Cheap Flights from Guadalajara to Chicago
Browse current best options from Guadalajara. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Guadalajara
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 Guadalajara to Chicago
Explore current cheapest deals departing from Guadalajara to Chicago
Round trip
Sort by: Cheapest
September 24 - September 27
GDL - Chicago
$319
$272
Round trip
September 24 - October 5
GDL - Chicago
$292
$279
Round trip
September 24 - October 10
GDL - Chicago
$285
$279
Round trip
September 24 - October 17
GDL - Chicago
$282
$280
Round trip
September 24 - September 30
GDL - Chicago
$315
$280
Round trip
September 24 - October 24
GDL - Chicago
$282
$280
Round trip
November 5 - November 9
GDL - Chicago
$329
$282
Round trip
October 17 - October 24
GDL - Chicago
$391
$284
Round trip
September 23 - September 30
GDL - Chicago
$315
$285
Round trip
October 3 - October 10
GDL - Chicago
$372
$286
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 Guadalajara to Chicago
How much is a round trip from Guadalajara to Chicago
Regular price: $272 - $600
Prices for flights from Guadalajara to Chicago are currently within the regular range.
The regular price range for this route is between $272 and $600. The current lowest deal is $272 with Aeroenlaces Nacionales, for travel from Sep 24-Sep 27.
now $272
Low $272
High $600
The cheapest time to fly from Guadalajara to Chicago
Flights from GDL to CHI are cheapest in September, with a median price of $254. The most expensive month to fly is October, with a median price of $589. Prices are generally lower from February to December.
September
Flights from $254
October
Flights from $589
Direct flights from Guadalajara to Chicago
Aeroenlaces Nacionales
Volaris
Last-minute flights going from Guadalajara to Chicago
Wed, Jun 17
GDL - Chicago
Guadalajara (GDL) - Chicago (ORD)
Volaris
$501
$360
One-way
Wed, Jun 17
GDL - Chicago
Guadalajara (GDL) - Chicago (ORD)
Volaris
$547
$378
One-way
Thu, Jun 18
GDL - Chicago
Guadalajara (GDL) - Chicago (ORD)
United Airlines
$470
$342
One-way
Thu, Jun 18
GDL - Chicago
Guadalajara (GDL) - Chicago (ORD)
$550
$342
One-way
Thu, Jun 18
GDL - Chicago
Guadalajara (GDL) - Chicago (ORD)
United Airlines
$467
$343
One-way
Thu, Jun 18
GDL - Chicago
Guadalajara (GDL) - Chicago (ORD)
Aeroenlaces Nacionales
$501
$351
One-way
Biggest price drops on these dates for flights from Guadalajara to Chicago
Oct 8 - Oct 11
$672 → $385
43%
Oct 8 - Oct 17
$654 → $382
42%
Oct 8 - Oct 15
$656 → $440
33%
Jun 18 - Jun 20
$550 → $342
38%
Popular Airports to fly from Guadalajara to Chicago
Guadalajara - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from Guadalajara to Chicago are below the typical level, with 42% good prices.
📅 Best time to fly
September is historically the cheapest month
Historically, September is the cheapest month to fly from Guadalajara to Chicago, with a median price of $254.
⏱️ Flight duration
Flights are typically 11h 37m long
A flight from Guadalajara to Chicago typically takes 11 hours and 37 minutes, covering 2780 km.
✈️ Airlines & availability
Connecting flights are dominant on this route
Connecting flights are dominant, making up 71.5% of deals, with a median of 2 stopovers.
🏆 Airline highlight
Aeroenlaces Nacionales offers direct flights
Aeroenlaces Nacionales is one of the airlines offering direct flights on the Guadalajara to Chicago route.
🎯 Booking tip
Deals appear frequently (1 per day)
Deals from Guadalajara to Chicago appear frequently, with about 1 deal per day.
Guadalajara main airports to depart from
Guadalajara International (GDL)
Guadalajara International is a good option for flights from Guadalajara to Chicago.
📍 ~20 km from Guadalajara (reachable by car)
💸 Flights from ~$272
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights from Guadalajara to Chicago.
📍 ~25 km from Chicago (reachable by car)
💸 Flights from ~$272
Chicago Midway International (MDW)
Chicago Midway International Airport is an alternative for flights from Guadalajara to Chicago.
