Cheap Flights from Fort Myers to Chicago
Browse current best options from Fort Myers. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Fort Myers
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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 Fort Myers to Chicago
Explore current cheapest deals departing from Fort Myers to Chicago
Round trip
Sort by: Cheapest
August 26 - August 31
RSW - Chicago
$198
$210
Round trip
August 25 - August 27
RSW - Chicago
$197
$210
Round trip
August 13 - August 17
RSW - Chicago
$197
$230
Round trip
September 3 - September 7
RSW - Chicago
$168
$230
Round trip
August 11 - August 13
RSW - Chicago
$347
$236
Round trip
October 29 - October 31
RSW - Chicago
$339
$240
Round trip
August 3 - August 5
RSW - Chicago
$200
$243
Round trip
July 8 - July 15
RSW - Chicago
$480
$257
Round trip
July 14 - July 21
RSW - Chicago
$621
$257
Round trip
August 4 - August 11
RSW - Chicago
$324
$257
Round trip
Unlock all 500+ flight deals to Chicago and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Fort Myers to Chicago
How much is a round trip from Fort Myers to Chicago
Regular price: $152 - $398
Prices are currently within the regular range.
The regular price range for flights from Fort Myers to Chicago is $152 to $398. The current lowest deal is $210 with United Airlines for travel from Aug 26-Aug 31.
now $210
Low $152
High $398
The cheapest time to fly from Fort Myers to Chicago
The cheapest month to fly from Fort Myers to Chicago is April, with a median price of $271. The most expensive month is February, with a median price of $931. Prices are generally lower from April to November.
April
Flights from $271
February
Flights from $931
Direct flights from Fort Myers to Chicago
American Airlines
Southwest Airlines
Last-minute flights going from Fort Myers to Chicago
Wed, Jul 1
RSW - Chicago
Fort Myers (RSW) - Chicago (ORD)
$487
$303
One-way
Wed, Jul 1
RSW - Chicago
Fort Myers (RSW) - Chicago (ORD)
$652
$358
One-way
Fri, Jul 3
RSW - Chicago
Fort Myers (RSW) - Chicago (ORD)
American Airlines
$484
$304
One-way
Fri, Jul 3
RSW - Chicago
Fort Myers (RSW) - Chicago (ORD)
American Airlines
$470
$324
One-way
Sat, Jul 4
RSW - Chicago
Fort Myers (RSW) - Chicago (ORD)
American Airlines
$511
$341
One-way
Sat, Jul 4
RSW - Chicago
Fort Myers (RSW) - Chicago (ORD)
Sun Country Airlines
$640
$414
One-way
Biggest price drops on these dates for flights from Fort Myers to Chicago
Jul 14 - Jul 15
$640 → $267
58%
Jul 14 - Jul 21
$621 → $257
59%
Jul 14 - Jul 16
$641 → $296
54%
Jul 16 - Jul 21
$632 → $296
53%
Popular Airports to fly from Fort Myers to Chicago
Fort Myers - Chicago route insights
💸 Price insights
Recent fares are above the typical level
Recent fares from Fort Myers to Chicago are above the typical level, with a median price of $340.
📅 Best time to fly
April is historically the cheapest month to fly
Historically, April is the cheapest month to fly from Fort Myers to Chicago, with a median price of $271.
⏱️ Flight duration
Flights are typically 16h 2m long
The median flight duration from Fort Myers to Chicago is 16 hours and 2 minutes, including layovers.
✈️ Airlines & availability
Connecting flights are dominant on this route
About 32.9% of recent deals from Fort Myers to Chicago are for direct flights.
🏆 Airline highlight
United Airlines offers a recent deal for $210
A recent deal on United Airlines from Fort Myers to Chicago was found for $210.
🎯 Booking tip
Deals appear frequently, about 1 per day
Deals from Fort Myers to Chicago appear frequently, with about 1 deal per day historically.
Fort Myers main airports to depart from
Southwest Florida International (RSW)
Southwest Florida International Airport offers a great option for flights from Fort Myers to Chicago.
