Cheap flights from Chicago to San Diego from $124
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to San Diego departing on 10/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Fly from
Fly to
Route
Depart
Return
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Tue 11/24
5:15 am-3:34 pm
1 stop12h 19m
San Diego
Tue 12/1
9:58 am-12:53 am
2 stops12h 55m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Sat 11/14
6:30 am-3:58 pm
1 stop11h 28m
San Diego
Tue 11/24
11:26 am-12:53 am
2 stops11h 27m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Mon 11/2
6:20 am-10:48 am
1 stop6h 28m
San Diego
Mon 11/9
10:10 pm-7:49 am
1 stop7h 39m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Mon 10/26
7:15 pm-11:55 pm
1 stop6h 40m
San Diego
Mon 11/2
2:10 pm-11:57 pm
1 stop7h 47m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Sun 11/22
5:15 am-7:55 am
1 stop28h 40m
San Diego
Thu 11/26
7:00 am-1:18 pm
Nonstop4h 18m
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Thu 11/5
9:20 pm-11:50 pm
Nonstop4h 30m
San Diego
Sat 11/7
5:00 pm-10:55 pm
Nonstop3h 55m
ChicagoSan Diego
MDW Chicago Midway - SAN San Diego
MDWSAN
Chicago Midway
Sat 1/16
6:10 pm-8:40 pm
Nonstop4h 30m
San Diego
Tue 1/19
9:30 am-7:15 pm
1 stop7h 45m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Fri 12/25
7:00 am-9:46 am
Nonstop4h 46m
San Diego
Wed 12/30
11:45 am-12:30 am
1 stop10h 45m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Sat 10/31
8:01 pm-10:35 pm
Nonstop4h 34m
San Diego
Sat 11/7
10:11 am-4:29 pm
Nonstop4h 18m
ChicagoSan Diego
ORD Chicago O'Hare Intl - SAN San Diego
ORDSAN
Chicago O'Hare Intl
Thu 11/5
9:20 pm-11:54 pm
Nonstop4h 34m
San Diego
Thu 11/12
11:50 am-6:13 pm
Nonstop4h 23m
See travel insights to San Diego from
How to get the cheapest flight ticket from Chicago to San Diego
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Chicago and San Diego?
Prices are currently low for flights on this route.
Typical prices usually range from $277 to $381.The lowest price recently found on this route was $259.
What is the cheapest month to fly to San Diego?
If you are unable to visit San Diego during the month of February, then departing from Chicago during the month January is also very affordable. Most momondo users find prices during this month for around $259.
What is the cheapest day to depart on your flight to San Diego?
The cheapest day to depart from Chicago to San Diego is on a Thursday. Travelers who choose to depart for San Diego on a Thursday will often find tickets for as low as $335. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $371. These prices are subject to change though, so be sure to set up a Price Alert for flights to San Diego.
What is the cheapest time of day to depart on your flight to San Diego?
The cheapest time of day to fly to San Diego is in the evening when flights can be purchased for as low as $308. Flights at noon are often more expensive with an average ticket price of $359.
What is the cheapest Chicago to San Diego flight route?
Fly from Chicago Midway to San Diego for the best Chicago - San Diego flight prices
How far in advance should I book a flight from Chicago to San Diego?
You are more likely to see cheaper flights to San Diego from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $318 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San Diego from Chicago for as low as $273 on momondo.
What cabin class options are available on Chicago to San Diego flights?
There are 4 cabin classes available to choose from on Chicago to San Diego flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Chicago to San Diego?
Southwest, United Airlines, and Delta are the most popular carriers operating from Chicago to San Diego
What airlines fly to San Diego?
American Airlines, United Airlines and Alaska Airlines are the top three most popular airlines that fly to San Diego from Chicago according to our data. American Airlines is the first choice among our users, with 40% of people opting to fly with this airline when traveling to San Diego. Keep in mind that there are 8 different airlines that fly to San Diego on a routine basis, so you have a few additional options to choose from.
