Cheap Flights from Chicago to San Diego
Browse current best options from Chicago. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
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RatePunk searches hundreds of travel sites at once for deals on flights to San Diego
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 Diego
Explore current cheapest deals departing from Chicago to San Diego
Round trip
Sort by: Cheapest
September 15 - October 14
ORD - San Diego
$217
$195
Round trip
September 15 - September 30
ORD - San Diego
$221
$195
Round trip
October 21 - November 11
ORD - San Diego
$241
$198
Round trip
October 20 - November 11
ORD - San Diego
$241
$198
Round trip
October 21 - October 28
ORD - San Diego
$268
$198
Round trip
October 20 - November 4
ORD - San Diego
$245
$198
Round trip
October 20 - October 28
ORD - San Diego
$266
$198
Round trip
August 17 - August 25
RFD - San Diego
$317
$200
Round trip
September 2 - September 8
ORD - San Diego
$182
$203
Round trip
August 20 - August 25
ORD - San Diego
$196
$208
Round trip
Unlock all 500+ flight deals to San Diego and get alerts when great deals appear
Route Intelligence — 486,190 Searches this Week
Insights for flights from Chicago to San Diego
How much is a round trip from Chicago to San Diego
Regular price: $185 - $360
Prices for flights from Chicago to San Diego are currently within the regular range.
The regular price range for flights from Chicago to San Diego is between $185 and $360. The current lowest deal is $195 with Frontier Airlines, for travel from Sep 15-Oct 14.
now $195
Low $185
High $360
The cheapest time to fly from Chicago to San Diego
Flights from Chicago to San Diego are cheapest in April, with a median price of $234. The most expensive month to fly is December, with a median price of $709. Generally, prices are lower from February to November.
April
Flights from $234
December
Flights from $709
Direct flights from Chicago to San Diego
Alaska Airlines, Inc.
Last-minute flights going from Chicago to San Diego
Tue, Jun 16
ORD - San Diego
Chicago (ORD) - San Diego (SAN)
Frontier Airlines
$421
$270
One-way
Wed, Jun 17
ORD - San Diego
Chicago (ORD) - San Diego (SAN)
Frontier Airlines
$379
$270
One-way
Wed, Jun 17
ORD - San Diego
Chicago (ORD) - San Diego (SAN)
Frontier Airlines
$425
$270
One-way
Wed, Jun 17
ORD - San Diego
Chicago (ORD) - San Diego (SAN)
Alaska Airlines, Inc.
$351
$305
One-way
Thu, Jun 18
ORD - San Diego
Chicago (ORD) - San Diego (SAN)
Frontier Airlines
$377
$270
One-way
Thu, Jun 18
ORD - San Diego
Chicago (ORD) - San Diego (SAN)
Frontier Airlines
$414
$270
One-way
Biggest price drops on these dates for flights from Chicago to San Diego
Jun 17 - Jun 19
$425 → $270
37%
Jun 16 - Jun 19
$421 → $270
36%
Jun 20 - Jun 22
$421 → $270
36%
Jun 19 - Jun 22
$416 → $270
35%
Popular Airports to fly from Chicago to San Diego
Chicago - San Diego route insights
💸 Price insights
Recent fares are above the typical level
Recent fares for Chicago to San Diego are above the typical level at $195.
📅 Best time to fly
April offers the lowest median price
Historically, April, May, and September offer the lowest median prices for this route.
⏱️ Flight duration
Typically 8h 51m to San Diego
Flights from Chicago to San Diego typically take 8 hours and 51 minutes.
✈️ Airlines & availability
Mixed availability of direct flights
About 55.7% of recent deals are for direct flights, with Frontier Airlines offering a recent deal.
🏆 Airline highlight
Frontier Airlines offers a recent deal
A recent deal from Chicago to San Diego was found on Frontier Airlines for $195.
🎯 Booking tip
Deals are frequent for this route
Deals for flights from Chicago to San Diego are frequent, with over 1 deal per day.
Chicago main airports to depart from
O Hare International (ORD)
O'Hare International Airport offers flights to San Diego and is often the cheapest option from Chicago.
📍 ~25 km from Chicago city center (reachable by car or train)
💸 Flights from ~$195
Chicago Midway International (MDW)
Chicago Midway International Airport is another convenient option for flights from Chicago to San Diego.