📍 ~15 km from Fort Myers (reachable by car)
💸 Flights from ~$210
Chicago main airports to arrive at
Chicago Midway International (MDW)
Chicago Midway International is a convenient arrival option for flights from Fort Myers to Chicago.
📍 ~15 km from Chicago city center (reachable by car)
💸 Flights from ~$210
Chicago Rockford International (RFD)
Chicago Rockford International offers an alternative arrival point for flights from Fort Myers to Chicago.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$318
O Hare International (ORD)
O Hare International is a major arrival airport for flights from Fort Myers to Chicago.
📍 ~30 km from Chicago city center (reachable by car)
💸 Flights from ~$210
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options.
📍 ~145 km from Chicago (reachable by car, train)
💸 Flights from ~$330
South Bend International (SBN)
South Bend International is geographically the closest alternative to the Chicago area.
📍 ~135 km from Chicago (reachable by car, train)
💸 Flights from ~$154
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub with high popularity and reliability.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$267
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service levels.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$159
Fort Wayne International (FWA)
Fort Wayne International offers stable regional service with multiple cabin class options.
📍 ~240 km from Chicago (reachable by car)
💸 Flights from ~$310
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Fort Myers to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From RSW
Elite
Aug 04
Chicago, United States
81% AI deal score
$1,249
$797
Save $452
From RSW
Elite
Jul 03
Chicago, United States
81% AI deal score
$1,693
$906
Save $787
From RSW
Elite
Aug 19
Chicago, United States
80% AI deal score
$1,196
$797
Save $399
From RSW
Elite
Oct 10
Chicago, United States
80% AI deal score
$1,192
$821
Save $371
From RSW
Elite
Jul 04
Chicago, United States
80% AI deal score
$1,480
$833
Save $647
From RSW
Elite
Jul 03
Chicago, United States
80% AI deal score
$1,612
$906
Save $706
From RSW
Elite
Sep 21
Chicago, United States
79% AI deal score
$1,134
$821
Save $313
From RSW
Elite
Sep 17
Chicago, United States
79% AI deal score
$1,129
$821
Save $308
From RSW
Elite
Jul 04
Chicago, United States
79% AI deal score
$1,448
$833
Save $615
From RSW
Elite
Jun 30
Chicago, United States
79% AI deal score
$1,145
$843
Save $302
From RSW
Elite
Aug 04
Chicago, United States
79% AI deal score
$945
$619
Save $326
From RSW
Elite
Aug 12
Chicago, United States
78% AI deal score
$1,427
$849
Save $578
From RSW
Elite
Jun 30
Chicago, United States
78% AI deal score
$1,447
$889
Save $558
From RSW
Elite
Jul 06
Chicago, United States
78% AI deal score
$1,492
$903
Save $589
From RSW
Elite
Jul 06
Chicago, United States
78% AI deal score
$1,494
$903
Save $591
From RSW
Elite
Jul 03
Chicago, United States
78% AI deal score
$1,505
$954
Save $551
From RSW
Elite
Aug 05
Chicago, United States
78% AI deal score
$934
$619
Save $315
From RSW
Elite
Aug 29
Chicago, United States
78% AI deal score
$956
$631
Save $325
From RSW
Elite
Aug 20
Chicago, United States
78% AI deal score
$962
$631
Save $331
From RSW
Elite
Aug 03
Chicago, United States
78% AI deal score
$986
$638
Save $348
From RSW
Elite
Aug 27
Chicago, United States
78% AI deal score
