Cheap Flights from San Diego to Chicago
Browse current best options from San Diego. Become a member to unlock all deals and get alerts when new deals appear.
Deals from
San Diego
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
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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 San Diego to Chicago
Explore current cheapest deals departing from San Diego to Chicago
Round trip
Sort by: Cheapest
October 28 - November 17
SAN - Chicago
$258
$187
Round trip
November 4 - November 17
SAN - Chicago
$273
$187
Round trip
September 30 - October 20
SAN - Chicago
$221
$187
Round trip
October 14 - October 20
SAN - Chicago
$277
$189
Round trip
August 19 - August 25
SAN - Chicago
$249
$192
Round trip
November 11 - November 17
SAN - Chicago
$286
$192
Round trip
September 30 - October 21
SAN - Chicago
$221
$194
Round trip
August 21 - August 24
SAN - Chicago
$190
$208
Round trip
August 5 - August 11
SAN - Chicago
$179
$208
Round trip
August 10 - August 14
SAN - Chicago
$191
$208
Round trip
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Route Intelligence — 486,190 Searches this Week
Insights for flights from San Diego to Chicago
How much is a round trip from San Diego to Chicago
Regular price: $215 - $347
Prices are currently below the regular range.
The regular price range for flights from San Diego to Chicago is $215 to $347. The current lowest deal is $187 with Frontier Airlines, for travel from Oct 28-Nov 17.
now $187
Low $215
High $347
The cheapest time to fly from San Diego to Chicago
The cheapest month to fly from San Diego to Chicago is January, with a median price of $174. The most expensive month is August, with a median price of $613. Prices are generally lower from January to November.
January
Flights from $174
August
Flights from $613
Direct flights from San Diego to Chicago
Alaska Airlines, Inc.
Last-minute flights going from San Diego to Chicago
Wed, Jun 17
SAN - Chicago
San Diego (SAN) - Chicago (ORD)
Frontier Airlines
$380
$317
One-way
Thu, Jun 18
SAN - Chicago
San Diego (SAN) - Chicago (ORD)
Frontier Airlines
$339
$270
One-way
Thu, Jun 18
SAN - Chicago
San Diego (SAN) - Chicago (ORD)
Frontier Airlines
$373
$270
One-way
Thu, Jun 18
SAN - Chicago
San Diego (SAN) - Chicago (ORD)
Frontier Airlines
$376
$316
One-way
Fri, Jun 19
SAN - Chicago
San Diego (SAN) - Chicago (ORD)
Frontier Airlines
$377
$290
One-way
Sat, Jun 20
SAN - Chicago
San Diego (SAN) - Chicago (ORD)
Frontier Airlines
$377
$270
One-way
Biggest price drops on these dates for flights from San Diego to Chicago
Jul 13 - Jul 18
$640 → $360
44%
Jun 21 - Jun 22
$468 → $334
29%
Jun 21 - Jun 28
$396 → $270
32%
Jun 20 - Jun 22
$377 → $270
28%
Popular Airports to fly from San Diego to Chicago
San Diego - Chicago route insights
💸 Price insights
Recent fares are below the typical level
Recent fares from San Diego to Chicago are below the typical level, starting at $187.
📅 Best time to fly
Fly in January, September, or November for the best prices
Historically, January, September, and November offer the lowest median prices at $174.
⏱️ Flight duration
Flights typically take 10h 34m
The median flight duration from San Diego to Chicago is 10 hours and 34 minutes.
✈️ Airlines & availability
Frequent deals, mixed direct flight availability
Deals are frequent, with a mixed share of direct flights available on this route.
🏆 Airline highlight
Alaska Airlines offers direct flights
Alaska Airlines is one of the carriers that offers direct flights for this route.
🎯 Booking tip
Consider booking in January, September, or November
Historically, the cheapest months to fly are January, September, and November.
San Diego main airports to depart from
San Diego International (SAN)
San Diego International is often a convenient option for flights from San Diego to Chicago.
