$110+ Cheap flights from San Diego (SAN) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — CHI
May 17 — May 241
Round-trip
1 adult, Economy
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Find cheap flights from San Diego to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from San Diego to Chicago are usually found in February or September, booked 44 days in advance, depart on a Friday or Thursday and return on a Saturday
Cheap flight deals from San Diego to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from San Diego to ChicagoExplore the most affordable flight options available from San Diego to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
Explore the most affordable flight options available from San Diego to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 17, 2026.
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:25 am
SAN
- ORD
1 stop12h 07m
Multiple Airlines
Sat 5/98:50 am
ORD
- SAN
Nonstop4h 40m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:25 am
SAN
- ORD
1 stop27h 15m
Frontier
Sat 5/239:37 pm
ORD
- SAN
1 stop13h 05m
Frontier
Deal found 4/12![Frontier logo]()
$215
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:12 pm
SAN
- ORD
1 stop13h 56m
Frontier
Tue 5/59:37 pm
ORD
- SAN
1 stop28h 13m
Frontier
Deal found 4/13![Frontier logo]()
$217
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 5/96:15 am
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 4/12![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:49 pm
SAN
- ORD
1 stop7h 19m
Frontier
Mon 5/44:58 pm
ORD
- SAN
2 stops56h 52m
Frontier
Deal found 4/12![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:25 am
SAN
- ORD
2 stops31h 37m
Frontier
Fri 5/89:37 pm
ORD
- SAN
1 stop28h 13m
Frontier
Deal found 4/12![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:25 am
SAN
- ORD
1 stop27h 15m
Multiple Airlines
Thu 5/76:15 am
ORD
- SAN
1 stop14h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$220
This CheapOair deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:25 am
SAN
- ORD
1 stop12h 07m
Frontier
Tue 5/199:37 pm
ORD
- SAN
1 stop28h 13m
Frontier
Deal found 4/12![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:25 am
SAN
- ORD
2 stops25h 29m
Multiple Airlines
Wed 6/107:12 am
ORD
- SAN
1 stop15h 46m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$222
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:53 am
SAN
- MDW
1 stop8h 16m
Delta
Tue 5/199:22 am
MDW
- SAN
1 stop6h 58m
Delta
Deal found 4/15![Delta logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:25 am
SAN
- ORD
1 stop12h 07m
Frontier
Sat 5/169:37 pm
ORD
- SAN
1 stop13h 05m
Frontier
Deal found 4/13![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:25 am
SAN
- MDW
1 stop29h 47m
Frontier
Tue 5/196:00 am
MDW
- SAN
2 stops17h 04m
Frontier
Deal found 4/14![Frontier logo]()
$223
Best flights from San Diego to ChicagoDiscover carefully curated flight deals from San Diego to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
Discover carefully curated flight deals from San Diego to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 17, 2026.
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Wed 6/32:15 pm
MDW
- SAN
1 stop6h 00m
Southwest
Deal found 4/12![Southwest logo]()
$247
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/316:15 am
SAN
- ORD
1 stop9h 50m
Delta
Sun 6/76:30 am
ORD
- SAN
1 stop6h 13m
Delta
Deal found 4/16![Delta logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:38 pm
SAN
- RFD
1 stop28h 07m
Multiple Airlines
Mon 5/118:35 pm
RFD
- SAN
1 stop20h 56m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$260
This Alaska Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:44 pm
SAN
- ORD
Nonstop4h 11m
Alaska Airlines
Mon 5/187:59 pm
ORD
- SAN
Nonstop4h 37m
Alaska Airlines
Deal found 4/16![Alaska Airlines logo]()
$267
This United Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:40 am
SAN
- ORD
Nonstop4h 29m
United Airlines
Sat 5/305:00 am
ORD
- SAN
1 stop6h 02m
United Airlines
Deal found 4/15![United Airlines logo]()
$277
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/272:40 pm
SAN
- ORD
1 stop7h 15m
Southwest
Wed 6/310:30 am
ORD
- SAN
2 stops9h 15m
Southwest
Deal found 4/12![Southwest logo]()
$272
This Alaska Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:34 pm
SAN
- ORD
Nonstop4h 16m
Alaska Airlines
Mon 6/87:59 pm
ORD
- SAN
Nonstop4h 37m
Alaska Airlines
Deal found 4/12![Alaska Airlines logo]()
$292
This Alaska Airlines deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:44 pm
SAN
- ORD
Nonstop4h 11m
Alaska Airlines
Sun 5/319:00 am
ORD
- SAN
Nonstop4h 37m
Alaska Airlines
Deal found 4/12![Alaska Airlines logo]()
$297
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2710:10 pm
SAN
- MDW
1 stop8h 37m
Delta
Thu 4/301:24 pm
MDW
- SAN
1 stop6h 55m
Delta
Deal found 4/15![Delta logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/234:17 pm