$981
$643
Save $338
From RSW
Elite
Aug 20
Chicago, United States
78% AI deal score
$993
$643
Save $350
From RSW
Elite
Aug 01
Chicago, United States
77% AI deal score
$1,083
$818
Save $265
From RSW
Elite
Aug 10
Chicago, United States
77% AI deal score
$1,130
$838
Save $292
From RSW
Elite
Jul 03
Chicago, United States
77% AI deal score
$1,432
$999
Save $433
From RSW
Elite
Sep 14
Chicago, United States
77% AI deal score
$922
$631
Save $291
From RSW
Elite
Aug 15
Chicago, United States
77% AI deal score
$933
$643
Save $290
From RSW
Elite
Jun 24
Chicago, United States
76% AI deal score
$1,427
$987
Save $440
From RSW
Elite
Jul 03
Chicago, United States
76% AI deal score
$1,437
$1,022
Save $415
From RSW
Elite
Jul 02
Chicago, United States
75% AI deal score
$1,381
$952
Save $429
From RSW
Elite
Jun 25
Chicago, United States
75% AI deal score
$1,496
$1,045
Save $451
From RSW
Elite
Jun 26
Chicago, United States
75% AI deal score
$1,511
$1,045
Save $466
From RSW
Elite
Jul 04
Chicago, United States
74% AI deal score
$1,186
$904
Save $282
From RSW
Elite
Nov 20
Chicago, United States
74% AI deal score
$1,184
$915
Save $269
From RSW
Elite
Jul 06
Chicago, United States
74% AI deal score
$1,374
$974
Save $400
From RSW
Elite
Jul 06
Chicago, United States
74% AI deal score
$1,440
$1,019
Save $421
From RSW
Elite
Jun 28
Chicago, United States
74% AI deal score
$1,505
$1,071
Save $434
From RSW
Elite
Jun 28
Chicago, United States
74% AI deal score
$1,453
$1,071
Save $382
From RSW
Elite
Jun 29
Chicago, United States
74% AI deal score
$1,446
$1,071
Save $375
From RSW
Elite
Jun 27
Chicago, United States
74% AI deal score
$1,527
$1,091
Save $436
From RSW
Elite
Jun 25
Chicago, United States
74% AI deal score
$1,551
$1,147
Save $404
From RSW
Elite
Aug 28
Chicago, United States
74% AI deal score
$1,957
$1,354
Save $603
From RSW
Elite
Jul 06
Chicago, United States
73% AI deal score
$1,472
$1,068
Save $404
From RSW
Elite
Jun 26
Chicago, United States
73% AI deal score
$1,531
$1,147
Save $384
From RSW
Elite
Jul 15
Chicago, United States
72% AI deal score
$947
$787
Save $160
From RSW
Elite
Aug 22
Chicago, United States
72% AI deal score
$1,019
$811
Save $208
From RSW
Elite
Aug 08
Chicago, United States
72% AI deal score
$1,028
$811
Save $217
From RSW
Elite
Jun 27
Chicago, United States
72% AI deal score
$1,158
$904
Save $254
From RSW
Elite
Sep 15
Chicago, United States
72% AI deal score
$867
$619
Save $248
From RSW
Elite
Sep 01
Chicago, United States
72% AI deal score
$848
$619
Save $229
From RSW
Elite
Sep 12
Chicago, United States
72% AI deal score
$872
$631
Save $241
From RSW
Elite
Sep 01
Chicago, United States
72% AI deal score
$906
$631
Save $275
From RSW
Elite
Sep 19
Chicago, United States
72% AI deal score
$915
$643
Save $272
From RSW
Elite
Sep 17
Chicago, United States
72% AI deal score
$915
$643
Save $272
From RSW
Elite
Sep 19
Chicago, United States
72% AI deal score
$884
$643
Save $241
From RSW
Elite
Sep 02
Chicago, United States
71% AI deal score
$948
$787
Save $161
From RSW
Elite
Jul 18
Chicago, United States
71% AI deal score
$947
$825
Save $122
From RSW
Elite
Jun 24
Chicago, United States
71% AI deal score
$1,068
$904
Save $164
From RSW
Elite
Jun 23
Chicago, United States
71% AI deal score
$1,068
$904
Save $164
From RSW
Elite
Jul 20
Chicago, United States
71% AI deal score
$748
$638
Save $110
From RSW
Elite
Jul 20
