Cheap Flights from San Diego, CA to Chicago, IL from $40

One way Round trip

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On Cheapflightsplus.com you will find 13 direct and 281 connecting flights from San Diego to Chicago. You can compare airfare deals from 5 airlines and multiple travel sites from $40, 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: $40 (one-way), $69 (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 $40. The fastest direct flight takes 3h 53m and the fastest connecting – 5h 40m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $346 Find flight	11:10 San Diego San Diego	17:10 Chicago O'Hare International	4h 0m	United Airlines	UA714
from $405 Find flight	06:15 San Diego San Diego	12:08 Chicago O'Hare International	3h 53m	Alaska Airlines	AS4323
from $594 Find flight	22:44 San Diego San Diego	05:00+1 день Chicago O'Hare International	4h 16m	Alaska Airlines	AS6893
from $40 Find flight	15:10 San Diego San Diego	04:45+1 день Chicago O'Hare International	11h 35m layover 6h 47m - Las Vegas	Spirit Airlines	NK3792 NK182
from $64 Find flight	06:25 San Diego San Diego	15:50 Chicago Midway	7h 25m layover 2h 29m - Denver	Frontier Airlines	F92818 F91228
from $72 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 $77 Find flight	12:41 San Diego San Diego	12:15+1 день Chicago O'Hare International	21h 34m layover 16h 27m - Denver	Frontier Airlines	F94990 F93174
from $83 Find flight	18:57 San Diego San Diego	04:45+1 день Chicago O'Hare International	7h 48m layover 3h 1m - Las Vegas	Spirit Airlines	NK2908 NK182
from $83 Find flight	18:57 San Diego San Diego	11:52+1 день Chicago O'Hare International	14h 55m layover 9h 59m - Las Vegas	Spirit Airlines	NK2908 NK187
from $85 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 $85 Find flight	20:41 San Diego San Diego	06:33+1 день Chicago Midway	7h 52m layover 2h 44m - Las Vegas	Frontier Airlines	F91470 F92330
from $85 Find flight	12:12 San Diego San Diego	23:16 Chicago O'Hare International	9h 4m layover 3h 58m - Denver	Frontier Airlines	F94928 F93174
from $90 Find flight	08:42 San Diego San Diego	19:45 Chicago O'Hare International	9h 3m layover 4h 18m - Phoenix	Frontier Airlines	F91572 F91830
from $91 Find flight	10:53 San Diego San Diego	22:15 Chicago Midway	9h 22m layover 4h 23m - Denver	Frontier Airlines	F94928 F91228
from $91 Find flight	12:12 San Diego San Diego	17:30+1 день Chicago O'Hare International	27h 18m layover 22h 10m - Denver	Frontier Airlines	F94928 F92048
from $92 Find flight	21:25 San Diego San Diego	06:10+1 день Chicago O'Hare International	6h 45m layover 1h 47m - Las Vegas	Spirit Airlines	NK1480 NK182