📍 ~5 km from San Diego (reachable by car)
💸 Flights from ~$187
McClellan–Palomar (CLD)
McClellan–Palomar provides an alternative departure point for your journey to Chicago from San Diego.
📍 ~45 km from San Diego (reachable by car)
💸 Flights from ~$348
Chicago main airports to arrive at
O Hare International (ORD)
O'Hare International Airport is a good option for flights from San Diego to Chicago.
📍 ~20 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$187
Chicago Midway International (MDW)
Chicago Midway International Airport offers another convenient arrival point for flights from San Diego.
📍 ~15 km from Chicago city center (reachable by car, train, and bus).
💸 Flights from ~$227
Chicago Rockford International (RFD)
Chicago Rockford International Airport serves as an alternative arrival airport for flights to the Chicago area.
📍 ~120 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 and diverse cabin class availability.
📍 ~135 km from Chicago (reachable by rail)
💸 Flights from ~$241
South Bend International (SBN)
South Bend International is geographically the closest alternative to the Chicago area, offering easier security and parking.
📍 ~120 km from Chicago (reachable by rail)
💸 Flights from ~$249
Gerald R. Ford International (GRR)
Gerald R. Ford International is a major regional hub with high popularity, reliability, and a wide range of cabin classes.
📍 ~200 km from Chicago (reachable by car)
💸 Flights from ~$208
Dane County Regional (MSN)
Dane County Regional is a reliable regional airport with consistent service levels and less congestion.
📍 ~205 km from Chicago (reachable by car)
💸 Flights from ~$250
Fort Wayne International (FWA)
Fort Wayne International provides stable regional service and multiple cabin class options for travelers in southeastern Chicago suburbs.
📍 ~230 km from Chicago (reachable by car)
💸 Flights from ~$237
Business & First Class Flight Deals to Chicago
Discover luxury on the budget with premium cabin class on flights from San Diego to Chicago.
Elite
Best Elite deals to Chicago
Exclusive daily First Class, Business Class, and Premium Economy flight deals, refreshed every 24 hours.
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,306
$727
Save $579
From SAN
Elite
Sep 03
Chicago, United States
90% AI deal score
$1,263
$727
Save $536
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,315
$727
Save $588
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,287
$727
Save $560
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,270
$727
Save $543
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,253
$727
Save $526
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,282
$727
Save $555
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,279
$727
Save $552
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,308
$727
Save $581
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,247
$727
Save $520
From SAN
Elite
Sep 05
Chicago, United States
90% AI deal score
$1,262
$727
Save $535
From SAN
Elite
Aug 25
Chicago, United States
90% AI deal score
$1,286
$727
Save $559
From SAN
Elite
Aug 25
Chicago, United States
90% AI deal score
$1,315
$727
Save $588
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,283
$727
Save $556
From SAN
Elite
Aug 25
Chicago, United States
90% AI deal score
$1,315
$727
Save $588
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,283
$727
Save $556
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,298
$727
Save $571
From SAN
Elite
Aug 25
Chicago, United States
