Cheap Flights from Chicago to San Juan
Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
Chicago
RatePunk searches hundreds of travel sites at once for deals on flights to San Juan
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 Chicago to San Juan
Explore current cheapest deals departing from Chicago to San Juan
Round trip
Sort by: Cheapest
August 29 - September 3
ORD - San Juan
$223
$137
Round trip
August 25 - September 3
ORD - San Juan
$211
$137
Round trip
August 25 - September 1
ORD - San Juan
$217
$137
Round trip
August 24 - September 1
ORD - San Juan
$212
$137
Round trip
August 27 - September 1
ORD - San Juan
$223
$137
Round trip
August 29 - September 1
ORD - San Juan
$224
$137
Round trip
August 24 - September 3
ORD - San Juan
$205
$137
Round trip
August 27 - September 3
ORD - San Juan
$217
$137
Round trip
August 24 - September 5
ORD - San Juan
$202
$137
Round trip
August 29 - September 5
ORD - San Juan
$217
$137
Round trip
Unlock all 500+ flight deals to San Juan and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to San Juan
How much is a round trip from Chicago to San Juan
Regular price: $184 - $327
Prices are currently below the regular range.
The regular price range for flights from Chicago to San Juan is $184 to $327. The current lowest deal is $137 with Frontier Airlines, for travel from Aug 25-Sep 1.
now $137
Low $184
High $327
The cheapest time to fly from Chicago to San Juan
Flights from Chicago to San Juan are cheapest in September, with a median price of $168. The most expensive month to fly is February, with a median price of $1006. Prices are generally lower from April to December.
September
Flights from $168
February
Flights from $1,006
Direct flights from Chicago to San Juan
Frontier Airlines
Last-minute flights going from Chicago to San Juan
Fri, Jun 19
ORD - San Juan
Chicago (ORD) - San Juan (SJU)
United Airlines
$514
$366
One-way
Sat, Jun 20
ORD - San Juan
Chicago (ORD) - San Juan (SJU)
United Airlines
$517
$374
One-way
Sat, Jun 20
ORD - San Juan
Chicago (ORD) - San Juan (SJU)
United Airlines
$514
$374
One-way
Sun, Jun 21
ORD - San Juan
Chicago (ORD) - San Juan (SJU)
United Airlines
$523
$360
One-way
Sun, Jun 21
ORD - San Juan
Chicago (ORD) - San Juan (SJU)
United Airlines
$517
$378
One-way
Sat, Aug 8
ORD - San Juan
Chicago (ORD) - San Juan (SJU)
Frontier Airlines
$191
$169
One-way
Biggest price drops on these dates for flights from Chicago to San Juan
Jun 21 - Jun 23
$523 → $360
31%
Jun 19 - Jun 23
$514 → $366
29%
Jun 20 - Jun 23
$517 → $374
28%
Jun 20 - Jun 24
$514 → $374
27%
Popular Airports to fly from Chicago to San Juan
Chicago - San Juan route insights
💸 Price insights
Recent fares are above the typical level.
Recent fares for Chicago to San Juan are above the typical level, with deals from $137.
📅 Best time to fly
September is historically the cheapest month to fly.
Historically, September is the cheapest month to fly, with a median price of $168.
⏱️ Flight duration
Flights typically last 12h 46m.
The typical flight duration from Chicago to San Juan is 12h 46m.
✈️ Airlines & availability
Connecting flights are dominant on this route.
Connecting flights make up 62% of deals, with a median of 2 stopovers.
🏆 Airline highlight
Frontier Airlines offers direct flights.
Frontier Airlines is one of the carriers that offers direct flights on this route.
🎯 Booking tip
Deals appear frequently for this route.
Deals for flights from Chicago to San Juan appear frequently, with over 1 deal per day.
Chicago main airports to depart from
O Hare International (ORD)
O'Hare International Airport offers flights to San Juan from Chicago, with prices starting from $137.
📍 ~23 km from Chicago (reachable by car or train).
💸 Flights from ~$137
Chicago Midway International (MDW)
Chicago Midway International Airport is an alternative for flights to San Juan from Chicago.
