Cheap flights from Chicago Midway Airport to San Diego from $81
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 Midway Airport to San Diego departing on 8/12. 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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Delta flights from Chicago Midway Airport to San Diego
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Southwest flights from Chicago Midway Airport to San Diego
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How to get the cheapest flight ticket from Chicago Midway Airport 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 cheapest month to fly to San Diego?
If you are unable to visit San Diego during the month of January, then departing from Chicago Midway Airport during the month April is also very affordable. Most momondo users find prices during this month for around $318.
What is the cheapest day to depart on your flight to San Diego?
The cheapest day to depart from Chicago Midway Airport 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 $403. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $470. 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 $372. Flights in the evening are often more expensive with an average ticket price of $461.
What is the cheapest Chicago Midway to San Diego flight route?
Fly from Chicago Midway to San Diego for the best Chicago Midway - 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 Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to San Diego for around $382 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 Midway Airport for as low as $287 on momondo.
What cabin class options are available on Chicago Midway to San Diego flights?
There are 1 cabin classes available to choose from on Chicago Midway 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 Midway Airport to San Diego flights?
You could potentially save up to 11% on your flight if you consider stops on a Chicago Midway Airport to San Diego flight.
How have Chicago Midway Airport to San Diego flight prices changed over time?
As of June 2025, prices for Chicago Midway Airport to San Diego flights are approximately 4% cheaper when compared to flights at the same time last year.
How many flights depart from Chicago Midway Airport to San Diego on average per day?
2 flights are operational daily from Chicago Midway Airport to San Diego as of June 2025. The most popular departure time for this route is 7:00AM, with 40% of flights per day taking off in the afternoon.
How many flights depart from Chicago Midway Airport to San Diego on average per week?
As of June 2025, there are 18 flights per week flying from Chicago Midway Airport to San Diego. The most common day of the week flights depart is Mon, with 22% of flights taking off on this day.
When to book flights from Chicago Midway Airport to San Diego
Cheap Chicago Midway Airport to San Diego (MDW to SAN) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to San Diego
How far is Chicago Midway to San Diego by plane?
San Diego is 1723.1 mi away from Chicago Midway. Flights usually cover this in 4h 10m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Chicago Midway Airport to San Diego Airport?
Prices for flights from Chicago Midway Airport to San Diego Airport are updated daily.
How many operators does momondo search for flights from Chicago Midway Airport to San Diego Airport?
There are 2 operators available for flights from Chicago Midway Airport to San Diego Airport as of June 2025.
How old do you have to be to fly from Chicago Midway Airport 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 Midway Airport to San Diego Airport.
What documentation or ID do you need to fly to San Diego Airport?
The necessary travel and health documents for your San Diego Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Chicago Midway Airport to San Diego?
momondo data reveals that the most frequently booked plane model on the route from Chicago Midway Airport to San Diego is Boeing 737-800, representing 28.24% of all bookings. The subsequent popular models are Boeing 737 MAX 8 at 19.17%, Airbus A321neo at 12.81%, and Airbus A321-100/200 at 11.79%.
What is the most popular airline from Chicago Midway Airport to San Diego?
momondo data reveals that the most frequently booked airline on the route from Chicago Midway Airport to San Diego is Southwest, representing 66% of all bookings. The subsequent popular airline is Frontier at 34%.
Best airlines flying from Chicago Midway Airport to San Diego
Compare and see reviews for airlines that fly from Chicago Midway Airport to San Diego with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $108 | Free Cancellation | Rating 5.9 3,301 reviews | |||
| PriceFrom $223 | Free Cancellation | Rating 8.0 4,280 reviews |
Southwest Flights From Chicago Midway Airport to San Diego
Southwest operates around 18 flights from Chicago Midway Airport to San Diego every week. The average price of these flights found in the last 72 hours has been $437, but momondo users have found Southwest deals from Chicago Midway Airport to San Diego from as low as $223 round-trip. Southwest has been scored 8.0/10 in 4,280 reviews.
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?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to San Diego from Chicago.
Can I find flights from Chicago to San Diego with flexible booking policies on momondo?
Yes. momondo enables you to select and highlight flights to San Diego from Chicago with this policy.
How can momondo help me find flights from Chicago to San Diego?
Once you have performed a search for Chicago to San Diego 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 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.