Cheap Flights from Cancún to Chicago
Browse current best options from Cancún. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Cancún
RatePunk searches hundreds of travel sites at once for deals on flights to Chicago
Prices updated 24 days ago
486,190 searches this week
171 airlines compared
80%+ AI score for best value
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 Cancún to Chicago
Explore current cheapest deals departing from Cancún to Chicago
Round trip
Sort by: Cheapest
July 4 - July 8
CUN - Chicago
$356
$270
Round trip
July 2 - July 7
CUN - Chicago
$352
$270
Round trip
July 4 - July 7
CUN - Chicago
$356
$270
Round trip
July 2 - July 8
CUN - Chicago
$347
$270
Round trip
September 3 - September 26
CUN - Chicago
$313
$276
Round trip
September 3 - September 15
CUN - Chicago
$322
$276
Round trip
September 3 - September 11
CUN - Chicago
$339
$277
Round trip
September 3 - September 9
CUN - Chicago
$350
$277
Round trip
September 4 - September 11
CUN - Chicago
$351
$278
Round trip
September 4 - September 9
CUN - Chicago
$358
$279
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 Cancún to Chicago
How much is a round trip from Cancún to Chicago
Regular price: $306 - $415
Prices are currently below the regular range.
The regular price range for flights from Cancún to Chicago is $306 to $415. The current lowest deal is $270 with Volaris. This deal is for travel from Jul 4-Jul 8.
now $270
Low $306
High $415
The cheapest time to fly from Cancún to Chicago
The cheapest month to fly from Cancun to Chicago is January, with a median price of $162. The most expensive month is October, with a median price of $737. Prices are generally lower from January to December.
January
Flights from $162
October
Flights from $737
Direct flights from Cancún to Chicago
Frontier Airlines
Southwest Airlines
Last-minute flights going from Cancún to Chicago
Thu, Jun 18
CUN - Chicago
Cancún (CUN) - Chicago (ORD)
Volaris
$485
$314
One-way
Thu, Jun 18
CUN - Chicago
Cancún (CUN) - Chicago (ORD)
Volaris
$451
$323
One-way
Thu, Jun 18
CUN - Chicago
Cancún (CUN) - Chicago (ORD)
Volaris
$433
$323
One-way
Thu, Jun 18
CUN - Chicago
Cancún (CUN) - Chicago (ORD)
Volaris
$488
$348
One-way
Fri, Jun 19
CUN - Chicago
Cancún (CUN) - Chicago (ORD)
Volaris
$451
$323
One-way
Fri, Jun 19
CUN - Chicago
Cancún (CUN) - Chicago (ORD)
Volaris
$416
$325
One-way
Biggest price drops on these dates for flights from Cancún to Chicago
Jun 18 - Jun 22
$485 → $314
35%
Jun 20 - Jun 21
$491 → $320
35%
Jun 19 - Jun 22
$488 → $335
31%
Jun 23 - Jun 26
$466 → $320
31%
Popular Airports to fly from Cancún to Chicago
Cancún - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Cancún to Chicago are currently around $270, which is below the typical level.
📅 Best time to fly
January is historically cheapest
Historically, January is the cheapest month to fly from Cancún to Chicago, with a median price of $162.
⏱️ Flight duration
Connecting flights average 11h 20m
The typical flight duration for this route, including layovers, is 11 hours and 20 minutes.
✈️ Airlines & availability
Connecting flights are dominant
Connecting flights make up 72.3% of deals, with a median of 2 stopovers for this route.
🏆 Airline highlight
Volaris offers a recent deal
Volaris recently offered a flight for $270 from Cancún to Chicago (Jul 4-Jul 8).
🎯 Booking tip
Deals are frequent on this route
Deals for flights from Cancún to Chicago appear frequently, averaging 1.03 deals per day.
Cancún main airports to depart from
Cancún International (CUN)
Cancún International offers flights to Chicago, providing a convenient departure point for your trip.
