United Airlines San Diego to Chicago Flights

Return flight: Chicago – San Diego

Cheapflightsplus.com will find cheap United Airlines flights from San Diego to Chicago. Compare airline ticket prices and book air tickets starting from $226 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of United Airlines, arrivals and departure details below.

Find Cheap Airfare San Diego (CA) — Chicago (IL) by United 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 april: one-way - $226, two-way – $388.
Direct flights
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Below is a detailed 2025 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
10:25 pm — 4:20 am
+1 day
10:25 pm — 4:20 am UA2633 United Airlines
San Diego — Chicago
3h 55m
Find flight
from$338
10:30 pm — 4:35 am
+1 day
10:30 pm — 4:35 am UA2352 United Airlines
San Diego — Chicago
4h 5m
Find flight
from$318
11:10 am — 5:10 pm
11:10 am — 5:10 pm UA714 United Airlines
San Diego — Chicago
4h
Find flight
from$318
12:46 pm — 6:55 pm
12:46 pm — 6:55 pm UA349 United Airlines
San Diego — Chicago
4h 9m
Find flight
from$345
2:14 pm — 8:25 pm
2:14 pm — 8:25 pm UA1998 United Airlines
San Diego — Chicago
4h 11m
Find flight
from$334
2:23 pm — 8:25 pm
2:23 pm — 8:25 pm UA1023 United Airlines
San Diego — Chicago
4h 2m
Find flight
from$318
4:40 pm — 10:45 pm
4:40 pm — 10:45 pm UA2486 United Airlines
San Diego — Chicago
4h 5m
Find flight
from$345
7:00 am — 1:09 pm
7:00 am — 1:09 pm UA797 United Airlines
San Diego — Chicago
4h 9m
Find flight
from$318
7:00 am — 1:04 pm
7:00 am — 1:04 pm UA1502 United Airlines
San Diego — Chicago
4h 4m
Find flight
from$338
10:35 am — 11:12 pm
10:35 am — 12:14 pm UA2309 United Airlines
San Diego — San Francisco
4h 41m stop
4:55 pm — 11:12 pm UA373 United Airlines
San Francisco — Chicago
10h 37m
including layover
Find flight
from$304
11:15 am — 10:51 pm
11:15 am — 2:43 pm UA264 United Airlines
San Diego — Denver
4h 37m stop
7:20 pm — 10:51 pm UA2258 United Airlines
Denver — Chicago
9h 36m
including layover
Find flight
from$290
11:20 am — 11:59 pm
11:15 am — 2:43 pm UA264 United Airlines
San Diego — Denver
5h 41m stop
8:25 pm — 11:57 pm UA377 United Airlines
Denver — Chicago
10h 39m
including layover
Find flight
from$265
12:12 pm — 9:18 pm
12:12 pm — 5:25 pm UA1640 United Airlines
San Diego — Houston
1h 15m stop
6:40 pm — 9:18 pm UA787 United Airlines
Houston — Chicago
7h 6m
including layover
Find flight
from$329
12:12 pm — 10:44 pm
12:12 pm — 5:25 pm UA1640 United Airlines
San Diego — Houston
2h 41m stop
8:06 pm — 10:44 pm UA321 United Airlines
Houston — Chicago
8h 32m
including layover
Find flight
from$330
1:34 pm — 10:44 pm
1:34 pm — 6:46 pm UA1382 United Airlines
San Diego — Houston
1h 20m stop
8:06 pm — 10:44 pm UA321 United Airlines
Houston — Chicago
7h 10m
including layover
Find flight
from$329
1:34 pm — 11:29 pm
1:34 pm — 6:46 pm UA1382 United Airlines
San Diego — Houston
2h 14m stop
9:00 pm — 11:29 pm UA750 United Airlines
Houston — Chicago
7h 55m
including layover
Find flight
from$329
3:25 pm — 11:59 pm
3:25 pm — 8:32 pm UA556 United Airlines
San Diego — Houston
58m stop
9:30 pm — 11:59 pm UA750 United Airlines
Houston — Chicago
6h 34m
including layover
Find flight
from$344
3:58 pm — 5:20 am
+1 day
3:58 pm — 5:43 pm UA2117 United Airlines
San Diego — San Francisco
5h 12m stop
10:55 pm — 5:20 am UA1494 United Airlines
San Francisco — Chicago
11h 22m
including layover
Find flight
from$288
4:01 pm — 0:59 am
+1 day
4:01 pm — 5:47 pm UA2117 United Airlines
San Diego — San Francisco
54m stop
6:41 pm — 0:59 am UA2117 United Airlines
San Francisco — Chicago
6h 58m
including layover
Find flight
from$342
4:10 pm — 5:06 am
+1 day
3:40 pm — 5:19 pm UA2117 United Airlines
San Diego — San Francisco
5h 1m stop
10:50 pm — 5:06 am UA456 United Airlines
San Francisco — Chicago
10h 56m
including layover
Find flight
from$304
5:15 pm — 5:57 am