📍 ~15 km from Chicago (reachable by car)
💸 Flights from ~$366
Chicago Rockford International (RFD)
Chicago Rockford International Airport is another choice for flights from Guadalajara to Chicago.
📍 ~120 km from Chicago (reachable by car)
💸 Flights from ~$475
Airports nearby Chicago used as alternative
General Mitchell International (MKE)
Consider MKE for its excellent proximity to Chicago and high-frequency flight options, despite potential traffic.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$590
South Bend International (SBN)
SBN is a close alternative to Chicago, offering easier security and parking, with direct rail access.
📍 ~130 km from Chicago (reachable by rail)
💸 Flights from ~$513
Gerald R. Ford International (GRR)
GRR is a major regional hub with diverse cabin classes, suitable for travelers on Chicago's eastern side.
📍 ~235 km from Chicago (reachable by car)
💸 Flights from ~$502
Dane County Regional (MSN)
MSN is a reliable, less congested regional airport with full cabin class options, though it is further out.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$517
Fort Wayne International (FWA)
FWA offers stable regional service and is an alternative for travelers in Chicago's southeastern suburbs.
📍 ~250 km from Chicago (reachable by car)
💸 Flights from ~$496
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from Guadalajara to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From GDL
Elite
Aug 05
Chicago, United States
90% AI deal score
$1,829
$632
Save $1,197
From GDL
Elite
Jul 22
Chicago, United States
90% AI deal score
$1,885
$647
Save $1,238
From GDL
Elite
Jul 28
Chicago, United States
90% AI deal score
$1,885
$647
Save $1,238
From GDL
Elite
Jul 15
Chicago, United States
90% AI deal score
$1,914
$663
Save $1,251
From GDL
Elite
Aug 02
Chicago, United States
90% AI deal score
$1,852
$674
Save $1,178
From GDL
Elite
Aug 11
Chicago, United States
90% AI deal score
$1,531
$793
Save $738
From GDL
Elite
Jun 23
Chicago, United States
90% AI deal score
$1,662
$833
Save $829
From GDL
Elite
Jul 13
Chicago, United States
89% AI deal score
$1,835
$648
Save $1,187
From GDL
Elite
Jul 17
Chicago, United States
89% AI deal score
$1,836
$653
Save $1,183
From GDL
Elite
Jul 19
Chicago, United States
89% AI deal score
$1,834
$674
Save $1,160
From GDL
Elite
Jul 21
Chicago, United States
89% AI deal score
$1,876
$674
Save $1,202
From GDL
Elite
Aug 17
Chicago, United States
89% AI deal score
$1,743
$674
Save $1,069
From GDL
Elite
Sep 15
Chicago, United States
89% AI deal score
$1,810
$683
Save $1,127
From GDL
Elite
Sep 08
Chicago, United States
89% AI deal score
$1,787
$683
Save $1,104
From GDL
Elite
Sep 10
Chicago, United States
89% AI deal score
$1,828
$683
Save $1,145
From GDL
Elite
Jun 23
Chicago, United States
89% AI deal score
$1,625
$833
Save $792
From GDL
Elite
Jun 19
Chicago, United States
89% AI deal score
$1,607
$833
Save $774
From GDL
Elite
Jul 14
Chicago, United States
88% AI deal score
$1,330
$738
Save $592
From GDL
Elite
Jul 15
Chicago, United States
88% AI deal score
$1,338
$738
Save $600
From GDL
Elite
Jul 14
Chicago, United States
88% AI deal score
$1,338
$738
Save $600
From GDL
Elite
Jul 15
Chicago, United States
88% AI deal score
$1,338
$738
Save $600
From GDL
Elite
Jul 14
Chicago, United States
88% AI deal score
$1,333
$743
Save $590
From GDL
Elite