📍 ~15 km from Cancún city center (reachable by car)
💸 Flights from ~$270
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a major hub for flights to Chicago, offering a wide range of connections.
📍 ~25 km from Chicago city center (reachable by car, train, and bus)
💸 Flights from ~$270
Chicago Midway International (MDW)
Chicago Midway International Airport provides convenient access to the city, especially for those traveling from Cancún.
📍 ~15 km from Chicago city center (reachable by car, train, and bus)
💸 Flights from ~$392
Chicago Rockford International (RFD)
Chicago Rockford International Airport is an alternative for travelers heading to the wider Chicago area.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$486
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
General Mitchell International offers excellent proximity to Chicago with high-frequency flight options and direct rail access.
📍 ~135 km from Chicago (reachable by car or rail)
💸 Flights from ~$481
South Bend International (SBN)
South Bend International is geographically the closest alternative to Chicago, connected via the South Shore Line.
📍 ~120 km from Chicago (reachable by car or rail)
💸 Flights from ~$478
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub, offering a wide range of cabin classes.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$442
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport, less congested than major Chicago or Milwaukee airports.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$468
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service for travelers in the southeastern Chicago suburbs.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$495
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Cancún to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From CUN
Elite
Aug 12
Chicago, United States
88% AI deal score
$1,573
$807
Save $766
From CUN
Elite
Oct 22
Chicago, United States
86% AI deal score
$1,717
$858
Save $859
From CUN
Elite
Aug 20
Chicago, United States
85% AI deal score
$1,188
$736
Save $452
From CUN
Elite
Jul 23
Chicago, United States
84% AI deal score
$1,245
$747
Save $498
From CUN
Elite
Oct 02
Chicago, United States
83% AI deal score
$1,655
$970
Save $685
From CUN
Elite
Aug 20
Chicago, United States
82% AI deal score
$1,114
$793
Save $321
From CUN
Elite
Jul 13
Chicago, United States
82% AI deal score
$1,189
$793
Save $396
From CUN
Elite
Aug 03
Chicago, United States
82% AI deal score
$1,163
$793
Save $370
From CUN
Elite
Jul 09
Chicago, United States
82% AI deal score
$1,235
$793
Save $442
From CUN
Elite
Jul 22
Chicago, United States
82% AI deal score
$1,225
$806
Save $419
From CUN
Elite
Oct 30
Chicago, United States
82% AI deal score
$1,332
$836
Save $496
From CUN
Elite
Nov 17
Chicago, United States
82% AI deal score
$1,266
$836
Save $430
From CUN
Elite
Nov 05
Chicago, United States
82% AI deal score
$1,268
$836
Save $432
From CUN
Elite
Nov 05
Chicago, United States
82% AI deal score
$1,271
$836
Save $435
From CUN
Elite
Oct 27
Chicago, United States
82% AI deal score
$1,340
$837
Save $503
From CUN
Elite
Oct 27
Chicago, United States
82% AI deal score
$1,339
$837
Save $502
From CUN
Elite
Oct 28
Chicago, United States
82% AI deal score
$1,340
$841
Save $499
From CUN
Elite
Oct 27
Chicago, United States
82% AI deal score
$1,340
$841
Save $499
From CUN
Elite
Oct 28
Chicago, United States
