MDW - SAN

$79 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 5/5. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$167
Overall average: $387
Southwest
Tue 3/10Tue 3/17
MDW - SAN • Non-stop
Cheapest one-way
$79
Typical prices: $150-$267
Southwest
Tue 5/5
MDW - SAN • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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
Southwest
Cheapest • from $167 (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 38% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 37% price drop
April
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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!
Flight Deals
Booking Insights
Expert advice
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

Tue, Mar 10 - Tue, Mar 17
Southwest Logo
5:45 am - 8:10 am
MDW
-
SAN
4h 25mnonstop
Southwest Logo
6:30 am - 12:35 pm
SAN
-
MDW
4h 05mnonstop
$167Southwest
Fri, Apr 24 - Tue, Apr 28
Frontier Logo
6:15 am - 2:25 pm
MDW
-
SAN
10h 10m
1 stop
Frontier Logo
7:15 am - 10:19 pm
SAN
-
MDW
13h 04m
2 stops
$169Frontier
Mon, Apr 20 - Sun, Apr 26
Frontier Logo
6:15 am - 2:25 pm
MDW
-
SAN
10h 10m
1 stop
Frontier Logo
6:55 am - 10:21 pm
SAN
-
MDW
13h 26m
1 stop
$170Frontier
Thu, May 7 - Sun, May 10
Frontier Logo
6:15 am - 2:25 pm
MDW
-
SAN
10h 10m
1 stop
Frontier Logo
3:20 pm - 2:49 pm
SAN
-
MDW
21h 29m
1 stop
$171Frontier
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
6:15 am - 2:25 pm
MDW
-
SAN
10h 10m
1 stop
Frontier Logo
6:55 am - 10:21 pm
SAN
-
MDW
13h 26m
1 stop
$172Frontier
Sun, May 3 - Sat, May 9
Frontier Logo
6:15 am - 2:25 pm
MDW
-
SAN
10h 10m
1 stop
Frontier Logo
7:05 am - 10:19 pm
SAN
-
MDW
13h 14m
2 stops
$174Frontier
Wed, Mar 11 - Fri, Mar 13
Southwest Logo
5:10 pm - 7:40 pm
MDW
-
SAN
4h 30mnonstop
Southwest Logo
4:45 pm - 10:35 pm
SAN
-
MDW
3h 50mnonstop
$177Southwest
Wed, Mar 11 - Sun, Mar 15
Frontier Logo
11:25 am - 12:08 am
MDW
-
SAN
14h 43m
2 stops
Frontier Logo
6:55 am - 1:18 pm
SAN
-
MDW
28h 23m
1 stop
$179Frontier
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
5:55 am - 11:00 am
MDW
-
SAN
7h 05m
1 stop
Southwest Logo
6:30 am - 12:35 pm
SAN
-
MDW
4h 05mnonstop
$184Southwest
Thu, Mar 12 - Mon, Mar 16
Frontier Logo
4:55 pm - 12:31 am
MDW
-
SAN
9h 36m
1 stop
Frontier Logo
9:08 pm - 10:25 am
SAN
-
MDW
35h 17m
2 stops
$185Frontier
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 Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday 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 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 February, where tickets cost $207 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $451 and $387 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 $286 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 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Expert advice

Expert advice for your flight from Midway to San Diego

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Brandon Schultz

Brandon Schultz

Expert on SAN

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.

Stefanie Waldek

Stefanie Waldek

Expert on MDW

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.

Good to know

Low seasonSeptember
Cheapest flight$79
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 10% 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 $79 for a one-way ticket and $167 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 JetBlue 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 MAX 8 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 $358 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 $308 and an overall rating of 5.7.

  • 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 $88 or less one-way and $252 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 4280 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

3 hour delay. Had to change plans and was still delayed.

2.0 MediocreAnonymous, Jan 2026
SFO - SAN
Read more Southwest reviews

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

There was no food and no entertainment, so I'm not sure why these are even in the survey, as my understanding is frontier does not ever offer food without a few, not even a snack, and there are no screens so unless the flight safety talk is our entertainment why ask how we liked it?. One of the flight attendants say in the back of the plane as people filed in to their seats, yelling orders about where to put baggage and telling people to hurry up. It was the least professional experience I've ever had on a flight.

Very well recently! Frontier is improving and less harrassing customer on luggages! Positive!

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

Better than expected. Staff were friendly and nice on both flights.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

i was unable to check in the flight. refund requested

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.

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