Cheap Flights from San Diego, CA to Chicago, IL from $54

One way Round trip

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On Cheapflightsplus.com you will find 24 direct and 298 connecting flights from San Diego to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $54, 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: $54 (one-way), $93 (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 $54. The fastest direct flight takes 4h 3m and the fastest connecting – 5h 33m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $74 Find flight	16:53 San Diego San Diego	22:56 Chicago O'Hare International	4h 3m	Frontier Airlines	F91856
from $93 Find flight	12:20 San Diego San Diego	18:59 Chicago O'Hare International	4h 39m	Hawaiian Airlines	HA6419
from $96 Find flight	12:20 San Diego San Diego	18:59 Chicago O'Hare International	4h 39m	Alaska Airlines	AS1186
from $121 Find flight	22:20 San Diego San Diego	04:30+1 день Chicago O'Hare International	4h 10m	United Airlines	UA1513
from $162 Find flight	10:41 San Diego San Diego	17:00 Chicago O'Hare International	4h 19m	United Airlines	UA1712
from $186 Find flight	22:38 San Diego San Diego	04:45+1 день Chicago O'Hare International	4h 7m	Alaska Airlines	AS4668
from $187 Find flight	10:33 San Diego San Diego	16:48 Chicago O'Hare International	4h 15m	Alaska Airlines	AS4232
from $228 Find flight	10:41 San Diego San Diego	16:57 Chicago O'Hare International	4h 16m	United Airlines	UA2677
from $54 Find flight	06:41 San Diego San Diego	20:53 Chicago Midway	12h 12m layover 7h 14m - Denver	Frontier Airlines	F92818 F92210
from $66 Find flight	16:57 San Diego San Diego	06:03+1 день Chicago O'Hare International	11h 6m layover 6h 15m - Las Vegas	Spirit Airlines	NK1157 NK1053
from $75 Find flight	15:10 San Diego San Diego	23:43 Chicago O'Hare International	6h 33m layover 1h 23m - Las Vegas	Spirit Airlines	NK3792 NK184
from $75 Find flight	13:00 San Diego San Diego	23:43 Chicago O'Hare International	8h 43m layover 3h 32m - Las Vegas	Spirit Airlines	NK1499 NK184
from $75 Find flight	11:40 San Diego San Diego	23:43 Chicago O'Hare International	10h 3m layover 4h 54m - Las Vegas	Spirit Airlines	NK1480 NK184
from $83 Find flight	13:10 San Diego San Diego	22:42 Chicago O'Hare International	7h 32m layover 2h 27m - Phoenix	Frontier Airlines	F94578 F91828
from $84 Find flight	06:15 San Diego San Diego	14:46 Chicago O'Hare International	6h 31m layover 1h 27m - Las Vegas	Spirit Airlines	NK1153 NK1269
from $84 Find flight	21:25 San Diego San Diego	06:03+1 день Chicago O'Hare International	6h 38m layover 1h 44m - Las Vegas	Spirit Airlines	NK1151 NK1053