📍 ~15 km from Chicago (reachable by car or train).
💸 Flights from ~$236
Chicago Rockford International (RFD)
Chicago Rockford International Airport is another option for flights to San Juan from Chicago.
📍 ~110 km from Chicago (reachable by car).
💸 Flights from ~$276
San Juan main airports to arrive at
Luis Muñoz Marín International (SJU)
Luis Muñoz Marín International Airport is a good option for flights from Chicago to San Juan.
📍 ~10 km from San Juan (reachable by car)
💸 Flights from ~$137
Fernando Luis Ribas Dominicci (SIG)
Fernando Luis Ribas Dominicci Airport is another option for flights from Chicago to San Juan.
📍 ~1 km from San Juan (reachable by car)
Airports nearby San Juan used as alternative
Aguadilla Rafael Hernandez (BQN)
Aguadilla Rafael Hernandez is a reliable alternative for travelers on the western side of the island.
📍 ~95 km from San Juan (reachable by car)
💸 Flights from ~$331
Mercedita (PSE)
Mercedita is geographically the closest commercial alternative on the main island, serving the southern region.
📍 ~55 km from San Juan (reachable by car)
💸 Flights from ~$342
Cyril E. King (STT)
Cyril E. King is a major international hub in the US Virgin Islands with extensive US mainland connectivity.
📍 ~115 km from San Juan (reachable by inter-island flight or ferry)
💸 Flights from ~$339
Punta Cana International (PUJ)
Punta Cana International is a massive international hub with global connections, often offering lower fares.
📍 ~250 km from San Juan (requires international travel)
💸 Flights from ~$288
Henry E. Rohlsen (STX)
Henry E. Rohlsen is an alternative US territory airport with direct links to the US mainland.
📍 ~150 km from San Juan (requires additional air travel)
💸 Flights from ~$356
Business & First Class Flight Deals to San Juan
Discover luxury on the budget with premium cabin class on flights from Chicago to San Juan.
Elite
Best Elite deals to San Juan
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Aug 22
San Juan, United States
91% AI deal score
$1,359
$762
Save $597
From ORD
Elite
Jul 04
San Juan, United States
91% AI deal score
$1,335
$777
Save $558
From ORD
Elite
Aug 15
San Juan, United States
91% AI deal score
$1,563
$898
Save $665
From ORD
Elite
Aug 10
San Juan, United States
91% AI deal score
$1,564
$898
Save $666
From ORD
Elite
Aug 29
San Juan, United States
90% AI deal score
$1,440
$816
Save $624
From ORD
Elite
Aug 19
San Juan, United States
90% AI deal score
$1,369
$852
Save $517
From ORD
Elite
Aug 26
San Juan, United States
90% AI deal score
$1,499
$898
Save $601
From ORD
Elite
Aug 22
San Juan, United States
90% AI deal score
$1,499
$907
Save $592
From ORD
Elite
Aug 22
San Juan, United States
90% AI deal score
$1,531
$907
Save $624
From ORD
Elite
Aug 25
San Juan, United States
90% AI deal score
$1,532
$907
Save $625
From ORD
Elite
Aug 18
San Juan, United States
89% AI deal score
$1,338
$907
Save $431
From ORD
Elite
Aug 18
San Juan, United States
89% AI deal score
$1,376
$912
Save $464
From ORD
Elite
Sep 19
San Juan, United States
89% AI deal score
$1,476
$927
Save $549
From ORD
Elite
Jul 04
San Juan, United States
89% AI deal score
$1,434
$927
Save $507
From ORD
Elite
Jul 04
San Juan, United States
89% AI deal score
$1,498
$927
Save $571
From ORD
Elite
Sep 25
