Alaska Airlines San Diego to Chicago Flights

Return flight: Chicago – San Diego

Cheapflightsplus.com will find cheap Alaska Airlines flights from San Diego to Chicago. Compare airline ticket prices and book air tickets starting from $572 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of Alaska Airlines, arrivals and departure details below.

Find Cheap Airfare San Diego (CA) — Chicago (IL) by Alaska Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in may: one-way - $572, two-way – $981.
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Below is a detailed 2024 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:46 pm — 5:01 am
+1 day
10:46 pm — 5:01 am AS4093 Alaska Airlines
San Diego — Chicago
4h 15m
Find flight
from$973
11:31 am — 5:45 pm
11:31 am — 5:45 pm AS6057 Alaska Airlines
San Diego — Chicago
4h 14m
Find flight
from$973
6:15 am — 12:31 pm
6:15 am — 12:31 pm AS6050 Alaska Airlines
San Diego — Chicago
4h 16m
Find flight
from$1343
12:30 pm — 1:11 am
+1 day
12:30 pm — 2:05 pm AS3331 Alaska Airlines
San Diego — San Francisco
4h 57m stop
6:57 pm — 1:11 am UA468 United Airlines
San Francisco — Chicago
10h 41m
including layover
Find flight
from$904
12:30 pm — 11:01 pm
12:30 pm — 2:05 pm AS3331 Alaska Airlines
San Diego — San Francisco
2h 44m stop
4:44 pm — 11:01 pm UA729 United Airlines
San Francisco — Chicago
8h 31m
including layover
Find flight
from$904
1:50 pm — 11:55 pm
1:45 pm — 4:46 pm AS1097 Alaska Airlines
San Diego — Seattle
1h 16m stop
6:00 pm — 11:53 pm AS538 Alaska Airlines
Seattle — Chicago
8h 5m
including layover
Find flight
from$866
2:15 pm — 6:17 am
+1 day
2:15 pm — 3:45 pm AS3352 Alaska Airlines
San Diego — San Francisco
8h 14m stop
11:59 pm — 6:17 am AA2828 American Airlines
San Francisco — Chicago
14h 2m
including layover
Find flight
from$789
2:15 pm — 1:11 am
+1 day
2:15 pm — 3:50 pm AS3352 Alaska Airlines
San Diego — San Francisco
3h 12m stop
6:57 pm — 1:11 am UA468 United Airlines
San Francisco — Chicago
8h 56m
including layover
Find flight
from$795
3:45 pm — 5:00 am
+1 day
3:45 pm — 6:40 pm AS1295 Alaska Airlines
San Diego — Seattle
4h 28m stop
11:08 pm — 5:00 am AS328 Alaska Airlines
Seattle — Chicago
11h 15m
including layover
Find flight
from$1229
4:55 pm — 6:17 am
+1 day
4:55 pm — 6:24 pm AS3482 Alaska Airlines
San Diego — San Francisco
5h 35m stop
11:59 pm — 6:17 am AA2828 American Airlines
San Francisco — Chicago
11h 22m
including layover
Find flight
from$789
5:55 pm — 5:53 am
+1 day
5:55 pm — 8:47 pm AS1135 Alaska Airlines
San Diego — Seattle
3h 7m stop
11:54 pm — 5:53 am UA747 United Airlines
Seattle — Chicago
9h 58m
including layover
Find flight
from$1977
5:55 pm — 6:41 am
+1 day
5:55 pm — 8:47 pm AS1135 Alaska Airlines
San Diego — Seattle
3h 58m stop
0:45 am — 6:41 am UA523 United Airlines
Seattle — Chicago
10h 46m
including layover
Find flight
from$1977
6:15 am — 6:50 pm
6:15 am — 7:51 am AS3451 Alaska Airlines
San Diego — San Francisco
4h 56m stop
12:47 pm — 6:50 pm F92482 Frontier Airlines
San Francisco — Chicago
10h 35m
including layover
Find flight
from$609
6:15 am — 6:58 pm
6:15 am — 7:56 am AS3451 Alaska Airlines
San Diego — San Francisco
4h 44m stop
12:35 pm — 7:01 pm AS332 Alaska Airlines
San Francisco — Chicago
10h 43m
including layover
Find flight
from$665
7:15 am — 6:50 pm
7:15 am — 8:56 am AS3455 Alaska Airlines
San Diego — San Francisco
3h 56m stop
8:36 am — 2:39 pm F92482 Frontier Airlines
San Francisco — Chicago
9h 35m
including layover
Find flight
from$572
7:15 am — 6:58 pm
7:15 am — 8:56 am AS3455 Alaska Airlines
San Diego — San Francisco
3h 44m stop
12:35 pm — 7:01 pm AS332 Alaska Airlines
San Francisco — Chicago
9h 43m
including layover
Find flight
from$646
8:00 am — 8:10 pm
8:00 am — 11:00 am AS1154 Alaska Airlines