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 14, 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$405
07:00 — 13:09	07:00 — 13:09 UA797 United Airlines San Diego — Chicago	4h 9m	Find flight from$346
07:00 — 13:04	07:00 — 13:04 UA1502 United Airlines San Diego — Chicago	4h 4m	Find flight from$367
11:10 — 17:10	11:10 — 17:10 UA714 United Airlines San Diego — Chicago	4h	Find flight from$346
12:46 — 18:55	12:46 — 18:55 UA349 United Airlines San Diego — Chicago	4h 9m	Find flight from$374
13:34 — 19:39	13:34 — 19:39 AS4232 Alaska Airlines San Diego — Chicago	4h 5m	Find flight from$405
14:14 — 20:25	14:14 — 20:25 UA1998 United Airlines San Diego — Chicago	4h 11m	Find flight from$362
14:23 — 20:25	14:23 — 20:25 UA1023 United Airlines San Diego — Chicago	4h 2m	Find flight from$346
16:40 — 22:45	16:40 — 22:45 UA2486 United Airlines San Diego — Chicago	4h 5m	Find flight from$374
22:25 — 04:20 +1 day	22:25 — 04:20 UA2633 United Airlines San Diego — Chicago	3h 55m	Find flight from$367
22:30 — 04:35 +1 day	22:30 — 04:35 UA2352 United Airlines San Diego — Chicago	4h 5m	Find flight from$346
22:39 — 04:34 +1 day	22:39 — 04:34 AS6037 Alaska Airlines San Diego — Chicago	3h 55m	Find flight from$405
22:44 — 05:00 +1 day	22:44 — 05:00 AS6893 Alaska Airlines San Diego — Chicago	4h 16m	Find flight from$594
06:25 — 15:50	06:25 — 09:59 F92818 Frontier Airlines San Diego — Denver 2h 29m stop 12:28 — 15:50 F91228 Frontier Airlines Denver — Chicago	7h 25m including layover	Find flight from$64
06:25 — 17:30	06:25 — 09:59 F92818 Frontier Airlines San Diego — Denver 3h 55m stop 13:54 — 17:30 F93426 Frontier Airlines Denver — Chicago	9h 5m including layover	Find flight from$70
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$177
08:42 — 19:45	08:42 — 10:59 F91572 Frontier Airlines San Diego — Phoenix 4h 18m stop 15:17 — 19:45 F91830 Frontier Airlines Phoenix — Chicago	9h 3m including layover	Find flight from$90
08:42 — 20:14	08:56 — 11:22 F91572 Frontier Airlines San Diego — Phoenix 4h 56m stop 17:38 — 21:58 F91736 Frontier Airlines Phoenix — Chicago	9h 32m including layover	Find flight from$92
10:35 — 19:30	13:31 — 14:57 F91326 Frontier Airlines San Diego — Las Vegas 1h 38m stop 18:18 — 23:59 F92146 Frontier Airlines Las Vegas — Chicago	6h 55m including layover	Find flight from$112
10:53 — 22:15	12:12 — 15:44 F94928 Frontier Airlines San Diego — Denver 4h 23m stop 12:28 — 15:50 F91228 Frontier Airlines Denver — Chicago	9h 22m including layover	Find flight from$91
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$72
12:41 — 09:47 +1 day	12:41 — 16:13 F94990 Frontier Airlines San Diego — Denver 13h 57m stop 06:10 — 09:47 F91484 Frontier Airlines Denver — Chicago	19h 6m including layover	Find flight from$71
12:41 — 12:15 +1 day	12:41 — 16:13 F94990 Frontier Airlines San Diego — Denver 16h 27m stop 08:40 — 12:15 F93174 Frontier Airlines Denver — Chicago	21h 34m including layover	Find flight from$77
15:10 — 04:45 +1 day	15:10 — 16:30 NK3792 Spirit Airlines San Diego — Las Vegas 6h 47m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	11h 35m including layover	Find flight from$40
15:38 — 00:13 +1 day	12:41 — 16:13 F94990 Frontier Airlines San Diego — Denver 1h 51m stop 08:50 — 12:13 F92210 Frontier Airlines Denver — Chicago	6h 35m including layover	Find flight from$71
16:24 — 06:10 +1 day	16:24 — 17:46 NK1767 Spirit Airlines San Diego — Las Vegas 6h 44m stop 00:30 — 06:10 NK153 Spirit Airlines Las Vegas — Chicago	11h 46m including layover	Find flight from$159
18:57 — 04:45 +1 day	18:57 — 20:16 NK2908 Spirit Airlines San Diego — Las Vegas 3h 1m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	7h 48m including layover	Find flight from$83
18:57 — 11:52 +1 day	18:57 — 20:16 NK2908 Spirit Airlines San Diego — Las Vegas 9h 59m stop 06:15 — 11:52 NK187 Spirit Airlines Las Vegas — Chicago	14h 55m including layover	Find flight from$83
19:01 — 14:11 +1 day	19:01 — 22:34 F92712 Frontier Airlines San Diego — Denver 12h 1m stop 10:35 — 14:11 F93172 Frontier Airlines Denver — Chicago	17h 10m including layover	Find flight from$93
19:01 — 00:17 +2 days	19:01 — 22:34 F92712 Frontier Airlines San Diego — Denver 22h 21m stop 20:55 — 00:17 F92210 Frontier Airlines Denver — Chicago	27h 16m including layover	Find flight from$93
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$85
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$85
21:25 — 06:10 +1 day	13:45 — 15:05 NK1480 Spirit Airlines San Diego — Las Vegas 1h 47m stop 23:17 — 04:45 NK182 Spirit Airlines Las Vegas — Chicago	6h 45m including layover	Find flight from$92
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$131
09:08 — 00:24 +1 day	09:08 — 10:30 NK376 Spirit Airlines San Diego — Las Vegas 1h 34m stop 12:04 — 17:05 NK3727 Spirit Airlines Las Vegas — Houston 4h 42m stop 21:47 — 00:24 NK962 Spirit Airlines Houston — Chicago	13h 16m including layover	Find flight from$157
13:45 — 06:25 +1 day	13:45 — 15:05 NK1480 Spirit Airlines San Diego — Las Vegas 3h 25m stop 18:30 — 19:48 NK465 Spirit Airlines Las Vegas — Los Angeles 4h 35m stop 00:23 — 06:25 NK486 Spirit Airlines Los Angeles — Chicago	14h 40m including layover	Find flight from$147
13:45 — 09:25 +1 day	13:45 — 15:05 NK1480 Spirit Airlines San Diego — Las Vegas 6h 15m stop 21:20 — 04:55 NK954 Spirit Airlines Las Vegas — Miami 2h 10m stop 07:15 — 09:35 NK2 Spirit Airlines Miami — Chicago	17h 40m including layover	Find flight from$147
17:58 — 10:55 +1 day	17:58 — 19:18 NK1480 Spirit Airlines San Diego — Las Vegas 4h 41m stop 23:59 — 05:05 SY778 Sun Country Airlines Las Vegas — Minneapolis 4h 2m stop 09:47 — 11:35 SY259 Sun Country Airlines Minneapolis — Chicago	14h 57m including layover	Find flight from$177