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on June 24, 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
06:20 — 12:40	06:20 — 12:40 AS6893 Alaska Airlines San Diego — Chicago	4h 20m	Find flight from$186
06:35 — 12:54	06:35 — 12:54 UA2343 United Airlines San Diego — Chicago	4h 19m	Find flight from$128
08:10 — 14:50	08:10 — 14:50 HA6417 Hawaiian Airlines San Diego — Chicago	4h 40m	Find flight from$93
08:10 — 14:50	08:10 — 14:50 AS1184 Alaska Airlines San Diego — Chicago	4h 40m	Find flight from$96
09:47 — 15:59	09:47 — 15:59 AS4024 Alaska Airlines San Diego — Chicago	4h 12m	Find flight from$186
10:33 — 16:48	10:33 — 16:48 AS4232 Alaska Airlines San Diego — Chicago	4h 15m	Find flight from$187
10:41 — 17:00	10:41 — 17:00 UA1712 United Airlines San Diego — Chicago	4h 19m	Find flight from$162
10:41 — 16:57	10:41 — 16:57 UA2677 United Airlines San Diego — Chicago	4h 16m	Find flight from$228
12:20 — 18:59	12:20 — 18:59 HA6419 Hawaiian Airlines San Diego — Chicago	4h 39m	Find flight from$93
12:20 — 18:59	12:20 — 18:59 AS1186 Alaska Airlines San Diego — Chicago	4h 39m	Find flight from$96
13:08 — 19:25	13:08 — 19:25 AS6057 Alaska Airlines San Diego — Chicago	4h 17m	Find flight from$186
14:05 — 20:20	14:05 — 20:20 UA2628 United Airlines San Diego — Chicago	4h 15m	Find flight from$128
14:11 — 20:25	14:11 — 20:25 UA1779 United Airlines San Diego — Chicago	4h 14m	Find flight from$128
14:50 — 21:09	14:50 — 21:09 AS4010 Alaska Airlines San Diego — Chicago	4h 19m	Find flight from$186
14:52 — 21:09	14:52 — 21:09 AS4762 Alaska Airlines San Diego — Chicago	4h 17m	Find flight from$186
14:54 — 21:11	14:54 — 21:11 AS6492 Alaska Airlines San Diego — Chicago	4h 17m	Find flight from$188
16:53 — 22:56	16:53 — 22:56 F91856 Frontier Airlines San Diego — Chicago	4h 3m	Find flight from$74
17:01 — 23:14	17:01 — 23:14 UA2486 United Airlines San Diego — Chicago	4h 13m	Find flight from$121
17:19 — 23:59	17:19 — 23:59 HA6430 Hawaiian Airlines San Diego — Chicago	4h 40m	Find flight from$93
17:19 — 23:59	17:19 — 23:59 AS1188 Alaska Airlines San Diego — Chicago	4h 40m	Find flight from$96
22:20 — 04:30 +1 day	22:20 — 04:30 UA1513 United Airlines San Diego — Chicago	4h 10m	Find flight from$121
22:20 — 04:30 +1 day	22:20 — 04:30 UA1726 United Airlines San Diego — Chicago	4h 10m	Find flight from$128
22:30 — 04:37 +1 day	22:30 — 04:37 UA2624 United Airlines San Diego — Chicago	4h 7m	Find flight from$128
22:38 — 04:45 +1 day	22:38 — 04:45 AS4668 Alaska Airlines San Diego — Chicago	4h 7m	Find flight from$186
06:15 — 14:46	06:15 — 07:37 NK1153 Spirit Airlines San Diego — Las Vegas 1h 27m stop 09:04 — 14:46 NK1269 Spirit Airlines Las Vegas — Chicago	6h 31m including layover	Find flight from$84
06:41 — 20:53	06:25 — 09:59 F92818 Frontier Airlines San Diego — Denver 7h 14m stop 08:50 — 12:13 F92210 Frontier Airlines Denver — Chicago	12h 12m including layover	Find flight from$54
08:36 — 22:01	08:36 — 10:04 F91572 Frontier Airlines San Diego — Phoenix 6h 31m stop 16:35 — 22:01 F91736 Frontier Airlines Phoenix — Chicago	11h 25m including layover	Find flight from$94
10:31 — 22:04	09:30 — 12:37 HA6499 Hawaiian Airlines San Diego — Seattle 2h 19m stop 15:59 — 22:04 HA6821 Hawaiian Airlines Seattle — Chicago	9h 33m including layover	Find flight from$98
11:40 — 23:43	11:40 — 13:02 NK1480 Spirit Airlines San Diego — Las Vegas 4h 54m stop 17:56 — 23:43 NK184 Spirit Airlines Las Vegas — Chicago	10h 3m including layover	Find flight from$75
11:40 — 14:16 +1 day	11:40 — 13:02 NK1480 Spirit Airlines San Diego — Las Vegas 19h 30m stop 08:32 — 14:16 NK187 Spirit Airlines Las Vegas — Chicago	24h 36m including layover	Find flight from$90
12:05 — 20:54	06:25 — 09:56 F94928 Frontier Airlines San Diego — Denver 1h 44m stop 20:55 — 00:17 F92210 Frontier Airlines Denver — Chicago	6h 49m including layover	Find flight from$89
13:00 — 23:43	13:00 — 14:24 NK1499 Spirit Airlines San Diego — Las Vegas 3h 32m stop 17:56 — 23:43 NK184 Spirit Airlines Las Vegas — Chicago	8h 43m including layover	Find flight from$75
13:10 — 22:42	12:17 — 13:47 F94578 Frontier Airlines San Diego — Phoenix 2h 27m stop 18:15 — 23:41 F91828 Frontier Airlines Phoenix — Chicago	7h 32m including layover	Find flight from$83
14:03 — 23:59	14:03 — 16:44 HA6519 Hawaiian Airlines San Diego — Portland 1h 6m stop 17:50 — 23:59 HA4829 Hawaiian Airlines Portland — Chicago	7h 56m including layover	Find flight from$98
14:03 — 23:59	14:03 — 16:44 AS1297 Alaska Airlines San Diego — Portland 1h 6m stop 17:50 — 23:59 AS370 Alaska Airlines Portland — Chicago	7h 56m including layover	Find flight from$104
15:10 — 23:43	15:10 — 16:33 NK3792 Spirit Airlines San Diego — Las Vegas 1h 23m stop 17:56 — 23:43 NK184 Spirit Airlines Las Vegas — Chicago	6h 33m including layover	Find flight from$75
15:10 — 14:16 +1 day	15:10 — 16:33 NK3792 Spirit Airlines San Diego — Las Vegas 15h 59m stop 08:32 — 14:16 NK187 Spirit Airlines Las Vegas — Chicago	21h 6m including layover	Find flight from$90
16:57 — 06:03 +1 day	16:57 — 18:19 NK1157 Spirit Airlines San Diego — Las Vegas 6h 15m stop 00:34 — 06:03 NK1053 Spirit Airlines Las Vegas — Chicago	11h 6m including layover	Find flight from$66
17:50 — 10:50 +1 day	17:43 — 19:01 NK2507 Spirit Airlines San Diego — Las Vegas 10h 4m stop 05:15 — 10:55 NK2619 Spirit Airlines Las Vegas — Chicago	15h including layover	Find flight from$93
19:31 — 10:50 +1 day	18:58 — 20:17 NK2296 Spirit Airlines San Diego — Las Vegas 8h 26m stop 05:15 — 10:55 NK2619 Spirit Airlines Las Vegas — Chicago	13h 19m including layover	Find flight from$86
20:37 — 11:40 +1 day	19:19 — 23:00 F94990 Frontier Airlines San Diego — Denver 7h 54m stop 17:26 — 20:53 F92210 Frontier Airlines Denver — Chicago	13h 3m including layover	Find flight from$94
20:37 — 23:59 +1 day	19:19 — 23:00 F94990 Frontier Airlines San Diego — Denver 20h stop 20:22 — 23:52 F93174 Frontier Airlines Denver — Chicago	25h 22m including layover	Find flight from$96
21:25 — 06:03 +1 day	21:25 — 22:50 NK1151 Spirit Airlines San Diego — Las Vegas 1h 44m stop 00:34 — 06:03 NK1053 Spirit Airlines Las Vegas — Chicago	6h 38m including layover	Find flight from$84
09:09 — 23:31 +1 day	09:09 — 10:31 NK1499 Spirit Airlines San Diego — Las Vegas 18h 29m stop 05:00 — 06:18 NK465 Spirit Airlines Las Vegas — Los Angeles 11h 6m stop 17:24 — 23:31 NK3010 Spirit Airlines Los Angeles — Chicago	36h 22m including layover	Find flight from$102