SAN
- RFD
1 stop26h 06m
Multiple Airlines
Sun 7/261:14 pm
RFD
- SAN
1 stop9h 44m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1710:40 pm
SAN
- ORD
Nonstop4h 11m
United Airlines
Sun 7/197:05 am
ORD
- SAN
Nonstop4h 28m
United Airlines
Deal found 4/14![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:50 am
SAN
- MDW
2 stops7h 05m
Southwest
Sat 5/163:05 pm
MDW
- SAN
1 stop7h 20m
Southwest
Deal found 4/13![Southwest logo]()
$317
This eDestinos deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:53 pm
SAN
- RFD
1 stop12h 31m
Multiple Airlines
Sun 7/261:14 pm
RFD
- SAN
1 stop9h 44m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/510:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Sun 6/76:05 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 4/16![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/3010:17 pm
SAN
- MDW
1 stop8h 57m
Delta
Thu 7/29:17 am
MDW
- SAN
1 stop6h 55m
Delta
Deal found 4/15![Delta logo]()
$355
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/124:17 pm
SAN
- RFD
1 stop17h 57m
Multiple Airlines
Sun 6/141:13 pm
RFD
- SAN
1 stop8h 21m
Multiple Airlines
Deal found 4/12![Multiple Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1610:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Mon 5/188:45 pm
MDW
- SAN
Nonstop4h 25m
Southwest
Deal found 4/16![Southwest logo]()
$317
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/13:00 pm
SAN
- ORD
1 stop6h 18m
Delta
Mon 7/65:57 pm
ORD
- SAN
1 stop7h 38m
Delta
Deal found 4/15![Delta logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/194:17 pm
SAN
- RFD
1 stop25h 48m
Multiple Airlines
Fri 5/229:13 pm
RFD
- SAN
1 stop20h 18m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/110:30 pm
SAN
- MDW
1 stop8h 12m
Delta
Mon 10/59:30 am
MDW
- SAN
1 stop6h 38m
Delta
Deal found 4/15![Delta logo]()
$361
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/2310:07 pm
SAN
- RFD
1 stop12h 14m
Multiple Airlines
Thu 5/281:11 pm
RFD
- SAN
1 stop10h 01m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1210:40 pm
SAN
- MDW
Nonstop4h 00m
Southwest
Sun 6/145:15 am
MDW
- SAN
1 stop5h 45m
Southwest
Deal found 4/12![Southwest logo]()
$357
This Delta deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/93:00 pm
SAN
- ORD
1 stop6h 18m
Delta
Sun 7/196:30 am
ORD
- SAN
1 stop8h 54m
Delta
Deal found 4/12![Delta logo]()
$367
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/305:30 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sun 8/25:15 am
MDW
- SAN
1 stop5h 45m
Southwest
Deal found 4/12![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/304:17 pm
SAN
- RFD
1 stop26h 06m
Multiple Airlines
Sun 8/21:14 pm
RFD
- SAN
1 stop9h 44m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$358
This Southwest deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/310:40 pm
SAN
- MDW
Nonstop3h 50m
Southwest
Mon 9/75:30 am
MDW
- SAN
1 stop6h 25m
Southwest
Deal found 4/13![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/214:17 pm
SAN
- RFD
1 stop25h 42m
Multiple Airlines
Mon 8/39:13 pm
RFD
- SAN
1 stop20h 19m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$380
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1311:30 am
SAN
- MDW
1 stop7h 25m
Southwest
Wed 6/246:00 am
MDW
- SAN
Nonstop4h 10m
Southwest
Deal found 4/12![Southwest logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/254:17 pm
SAN
- RFD
1 stop26h 58m
Multiple Airlines
Mon 6/2910:05 pm
RFD
- SAN
1 stop19h 27m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$386
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/910:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sun 5/179:10 pm
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 4/16![Southwest logo]()
$362
Last-minute flights from San Diego to ChicagoDiscover last-minute flight deals from San Diego to Chicago. Data last updated April 17, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Chicago. Data last updated April 17, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:12 pm
SAN
- ORD
1 stop13h 56m
Frontier
Tue 5/59:37 pm
ORD
- SAN
1 stop28h 13m
Frontier
Deal found 4/13![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/18:49 pm
SAN
- ORD
1 stop7h 19m
Frontier
Mon 5/44:58 pm
ORD
- SAN
2 stops56h 52m
Frontier
Deal found 4/12![Frontier logo]()
$218
This Southwest deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/210:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Sat 5/96:15 am
MDW
- SAN
Nonstop4h 15m
Southwest
Deal found 4/12![Southwest logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/36:25 am
SAN
- ORD
2 stops31h 37m
Frontier
Fri 5/89:37 pm
ORD
- SAN
1 stop28h 13m
Frontier
Deal found 4/12![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/56:25 am
SAN
- ORD
1 stop27h 15m
Multiple Airlines
Thu 5/76:15 am
ORD
- SAN
1 stop14h 10m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$220
