Cheap Flights from San Diego, CA to Chicago, IL from $67

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On Cheapflightsplus.com you will find 7 direct and 26 connecting flights from San Diego to Chicago. You can compare airfare deals from 4 airlines and multiple travel sites from $67, book and save on cheap plane tickets and last minute offers. Also check out SAN-CHI flight schedule to find best flight time, convenient departure and arrival airports.

Find One-Way and Round-Trip San Diego to Chicago Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $67 (one-way), $115 (round-trip).

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Best Flights from San Diego to Chicago Today

Take a look at the list of non stop flights and flights with layovers from San Diego to Chicago with the lowest price of $67. The fastest direct flight takes 3h 53m and the fastest connecting – 5h 56m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $318 Find flight	11:10 San Diego San Diego	17:10 Chicago O'Hare International	4h 0m	United Airlines	UA714
from $373 Find flight	06:15 San Diego San Diego	12:08 Chicago O'Hare International	3h 53m	Alaska Airlines	AS4323
from $67 Find flight	11:09 San Diego San Diego	06:33+1 день Chicago Midway	17h 24m layover 12h 20m - Las Vegas	Frontier Airlines	F91326 F92330
from $79 Find flight	20:41 San Diego San Diego	04:47+1 день Chicago O'Hare International	6h 6m layover 0h 44m - Las Vegas	Frontier Airlines	F91470 F92146
from $120 Find flight	21:30 San Diego San Diego	10:42+1 день Chicago Midway	11h 12m layover 6h 16m - Phoenix	Frontier Airlines	F92888 F91736
from $147 Find flight	20:58 San Diego San Diego	12:14+1 день Chicago O'Hare International	13h 16m layover 8h 7m - Las Vegas	Spirit Airlines	NK1480 NK187
from $163 Find flight	07:24 San Diego San Diego	01:03+1 день Chicago O'Hare International	15h 39m layover 10h 26m - Denver	Frontier Airlines	F92818 F93172
from $188 Find flight	21:59 San Diego San Diego	17:00+1 день Chicago O'Hare International	17h 1m layover 11h 3m - San Francisco	Alaska Airlines	AS3458 AS598
from $189 Find flight	17:27 San Diego San Diego	17:00+1 день Chicago O'Hare International	21h 33m layover 15h 39m - San Francisco	Alaska Airlines	AS3423 AS598
from $205 Find flight	08:00 San Diego San Diego	16:58 Chicago O'Hare International	6h 58m layover 1h 2m - San Francisco	Alaska Airlines	AS3463 AS598
from $205 Find flight	06:15 San Diego San Diego	16:58 Chicago O'Hare International	8h 43m layover 2h 46m - San Francisco	Alaska Airlines	AS2180 AS598
from $237 Find flight	17:59 San Diego San Diego	13:04+1 день Chicago O'Hare International	17h 5m layover 10h 21m - Portland	Alaska Airlines	AS1294 AS324
from $214 Find flight	08:18 San Diego San Diego	01:13+1 день Chicago O'Hare International	14h 55m layover 3h 17m - San Jose 4h 23m - Dallas	Spirit Airlines	NK1497 NK1942 NK828
from $219 Find flight	08:00 San Diego San Diego	23:59 Chicago O'Hare International	13h 59m layover 4h 59m - San Francisco 1h 4m - Seattle	Alaska Airlines	AS3463 AS1059 AS538
from $231 Find flight	13:39 San Diego San Diego	05:53+1 день Chicago O'Hare International	14h 14m layover 2h 24m - San Francisco 3h 59m - Seattle	Alaska Airlines	AS3352 AS971 AS461
from $262 Find flight	08:00 San Diego San Diego	23:59 Chicago O'Hare International	13h 59m layover 1h 51m - San Francisco 4h 10m - Seattle	Alaska Airlines	AS3463 AS1225 AS538

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on March 01, 2025

Flight Schedule San Diego (California) to Chicago (Illinois)

Full flight schedule will help you in detecting at what time planes fly from San Diego to Chicago. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.