82% AI deal score
$1,340
$841
Save $499
From CUN
Elite
Oct 29
Chicago, United States
82% AI deal score
$1,330
$841
Save $489
From CUN
Elite
Nov 05
Chicago, United States
82% AI deal score
$1,276
$841
Save $435
From CUN
Elite
Oct 30
Chicago, United States
82% AI deal score
$1,331
$841
Save $490
From CUN
Elite
Oct 29
Chicago, United States
82% AI deal score
$1,318
$841
Save $477
From CUN
Elite
Oct 21
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 16
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 23
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 21
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 13
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 23
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 14
Chicago, United States
82% AI deal score
$1,345
$847
Save $498
From CUN
Elite
Oct 22
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Oct 22
Chicago, United States
82% AI deal score
$1,344
$847
Save $497
From CUN
Elite
Sep 24
Chicago, United States
81% AI deal score
$1,172
$806
Save $366
From CUN
Elite
Jul 29
Chicago, United States
81% AI deal score
$1,170
$806
Save $364
From CUN
Elite
Jul 29
Chicago, United States
81% AI deal score
$1,188
$806
Save $382
From CUN
Elite
Aug 06
Chicago, United States
81% AI deal score
$1,120
$818
Save $302
From CUN
Elite
Jul 24
Chicago, United States
81% AI deal score
$1,183
$818
Save $365
From CUN
Elite
Aug 06
Chicago, United States
81% AI deal score
$1,168
$831
Save $337
From CUN
Elite
Aug 01
Chicago, United States
81% AI deal score
$1,163
$840
Save $323
From CUN
Elite
Nov 13
Chicago, United States
81% AI deal score
$1,256
$836
Save $420
From CUN
Elite
Nov 11
Chicago, United States
81% AI deal score
$1,257
$836
Save $421
From CUN
Elite
Nov 04
Chicago, United States
81% AI deal score
$1,268
$841
Save $427
From CUN
Elite
Nov 04
Chicago, United States
81% AI deal score
$1,271
$841
Save $430
From CUN
Elite
Nov 11
Chicago, United States
81% AI deal score
$1,257
$841
Save $416
From CUN
Elite
Nov 13
Chicago, United States
81% AI deal score
$1,247
$841
Save $406
From CUN
Elite
Nov 03
Chicago, United States
81% AI deal score
$1,276
$847
Save $429
From CUN
Elite
Nov 03
Chicago, United States
81% AI deal score
$1,277
$847
Save $430
From CUN
Elite
Jul 24
Chicago, United States
80% AI deal score
$1,177
$831
Save $346
From CUN
Elite
Jul 22
Chicago, United States
80% AI deal score
$1,171
$831
Save $340
From CUN
Elite
Aug 02
Chicago, United States
80% AI deal score
$1,163
$858
Save $305
From CUN
Elite
Aug 19
Chicago, United States
80% AI deal score
$1,169
$863
Save $306
From CUN
Elite
Sep 16
Chicago, United States
80% AI deal score
$1,314
$895
Save $419
From CUN
Elite
Aug 01
Chicago, United States
79% AI deal score
$1,115
$853
Save $262
From CUN
Elite
Jul 30
Chicago, United States
79% AI deal score
$1,185
$858
Save $327
From CUN
Elite
Jul 15
Chicago, United States
79% AI deal score
$1,187
$858
Save $329
From CUN
Elite
Sep 30
Chicago, United States
75% AI deal score
$1,143
$858
Save $285
From CUN
Elite
Sep 22
Chicago, United States
74% AI deal score
$1,110
$858
Save $252
From CUN
Elite
Jul 19
Chicago, United States
74% AI deal score
$1,179
$900
Save $279
From CUN
Elite
Dec 04
Chicago, United States
74% AI deal score
$1,253
$905
Save $348
From CUN
Elite
Aug 22
Chicago, United States
74% AI deal score
$1,114
$905
Save $209
From CUN
Elite
Aug 21
Chicago, United States
74% AI deal score
$1,114