Jul 15
Chicago, United States
88% AI deal score
$1,330
$743
Save $587
From GDL
Elite
Jul 15
Chicago, United States
87% AI deal score
$1,333
$770
Save $563
From GDL
Elite
Jul 12
Chicago, United States
87% AI deal score
$1,334
$793
Save $541
From GDL
Elite
Jul 27
Chicago, United States
87% AI deal score
$1,368
$793
Save $575
From GDL
Elite
Jul 27
Chicago, United States
87% AI deal score
$1,369
$793
Save $576
From GDL
Elite
Jul 20
Chicago, United States
86% AI deal score
$1,336
$798
Save $538
From GDL
Elite
Jul 20
Chicago, United States
86% AI deal score
$1,336
$798
Save $538
From GDL
Elite
Jul 14
Chicago, United States
85% AI deal score
$835
$567
Save $268
From GDL
Elite
Jul 15
Chicago, United States
85% AI deal score
$836
$567
Save $269
From GDL
Elite
Jul 14
Chicago, United States
85% AI deal score
$835
$567
Save $268
From GDL
Elite
Jul 15
Chicago, United States
85% AI deal score
$836
$567
Save $269
From GDL
Elite
Jul 14
Chicago, United States
85% AI deal score
$839
$572
Save $267
From GDL
Elite
Jul 15
Chicago, United States
85% AI deal score
$836
$572
Save $264
From GDL
Elite
Aug 13
Chicago, United States
85% AI deal score
$971
$604
Save $367
From GDL
Elite
Aug 13
Chicago, United States
85% AI deal score
$972
$604
Save $368
From GDL
Elite
Jul 10
Chicago, United States
84% AI deal score
$1,342
$906
Save $436
From GDL
Elite
Jul 15
Chicago, United States
84% AI deal score
$1,369
$906
Save $463
From GDL
Elite
Jul 14
Chicago, United States
84% AI deal score
$1,362
$906
Save $456
From GDL
Elite
Jul 07
Chicago, United States
84% AI deal score
$1,386
$911
Save $475
From GDL
Elite
Jul 15
Chicago, United States
84% AI deal score
$839
$598
Save $241
From GDL
Elite
Aug 14
Chicago, United States
84% AI deal score
$972
$609
Save $363
From GDL
Elite
Aug 11
Chicago, United States
84% AI deal score
$970
$622
Save $348
From GDL
Elite
Sep 29
Chicago, United States
83% AI deal score
$3,693
$2,314
Save $1,379
From GDL
Elite
Sep 22
Chicago, United States
83% AI deal score
$3,630
$2,325
Save $1,305
From GDL
Elite
Sep 29
Chicago, United States
83% AI deal score
$3,660
$2,331
Save $1,329
From GDL
Elite
Sep 21
Chicago, United States
83% AI deal score
$3,651
$2,332
Save $1,319
From GDL
Elite
Sep 23
Chicago, United States
83% AI deal score
$3,660
$2,332
Save $1,328
From GDL
Elite
Oct 01
Chicago, United States
83% AI deal score
$3,590
$2,332
Save $1,258
From GDL
Elite
Sep 16
Chicago, United States
83% AI deal score
$3,613
$2,332
Save $1,281
From GDL
Elite
Sep 22
Chicago, United States
83% AI deal score
$3,667
$2,341
Save $1,326
From GDL
Elite
Sep 21
Chicago, United States
83% AI deal score
$3,635
$2,348
Save $1,287
From GDL
Elite
Sep 23
Chicago, United States
83% AI deal score
$3,693
$2,349
Save $1,344
From GDL
Elite
Jul 10
Chicago, United States
83% AI deal score
$839
$618
Save $221
From GDL
Elite
Jul 14
Chicago, United States
83% AI deal score
$835
$618
Save $217
From GDL
Elite
Jul 14
Chicago, United States
83% AI deal score
$835
$618
Save $217
From GDL
Elite
Jul 15
Chicago, United States
83% AI deal score
$836
$618
Save $218
From GDL
Elite
Jul 15
Chicago, United States
83% AI deal score
$836
$618
Save $218
From GDL
Elite
Jul 27
Chicago, United States
83% AI deal score
$836
$622
Save $214
From GDL
Elite
Jul 12
Chicago, United States
83% AI deal score
$839
$622
Save $217
From GDL
Elite
Oct 13
Chicago, United States