Departure	Flight Details	Flight Duration	Price
06:15 — 12:08	06:15 — 12:08 AS4323 Alaska Airlines San Diego — Chicago	3h 53m	Find flight from$373
07:00 — 13:04	07:00 — 13:04 UA1502 United Airlines San Diego — Chicago	4h 4m	Find flight from$338
11:10 — 17:10	11:10 — 17:10 UA714 United Airlines San Diego — Chicago	4h	Find flight from$318
13:34 — 19:39	13:34 — 19:39 AS4232 Alaska Airlines San Diego — Chicago	4h 5m	Find flight from$373
14:23 — 20:25	14:23 — 20:25 UA1023 United Airlines San Diego — Chicago	4h 2m	Find flight from$318
22:25 — 04:20 +1 day	22:25 — 04:20 UA2633 United Airlines San Diego — Chicago	3h 55m	Find flight from$338
22:39 — 04:34 +1 day	22:39 — 04:34 AS6037 Alaska Airlines San Diego — Chicago	3h 55m	Find flight from$373
06:15 — 16:58	06:15 — 08:00 AS2180 Alaska Airlines San Diego — San Francisco 2h 46m stop 10:46 — 16:58 AS598 Alaska Airlines San Francisco — Chicago	8h 43m including layover	Find flight from$205
07:00 — 19:50	07:00 — 10:28 UA2270 United Airlines San Diego — Denver 5h 49m stop 16:17 — 19:50 UA1495 United Airlines Denver — Chicago	10h 50m including layover	Find flight from$313
07:24 — 01:03 +1 day	06:25 — 09:56 F92818 Frontier Airlines San Diego — Denver 10h 26m stop 20:59 — 00:35 F93172 Frontier Airlines Denver — Chicago	15h 39m including layover	Find flight from$163
08:00 — 16:58	08:00 — 09:44 AS3463 Alaska Airlines San Diego — San Francisco 1h 2m stop 10:46 — 16:58 AS598 Alaska Airlines San Francisco — Chicago	6h 58m including layover	Find flight from$205
10:59 — 18:55	10:22 — 11:28 UA5249 United Airlines San Diego — Los Angeles 40m stop 12:40 — 18:53 UA1069 United Airlines Los Angeles — Chicago	5h 56m including layover	Find flight from$329
11:09 — 06:33 +1 day	10:35 — 12:01 F91326 Frontier Airlines San Diego — Las Vegas 12h 20m stop 06:11 — 11:48 F92330 Frontier Airlines Las Vegas — Chicago	17h 24m including layover	Find flight from$67
15:11 — 00:15 +1 day	15:11 — 20:20 UA1998 United Airlines San Diego — Houston 1h 18m stop 21:38 — 00:15 UA1692 United Airlines Houston — Chicago	7h 4m including layover	Find flight from$347
16:01 — 00:59 +1 day	16:01 — 17:47 UA2117 United Airlines San Diego — San Francisco 54m stop 18:41 — 00:59 UA2117 United Airlines San Francisco — Chicago	6h 58m including layover	Find flight from$342
17:27 — 17:00 +1 day	17:27 — 19:09 AS3423 Alaska Airlines San Diego — San Francisco 15h 39m stop 10:48 — 17:00 AS598 Alaska Airlines San Francisco — Chicago	21h 33m including layover	Find flight from$189
17:59 — 13:04 +1 day	17:59 — 20:39 AS1294 Alaska Airlines San Diego — Portland 10h 21m stop 07:00 — 13:04 AS324 Alaska Airlines Portland — Chicago	17h 5m including layover	Find flight from$237
18:53 — 05:53 +1 day	18:53 — 22:00 AS1071 Alaska Airlines San Diego — Seattle 1h 59m stop 23:59 — 05:53 AS461 Alaska Airlines Seattle — Chicago	9h including layover	Find flight from$328
20:41 — 04:47 +1 day	20:41 — 22:15 F91470 Frontier Airlines San Diego — Las Vegas 44m stop 22:59 — 04:47 F92146 Frontier Airlines Las Vegas — Chicago	6h 6m including layover	Find flight from$79
20:41 — 06:33 +1 day	20:41 — 22:15 F91470 Frontier Airlines San Diego — Las Vegas 2h 44m stop 00:59 — 06:33 F92330 Frontier Airlines Las Vegas — Chicago	7h 52m including layover	Find flight from$79
21:30 — 10:42 +1 day	21:30 — 00:04 F92888 Frontier Airlines San Diego — Phoenix 6h 16m stop 06:20 — 10:42 F91736 Frontier Airlines Phoenix — Chicago	11h 12m including layover	Find flight from$120
21:59 — 17:00 +1 day	21:59 — 23:45 AS3458 Alaska Airlines San Diego — San Francisco 11h 3m stop 10:48 — 17:00 AS598 Alaska Airlines San Francisco — Chicago	17h 1m including layover	Find flight from$188
08:18 — 01:13 +1 day	08:18 — 09:41 NK1497 Spirit Airlines San Diego — San Jose 3h 17m stop 12:58 — 18:36 NK1942 Spirit Airlines San Jose — Dallas 4h 23m stop 22:59 — 01:13 NK828 Spirit Airlines Dallas — Chicago	14h 55m including layover	Find flight from$214
10:24 — 23:59	10:24 — 12:15 AS2058 Alaska Airlines San Diego — San Francisco 2h 28m stop 14:43 — 16:59 AS1059 Alaska Airlines San Francisco — Seattle 1h 4m stop 18:03 — 23:59 AS538 Alaska Airlines Seattle — Chicago	11h 35m including layover	Find flight from$279
13:39 — 05:53 +1 day	13:39 — 15:26 AS3352 Alaska Airlines San Diego — San Francisco 2h 24m stop 17:50 — 20:00 AS971 Alaska Airlines San Francisco — Seattle 3h 59m stop 23:59 — 05:53 AS461 Alaska Airlines Seattle — Chicago	14h 14m including layover	Find flight from$231
15:58 — 05:53 +1 day	15:58 — 17:40 AS3473 Alaska Airlines San Diego — San Francisco 1h 10m stop 18:50 — 21:00 AS157 Alaska Airlines San Francisco — Seattle 2h 59m stop 23:59 — 05:53 AS461 Alaska Airlines Seattle — Chicago	11h 55m including layover	Find flight from$266

