SAN - MDW

$155 Find Cheap Flights from San Diego to Chicago Midway Airport - Compare and Save

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 7/18. 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

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Everything you should know

Cheapest round-trip
$297
Typical prices: $215-$419
Southwest
Fri 9/11Wed 9/16
SAN - MDW • Non-stop
Cheapest non-stop
$297
Typical prices: $205-$417
Southwest
Fri 9/4Sat 9/5
SAN - MDW • Non-stop
Top airlines
Cheapest • from $297 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
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Nonstop flights
You can fly direct with Southwest. Average duration is 4h 00m
Direct flights
Direct flights
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Direct flights
Direct flights
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Top layover airports
Cheapest • Avg $410 (round-trip)
Shortest trip • 8h 37m (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 49% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
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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

Fri, Sep 11 - Wed, Sep 16
Southwest Logo
11:05 am - 5:00 pm
SAN
-
MDW
3h 55mnonstop
Southwest Logo
3:05 pm - 5:10 pm
MDW
-
SAN
4h 05mnonstop
$297Southwest
Wed, Aug 12 - Tue, Sep 1
Southwest Logo
10:40 pm - 4:30 am
SAN
-
MDW
3h 50mnonstop
Southwest Logo
8:25 pm - 10:35 pm
MDW
-
SAN
4h 10mnonstop
$300Southwest
Fri, Aug 21 - Wed, Aug 26
Southwest Logo
6:45 am - 12:45 pm
SAN
-
MDW
4h 00mnonstop
Southwest Logo
2:05 pm - 6:20 pm
MDW
-
SAN
6h 15m
1 stop
$303Southwest
Wed, Aug 12 - Tue, Sep 1
Southwest Logo
10:40 pm - 4:30 am
SAN
-
MDW
3h 50mnonstop
Southwest Logo
3:10 pm - 6:55 pm
MDW
-
SAN
5h 45m
1 stop
$306Southwest
Thu, Sep 3 - Tue, Sep 8
Southwest Logo
2:55 pm - 11:45 pm
SAN
-
MDW
6h 50m
1 stop
Southwest Logo
8:25 pm - 10:35 pm
MDW
-
SAN
4h 10mnonstop
$307Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
6:15 pm - 5:00 am
SAN
-
MDW
8h 45m
1 stop
Southwest Logo
10:00 am - 12:10 pm
MDW
-
SAN
4h 10mnonstop
$310Southwest
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
6:15 pm - 5:00 am
SAN
-
MDW
8h 45m
1 stop
Southwest Logo
1:45 pm - 5:10 pm
MDW
-
SAN
5h 25m
1 stop
$312Southwest
Sat, Aug 8 - Wed, Aug 12
Frontier Logo
4:28 pm - 9:51 am
SAN
-
MDW
15h 23m
2 stops
Frontier Logo
4:45 pm - 7:00 pm
MDW
-
SAN
28h 15m
1 stop
$314Frontier
Wed, Aug 12 - Tue, Sep 1
Southwest Logo
10:40 pm - 7:10 am
SAN
-
MDW
6h 30m
1 stop
Southwest Logo
3:10 pm - 6:55 pm
MDW
-
SAN
5h 45m
1 stop
$315Southwest
Fri, Aug 28 - Mon, Aug 31
Southwest Logo
10:40 pm - 4:30 am
SAN
-
MDW
3h 50mnonstop
Southwest Logo
6:15 am - 8:20 am
MDW
-
SAN
4h 05mnonstop
$317Southwest
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 September.

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 Sunday 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 $251 (return) on average. On the other hand, the most expensive months are June and April, where the average cost of round-trip tickets is $457 and $442 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.

No, with an average price for the route of $387, prices are generally cheapest when you fly direct.

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 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 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$155
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 40% 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 5 days, the lowest price for a flight from San Diego to Chicago Midway Airport was $155 for a one-way ticket and $297 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?

    Alaska Airlines, American Airlines, Delta, and JetBlue 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 737-800 Passenger/BBJ2 (winglets) 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 $367 and an overall rating of 7.9, Southwest is the most popular choice. Frontier is also a great choice for the route, with an average price of $238 and an overall rating of 5.6.

  • 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 $178 or less one-way and $375 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.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

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.

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

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Wifi didn’t work, no service, seats are hard as rocks

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

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

Every day about it was very different all the boarding pass where all wrong l miss flight no refund all crazy

The trip was good but the last minute changes I didn’t like because I had already talked to the attendee and they didn’t help me with my ticket I was having trouble checking in and when the time was up they help me but charge me for that and last minute luggage it was a small bag. After I was in the airplane I realized you were charging because the flight was almost empty and you have to get the money some how. Thanks for everything.

The trip was unremarkable which is good. Crew was very professional and courteous.

I was singled out for being a Latina flying solo and the attendants took me out of line to put my luggage in the personal item bin to see if it would fly. Keep In mind I had just flown with the same luggage with no problem not even 5 days ago. The tag was sticking out a bit and the attendant was belligerent about charging me $100. I could not refuse because I didn’t wanna cause a scene. But today I felt targeted and embarrassed. I went online and found out that this happens a lot with this airline and to many minority women.

Nothing I missed my first flight because my boarding pass said one thing and another passenger on the same flight said another. I didn’t get notified of a gate change until 8:39 pm which was one minute before the flight departed at 8:40pm when we explained this to gate agent Dorsey prior to the flight departing she was extremely short and had nasty attitude. Some of the passengers in my party including myself needed to catch that flight due work the next which included presentations and court litigation. We were deeply saddened and frustrated how Frontier handled this situation. We were told that the flight was over booked by 19 seats and they constantly change gates to make people miss their flight. If that is true I will ensure there will be a class action lawsuit against frontier airlines.

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

Information on your arrival and departure airports