This Expedia deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:25 am
SAN
- ORD
1 stop12h 07m
Multiple Airlines
Sat 5/98:50 am
ORD
- SAN
Nonstop4h 40m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$214
This Delta deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:00 am
SAN
- ORD
1 stop10h 24m
Delta
Sat 5/166:24 am
ORD
- SAN
1 stop8h 53m
Delta
Deal found 4/14![Delta logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:25 am
SAN
- ORD
1 stop12h 07m
Frontier
Sat 5/169:37 pm
ORD
- SAN
1 stop13h 05m
Frontier
Deal found 4/13![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:25 am
SAN
- MDW
1 stop29h 47m
Frontier
Tue 5/196:00 am
MDW
- SAN
2 stops17h 04m
Frontier
Deal found 4/14![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/136:25 am
SAN
- ORD
1 stop12h 07m
Frontier
Tue 5/199:37 pm
ORD
- SAN
1 stop28h 13m
Frontier
Deal found 4/12![Frontier logo]()
$221
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:53 am
SAN
- MDW
1 stop8h 16m
Delta
Tue 5/199:22 am
MDW
- SAN
1 stop6h 58m
Delta
Deal found 4/15![Delta logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:25 am
SAN
- ORD
1 stop27h 15m
Frontier
Sat 5/239:37 pm
ORD
- SAN
1 stop13h 05m
Frontier
Deal found 4/12![Frontier logo]()
$215
One-way flights from San Diego to ChicagoSearch for one-way flight options from San Diego to Chicago. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
Search for one-way flight options from San Diego to Chicago. Find affordable one-way fares based on user searches. Data last updated April 17, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/96:25 am
SAN
- ORD
1 stop12h 07m
Frontier
Deal found 4/12![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:25 am
SAN
- ORD
1 stop12h 18m
Frontier
Deal found 4/12![Frontier logo]()
$111
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/99:53 pm
SAN
- ORD
1 stop29h 39m
Frontier
Deal found 4/12![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/199:59 pm
SAN
- ORD
2 stops23h 02m
Frontier
Deal found 4/14![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/119:37 am
SAN
- MDW
2 stops26h 35m
Frontier
Deal found 4/12![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:25 am
SAN
- ORD
1 stop27h 39m
Multiple Airlines
Deal found 4/13![Multiple Airlines logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 4/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:25 am
SAN
- MDW
1 stop29h 47m
Frontier
Deal found 4/11![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:38 pm
SAN
- ORD
2 stops15h 01m
Frontier
Deal found 4/13![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:00 pm
SAN
- ORD
2 stops35h 23m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/194:17 pm
SAN
- MDW
2 stops43h 55m
Frontier
Deal found 4/14![Frontier logo]()
$118
This Alaska Airlines deal was found by Cheapflights users on 4/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/137:00 am
SAN
- ORD
Nonstop4h 14m
Alaska Airlines
Deal found 4/13![Alaska Airlines logo]()
$119
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/1310:40 pm
SAN
- MDW
Nonstop3h 55m
Southwest
Deal found 4/16![Southwest logo]()
$119
Find flight deals from San Diego to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated April 17, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $214 (Expedia) |
One-way from | $110 (Kiwi.com) |
Popular in | April |
Cheapest in | February |
Average price | $310 |
Good round-trip deal | $339 or less |
Good one-way deal | $209 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
Use the filters below to find and compare flights from San Diego to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Wed 5/27
10:40 pm-4:35 am
Nonstop3h 55m
Chicago Midway
Wed 6/3
2:15 pm-6:15 pm
1 stop6h 00m
$247
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sun 5/31
6:15 am-6:05 pm
1 stop9h 50m
Chicago O'Hare Intl
Sun 6/7
6:30 am-10:43 am
1 stop6h 13m
$252
San DiegoChicago
SAN - RFD
SANRFD
San Diego
Thu 5/7
1:38 pm-7:45 pm
1 stop28h 07m
Chicago Greater Rockford
Mon 5/11
8:35 pm-3:31 pm
1 stop20h 56m
$260
San DiegoChicago
SAN - ORD
SANORD
San Diego
Sat 5/16
5:44 pm-11:55 pm
Nonstop4h 11m
Chicago O'Hare Intl
Mon 5/18
7:59 pm-10:36 pm
Nonstop4h 37m
$267
San DiegoChicago
SAN - ORD
SANORD
San Diego
Wed 5/27
2:40 pm-11:55 pm
1 stop7h 15m
Chicago O'Hare Intl
Wed 6/3
10:30 am-5:45 pm
2 stops9h 15m
$272
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 5/28
6:40 am-1:09 pm
Nonstop4h 29m
Chicago O'Hare Intl
Sat 5/30
5:00 am-9:02 am
1 stop6h 02m
$277
San DiegoChicago
SAN - ORD
SANORD
San Diego
Mon 6/8
12:34 pm-6:50 pm
Nonstop4h 16m
Chicago O'Hare Intl
Mon 6/8
7:59 pm-10:36 pm
Nonstop4h 37m
$292
San DiegoChicago
SAN - ORD
SANORD
San Diego
Thu 5/28
5:44 pm-11:55 pm
Nonstop4h 11m
Chicago O'Hare Intl
Sun 5/31
9:00 am-11:37 am
Nonstop4h 37m
$297
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Sat 5/9
8:50 am-5:55 pm
2 stops7h 05m
Chicago Midway
Sat 5/16
