MDW - SAN

$52 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 8/26. 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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Flights 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

Tue, Oct 7 - Wed, Oct 15
Southwest Logo
7:10 am - 9:30 amMDW-SAN
4h 20mnonstop
Southwest Logo
6:25 pm - 12:25 amSAN-MDW
4h 00mnonstop
$104Southwest
Find Deal
Mon, Aug 18 - Tue, Aug 26
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
4:05 pm - 10:00 pmSAN-MDW
3h 55mnonstop
$109Southwest
Find Deal
Thu, Aug 14 - Thu, Aug 21
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
1:40 pm - 7:40 pmSAN-MDW
4h 00mnonstop
$114Southwest
Find Deal
Mon, Aug 25 - Wed, Sep 3
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
1:05 pm - 9:35 pmSAN-MDW
6h 30m1 stop
$119Southwest
Find Deal
Mon, Aug 18 - Tue, Aug 26
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
6:35 am - 3:55 pmSAN-MDW
7h 20m2 stops
$124Southwest
Find Deal
Fri, Sep 19 - Tue, Sep 23
Southwest Logo
12:10 pm - 2:20 pmMDW-SAN
4h 10mnonstop
Southwest Logo
4:05 pm - 10:00 pmSAN-MDW
3h 55mnonstop
$126Southwest
Find Deal
Tue, Aug 26 - Thu, Sep 4
Southwest Logo
4:05 pm - 8:55 pmMDW-SAN
6h 50m2 stops
Southwest Logo
4:20 pm - 12:15 amSAN-MDW
5h 55m1 stop
$129Southwest
Find Deal
Thu, Oct 2 - Sun, Oct 5
Southwest Logo
3:25 pm - 5:45 pmMDW-SAN
4h 20mnonstop
Southwest Logo
6:45 pm - 12:45 amSAN-MDW
4h 00mnonstop
$131Southwest
Find Deal
Sat, Aug 30 - Sat, Sep 6
Southwest Logo
10:05 am - 4:20 pmMDW-SAN
8h 15m1 stop
Southwest Logo
10:45 am - 4:45 pmSAN-MDW
4h 00mnonstop
$134Southwest
Find Deal
Fri, Aug 15 - Tue, Aug 19
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
6:55 am - 3:20 pmSAN-MDW
6h 25m1 stop
$136Southwest
Find Deal
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
Useful Info

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.

How much is a round-trip flight from Chicago Midway Airport to San Diego?

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 Wednesday and avoiding Sundays 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 $292 (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.

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. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low seasonFebruary
High seasonApril
Cheapest flight$52
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 17% 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 $52 for a one-way ticket and $104 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 $431 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 $199 and an overall rating of 5.9.

  • 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 $118 or less one-way and $277 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 4250 reviews
8.1Boarding
8.6Crew
7.6Entertainment
8.0Comfort
7.0Food
Airline reviews

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

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

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.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

Very bad! No good service delayed my second connection flight

They canceled flight. Hard to believe there was even a plane incoming for us to get on

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

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

Information on your arrival and departure airports

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