San Juan, United States
89% AI deal score
$1,484
$937
Save $547
From ORD
Elite
Oct 14
San Juan, United States
89% AI deal score
$1,516
$942
Save $574
From ORD
Elite
Oct 02
San Juan, United States
89% AI deal score
$1,608
$957
Save $651
From ORD
Elite
Aug 18
San Juan, United States
89% AI deal score
$1,530
$958
Save $572
From ORD
Elite
Aug 18
San Juan, United States
89% AI deal score
$1,497
$962
Save $535
From ORD
Elite
Aug 10
San Juan, United States
89% AI deal score
$1,530
$972
Save $558
From ORD
Elite
Aug 01
San Juan, United States
89% AI deal score
$1,555
$987
Save $568
From ORD
Elite
Aug 05
San Juan, United States
89% AI deal score
$1,575
$987
Save $588
From ORD
Elite
Aug 02
San Juan, United States
89% AI deal score
$1,595
$997
Save $598
From ORD
Elite
Sep 10
San Juan, United States
88% AI deal score
$1,548
$932
Save $616
From ORD
Elite
Sep 06
San Juan, United States
88% AI deal score
$1,312
$898
Save $414
From ORD
Elite
Aug 22
San Juan, United States
88% AI deal score
$1,309
$898
Save $411
From ORD
Elite
Aug 22
San Juan, United States
88% AI deal score
$1,298
$907
Save $391
From ORD
Elite
Jul 04
San Juan, United States
88% AI deal score
$1,303
$927
Save $376
From ORD
Elite
Sep 18
San Juan, United States
88% AI deal score
$1,456
$937
Save $519
From ORD
Elite
Oct 27
San Juan, United States
88% AI deal score
$1,418
$937
Save $481
From ORD
Elite
Sep 25
San Juan, United States
88% AI deal score
$1,452
$942
Save $510
From ORD
Elite
Sep 02
San Juan, United States
88% AI deal score
$1,423
$957
Save $466
From ORD
Elite
Jul 20
San Juan, United States
88% AI deal score
$1,481
$987
Save $494
From ORD
Elite
Jul 06
San Juan, United States
88% AI deal score
$1,521
$997
Save $524
From ORD
Elite
Jul 06
San Juan, United States
88% AI deal score
$1,477
$997
Save $480
From ORD
Elite
Oct 28
San Juan, United States
88% AI deal score
$1,582
$1,012
Save $570
From ORD
Elite
Jul 04
San Juan, United States
87% AI deal score
$1,179
$785
Save $394
From ORD
Elite
Oct 04
San Juan, United States
87% AI deal score
$1,453
$932
Save $521
From ORD
Elite
Jul 08
San Juan, United States
87% AI deal score
$1,574
$1,002
Save $572
From ORD
Elite
Sep 12
San Juan, United States
87% AI deal score
$1,326
$937
Save $389
From ORD
Elite
Sep 19
San Juan, United States
87% AI deal score
$1,337
$937
Save $400
From ORD
Elite
Sep 18
San Juan, United States
87% AI deal score
$1,332
$937
Save $395
From ORD
Elite
Jul 05
San Juan, United States
87% AI deal score
$1,351
$958
Save $393
From ORD
Elite
Aug 05
San Juan, United States
87% AI deal score
$1,377
$997
Save $380
From ORD
Elite
Jul 21
San Juan, United States
87% AI deal score
$1,450
$997
Save $453
From ORD
Elite
Jul 31
San Juan, United States
87% AI deal score
$1,407
$997
Save $410
From ORD
Elite
Jul 31
San Juan, United States
87% AI deal score
$1,437
$997
Save $440
From ORD
Elite
Sep 17
San Juan, United States
87% AI deal score
$1,456
$1,012
Save $444
From ORD
Elite
Aug 07
San Juan, United States
86% AI deal score
$1,373
$952
Save $421
From ORD
Elite
Aug 07
San Juan, United States
86% AI deal score
$1,273
$958
Save $315
From ORD
Elite
Jul 06
San Juan, United States
86% AI deal score
$1,337
$987
Save $350
From ORD
Elite
Jul 12
San Juan, United States
86% AI deal score
$1,255
$987
Save $268
From ORD
Elite
Jul 22