📍 ~15 km from Chicago city center (reachable by car or train)
💸 Flights from ~$227
Chicago Rockford International (RFD)
Chicago Rockford International Airport provides an alternative departure point for your trip to San Diego.
📍 ~120 km from Chicago city center (reachable by car)
💸 Flights from ~$203
San Diego main airports to arrive at
San Diego International (SAN)
San Diego International Airport is a convenient arrival choice for flights from Chicago to San Diego.
📍 ~5 km from San Diego (reachable by car)
💸 Flights from ~$195
McClellan–Palomar (CLD)
McClellan–Palomar Airport offers an alternative arrival point for your trip to San Diego from Chicago.
📍 ~45 km from San Diego (reachable by car)
💸 Flights from ~$360
Airports nearby San Diego used as alternative
Tijuana International (TIJ)
Tijuana International (TIJ) is an excellent alternative for domestic Mexico flights with lower fares, requiring an international border crossing.
📍 ~25 km from San Diego (reachable by car)
💸 Flights from ~$299
John Wayne (SNA)
John Wayne (SNA) is a close major US domestic alternative, easier to navigate and less congested than LAX.
📍 ~120 km from San Diego (reachable by car)
💸 Flights from ~$215
Los Angeles International (LAX)
Los Angeles International (LAX) is a primary global hub with extensive international and domestic route options and competitive pricing.
📍 ~180 km from San Diego (reachable by car)
💸 Flights from ~$157
Ontario International (ONT)
Ontario International (ONT) is a reliable domestic alternative with growing service, often less congested than LAX or SNA.
📍 ~180 km from San Diego (reachable by car)
💸 Flights from ~$190
Long Beach (LGB)
Long Beach (LGB) is very easy to navigate with fast security processing, offering a good alternative for specific West Coast routes.
📍 ~150 km from San Diego (reachable by car)
💸 Flights from ~$240
Business & First Class Flight Deals to San Diego
Discover luxury on the budget with premium cabin class on flights from Chicago to San Diego.
Elite
Best Elite deals to San Diego
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From ORD
Elite
Aug 19
San Diego, United States
88% AI deal score
$1,303
$747
Save $556
From ORD
Elite
Aug 29
San Diego, United States
88% AI deal score
$1,303
$747
Save $556
From ORD
Elite
Aug 25
San Diego, United States
88% AI deal score
$1,210
$727
Save $483
From ORD
Elite
Aug 26
San Diego, United States
88% AI deal score
$1,223
$727
Save $496
From ORD
Elite
Oct 20
San Diego, United States
88% AI deal score
$1,179
$727
Save $452
From ORD
Elite
Aug 29
San Diego, United States
87% AI deal score
$1,190
$727
Save $463
From ORD
Elite
Sep 10
San Diego, United States
87% AI deal score
$1,280
$742
Save $538
From ORD
Elite
Sep 16
San Diego, United States
87% AI deal score
$1,334
$746
Save $588
From ORD
Elite
Aug 26
San Diego, United States
87% AI deal score
$1,244
$747
Save $497
From ORD
Elite
Sep 22
San Diego, United States
87% AI deal score
$1,285
$747
Save $538
From ORD
Elite
Sep 15
San Diego, United States
87% AI deal score
$1,317
$747
Save $570
From ORD
Elite
Sep 13
San Diego, United States
87% AI deal score
$1,335
$747
Save $588
From ORD
Elite
Aug 22
San Diego, United States
87% AI deal score
$1,082
$727
Save $355
From ORD
Elite
Oct 17
San Diego, United States
87% AI deal score
$1,090
$727
Save $363
From ORD
Elite
Jun 20
San Diego, United States
87% AI deal score
$1,478
$945
Save $533
From ORD
Elite
Aug 26
San Diego, United States
86% AI deal score
$1,162
$726