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

*Departure and arrival times - local. Updated on March 1, 2025

Flight Information

Below we will explain in detail what the flights cost on the destination from San Diego to Chicago depends on and how to choose the most interesting flight option for you.

Distance between San Diego and Chicago is 2788 miles. Time difference between the cities is 2h. Airplanes depart 06:15 to 22:39 from 11 San Diego airport and arrive 06:15 to 22:39 to 7 Chicago airports. Average flight time is 4h.

The fastest flight 3h 53m
Average flight time 4h
The earliest flight 06:15
The latest flight 22:39
Distance 1733 ml

The cheapest months to travel to Chicago are january (from 67 $), february (from 79 $), december (from 152 $).

The most expensive months are november (from 345 $), december (from 152 $), february (from 79 $).

What is the lowest airfare San Diego to Chicago?

The cheapest plane ticket found by our users is $67. This airfare is for economy class on one-way F91326 flight by Frontier Airlines for February 21, 2025 which leaves San Diego in San Diego at 11:09 am and arrives at Chicago Midway at 06:33.

Economy class

$67

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First class

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Popular Airlines on the Route

The flight San Diego — Chicago is served by 4 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by United Airlines - 10 departures per week at the price of from $ 313 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 373.

Direct flights

There are 7 nonstop flights on the route. The fastest direct flight is AS4323 by Alaska Airlines takes 3h 53m and the cheapest is F91326 by Frontier Airlines for $318.

UA - United Airlines

from $318

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AS - Alaska Airlines

from $373

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Connecting Flights

There are 26 flights with layovers on the route. The fastest connecting flight is UA5249 by United Airlines takes 5h 56m and the cheapest is F91326 by Frontier Airlines for $67.

UA - United Airlines

from $313

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AS - Alaska Airlines

from $188

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F9 - Frontier Airlines

from $67

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NK - Spirit Airlines

from $147

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Airports

You can fly from San Diego to Chicago from 11 airports (San Diego, San Diego Regional, Gillespie Field, Golden Triangle Reg., El Cajon, Lowndes County, Miramar NAS, Montgomery Field, North Island NAS, Brown Field Municipal, AFB).

San Diego airports

San Diego-SAN

from $67
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San Diego Regional-USA

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Gillespie Field-SEE

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Golden Triangle Reg.-GTR

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El Cajon-CJN

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Lowndes County-UBS

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Miramar NAS-NKX

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Montgomery Field-MYF

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North Island NAS-NZY

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Brown Field Municipal-SDM

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AFB-CBM

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Chicago airports

O'Hare International-ORD

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Midway-MDW

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Dupage County-DPA

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Chicago FSS-CHI

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Merrill C Meigs (closed)-CGX

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Pal-Waukee-PWK

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Chicago NAS-NOH

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Airplanes

There are flights to Chicago from San Diego by 4 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.

Top Domestic Destinations from San Diego

You may also consider searching for discounted plane tickets to some other popular places from San Diego within United States.

San Diego — Las Vegas

from $67

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San Diego — Seattle

from $56

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San Diego — New York

from $68

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San Diego — San Francisco

from $54

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San Diego — Denver

from $64

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San Diego — Phoenix

from $71

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San Diego — Chicago

from $57

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San Diego — Sacramento

from $76

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San Diego — Dallas

from $70

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San Diego — Boston

from $76

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Top International Destinations from San Diego

Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.

San Diego — San Jose

from $65

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San Diego — London

from $66

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San Diego — Vancouver

from $79

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San Diego — Tokyo

from $72

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San Diego — Cancun

from $72

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San Diego — Paris

from $79

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San Diego — Toronto

from $68

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San Diego — Rome

from $54

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San Diego — Madrid

from $65

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San Diego — Calgary

from $60

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How to book a plane 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 flight ticket.
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.
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