70
From ORD
Elite
Jul 25
Fort Myers, United States
67% AI deal score
$884
$856
Save $28
From ORD
Elite
Jul 19
Fort Myers, United States
67% AI deal score
$920
$887
Save $33
From ORD
Elite
Jul 09
Fort Myers, United States
67% AI deal score
$955
$922
Save $33
From ORD
Elite
Jul 26
Fort Myers, United States
66% AI deal score
$899
$887
Save $12
From ORD
Elite
Sep 26
Fort Myers, United States
66% AI deal score
$945
From MDW
Elite
Aug 06
Fort Myers, United States
66% AI deal score
$1,784
$1,519
Save $265
From MDW
Elite
Jul 03
Fort Myers, United States
65% AI deal score
$1,556
$1,388
Save $168
From MDW
Elite
Aug 01
Fort Myers, United States
65% AI deal score
$1,877
$1,614
Save $263
From MDW
Elite
Nov 08
Fort Myers, United States
50% AI deal score
$1,337
$1,209
Save $128
From MDW
Elite
Aug 19
Fort Myers, United States
50% AI deal score
$1,674
$1,495
Save $179
From MDW
Elite
Aug 03
Fort Myers, United States
50% AI deal score
$1,693
$1,519
Save $174
From MDW
Elite
Aug 05
Fort Myers, United States
49% AI deal score
$1,614
$1,507
Save $107
From MDW
Elite
Oct 03
Fort Myers, United States
48% AI deal score
$1,583
$1,483
Save $100
From MDW
Elite
Aug 19
Fort Myers, United States
48% AI deal score
$1,760
$1,655
Save $105
From MDW
Elite
Oct 15
Fort Myers, United States
47% AI deal score
$1,589
$1,563
Save $26
From MDW
Elite
Jun 23
Fort Myers, United States
47% AI deal score
$1,881
$1,851
Save $30
From MDW
Elite
Jul 11
Fort Myers, United States
46% AI deal score
$1,616
From ORD
Elite
Jul 10
Fort Myers, United States
45% AI deal score
$4,048
From ORD
Elite
Aug 28
Fort Myers, United States
44% AI deal score
$3,818
From ORD
Elite
Aug 07
Fort Myers, United States
44% AI deal score
$3,845
From ORD
Elite
Jul 31
Fort Myers, United States
44% AI deal score
$3,867
From ORD
Elite
Jul 31
Fort Myers, United States
44% AI deal score
$3,867
From ORD
Elite
Aug 07
Fort Myers, United States
44% AI deal score
$3,888
From ORD
Elite
Jul 10
Fort Myers, United States
44% AI deal score
$3,921
From ORD
Elite
Jul 10
Fort Myers, United States
44% AI deal score
$3,922
From ORD
Elite
Jul 10
Fort Myers, United States
44% AI deal score
$3,928
From ORD
Elite
Jul 31
Fort Myers, United States
44% AI deal score
$3,940
From ORD
Elite
Jul 10
Fort Myers, United States
44% AI deal score
$3,941
From ORD
Elite
Jul 10
Fort Myers, United States
44% AI deal score
$3,987
From ORD
Elite
Jul 30
Fort Myers, United States
44% AI deal score
$3,995
From ORD
Elite
Jul 13
Fort Myers, United States
44% AI deal score
$3,998
From ORD
Elite
Jul 13
Fort Myers, United States
44% AI deal score
$3,999
From ORD
Elite
Jul 13
Fort Myers, United States
44% AI deal score
$4,018
From ORD
Elite
Aug 07
Fort Myers, United States
43% AI deal score
$3,845
From ORD
Elite
Aug 07
Fort Myers, United States
43% AI deal score
$3,882
From ORD
Elite
Aug 07
Fort Myers, United States
43% AI deal score
$3,884
From ORD
Elite
Aug 07
Fort Myers, United States
43% AI deal score
$3,902
From ORD
Elite
Jul 31
Fort Myers, United States
43% AI deal score
$3,903
From ORD
Elite
Jul 30
Fort Myers, United States
43% AI deal score
$3,922
From ORD
Elite
Jul 10
Fort Myers, United States
43% AI deal score
$3,954
From ORD
Elite
Jul 30
Fort Myers, United States
43% AI deal score
$3,959
From ORD
Elite
Jul 10
Fort Myers, United States
43% AI deal score
$3,963
From ORD
Elite
Jul 10
Fort Myers, United States
43% AI deal score
$3,965
From ORD
Elite
Jul 20
Fort Myers, United States
43% AI deal score
$3,972
From ORD
Elite
Jul 31
Fort Myers, United States
43% AI deal score
$3,978
From ORD
Elite
Jul 31
Fort Myers, United States
43% AI deal score
$3,978
From ORD
Elite
Jul 10
Fort Myers, United States
43% AI deal score
$3,978