90% AI deal score
$1,305
$727
Save $578
From SAN
Elite
Aug 21
Chicago, United States
90% AI deal score
$1,294
$727
Save $567
From SAN
Elite
Aug 29
Chicago, United States
90% AI deal score
$1,305
$727
Save $578
From SAN
Elite
Aug 29
Chicago, United States
90% AI deal score
$1,288
$727
Save $561
From SAN
Elite
Oct 22
Chicago, United States
90% AI deal score
$1,235
$727
Save $508
From SAN
Elite
Oct 20
Chicago, United States
90% AI deal score
$1,317
$727
Save $590
From SAN
Elite
Oct 24
Chicago, United States
90% AI deal score
$1,324
$727
Save $597
From SAN
Elite
Oct 22
Chicago, United States
90% AI deal score
$1,319
$727
Save $592
From SAN
Elite
Oct 21
Chicago, United States
90% AI deal score
$1,342
$727
Save $615
From SAN
Elite
Oct 25
Chicago, United States
90% AI deal score
$1,359
$727
Save $632
From SAN
Elite
Aug 24
Chicago, United States
90% AI deal score
$1,305
$747
Save $558
From SAN
Elite
Aug 20
Chicago, United States
90% AI deal score
$1,306
$747
Save $559
From SAN
Elite
Aug 24
Chicago, United States
90% AI deal score
$1,301
$767
Save $534
From SAN
Elite
Aug 24
Chicago, United States
89% AI deal score
$1,358
$727
Save $631
From SAN
Elite
Aug 30
Chicago, United States
89% AI deal score
$1,355
$727
Save $628
From SAN
Elite
Aug 25
Chicago, United States
89% AI deal score
$1,374
$727
Save $647
From SAN
Elite
Oct 16
Chicago, United States
89% AI deal score
$1,361
$727
Save $634
From SAN
Elite
Sep 06
Chicago, United States
89% AI deal score
$1,258
$727
Save $531
From SAN
Elite
Sep 03
Chicago, United States
89% AI deal score
$1,241
$727
Save $514
From SAN
Elite
Aug 20
Chicago, United States
89% AI deal score
$1,246
$727
Save $519
From SAN
Elite
Aug 20
Chicago, United States
88% AI deal score
$1,257
$727
Save $530
From SAN
Elite
Aug 20
Chicago, United States
88% AI deal score
$1,242
$727
Save $515
From SAN
Elite
Aug 24
Chicago, United States
88% AI deal score
$1,250
$727
Save $523
From SAN
Elite
Aug 25
Chicago, United States
88% AI deal score
$1,260
$727
Save $533
From SAN
Elite
Aug 24
Chicago, United States
88% AI deal score
$1,200
$727
Save $473
From SAN
Elite
Aug 20
Chicago, United States
88% AI deal score
$1,202
$727
Save $475
From SAN
Elite
Aug 20
Chicago, United States
88% AI deal score
$1,251
$727
Save $524
From SAN
Elite
Aug 30
Chicago, United States
88% AI deal score
$1,219
$727
Save $492
From SAN
Elite
Aug 24
Chicago, United States
88% AI deal score
$1,267
$727
Save $540
From SAN
Elite
Oct 16
Chicago, United States
88% AI deal score
$1,262
$727
Save $535
From SAN
Elite
Oct 16
Chicago, United States
88% AI deal score
$1,337
$727
Save $610
From SAN
Elite
Aug 29
Chicago, United States
88% AI deal score
$1,222
$727
Save $495
From SAN
Elite
Sep 05
Chicago, United States
88% AI deal score
$1,349
$727
Save $622
From SAN
Elite
Oct 16
Chicago, United States
88% AI deal score
$1,261
$727
Save $534
From SAN
Elite
Oct 22
Chicago, United States
88% AI deal score
$1,349
$727
Save $622
From SAN
Elite
Aug 20
Chicago, United States
88% AI deal score
$1,252
$747
Save $505
From SAN
Elite
Aug 24
Chicago, United States
88% AI deal score
$1,297
$747
Save $550
From SAN
Elite
Sep 06
Chicago, United States
88% AI deal score
$1,142
$727
Save $415
From SAN
Elite
Oct 22
Chicago, United States
87% AI deal score
$1,268
$727
Save $541
From SAN
Elite
Oct 16
Chicago, United States
87% AI deal score
$1,264
$727
Save $537
From SAN
Elite
Sep 09
Chicago, United States
87% AI deal score
$1,244
$727
Save $517
From SAN
Elite
Sep 06
Chicago, United States
87% AI deal score
$1,101
$727