82% AI deal score
$3,532
$2,318
Save $1,214
From GDL
Elite
Oct 01
Chicago, United States
82% AI deal score
$3,560
$2,349
Save $1,211
From GDL
Elite
Sep 23
Chicago, United States
82% AI deal score
$3,580
$2,380
Save $1,200
From GDL
Elite
Oct 20
Chicago, United States
82% AI deal score
$3,600
$2,389
Save $1,211
From GDL
Elite
Jul 27
Chicago, United States
82% AI deal score
$835
$622
Save $213
From GDL
Elite
Jun 20
Chicago, United States
81% AI deal score
$1,710
$1,250
Save $460
From GDL
Elite
Sep 29
Chicago, United States
81% AI deal score
$3,395
$2,314
Save $1,081
From GDL
Elite
Sep 22
Chicago, United States
81% AI deal score
$3,435
$2,355
Save $1,080
From GDL
Elite
Sep 23
Chicago, United States
81% AI deal score
$3,499
$2,362
Save $1,137
From GDL
Elite
Oct 22
Chicago, United States
81% AI deal score
$3,603
$2,432
Save $1,171
From GDL
Elite
Jul 10
Chicago, United States
81% AI deal score
$836
$666
Save $170
From GDL
Elite
Jul 14
Chicago, United States
81% AI deal score
$835
$666
Save $169
From GDL
Elite
Jul 15
Chicago, United States
81% AI deal score
$835
$666
Save $169
From GDL
Elite
Jul 04
Chicago, United States
81% AI deal score
$808
$671
Save $137
From GDL
Elite
Jul 07
Chicago, United States
80% AI deal score
$822
$671
Save $151
From GDL
Elite
Jul 08
Chicago, United States
80% AI deal score
$821
$671
Save $150
From GDL
Elite
Jul 06
Chicago, United States
80% AI deal score
$821
$671
Save $150
From GDL
Elite
Jul 09
Chicago, United States
80% AI deal score
$821
$671
Save $150
From GDL
Elite
Oct 13
Chicago, United States
77% AI deal score
$3,293
$2,307
Save $986
From GDL
Elite
Oct 20
Chicago, United States
77% AI deal score
$3,420
$2,342
Save $1,078
From GDL
Elite
Sep 21
Chicago, United States
77% AI deal score
$3,315
$2,362
Save $953
From GDL
Elite
Sep 16
Chicago, United States
77% AI deal score
$3,318
$2,362
Save $956
From GDL
Elite
Sep 22
Chicago, United States
77% AI deal score
$3,482
$2,372
Save $1,110
From GDL
Elite
Sep 21
Chicago, United States
77% AI deal score
$3,427
$2,379
Save $1,048
From GDL
Elite
Sep 16
Chicago, United States
77% AI deal score
$3,458
$2,407
Save $1,051
From GDL
Elite
Oct 27
Chicago, United States
77% AI deal score
$3,571
$2,431
Save $1,140
From GDL
Elite
Jun 20
Chicago, United States
76% AI deal score
$1,481
$1,107
Save $374
From GDL
Elite
Oct 13
Chicago, United States
76% AI deal score
$3,277
$2,324
Save $953
From GDL
Elite
Oct 01
Chicago, United States
76% AI deal score
$3,248
$2,332
Save $916
From GDL
Elite
Sep 22
Chicago, United States
76% AI deal score
$3,148
$2,341
Save $807
From GDL
Elite
Sep 21
Chicago, United States
76% AI deal score
$3,119
$2,348
Save $771
From GDL
Elite
Nov 10
Chicago, United States
76% AI deal score
$3,270
$2,349
Save $921
From GDL
Elite
Sep 16
Chicago, United States
76% AI deal score
$3,268
$2,349
Save $919
From GDL
Elite
Oct 20
Chicago, United States
76% AI deal score
$3,249
$2,353
Save $896
From GDL
Elite
Nov 09
Chicago, United States
76% AI deal score
$3,207
$2,355
Save $852
From GDL
Elite
Nov 11
Chicago, United States
76% AI deal score
$3,341
$2,374
Save $967
From GDL
Elite
Sep 16
Chicago, United States
76% AI deal score
$3,286
$2,380
Save $906
From GDL
Elite
Sep 17
Chicago, United States
76% AI deal score
$3,286
$2,411
Save $875
From GDL
Elite
Sep 17
Chicago, United States
76% AI deal score
$3,286
$2,429
Save $857