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

*Departure and arrival times - local. Updated on June 24, 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 23:00 from 11 San Diego airport and arrive 06:15 to 23:00 to 7 Chicago airports. Average flight time is 4h 17m.

The fastest flight 4h 3m
Average flight time 4h 17m
The earliest flight 06:15
The latest flight 23:00
Distance 1733 ml

The cheapest months to travel to Chicago are november (from 73 $), june (from 73 $), july (from 88 $).

The most expensive months are october (from 108 $), september (from 106 $), august (from 100 $).

What is the lowest airfare San Diego to Chicago?

The cheapest plane ticket found by our users is $54. This airfare is for economy class on one-way F92818 flight by Frontier Airlines for June 25, 2025 which leaves San Diego in San Diego at 06:41 am and arrives at Chicago Midway at 20:53.

Economy class

$54

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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 7 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by United Airlines - 88 departures per week at the price of from $ 121 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 4840.

Direct flights

There are 24 nonstop flights on the route. The fastest direct flight is F91856 by Frontier Airlines takes 4h 3m and the cheapest is F92818 by Frontier Airlines for $74.

UA - United Airlines

from $121

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AS - Alaska Airlines

from $96

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F9 - Frontier Airlines

from $74

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HA - Hawaiian Airlines

from $93

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Connecting Flights

There are 298 flights with layovers on the route. The fastest connecting flight is NK1157 by Spirit Airlines takes 5h 33m and the cheapest is F92818 by Frontier Airlines for $54.

UA - United Airlines

from $147

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AS - Alaska Airlines

from $104

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F9 - Frontier Airlines

from $54

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SY - Sun Country Airlines

from $110

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HA - Hawaiian Airlines

from $97

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NK - Spirit Airlines

from $66

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G4 - Allegiant Air

from $136

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See more connecting flights

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 $54
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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 7 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.
To find a plane ticket, please select dates.