Cheap Flights from San Diego, CA to Chicago, IL from $68

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On Cheapflightsplus.com you will find 28 direct and 400 connecting flights from San Diego to Chicago. You can compare airfare deals from 7 airlines and multiple travel sites from $68, 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: $68 (one-way), $117 (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 $68. The fastest direct flight takes 4h 3m and the fastest connecting – 5h 33m.

Price	Departure	Arrival	Flight Duration	Airline	Flight
from $92 Find flight	16:53 San Diego San Diego	22:56 Chicago O'Hare International	4h 3m	Frontier Airlines	F91856
from $116 Find flight	12:20 San Diego San Diego	18:59 Chicago O'Hare International	4h 39m	Hawaiian Airlines	HA6419
from $119 Find flight	12:20 San Diego San Diego	18:59 Chicago O'Hare International	4h 39m	Alaska Airlines	AS1186
from $68 Find flight	06:41 San Diego San Diego	20:53 Chicago Midway	12h 12m layover 7h 14m - Denver	Frontier Airlines	F92818 F92210
from $69 Find flight	20:48 San Diego San Diego	05:25+1 день Chicago O'Hare International	6h 37m layover 1h 39m - Las Vegas	Spirit Airlines	NK2021 NK2186
from $107 Find flight	20:48 San Diego San Diego	08:55+1 день Chicago O'Hare International	10h 7m layover 0h 55m - Las Vegas 1h 48m - Atlanta	Spirit Airlines	NK2021 NK2573 NK2707
from $124 Find flight	15:10 San Diego San Diego	23:31+1 день Chicago O'Hare International	30h 21m layover 2h 14m - Las Vegas 21h 16m - Los Angeles	Spirit Airlines	NK3792 NK1495 NK3010

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*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 15, 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
06:35 — 12:54	06:35 — 12:54 UA2343 United Airlines San Diego — Chicago	4h 19m	Find flight from$160
08:10 — 14:50	08:10 — 14:50 HA6417 Hawaiian Airlines San Diego — Chicago	4h 40m	Find flight from$116
08:10 — 14:50	08:10 — 14:50 AS1184 Alaska Airlines San Diego — Chicago	4h 40m	Find flight from$119
09:47 — 15:59	09:47 — 15:59 AS4024 Alaska Airlines San Diego — Chicago	4h 12m	Find flight from$231
10:41 — 16:57	10:41 — 16:57 UA2677 United Airlines San Diego — Chicago	4h 16m	Find flight from$189
12:20 — 18:59	12:20 — 18:59 HA6419 Hawaiian Airlines San Diego — Chicago	4h 39m	Find flight from$116
12:20 — 18:59	12:20 — 18:59 AS1186 Alaska Airlines San Diego — Chicago	4h 39m	Find flight from$119
13:58 — 20:13	13:58 — 20:13 UA369 United Airlines San Diego — Chicago	4h 15m	Find flight from$189
14:11 — 20:25	14:11 — 20:25 UA1779 United Airlines San Diego — Chicago	4h 14m	Find flight from$159
16:53 — 22:56	16:53 — 22:56 F91856 Frontier Airlines San Diego — Chicago	4h 3m	Find flight from$92
17:01 — 23:14	17:01 — 23:14 UA2486 United Airlines San Diego — Chicago	4h 13m	Find flight from$159
17:19 — 23:59	17:19 — 23:59 HA6430 Hawaiian Airlines San Diego — Chicago	4h 40m	Find flight from$116
17:19 — 23:59	17:19 — 23:59 AS1188 Alaska Airlines San Diego — Chicago	4h 40m	Find flight from$119
22:20 — 04:30 +1 day	22:20 — 04:30 UA1513 United Airlines San Diego — Chicago	4h 10m	Find flight from$150
22:30 — 04:37 +1 day	22:30 — 04:37 UA2624 United Airlines San Diego — Chicago	4h 7m	Find flight from$159

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

*Departure and arrival times - local. Updated on September 15, 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 68 $), september (from 68 $), june (from 69 $).

The most expensive months are october (from 100 $), august (from 93 $), december (from 90 $).

What is the lowest airfare San Diego to Chicago?

The cheapest plane ticket found by our users is $68. This airfare is for economy class on one-way F92818 flight by Frontier Airlines for September 17, 2025 which leaves San Diego in San Diego at 06:41 am and arrives at Chicago Midway at 20:53.

Economy class

$68

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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 Alaska Airlines - 50 departures per week at the price of from $ 119 . And the most expensive tickets are offered by Alaska Airlines airline - from $ 6005.

Direct flights

There are 28 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 $92.

AS - Alaska Airlines

from $119

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F9 - Frontier Airlines

from $92

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HA - Hawaiian Airlines

from $116

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UA - United Airlines

from $150

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Connecting Flights

There are 400 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 $68.

AS - Alaska Airlines

from $129

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F9 - Frontier Airlines

from $68

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SY - Sun Country Airlines

from $137

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HA - Hawaiian Airlines

from $121

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UA - United Airlines

from $183

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NK - Spirit Airlines

from $69

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G4 - Allegiant Air

from $159

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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 $68
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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.
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