MDW - SAN

$78 Find Cheap Flights from Chicago Midway Airport to San Diego

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Diego departing on 12/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to San Diego

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Diego, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Diego, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Midway to San Diego (MDW-SAN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Diego that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to San Diego

Sat, Nov 1 - Wed, Nov 5
Frontier Logo
3:57 pm - 9:24 pmMDW-SAN
7h 27m1 stop
Frontier Logo
6:41 am - 11:30 amSAN-MDW
26h 49m1 stop
$152Frontier
Find Deal
Sat, Nov 8 - Wed, Nov 12
Southwest Logo
7:30 pm - 9:50 pmMDW-SAN
4h 20mnonstop
Southwest Logo
5:00 pm - 10:55 pmSAN-MDW
3h 55mnonstop
$157Southwest
Find Deal
Sat, Nov 8 - Sat, Nov 15
Frontier Logo
2:57 pm - 8:24 pmMDW-SAN
7h 27m1 stop
Frontier Logo
5:28 pm - 11:30 amSAN-MDW
16h 02m1 stop
$160Frontier
Find Deal
Mon, Nov 10 - Wed, Nov 12
Frontier Logo
8:30 am - 4:40 pmMDW-SAN
10h 10m1 stop
Frontier Logo
6:41 am - 11:30 amSAN-MDW
26h 49m1 stop
$161Frontier
Find Deal
Sat, Nov 8 - Wed, Nov 12
Frontier Logo
2:57 pm - 8:24 pmMDW-SAN
7h 27m1 stop
Frontier Logo
6:41 am - 11:30 amSAN-MDW
26h 49m1 stop
$164Frontier
Find Deal
Tue, Nov 11 - Tue, Nov 18
Southwest Logo
10:05 am - 3:35 pmMDW-SAN
7h 30m1 stop
Southwest Logo
6:30 am - 12:35 pmSAN-MDW
4h 05mnonstop
$165Southwest
Find Deal
Wed, Nov 5 - Sat, Nov 8
Southwest Logo
8:20 am - 10:50 amMDW-SAN
4h 30mnonstop
Southwest Logo
7:25 am - 4:40 pmSAN-MDW
7h 15m1 stop
$167Southwest
Find Deal
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
7:50 pm - 10:20 pmMDW-SAN
4h 30mnonstop
Southwest Logo
7:30 am - 4:35 pmSAN-MDW
7h 05m2 stops
$170Southwest
Find Deal
Sun, Dec 21 - Thu, Dec 25
Delta Logo
5:59 pm - 11:55 pmMDW-SAN
7h 56m1 stop
Delta Logo
6:15 am - 5:19 pmSAN-MDW
9h 04m1 stop
$237Delta
Find Deal
Fri, Oct 31 - Tue, Nov 4
Delta Logo
10:40 am - 4:08 pmMDW-SAN
7h 28m1 stop
Delta Logo
10:20 pm - 8:40 amSAN-MDW
8h 20m1 stop
$240Delta
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Midway's compact terminal allows quick check-ins.
Take Route 992 bus for a quick ride to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Frontier
Cheapest • from $152 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 28% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 28% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$152
Overall average: $317
Frontier
Sat 11/1Wed 11/5
MDW - SAN • 1 stop
Cheapest non-stop
$157
Typical prices: $385-$679
Southwest
Sat 11/8Wed 11/12
MDW - SAN • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Diego!
Booking Insights

KAYAK's insights & trends for Midway to San Diego flights

Get data-powered insights and trends into flights from Midway to San Diego to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago Midway Airport to San Diego?

The average price of all round-trip flights from Chicago Midway Airport to San Diego clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to San Diego on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Chicago Midway Airport to San Diego. For your return ticket, we recommend flying on a Tuesday and avoiding Mondays for the best deals.

What is the cheapest month to fly from Chicago Midway Airport to San Diego?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to San Diego, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to San Diego is January, where tickets cost $267 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $490 and $472 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to San Diego?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $252 on average.

How far in advance should I book a flight from Chicago Midway Airport to San Diego?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to San Diego, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to San Diego, you should book around 3 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Midway to San Diego

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway offers a compact terminal with easy navigation, making it ideal for quick check-ins and departures.

Read more about MDWby Stefanie Waldek
SAN

For a quick ride to downtown San Diego, take the Route 992 bus from SAN, running every 15 minutes.

Read more about SANby Brandon Schultz
Our travel experts
Brandon Schultz

Brandon Schultz

Expert on SAN

Brandon Schultz

Brandon Schultz

Brandon Schultz is an award-winning food and travel writer based in New York City. His work has appeared in Forbes, AAA, Thrillist, Travel + Leisure, and The Daily Meal, among many others, and he is the author of 6 books, including 3 cookbooks.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more

Good to know

Low seasonSeptember
Cheapest flight$78
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Chicago Midway Airport to San Diego

When to book flights from Midway to San Diego

Are your dates flexible? Find out the best times to travel from Midway to San Diego based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago Midway Airport to San Diego flights

  • What is the cheapest flight from Chicago Midway Airport to San Diego?

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to San Diego was $78 for a one-way ticket and $152 for a round-trip.

  • Do I need a passport to fly between Chicago Midway Airport and San Diego?

    No

  • Which airlines offer Wi-Fi service onboard planes from Chicago Midway Airport to San Diego?

    American Airlines, Alaska Airlines, and Hawaiian Airlines offer inflight Wi-Fi service on the Chicago Midway Airport to San Diego flight route.

  • Which aircraft models fly most regularly from Chicago Midway Airport to San Diego?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to San Diego flight route.

  • On which days can I fly direct from Chicago Midway Airport to San Diego?

    There are nonstop flights from Chicago Midway Airport to San Diego on a daily basis.

  • Which is the best airline for flights from Chicago to San Diego, Southwest or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to San Diego are Southwest and Frontier. With an average price for the route of $416 and an overall rating of 8.0, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $204 and an overall rating of 5.8.

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to San Diego?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago Midway Airport to San Diego.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to San Diego?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Diego from Chicago Midway Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago Midway Airport to San Diego?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San Diego with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and SAN can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to San Diego?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San Diego from Chicago Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Chicago Midway Airport to San Diego

  • Looking for a cheap flight? 25% of our users found flights on this route for $208 or less one-way and $250 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to San Diego?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Chicago Midway to San Diego.
Find which airlines fly direct from Chicago Midway Airport to San Diego Airport, which days they fly and book direct flights.

Direct departures

Chicago Midway to San Diego

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

San Diego to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airlines flying from Midway to San Diego

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Diego. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to San Diego? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4239 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

Connecting flight is on time and boarding was a breeze!

10.0 ExcellentGabriel, Sep 2025DEN - SMF
Read more Southwest reviews

Connecting flight is on time and boarding was a breeze!

Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

Great for the price. No wifi or entertainment, but gate agents and crew were fantastic and we boarded quickly and left on time.

Everything you need to know for your flight from Midway to San Diego

Information on your arrival and departure airports

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