United Airlines San Diego to Chicago Flights

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Cheapflightsplus.com will find cheap United Airlines flights from San Diego to Chicago. Compare airline ticket prices and book air tickets starting from $246 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 may: one-way - $246, two-way – $422.

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Cheap Flights from San Diego to Chicago by United Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by United Airlines, their prices start from $246. The fastest nonstop flight takes 3h 55m. The fastest connecting flight — 5h 40m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $346 Find flight	11:10 am San Diego San Diego	5:10 pm Chicago O'Hare International	4h 0m	United Airlines	UA714
from $246 Find flight	7:05 am San Diego San Diego	10:51 pm Chicago O'Hare International	13h 46m layover 8h 47m - Denver	United Airlines	UA2432 UA2258
from $288 Find flight	11:20 am San Diego San Diego	11:59 pm Chicago O'Hare International	10h 39m layover 5h 41m - Denver	United Airlines	UA264 UA377
from $288 Find flight	9:00 am San Diego San Diego	10:51 pm Chicago O'Hare International	11h 51m layover 6h 52m - Denver	United Airlines	UA2476 UA2258
from $293 Find flight	7:00 am San Diego San Diego	7:31 pm Chicago O'Hare International	10h 31m layover 5h 27m - Denver	United Airlines	UA1365 UA1495
from $293 Find flight	6:30 pm San Diego San Diego	9:38 am+1 день Chicago O'Hare International	13h 8m layover 8h 2m - Denver	United Airlines	UA1924 UA532
from $293 Find flight	7:00 am San Diego San Diego	9:25 pm Chicago O'Hare International	12h 25m layover 7h 27m - Denver	United Airlines	UA1365 UA1898
from $299 Find flight	6:15 am San Diego San Diego	7:59 pm Chicago O'Hare International	11h 44m layover 5h 40m - San Francisco	United Airlines	UA1986 UA2386
from $313 Find flight	7:35 am San Diego San Diego	7:59 pm Chicago O'Hare International	10h 24m layover 4h 20m - San Francisco	United Airlines	UA2051 UA2386
from $313 Find flight	3:58 pm San Diego San Diego	5:20 am+1 день Chicago O'Hare International	11h 22m layover 5h 12m - San Francisco	United Airlines	UA2117 UA1494
from $330 Find flight	4:10 pm San Diego San Diego	5:06 am+1 день Chicago O'Hare International	10h 56m layover 5h 1m - San Francisco	United Airlines	UA2117 UA456
from $330 Find flight	5:15 pm San Diego San Diego	5:57 am+1 день Chicago O'Hare International	10h 42m layover 4h 51m - San Francisco	United Airlines	UA2110 UA476
from $330 Find flight	8:00 am San Diego San Diego	9:05 pm Chicago O'Hare International	11h 5m layover 5h 6m - San Francisco	United Airlines	UA1898 UA2386
from $340 Find flight	7:00 am San Diego San Diego	7:50 pm Chicago O'Hare International	10h 50m layover 5h 49m - Denver	United Airlines	UA2270 UA1495
from $276 Find flight	8:49 pm San Diego San Diego	12:41 pm+1 день Chicago O'Hare International	13h 52m layover 0h 46m - Los Angeles 7h 1m - Las Vegas	United Airlines	UA5636 UA1279 UA664
from $437 Find flight	6:15 am San Diego San Diego	10:51 pm Chicago O'Hare International	14h 36m layover 1h 32m - Los Angeles 6h 58m - Denver	United Airlines	UA4723 UA1583 UA2258

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 04/28/2025

United Airlines Flight Schedule San Diego to Chicago

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	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$367
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$346
11:10 am — 5:10 pm	11:10 am — 5:10 pm UA714 United Airlines San Diego — Chicago	4h	Find flight from$346
12:46 pm — 6:55 pm	12:46 pm — 6:55 pm UA349 United Airlines San Diego — Chicago	4h 9m	Find flight from$374
2:14 pm — 8:25 pm	2:14 pm — 8:25 pm UA1998 United Airlines San Diego — Chicago	4h 11m	Find flight from$362
2:23 pm — 8:25 pm	2:23 pm — 8:25 pm UA1023 United Airlines San Diego — Chicago	4h 2m	Find flight from$346
4:40 pm — 10:45 pm	4:40 pm — 10:45 pm UA2486 United Airlines San Diego — Chicago	4h 5m	Find flight from$374
7:00 am — 1:09 pm	7:00 am — 1:09 pm UA797 United Airlines San Diego — Chicago	4h 9m	Find flight from$346
7:00 am — 1:04 pm	7:00 am — 1:04 pm UA1502 United Airlines San Diego — Chicago	4h 4m	Find flight from$367
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$330
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$314
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$288
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$357
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$358
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$357
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$357
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$374
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$313
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$371
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$330
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$330
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$374
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$299
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$293
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$246
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$246
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$288
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$349
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$276
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$314

Departure	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*Departure and arrival times are local. Last updated on 04/28/2025

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 246 $), december (from 246 $), january (from 293 $).

The most expensive and popular months are february (from 293 $), january (from 293 $), december (from 246 $).

The cheapest flight by United Airlines that our users were able to find is $246. 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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United Airlines Airplanes on the Route

List of the most popular United Airlines airplanes flying from San Diego to Chicago:

Airbus A320

from $415

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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 $405

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Connecting Flights

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

AS - Alaska Airlines

from $203

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F9 - Frontier Airlines

from $64

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SY - Sun Country Airlines

from $139

Find
NK - Spirit Airlines

from $40

Find

See more connecting flights

How to book an air ticket yourself?

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