Chicago, United States
71% AI deal score
$742
$638
Save $104
From RSW
Elite
Jul 29
Chicago, United States
71% AI deal score
$743
$638
Save $105
From RSW
Elite
Jul 18
Chicago, United States
71% AI deal score
$742
$638
Save $104
From RSW
Elite
Jul 16
Chicago, United States
71% AI deal score
$742
$638
Save $104
From RSW
Elite
Sep 12
Chicago, United States
71% AI deal score
$873
$643
Save $230
From RSW
Elite
Oct 09
Chicago, United States
71% AI deal score
$932
$708
Save $224
From RSW
Elite
Aug 21
Chicago, United States
70% AI deal score
$1,019
$865
Save $154
From RSW
Elite
Jun 27
Chicago, United States
70% AI deal score
$1,049
$904
Save $145
From RSW
Elite
Jul 03
Chicago, United States
70% AI deal score
$1,061
$906
Save $155
From RSW
Elite
Jul 16
Chicago, United States
70% AI deal score
$737
$638
Save $99
From RSW
Elite
Jul 16
Chicago, United States
70% AI deal score
$733
$638
Save $95
From RSW
Elite
Jul 14
Chicago, United States
70% AI deal score
$735
$638
Save $97
From RSW
Elite
Oct 08
Chicago, United States
70% AI deal score
$907
$711
Save $196
From RSW
Elite
Jul 31
Chicago, United States
69% AI deal score
$936
$865
Save $71
From RSW
Elite
Jul 04
Chicago, United States
69% AI deal score
$1,184
$949
Save $235
From RSW
Elite
Jul 02
Chicago, United States
69% AI deal score
$1,184
$952
Save $232
From RSW
Elite
Jun 24
Chicago, United States
69% AI deal score
$1,255
$1,023
Save $232
From RSW
Elite
Jul 05
Chicago, United States
69% AI deal score
$1,446
$1,072
Save $374
From RSW
Elite
Jun 30
Chicago, United States
69% AI deal score
$1,449
$1,117
Save $332
From RSW
Elite
Sep 25
Chicago, United States
68% AI deal score
$977
$906
Save $71
From RSW
Elite
Jun 29
Chicago, United States
68% AI deal score
$984
$906
Save $78
From RSW
Elite
Aug 10
Chicago, United States
68% AI deal score
$1,028
$964
Save $64
From RSW
Elite
Jun 29
Chicago, United States
68% AI deal score
$1,414
$1,137
Save $277
From RSW
Elite
Jul 12
Chicago, United States
67% AI deal score
$941
$903
Save $38
From RSW
Elite
Jul 07
Chicago, United States
67% AI deal score
$976
$929
Save $47
From RSW
Elite
Jul 05
Chicago, United States
67% AI deal score
$1,118
$952
Save $166
From RSW
Elite
Oct 20
Chicago, United States
67% AI deal score
$1,008
$952
Save $56
From RSW
Elite
Oct 01
Chicago, United States
67% AI deal score
$999
$964
Save $35
From RSW
Elite
Oct 17
Chicago, United States
67% AI deal score
$1,006
$964
Save $42
From RSW
Elite
Jul 02
Chicago, United States
67% AI deal score
$1,214
$1,023
Save $191
From RSW
Elite
Jun 25
Chicago, United States
67% AI deal score
$1,224
$1,081
Save $143
From RSW
Elite
Jun 24
Chicago, United States
67% AI deal score
$1,255
$1,091
Save $164
From RSW
Elite
Jun 25
Chicago, United States
67% AI deal score
$1,255
$1,091
Save $164
From RSW
Elite
Jun 26
Chicago, United States
67% AI deal score
$1,410
$1,183
Save $227
From RSW
Elite
Jun 26
Chicago, United States
67% AI deal score
$1,478
$1,212
Save $266
From RSW
Elite
Jun 29
Chicago, United States
67% AI deal score
$1,466
$1,229
Save $237
From RSW
Elite
Jul 05
Chicago, United States
66% AI deal score
$1,103
$952
Save $151
From RSW
Elite
Sep 16
Chicago, United States
66% AI deal score
$953
$952
Save $1
From RSW
Elite
Jul 02
Chicago, United States
66% AI deal score
$1,214
$1,068
Save $146
From RSW
Elite
Jun 26
Chicago, United States
66% AI deal score
$1,209
$1,091
Save $118