+1 day
5:15 pm — 6:54 pm UA2110 United Airlines
San Diego — San Francisco
4h 51m stop
11:45 pm — 5:57 am UA476 United Airlines
San Francisco — Chicago
10h 42m
including layover
Find flight
from$304
5:15 pm — 5:06 am
+1 day
5:15 pm — 6:54 pm UA2110 United Airlines
San Diego — San Francisco
3h 56m stop
10:50 pm — 5:06 am UA456 United Airlines
San Francisco — Chicago
9h 51m
including layover
Find flight
from$344
6:15 am — 7:59 pm
6:15 am — 7:54 am UA1986 United Airlines
San Diego — San Francisco
5h 40m stop
2:45 pm — 9:05 pm UA2386 United Airlines
San Francisco — Chicago
11h 44m
including layover
Find flight
from$276
6:30 pm — 9:38 am
+1 day
6:30 pm — 9:58 pm UA1924 United Airlines
San Diego — Denver
8h 2m stop
6:00 am — 9:38 am UA532 United Airlines
Denver — Chicago
13h 8m
including layover
Find flight
from$270
7:05 am — 10:51 pm
7:05 am — 10:33 am UA2432 United Airlines
San Diego — Denver
8h 47m stop
7:20 pm — 10:51 pm UA2258 United Airlines
Denver — Chicago
13h 46m
including layover
Find flight
from$226
7:05 am — 11:57 pm
7:05 am — 10:33 am UA2432 United Airlines
San Diego — Denver
9h 52m stop
8:25 pm — 11:57 pm UA377 United Airlines
Denver — Chicago
14h 52m
including layover
Find flight
from$226
9:00 am — 10:51 pm
9:00 am — 12:28 pm UA2476 United Airlines
San Diego — Denver
6h 52m stop
7:20 pm — 10:51 pm UA2258 United Airlines
Denver — Chicago
11h 51m
including layover
Find flight
from$265
9:00 am — 11:57 pm
9:00 am — 12:28 pm UA2476 United Airlines
San Diego — Denver
7h 57m stop
8:25 pm — 11:57 pm UA377 United Airlines
Denver — Chicago
12h 57m
including layover
Find flight
from$321
8:49 pm — 12:41 pm
+1 day
8:49 pm — 9:55 pm UA5636 United Airlines
San Diego — Los Angeles
46m stop
10:41 pm — 11:59 pm UA1279 United Airlines
Los Angeles — Las Vegas
7h 1m stop
7:00 am — 12:41 pm UA664 United Airlines
Las Vegas — Chicago
13h 52m
including layover
Find flight
from$254
8:49 pm — 12:41 pm
+1 day
8:49 pm — 9:55 pm UA5636 United Airlines
San Diego — Los Angeles
44m stop
10:39 pm — 11:57 pm UA2622 United Airlines
Los Angeles — Las Vegas
7h 3m stop
7:00 am — 12:41 pm UA664 United Airlines
Las Vegas — Chicago
13h 52m
including layover
Find flight
from$290
*Departure and arrival times are local. Last updated on 04/04/2025

Flight Information

There are 9 flights by United 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 9:45 pm. Nonstop flight is 3h 55m. The time difference between San Diego and Chicago is 2h.

  • The fastest flight 3h 55m
  • Average flight time 4h 5m
  • The earliest flight 10:00 am
  • The latest flight 9:45 pm
  • Distance 1733 ml

The cheapest months for traveling to Chicago are november (from 226 $), december (from 227 $), january (from 270 $).

The most expensive and popular months are february (from 270 $), january (from 270 $), december (from 227 $).

The cheapest flight by United Airlines that our users were able to find is $226. This airfare is economy class on one-way UA2432 flight for November 20, 2024 leaving San Diego in San Diego at 7:05 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides United Airlines there are other 4 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 13 direct flights every day from San Diego. Airlines and fares are below:

  • AS - Alaska Airlines
    from $373
    Find
See more direct flights

Connecting Flights

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

  • AS - Alaska Airlines
    from $187
    Find
  • F9 - Frontier Airlines
    from $59
    Find
  • SY - Sun Country Airlines
    from $128
    Find
  • NK - Spirit Airlines
    from $37
    Find
See more connecting flights

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How to book an air ticket yourself?
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  • 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.

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