San Juan, United States
86% AI deal score
$1,266
$997
Save $269
From ORD
Elite
Jul 06
San Juan, United States
86% AI deal score
$1,321
$997
Save $324
From ORD
Elite
Sep 28
San Juan, United States
86% AI deal score
$1,364
$1,022
Save $342
From ORD
Elite
Aug 29
San Juan, United States
86% AI deal score
$1,527
$1,098
Save $429
From ORD
Elite
Aug 06
San Juan, United States
85% AI deal score
$1,428
$1,026
Save $402
From ORD
Elite
Sep 16
San Juan, United States
85% AI deal score
$1,496
$1,027
Save $469
From ORD
Elite
Jul 28
San Juan, United States
85% AI deal score
$1,230
$987
Save $243
From ORD
Elite
Jul 27
San Juan, United States
85% AI deal score
$1,227
$987
Save $240
From ORD
Elite
Jul 20
San Juan, United States
85% AI deal score
$1,255
$997
Save $258
From ORD
Elite
Jul 21
San Juan, United States
85% AI deal score
$1,255
$997
Save $258
From ORD
Elite
Sep 09
San Juan, United States
85% AI deal score
$1,314
$1,022
Save $292
From ORD
Elite
Jul 22
San Juan, United States
84% AI deal score
$1,181
$987
Save $194
From ORD
Elite
Sep 17
San Juan, United States
84% AI deal score
$1,285
$1,022
Save $263
From ORD
Elite
Aug 15
San Juan, United States
83% AI deal score
$1,295
$1,108
Save $187
From ORD
Elite
Sep 24
San Juan, United States
77% AI deal score
$1,248
$1,012
Save $236
From ORD
Elite
Aug 05
San Juan, United States
76% AI deal score
$1,077
$955
Save $122
From ORD
Elite
Jul 12
San Juan, United States
76% AI deal score
$1,130
$987
Save $143
From ORD
Elite
Jul 22
San Juan, United States
76% AI deal score
$1,163
$997
Save $166
From ORD
Elite
Sep 11
San Juan, United States
76% AI deal score
$1,228
$1,012
Save $216
From ORD
Elite
Sep 17
San Juan, United States
76% AI deal score
$1,213
$1,022
Save $191
From ORD
Elite
Jul 22
San Juan, United States
75% AI deal score
$1,122
$987
Save $135
From ORD
Elite
Jul 22
San Juan, United States
75% AI deal score
$1,131
$997
Save $134
From ORD
Elite
Sep 17
San Juan, United States
75% AI deal score
$1,161
$1,022
Save $139
From ORD
Elite
Jul 30
San Juan, United States
74% AI deal score
$1,189
$1,105
Save $84
From ORD
Elite
Aug 29
San Juan, United States
74% AI deal score
$1,200
$1,108
Save $92
From ORD
Elite
Jul 10
San Juan, United States
74% AI deal score
$1,210
$1,108
Save $102
From ORD
Elite
Jul 09
San Juan, United States
74% AI deal score
$1,198
$1,108
Save $90
From ORD
Elite
Jul 25
San Juan, United States
74% AI deal score
$1,188
$1,108
Save $80
From ORD
Elite
Jun 30
San Juan, United States
73% AI deal score
$1,181
$1,095
Save $86
From ORD
Elite
Jul 29
San Juan, United States
73% AI deal score
$1,164
$1,108
Save $56
From ORD
Elite
Aug 14
San Juan, United States
72% AI deal score
$1,126
$1,098
Save $28
From ORD
Elite
Oct 25
San Juan, United States
72% AI deal score
$1,131
$1,098
Save $33
From ORD
Elite
Jul 15
San Juan, United States
72% AI deal score
$1,118
$1,102
Save $16
From ORD
Elite
Aug 02
San Juan, United States
72% AI deal score
$1,123
$1,104
Save $19
From ORD
Elite
Jul 28
San Juan, United States
72% AI deal score
$1,113
$1,108
Save $5
From ORD
Elite
Jul 14
San Juan, United States
72% AI deal score
$1,126
$1,108
Save $18
From ORD
Elite
Jul 15
San Juan, United States
72% AI deal score
$1,128
$1,108
Save $20
From ORD
Elite
Oct 29
San Juan, United States
71% AI deal score
$1,104