3:05 pm-8:25 pm
1 stop7h 20m
$317
Quickest round-trip
San DiegoChicago
SAN - MDW
SANMDW
San Diego
Fri 6/5
10:40 pm-4:40 am
Nonstop4h 00m
Chicago Midway
Sun 6/7
6:05 am-8:15 am
Nonstop4h 10m
$317
Showing 1-10 of 60 resultsSorted by cheapest first
Compare providers for flights from San Diego to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from San Diego to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*2 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy- | Trust Score*1 star | |
| Price Accuracy- | Trust Score*1 star |
- Most accurate provider: When it comes to deals on San Diego-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on San Diego-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for San Diego-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from San Diego to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from San Diego with our price prediction graph.
SAN-CHI
SAN-ORD
SAN-MDW
SAN-RFD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from San Diego to Chicago
SAN-CHI
SAN-ORD
SAN-MDW
SAN-RFD
How far ahead should I book a flight from San Diego to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from San Diego to Chicago. Price data was last updated on April 10, 2026.
The price you pay for your flight from San Diego to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 44 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from San Diego to Chicago?
Currently, February is the cheapest month in which you can book a flight from San Diego to Chicago (average of $91). Flying from San Diego to Chicago in December is currently the most expensive (average of $583). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from SAN to CHI?
Find hourly flight availability from San Diego to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 17, 2026.
It’s optimal to fly from San Diego to Chicago in the afternoon. By choosing this option you can save up to 34% on the cost of your flight, compared to a flight in the morning.
What is the cheapest day to fly from San Diego to Chicago?
Use this chart to determine the cheapest time to fly round-trip from San Diego to Chicago. Price data was last updated on April 11, 2026.
Travelers seeking maximum savings on their San Diego to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from San Diego to Chicago
Explore weekly flight availability from San Diego to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 17, 2026.
The most flights from SAN to CHI are scheduled on a Friday (51 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (34 on average).
How much does it cost to fly round-trip from San Diego to Chicago?
How often are flights from San Diego to Chicago delayed?
About 10% of weekly flights between San Diego and Chicago have experienced delays in the past year, with the average delay time being 178 minutes.
What is the most punctual flight time for San Diego to Chicago flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Tuesday tends to have the lowest number of delays on this route, whereas Friday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on San Diego to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 7% of flights being delayed.
The best insider tips for San Diego to Chicago flights
AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your San Diego to Chicago trip
Our travel experts
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated April 17, 2026.
Get a feel of what it's like to fly with Southwest,Alaska Airlines, andUnited Airlines from San Diego to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Boarding
8.1
Comfort
8.0
Food
7.0
Entertainment
7.5
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Diego to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Hammond
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 17, 2026.
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San Diego and Chicago flights
Browse other San Diego and Chicago flight options. Last updated on April 17, 2026.
Other flights from San Diego
Browse through other flights departing from San Diego. Flights are based on user searches made on Cheapflights and were last updated on April 17, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 7 airlines flying from San Diego to Chicago
Discover the top 7 airlines that operate flights from San Diego to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$92 | Average$221 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$109 | Average$214 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$139 | Average$197 | FlexibilityNo cancel fee | On-time85% | |
| Cheapest$145 | Average$280 | FlexibilityNo cancel fee | On-time75% | |
| Cheapest$157 | Average$305 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$166 | Average$349 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$205 | Average$340 | FlexibilityNo cancel fee | On-time63% |