Save $374
From SAN
Elite
Sep 03
Chicago, United States
87% AI deal score
$1,098
$727
Save $371
From SAN
Elite
Oct 01
Chicago, United States
87% AI deal score
$1,156
$742
Save $414
From SAN
Elite
Oct 01
Chicago, United States
87% AI deal score
$1,155
$742
Save $413
From SAN
Elite
Aug 21
Chicago, United States
87% AI deal score
$1,298
$857
Save $441
From SAN
Elite
Jun 23
Chicago, United States
87% AI deal score
$1,483
$945
Save $538
From SAN
Elite
Dec 10
Chicago, United States
86% AI deal score
$1,244
$785
Save $459
From SAN
Elite
Dec 10
Chicago, United States
86% AI deal score
$1,232
$785
Save $447
From SAN
Elite
Aug 20
Chicago, United States
86% AI deal score
$1,456
$727
Save $729
From SAN
Elite
Aug 20
Chicago, United States
86% AI deal score
$1,439
$727
Save $712
From SAN
Elite
Aug 20
Chicago, United States
86% AI deal score
$1,472
$727
Save $745
From SAN
Elite
Aug 20
Chicago, United States
86% AI deal score
$1,390
$727
Save $663
From SAN
Elite
Aug 21
Chicago, United States
86% AI deal score
$1,382
$727
Save $655
From SAN
Elite
Aug 25
Chicago, United States
86% AI deal score
$1,451
$727
Save $724
From SAN
Elite
Aug 21
Chicago, United States
86% AI deal score
$1,461
$727
Save $734
From SAN
Elite
Aug 21
Chicago, United States
86% AI deal score
$1,431
$727
Save $704
From SAN
Elite
Aug 21
Chicago, United States
86% AI deal score
$1,464
$727
Save $737
From SAN
Elite
Aug 25
Chicago, United States
86% AI deal score
$1,386
$727
Save $659
From SAN
Elite
Aug 21
Chicago, United States
86% AI deal score
$1,448
$727
Save $721
From SAN
Elite
Aug 29
Chicago, United States
86% AI deal score
$1,372
$727
Save $645
From SAN
Elite
Aug 29
Chicago, United States
86% AI deal score
$1,448
$727
Save $721
From SAN
Elite
Aug 29
Chicago, United States
86% AI deal score
$1,437
$727
Save $710
From SAN
Elite
Aug 20
Chicago, United States
86% AI deal score
$1,469
$727
Save $742
From SAN
Elite
Aug 26
Chicago, United States
86% AI deal score
$1,435
$731
Save $704
From SAN
Elite
Jun 19
Chicago, United States
86% AI deal score
$2,291
$1,096
Save $1,195
From SAN
Elite
Nov 22
Chicago, United States
85% AI deal score
$1,193
$799
Save $394
From SAN
Elite
Dec 10
Chicago, United States
85% AI deal score
$1,234
$801
Save $433
From SAN
Elite
Jun 23
Chicago, United States
85% AI deal score
$1,579
$943
Save $636
From SAN
Elite
Jun 22
Chicago, United States
85% AI deal score
$1,581
$947
Save $634
From SAN
Elite
Jul 20
Chicago, United States
85% AI deal score
$1,322
$785
Save $537
From SAN
Elite
Aug 24
Chicago, United States
84% AI deal score
$1,171
$729
Save $442
From SAN
Elite
Dec 01
Chicago, United States
83% AI deal score
$1,211
$864
Save $347
From SAN
Elite
Dec 01
Chicago, United States
83% AI deal score
$1,205
$864
Save $341
From SAN
Elite
Dec 01
Chicago, United States
83% AI deal score
$1,205
$864
Save $341
From SAN
Elite
Dec 01
Chicago, United States
83% AI deal score
$1,197
$864
Save $333
From SAN
Elite
Aug 22
Chicago, United States
83% AI deal score
$1,097
$729
Save $368
From SAN
Elite
Aug 22
Chicago, United States
83% AI deal score
$1,104
$739
Save $365
From SAN
Elite
Dec 01
Chicago, United States
82% AI deal score
$1,197
$880
Save $317
From SAN
Elite
Jul 22
Chicago, United States
82% AI deal score
$1,263
$864
Save $399
From SAN
Elite
Jun 19
Chicago, United States
82% AI deal score
$2,341
$1,041
Save $1,300
From SAN
Elite
Jul 09
Chicago, United States
82% AI deal score
$1,883
$1,107
Save $776
From SAN
Elite
Aug 28
Chicago, United States
82% AI deal score
$1,459
$1,117
Save $342