Cheap flights from Chicago to San Diego from $58
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 7/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
Discover deals from 900+ travel sites with momondo.
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.Price Alerts
Price Alerts
Not ready to book? to track prices.Find the cheapest flights from Chicago to San Diego
Cheap round-trip flights
Cheap one-way flights
Cheap last minute flights
Cheap direct flights
Southwest flights from Chicago to San Diego
Our best Southwest deals on Chicago to San Diego flight tickets
Spirit Airlines flights from Chicago to San Diego
Our best Spirit Airlines deals on Chicago to San Diego flight tickets
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?
What is the cheapest month to fly to San Diego?
If you are unable to visit San Diego during the month of June, then departing from Chicago during the month August is also very affordable. Most momondo users find prices during this month for around $342.
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 Wednesday. Travelers who choose to depart for San Diego on a Wednesday will often find tickets for as low as $409. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $471. 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 at noon when flights can be purchased for as low as $388. Flights in the evening are often more expensive with an average ticket price of $462.
What is the cheapest Chicago to San Diego flight route?
Fly from Chicago O'Hare Intl to San Diego for the best Chicago - San Diego flight prices
How far in advance should I book a flight to San Diego?
You are more likely to see cheaper flights to San Diego from Chicago when booking 11 weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $402 when searching 11 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 $311 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.
Can stopping save me money on Chicago to San Diego flights?
No. A direct flight is the cheapest option for a flight between Chicago to San Diego.
How have Chicago to San Diego flight prices changed over time?
As of June 2025, prices for Chicago to San Diego flights are approximately 17% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from Chicago to San Diego?
Frontier, Spirit Airlines, and Southwest are the most popular carriers operating from Chicago to San Diego
What airlines fly to San Diego?
American Airlines, United Airlines and Frontier 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 54% of people opting to fly with this airline when traveling to San Diego. Keep in mind that there are 7 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 41 per day as of June 2025. The most frequent departure time is 9:00PM, with 36% of daily flights leaving in the afternoon.
How many flights depart from Chicago to San Diego on average per week?
287 flights are operational weekly from Chicago to San Diego as of June 2025. The most popular departure day for this route is Thu, with 17% 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
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 10m.
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 June 2025, 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 Boeing 737-800 (33.29% of total bookings). The next most popular plane models are Airbus A321-100/200 (14.90%), Airbus A321neo (13.62%), and Boeing 737 MAX 8 (10.02%).
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 United Airlines, making up 31% of the total bookings. Other popular airlines include American Airlines with 31%, Frontier with 19%, and Southwest with 13%.
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 $97 | Free Cancellation | Rating 6.3 8,052 reviews | |||
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,295 reviews | |||
| PriceFrom $216 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $220 | Free Cancellation | Rating 8.0 4,287 reviews | |||
| PriceFrom $236 | Free Cancellation | Rating 8.0 7,950 reviews | |||
| PriceFrom $246 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $246 | Free Cancellation | Rating 7.4 8,790 reviews |
Southwest Flights From Chicago to San Diego
Southwest flies from Chicago to San Diego around 18 times per week, with 4,287 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Chicago to San Diego in the last 72 hours was $220 (round-trip), much lower than the average airfare cost of $469 for Southwest flights on this route.
Alaska Airlines Flights From Chicago to San Diego
$246 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 $566, however, with flight time and availability significantly affecting the price. Alaska Airlines (8.0/10 from 10,000 user reviews) flies into San Diego from Chicago 34 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.