San Diego — Seattle
3h 10m stop
2:15 pm — 8:20 pm AS362 Alaska Airlines
Seattle — Chicago
10h 10m
including layover
Find flight
from$1053
8:00 am — 6:20 pm
8:00 am — 11:00 am AS1154 Alaska Airlines
San Diego — Seattle
1h 20m stop
12:15 pm — 6:20 pm AS410 Alaska Airlines
Seattle — Chicago
8h 20m
including layover
Find flight
from$1053
9:50 am — 8:10 pm
9:47 am — 12:45 pm AS1167 Alaska Airlines
San Diego — Seattle
1h 27m stop
2:15 pm — 8:20 pm AS362 Alaska Airlines
Seattle — Chicago
8h 20m
including layover
Find flight
from$1343
10:20 am — 0:59 am
+1 day
10:20 am — 11:34 am AS3335 Alaska Airlines
San Diego — Fresno
5h 51m stop
5:25 pm — 8:03 pm DL4065 Delta Air Lines Inc.
Fresno — Salt Lake City
52m stop
8:55 pm — 0:59 am DL1712 Delta Air Lines Inc.
Salt Lake City — Chicago
12h 39m
including layover
Find flight
from$886
11:50 am — 6:24 am
+1 day
11:50 am — 2:50 pm AS1259 Alaska Airlines
San Diego — Seattle
1h 20m stop
4:10 pm — 11:59 pm AS492 Alaska Airlines
Seattle — Atlanta
5h 11m stop
5:10 am — 6:24 am F91574 Frontier Airlines
Atlanta — Chicago
16h 34m
including layover
Find flight
from$1634
1:57 pm — 0:59 am
+1 day
1:57 pm — 3:10 pm AS3481 Alaska Airlines
San Diego — Fresno
2h 15m stop
5:25 pm — 8:03 pm DL4065 Delta Air Lines Inc.
Fresno — Salt Lake City
52m stop
8:55 pm — 0:59 am DL1712 Delta Air Lines Inc.
Salt Lake City — Chicago
9h 2m
including layover
Find flight
from$886
3:39 pm — 10:20 am
+1 day
3:39 pm — 5:09 pm AS6140 Alaska Airlines
San Diego — Phoenix
5h 35m stop
10:44 pm — 6:06 am F91286 Frontier Airlines
Phoenix — Orlando
2h 27m stop
8:33 am — 10:20 am F91024 Frontier Airlines
Orlando — Chicago
16h 41m
including layover
Find flight
from$1301
4:55 pm — 8:43 am
+1 day
4:55 pm — 6:24 pm AS3482 Alaska Airlines
San Diego — San Francisco
5h 51m stop
0:15 am — 5:50 am DL1081 Delta Air Lines Inc.
San Francisco — Minneapolis
1h 17m stop
7:07 am — 8:43 am DL3746 Delta Air Lines Inc.
Minneapolis — Chicago
13h 48m
including layover
Find flight
from$773
9:47 am — 6:24 am
+1 day
9:47 am — 12:45 pm AS1167 Alaska Airlines
San Diego — Seattle
3h 25m stop
4:10 pm — 11:59 pm AS492 Alaska Airlines
Seattle — Atlanta
5h 11m stop
5:10 am — 6:24 am F91574 Frontier Airlines
Atlanta — Chicago
18h 37m
including layover
Find flight
from$1200
*Departure and arrival times are local. Last updated on 04/24/2024

Flight Information

There are 3 flights by Alaska Airlines from San Diego to Chicago every week with departures from San Diego, AFB, Golden Triangle Reg., Lowndes County, San Diego Regional, El Cajon, Montgomery Field, Miramar NAS, North Island NAS, Brown Field Municipal, Gillespie Field. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 10:00 am to 9:50 am. Nonstop flight is 4h 14m. The time difference between San Diego and Chicago is 2h.

  • The fastest flight 4h 14m
  • Average flight time 4h 15m
  • The earliest flight 10:00 am
  • The latest flight 9:50 am
  • Distance 1733 ml

The cheapest months for traveling to Chicago are august (from 572 $).

The cheapest flight by Alaska Airlines that our users were able to find is $572. This airfare is economy class on one-way AS3455 flight for August 29, 2023 leaving San Diego in San Diego at 7:15 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides Alaska Airlines there are other 8 airline carriers between San Diego and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from San Diego to Chicago.

Nonstop flights

There are 22 direct flights every day from San Diego. Airlines and fares are below:

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

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How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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