$905
Save $209
From CUN
Elite
Jul 18
Chicago, United States
74% AI deal score
$1,183
$905
Save $278
From CUN
Elite
Aug 24
Chicago, United States
74% AI deal score
$1,152
$912
Save $240
From CUN
Elite
Jul 16
Chicago, United States
74% AI deal score
$1,187
$918
Save $269
From CUN
Elite
Jul 16
Chicago, United States
74% AI deal score
$1,186
$918
Save $268
From CUN
Elite
Nov 24
Chicago, United States
74% AI deal score
$3,471
$2,565
Save $906
From CUN
Elite
Nov 25
Chicago, United States
74% AI deal score
$3,482
$2,583
Save $899
From CUN
Elite
Nov 24
Chicago, United States
74% AI deal score
$3,471
$2,607
Save $864
From CUN
Elite
Aug 05
Chicago, United States
73% AI deal score
$1,105
$918
Save $187
From CUN
Elite
Nov 24
Chicago, United States
73% AI deal score
$3,297
$2,512
Save $785
From CUN
Elite
Nov 23
Chicago, United States
73% AI deal score
$3,226
$2,576
Save $650
From CUN
Elite
Dec 11
Chicago, United States
73% AI deal score
$3,319
$2,620
Save $699
From CUN
Elite
Nov 25
Chicago, United States
73% AI deal score
$3,474
$2,625
Save $849
From CUN
Elite
Nov 23
Chicago, United States
73% AI deal score
$3,471
$2,629
Save $842
From CUN
Elite
Nov 20
Chicago, United States
73% AI deal score
$3,481
$2,629
Save $852
From CUN
Elite
Nov 22
Chicago, United States
73% AI deal score
$3,471
$2,632
Save $839
From CUN
Elite
Dec 10
Chicago, United States
73% AI deal score
$3,374
$2,654
Save $720
From CUN
Elite
Dec 12
Chicago, United States
73% AI deal score
$3,444
$2,662
Save $782
From CUN
Elite
Nov 20
Chicago, United States
73% AI deal score
$3,459
$2,671
Save $788
From CUN
Elite
Nov 23
Chicago, United States
73% AI deal score
$3,467
$2,671
Save $796
From CUN
Elite
Nov 22
Chicago, United States
73% AI deal score
$3,481
$2,674
Save $807
From CUN
Elite
Nov 21
Chicago, United States
73% AI deal score
$3,467
$2,689
Save $778
From CUN
Elite
Nov 21
Chicago, United States
73% AI deal score
$3,459
$2,731
Save $728
From CUN
Elite
Nov 24
Chicago, United States
72% AI deal score
$3,097
$2,525
Save $572
From CUN
Elite
Nov 25
Chicago, United States
72% AI deal score
$3,099
$2,543
Save $556
From CUN
Elite
Dec 04
Chicago, United States
72% AI deal score
$3,089
$2,577
Save $512
From CUN
Elite
Nov 22
Chicago, United States
72% AI deal score
$3,165
$2,578
Save $587
From CUN
Elite
Nov 23
Chicago, United States
72% AI deal score
$3,117
$2,589
Save $528
From CUN
Elite
Nov 20
Chicago, United States
72% AI deal score
$3,083
$2,589
Save $494
From CUN
Elite
Nov 22
Chicago, United States
72% AI deal score
$3,117
$2,592
Save $525
From CUN
Elite
Dec 04
Chicago, United States
72% AI deal score
$3,109
$2,620
Save $489
From CUN
Elite
Dec 03
Chicago, United States
72% AI deal score
$3,089
$2,620
Save $469
From CUN
Elite
Dec 02
Chicago, United States
72% AI deal score
$3,109
$2,620
Save $489
From CUN
Elite
Nov 21
Chicago, United States
72% AI deal score
$3,093
$2,649
Save $444
From CUN
Elite
Dec 10
Chicago, United States
72% AI deal score
$3,245
$2,696
Save $549
From CUN
Elite
Dec 08
Chicago, United States
72% AI deal score
$3,245
$2,747
Save $498
From CUN
Elite
Dec 09
Chicago, United States
72% AI deal score
$3,300
$2,789
Save $511
From CUN
Elite
Nov 20
Chicago, United States
71% AI deal score
$2,943
$2,576
Save $367
From CUN
Elite
Nov 21
Chicago, United States
71% AI deal score
$3,078
$2,636
Save $442
From CUN
Elite
Dec 03
Chicago, United States
71% AI deal score
$3,109
$2,662
Save $447