Cheap flights from San Diego to Chicago from $43
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Diego to Chicago departing on 8/6. 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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Southwest flights from San Diego to Chicago
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Spirit Airlines flights from San Diego to Chicago
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How to get the cheapest flight ticket from San Diego to Chicago
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 cheapest month to fly to Chicago?
The month of August is, on average, the cheapest month to fly to Chicago from San Diego, with most prices found around $307. If you’re not able to fly to Chicago in August, then June is your next best option. Flight prices from San Diego to Chicago during June average around $314.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $441. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from San Diego to Chicago for around $593.
What is the cheapest time of day to depart on your flight to Chicago?
Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from San Diego to Chicago during this time can be as low as $324. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $520.
What is the cheapest San Diego to Chicago flight route?
Fly from San Diego to Chicago O'Hare Intl for the best San Diego - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from San Diego when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $397 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from San Diego for as low as $307 on momondo.
What cabin class options are available on San Diego to Chicago flights?
There are 4 cabin classes available to choose from on San Diego to Chicago 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 San Diego to Chicago flights?
You could potentially save up to 3% on your flight if you consider stops on a San Diego to Chicago flight.
How have San Diego to Chicago flight prices changed over time?
As of July 2025, prices for San Diego to Chicago flights are approximately 24% cheaper when compared to flights at the same time last year.
What is the cheapest airline that flies from San Diego to Chicago?
Spirit Airlines, Southwest, and Frontier are the most popular carriers operating from San Diego to Chicago
What airlines fly to Chicago?
American Airlines, United Airlines and Frontier are the top three most popular airlines that fly to Chicago from San Diego according to our data. American Airlines is the first choice among our users, with 50% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from San Diego to Chicago on average per day?
48 flights are operational daily from San Diego to Chicago as of July 2025. The most popular departure time for this route is 6:00AM, with 58% of flights per day taking off at noon.
How many flights depart from San Diego to Chicago on average per week?
The number of flights available between San Diego and Chicago is 341 per week as of July 2025. The most frequent departure day is Tue, with 16% of weekly flights leaving on this day.
When to book flights from San Diego to Chicago
Cheap San Diego to Chicago (SAN to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from San Diego to Chicago
How far is San Diego to Chicago by plane?
The straight-line distance from San Diego to Chicago is 1730.3 mi. Typically, this will take 3h 55m by plane in normal conditions.
When did momondo last update prices for flights from San Diego Airport to Chicago?
Prices for flights from San Diego Airport to Chicago are refreshed on a daily basis.
How many operators does momondo search for flights from San Diego Airport to Chicago?
As of July 2025, there are 7 operators available to choose from for flights from San Diego Airport to Chicago.
How old do you have to be to fly from San Diego Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from San Diego Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents you'll need for your trip to Chicago 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 Chicago. 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 San Diego to Chicago?
Based on momondo bookings for flights between San Diego and Chicago, the leading plane model is Boeing 737-800, making up 31.21% of the total bookings. Other popular models include Airbus A321-100/200 with 12.19%, Airbus A321neo with 11.95%, and Boeing 737-900 with 8.92%.
What is the most popular airline from San Diego to Chicago?
Based on momondo bookings for flights between San Diego and Chicago, the leading airline is American Airlines, making up 33% of the total bookings. Other popular airlines include United Airlines with 22%, Frontier with 21%, and Southwest with 16%.
Best airlines flying from San Diego to Chicago
Compare and see reviews for airlines that fly from San Diego to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $92 | Free Cancellation | Rating 6.3 8,060 reviews | |||
| PriceFrom $116 | Free Cancellation | Rating 5.9 3,268 reviews | |||
| PriceFrom $210 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom $245 | Free Cancellation | Rating 7.4 8,843 reviews | |||
| PriceFrom $258 | Free Cancellation | Rating 8.0 7,958 reviews | |||
| PriceFrom $267 | Free Cancellation | Rating 8.0 10,000 reviews | |||
| PriceFrom $275 | Free Cancellation | Rating 8.0 4,253 reviews |
Alaska Airlines Flights From San Diego to Chicago
Alaska Airlines flight deals from San Diego to Chicago start from $267 round-trip. Over the 35 Alaska Airlines flights for this route in a normal week, average airfare is usually $680 round-trip - but some users have found much cheaper deals with momondo.
Southwest Flights From San Diego to Chicago
Southwest (8.0/10 from 4,252 reviews) operates around 18 flights from San Diego to Chicago in any given week. The average Southwest airfare for this route is around $446, with deals from around $275 rare but found on momondo. Referenced prices are for round-trip San Diego to Chicago flight searches in the last 72 hours.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from San Diego to Chicago?
Finding the right flight to Chicago from San Diego 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 Chicago quick and easy, saving you time and money.
Can I find flights from San Diego to Chicago with flexible booking policies on momondo?
All flight searches from San Diego to Chicago on momondo can be filtered to show those which offer flexible booking policies.
How can momondo help me find flights from San Diego to Chicago?
Once you have performed a search for San Diego to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.
I’m not ready to book a flight from San Diego to Chicago right now. Can momondo alert me if prices change?
If you are not ready to book a flight from San Diego to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.