Save $436
From ORD
Elite
Aug 19
San Diego, United States
86% AI deal score
$1,131
$727
Save $404
From ORD
Elite
Aug 26
San Diego, United States
86% AI deal score
$1,134
$727
Save $407
From ORD
Elite
Aug 19
San Diego, United States
86% AI deal score
$1,131
$727
Save $404
From ORD
Elite
Aug 29
San Diego, United States
86% AI deal score
$1,158
$727
Save $431
From ORD
Elite
Oct 24
San Diego, United States
86% AI deal score
$1,200
$742
Save $458
From ORD
Elite
Aug 24
San Diego, United States
86% AI deal score
$1,158
$746
Save $412
From ORD
Elite
Sep 16
San Diego, United States
86% AI deal score
$1,230
$746
Save $484
From ORD
Elite
Aug 28
San Diego, United States
86% AI deal score
$1,188
$746
Save $442
From ORD
Elite
Oct 22
San Diego, United States
86% AI deal score
$1,274
$746
Save $528
From ORD
Elite
Aug 19
San Diego, United States
86% AI deal score
$1,186
$747
Save $439
From ORD
Elite
Aug 26
San Diego, United States
86% AI deal score
$1,160
$747
Save $413
From ORD
Elite
Sep 15
San Diego, United States
86% AI deal score
$1,229
$747
Save $482
From ORD
Elite
Aug 29
San Diego, United States
86% AI deal score
$1,188
$747
Save $441
From ORD
Elite
Oct 10
San Diego, United States
86% AI deal score
$1,037
$727
Save $310
From ORD
Elite
Oct 14
San Diego, United States
86% AI deal score
$1,061
$727
Save $334
From ORD
Elite
Oct 13
San Diego, United States
86% AI deal score
$1,059
$727
Save $332
From ORD
Elite
Sep 26
San Diego, United States
86% AI deal score
$1,109
$727
Save $382
From ORD
Elite
Sep 29
San Diego, United States
86% AI deal score
$1,119
$727
Save $392
From ORD
Elite
Nov 10
San Diego, United States
85% AI deal score
$1,115
$727
Save $388
From ORD
Elite
Aug 26
San Diego, United States
85% AI deal score
$1,134
$746
Save $388
From ORD
Elite
Aug 20
San Diego, United States
85% AI deal score
$1,131
$746
Save $385
From ORD
Elite
Aug 19
San Diego, United States
85% AI deal score
$1,131
$747
Save $384
From ORD
Elite
Aug 24
San Diego, United States
85% AI deal score
$1,134
$747
Save $387
From ORD
Elite
Aug 19
San Diego, United States
85% AI deal score
$1,138
$747
Save $391
From ORD
Elite
Aug 29
San Diego, United States
85% AI deal score
$1,142
$747
Save $395
From ORD
Elite
Aug 29
San Diego, United States
85% AI deal score
$1,135
$747
Save $388
From ORD
Elite
Aug 28
San Diego, United States
85% AI deal score
$1,153
$747
Save $406
From ORD
Elite
Aug 20
San Diego, United States
85% AI deal score
$1,131
$747
Save $384
From ORD
Elite
Sep 19
San Diego, United States
85% AI deal score
$1,000
$727
Save $273
From ORD
Elite
Dec 04
San Diego, United States
84% AI deal score
$1,152
$785
Save $367
From ORD
Elite
Dec 03
San Diego, United States
84% AI deal score
$1,147
$785
Save $362
From ORD
Elite
Oct 03
San Diego, United States
84% AI deal score
$983
$727
Save $256
From ORD
Elite
Oct 06
San Diego, United States
84% AI deal score
$986
$727
Save $259
From ORD
Elite
Oct 07
San Diego, United States
84% AI deal score
$989
$727
Save $262
From ORD
Elite
Sep 15
San Diego, United States
84% AI deal score
$953
$727
Save $226
From ORD
Elite
Sep 16
San Diego, United States
84% AI deal score
$968
$727
Save $241
From ORD
Elite
Aug 27
San Diego, United States
84% AI deal score
$1,224
$739
Save $485
From ORD
Elite
Nov 21
San Diego, United States
83% AI deal score
$1,098
$796
Save $302
From ORD
Elite
Sep 05
San Diego, United States
83% AI deal score
$911
$727
Save $184
From ORD
Elite
Sep 26
San Diego, United States
83% AI deal score
$949
$727
Save $222