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

*Departure and arrival times - local. Updated on May 14, 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 22:44 from 11 San Diego airport and arrive 06:15 to 22:44 to 7 Chicago airports. Average flight time is 4h 5m.

The fastest flight 3h 53m
Average flight time 4h 5m
The earliest flight 06:15
The latest flight 22:44
Distance 1733 ml

The cheapest months to travel to Chicago are november (from 40 $), january (from 72 $), february (from 85 $).

The most expensive months are december (from 86 $), february (from 85 $), january (from 72 $).

What is the lowest airfare San Diego to Chicago?

The cheapest plane ticket found by our users is $40. This airfare is for economy class on one-way NK3792 flight by Spirit Airlines for November 20, 2024 which leaves San Diego in San Diego at 15:10 am and arrives at Chicago O'Hare International at 04:45.

Economy class

$40

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Business class

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First class

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Popular Airlines on the Route

The flight San Diego — Chicago is served by 5 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by United Airlines - 102 departures per week at the price of from $ 246 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 594.

Direct flights

There are 13 nonstop flights on the route. The fastest direct flight is AS4323 by Alaska Airlines takes 3h 53m and the cheapest is NK3792 by Spirit Airlines for $346.

UA - United Airlines

from $346

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AS - Alaska Airlines

from $405

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Connecting Flights

There are 281 flights with layovers on the route. The fastest connecting flight is UA264 by United Airlines takes 5h 40m and the cheapest is NK3792 by Spirit Airlines for $40.

UA - United Airlines

from $246

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AS - Alaska Airlines

from $203

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F9 - Frontier Airlines

from $64

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SY - Sun Country Airlines

from $139

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NK - Spirit Airlines

from $40

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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 $40
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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 5 airlines that use 1 aircraft brands. They range from huge modern airplanes to small-sized.

Airbus A320

from $415

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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.
To find a plane ticket, please select dates.