How many flights depart from Chicago to San Diego on average per day?
The number of flights available between Chicago and San Diego is 34 per day as of October 2026. The most frequent departure time is 8:00PM, with 36% of daily flights leaving in the afternoon.
How many flights depart from Chicago to San Diego on average per week?
244 flights are operational weekly from Chicago to San Diego as of October 2026. The most popular departure day for this route is Wed, with 21% of flights per week taking off on this day.
When to book flights from Chicago to San Diego
Cheap Chicago to San Diego (CHI to SAN) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago to San Diego
Frequently asked questions about flying from Chicago to San Diego
How far is Chicago to San Diego by plane?
There are 1730.3 mi between Chicago and San Diego. In terms of flight time, this usually takes a little over 4h 12m.
When did momondo last update prices for flights from Chicago to San Diego Airport?
Prices for flights from Chicago to San Diego Airport refresh daily.
How many operators does momondo search for flights from Chicago to San Diego Airport?
As of October 2026, there are 7 operators available to choose from for flights from Chicago to San Diego Airport.
How old do you have to be to fly from Chicago to San Diego Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to San Diego Airport.
What documentation or ID do you need to fly to San Diego Airport?
The travel and health documents you'll need for your trip to San Diego Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at San Diego Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago to San Diego?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Chicago to San Diego is Airbus A321-100/200 (18.17% of total bookings). The next most popular plane models are Boeing 737 MAX 9 (15.56%), Boeing 737-800 (15.39%), and Airbus A321neo (14.31%).
What is the most popular airline from Chicago to San Diego?
Based on momondo bookings for flights between Chicago and San Diego, the leading airline is Alaska Airlines, making up 32% of the total bookings. Other popular airlines include United Airlines with 31%, American Airlines with 25%, and Southwest with 9%.
Best airlines flying from Chicago to San Diego
Compare and see reviews for airlines that fly from Chicago to San Diego with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $124 | Free Cancellation | Rating 5.6 2,551 reviews | |||
| PriceFrom $153 | Free Cancellation | Rating 7.8 2,806 reviews | |||
| PriceFrom $157 | Free Cancellation | Rating 7.9 13,038 reviews | |||
| PriceFrom $161 | Free Cancellation | Rating 7.4 10,322 reviews | |||
| PriceFrom $166 | Free Cancellation | Rating 7.0 12,146 reviews | |||
| PriceFrom $186 | Free Cancellation | Rating 7.8 8,646 reviews | |||
| PriceFrom $187 | Free Cancellation | Rating 7.9 4,224 reviews |
Southwest Flights From Chicago to San Diego
Southwest flies from Chicago to San Diego around 10 times per week, with 4,224 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Chicago to San Diego in the last 72 hours was $187 (round-trip), much lower than the average airfare cost of $352 for Southwest flights on this route.
Alaska Airlines Flights From Chicago to San Diego
$157 is the best Alaska Airlines flight deal from Chicago to San Diego found on momondo over the last 72 hours. The average Alaska Airlines ticket price found was closer to $319, however, with flight time and availability significantly affecting the price. Alaska Airlines (7.9/10 from 13,038 user reviews) flies into San Diego from Chicago 2 times in an average week so prices can vary.
Traveling to a place near San Diego?
Book flights to San Diego if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Chicago to San Diego?
Finding the right flight to San Diego from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to San Diego quick and easy, saving you time and money.
Can I find flights from Chicago to San Diego with flexible booking policies on momondo?
Flights from Chicago to San Diego with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Chicago to San Diego?
momondo provides multiple filters to help you find the best flight to San Diego from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Chicago to San Diego right now. Can momondo alert me if prices change?
If you are simply researching potential flights to San Diego, momondo offers a useful price alert feature which will track prices for flights to San Diego from Chicago and alert you when they change.