From ORD
Elite
Sep 30
San Diego, United States
83% AI deal score
$951
$727
Save $224
From ORD
Elite
Sep 29
San Diego, United States
83% AI deal score
$951
$727
Save $224
From ORD
Elite
Oct 23
San Diego, United States
83% AI deal score
$1,064
$724
Save $340
From ORD
Elite
Oct 06
San Diego, United States
83% AI deal score
$1,121
$729
Save $392
From ORD
Elite
Aug 20
San Diego, United States
83% AI deal score
$1,195
$729
Save $466
From ORD
Elite
Aug 17
San Diego, United States
83% AI deal score
$1,164
$738
Save $426
From ORD
Elite
Oct 09
San Diego, United States
83% AI deal score
$1,121
$739
Save $382
From ORD
Elite
Oct 23
San Diego, United States
83% AI deal score
$1,111
$739
Save $372
From ORD
Elite
Aug 27
San Diego, United States
83% AI deal score
$1,197
$739
Save $458
From ORD
Elite
Sep 02
San Diego, United States
82% AI deal score
$908
$727
Save $181
From ORD
Elite
Sep 01
San Diego, United States
82% AI deal score
$908
$727
Save $181
From ORD
Elite
Oct 22
San Diego, United States
82% AI deal score
$1,058
$729
Save $329
From ORD
Elite
Oct 16
San Diego, United States
82% AI deal score
$1,072
$739
Save $333
From ORD
Elite
Oct 22
San Diego, United States
82% AI deal score
$1,067
$739
Save $328
From ORD
Elite
Dec 01
San Diego, United States
81% AI deal score
$1,139
$864
Save $275
From ORD
Elite
Sep 22
San Diego, United States
81% AI deal score
$989
$709
Save $280
From ORD
Elite
Sep 05
San Diego, United States
81% AI deal score
$1,014
$709
Save $305
From ORD
Elite
Sep 11
San Diego, United States
81% AI deal score
$1,057
$739
Save $318
From ORD
Elite
Sep 18
San Diego, United States
81% AI deal score
$1,050
$739
Save $311
From ORD
Elite
Sep 30
San Diego, United States
81% AI deal score
$1,014
$739
Save $275
From ORD
Elite
Sep 17
San Diego, United States
81% AI deal score
$1,023
$739
Save $284
From ORD
Elite
Sep 17
San Diego, United States
81% AI deal score
$1,039
$739
Save $300
From ORD
Elite
Sep 24
San Diego, United States
81% AI deal score
$1,015
$739
Save $276
From ORD
Elite
Sep 17
San Diego, United States
81% AI deal score
$1,013
$739
Save $274
From ORD
Elite
Nov 10
San Diego, United States
80% AI deal score
$900
$709
Save $191
From ORD
Elite
Nov 06
San Diego, United States
76% AI deal score
$940
$739
Save $201
From ORD
Elite
Sep 09
San Diego, United States
76% AI deal score
$985
$739
Save $246
From ORD
Elite
Sep 03
San Diego, United States
76% AI deal score
$1,013
$739
Save $274
From ORD
Elite
Sep 14
San Diego, United States
76% AI deal score
$990
$739
Save $251
From ORD
Elite
Sep 17
San Diego, United States
76% AI deal score
$995
$739
Save $256
From ORD
Elite
Nov 16
San Diego, United States
70% AI deal score
$1,110
$1,095
Save $15
From ORD
Elite
Sep 02
San Diego, United States
68% AI deal score
$1,075
From ORD
Elite
Dec 07
San Diego, United States
66% AI deal score
$1,253
From ORD
Elite
Oct 26
San Diego, United States
49% AI deal score
$1,251
From ORD
Elite
Nov 21
San Diego, United States
49% AI deal score
$1,257
From ORD
Elite
Sep 02
San Diego, United States
48% AI deal score
$1,432
From ORD
Elite
Nov 13
San Diego, United States
47% AI deal score
$1,517
From ORD
Elite
Dec 01
San Diego, United States
47% AI deal score
$1,635
From ORD
Elite
Nov 19
San Diego, United States
46% AI deal score
$1,615
From ORD
Elite
Nov 20
San Diego, United States
46% AI deal score
$1,615
From ORD
Elite
Nov 12
San Diego, United States
46% AI deal score
$1,635
From ORD
Elite
Oct 28
San Diego, United States
46% AI deal score
$1,635