SAN - MDW

$104 Find Cheap Flights from San Diego to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Diego to Midway departing on 4/16. 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 Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Chicago, 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 San Diego to Chicago, 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
$206
Typical prices: $431-$298
Southwest
Tue 5/26Mon 6/1
SAN - MDW • Non-stop
Cheapest one-way
$104
Typical prices: $178-$463
Frontier
Thu 4/16
SAN - MDW • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Security lines at SAN are generally manageable.
The CTA Orange Line offers a direct route to downtown.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $206 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Southwest. Average duration is 3h 56m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Top layover airports
Cheapest • Avg $296 (round-trip)
Shortest trip • 6h 00m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 37% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 19% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
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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 Midway!
Flight Deals
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Expert advice
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Diego to Midway 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 San Diego to Midway

Tue, May 26 - Mon, Jun 1
Southwest Logo
10:40 pm - 4:35 am
SAN
-
MDW
3h 55mnonstop
Southwest Logo
6:40 am - 8:55 am
MDW
-
SAN
4h 15mnonstop
$206Southwest
Thu, Apr 16 - Mon, Apr 20
Frontier Logo
7:52 am - 10:22 pm
SAN
-
MDW
12h 30m
1 stop
Frontier Logo
4:14 pm - 11:29 pm
MDW
-
SAN
9h 15m
1 stop
$211Frontier
Sat, May 2 - Sat, May 23
Southwest Logo
6:25 am - 2:20 pm
SAN
-
MDW
5h 55m
1 stop
Southwest Logo
6:10 pm - 8:30 pm
MDW
-
SAN
4h 20mnonstop
$212Southwest
Tue, May 5 - Sat, May 9
Frontier Logo
6:25 am - 2:12 pm
SAN
-
MDW
29h 47m
1 stop
Frontier Logo
3:07 pm - 11:50 pm
MDW
-
SAN
10h 43m
2 stops
$213Frontier
Fri, Apr 24 - Mon, Apr 27
Frontier Logo
11:01 am - 9:50 pm
SAN
-
MDW
8h 49m
1 stop
Frontier Logo
1:35 pm - 1:17 pm
MDW
-
SAN
25h 42m
2 stops
$215Frontier
Tue, May 26 - Mon, Jun 1
Southwest Logo
9:00 pm - 5:45 am
SAN
-
MDW
6h 45m
1 stop
Southwest Logo
8:45 pm - 11:10 pm
MDW
-
SAN
4h 25mnonstop
$216Southwest
Sat, May 2 - Sat, May 23
Southwest Logo
6:25 am - 4:50 pm
SAN
-
MDW
8h 25m
2 stops
Southwest Logo
6:10 pm - 8:30 pm
MDW
-
SAN
4h 20mnonstop
$221Southwest
Mon, May 11 - Fri, May 15
Frontier Logo
10:07 pm - 2:12 pm
SAN
-
MDW
14h 05m
2 stops
Frontier Logo
3:07 pm - 6:25 pm
MDW
-
SAN
29h 18m
1 stop
$223Frontier
Tue, May 5 - Sat, May 9
Frontier Logo
6:25 am - 2:12 pm
SAN
-
MDW
29h 47m
1 stop
Frontier Logo
3:07 pm - 11:50 pm
MDW
-
SAN
10h 43m
2 stops
$224Frontier
Tue, May 26 - Mon, Jun 1
Southwest Logo
8:50 pm - 5:25 am
SAN
-
MDW
6h 35m
1 stop
Southwest Logo
5:00 pm - 9:55 pm
MDW
-
SAN
6h 55m
1 stop
$226Southwest
Booking Insights

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

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

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from San Diego to Chicago Midway Airport departing in May.

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

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

For San Diego to Chicago Midway Airport, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway Airport back to San Diego, the best deals are generally found on Sunday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Diego to Chicago Midway Airport, 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 San Diego to Chicago Midway Airport is December, where tickets cost $247 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $428 and $360 respectively.

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

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 $264 on average.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San Diego to Chicago Midway Airport, 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 San Diego to Chicago Midway Airport, you should book around 3 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Expert advice

Expert advice for your flight from San Diego to Midway

 
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 seasonFebruary
Cheapest flight$104
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from San Diego to Chicago Midway Airport

When to book flights from San Diego to Midway

Are your dates flexible? Find out the best times to travel from San Diego to Midway 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 San Diego to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from San Diego to Chicago Midway Airport was $104 for a one-way ticket and $206 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

    The Boeing 737 MAX 8 is the aircraft model that flies most regularly on the San Diego to Chicago Midway Airport flight route.

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

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

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

    The two airlines most popular with KAYAK users for flights from San Diego to Chicago are Southwest and Frontier. With an average price for the route of $334 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 $233 and an overall rating of 5.7.

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

    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 San Diego to Chicago Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from San Diego 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 San Diego to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to San Diego with another airline. Booking your flights between San Diego and MDW 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 San Diego to Chicago Midway Airport?

    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 Chicago Midway Airport from San Diego 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 San Diego to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $208 or less one-way and $331 or less round-trip.

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

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

Direct departures

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

Direct returns

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

Reviews of the top airlines flying from San Diego to Midway

 
See real verified KAYAK customer reviews for airlines flying from San Diego to Chicago. 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 San Diego to Midway? 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 4339 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

10.0 ExcellentAnthony & Kathy, Mar 2026
LAX - PHX
Read more Southwest reviews

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Remind customers of the need to have passport or new ID for boarding.

The flight never took off and we spent 7 hours at the airport

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.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

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.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Severe turbulence. Captain never came on to reassure passengers after things settled down.

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

Information on your arrival and departure airports