SAN - MDW

$58 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 9/4. 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 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
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Flights 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

Mon, Sep 1 - Thu, Sep 4
Frontier Logo
6:25 am - 12:24 amSAN-MDW
15h 59m1 stop
Frontier Logo
10:18 am - 4:42 pmMDW-SAN
8h 24m1 stop
$122Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Frontier Logo
7:11 pm - 10:28 amSAN-MDW
13h 17m1 stop
Frontier Logo
7:15 am - 6:16 pmMDW-SAN
13h 01m1 stop
$124Frontier
Find Deal
Thu, Sep 18 - Mon, Sep 22
Frontier Logo
1:18 pm - 9:58 pmSAN-MDW
6h 40m1 stop
Frontier Logo
4:48 pm - 11:53 pmMDW-SAN
9h 05m1 stop
$128Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Frontier Logo
8:36 am - 10:01 pmSAN-MDW
11h 25m1 stop
Frontier Logo
4:29 pm - 11:50 pmMDW-SAN
9h 21m1 stop
$129Frontier
Find Deal
Thu, Aug 28 - Mon, Sep 1
Frontier Logo
8:26 pm - 12:24 amSAN-MDW
25h 58m1 stop
Frontier Logo
6:31 pm - 11:52 pmMDW-SAN
7h 21m1 stop
$139Frontier
Find Deal
Fri, Sep 12 - Mon, Sep 15
Frontier Logo
7:11 pm - 10:28 amSAN-MDW
13h 17m1 stop
Frontier Logo
4:48 pm - 11:53 pmMDW-SAN
9h 05m1 stop
$140Frontier
Find Deal
Wed, Jul 30 - Sat, Aug 9
Frontier Logo
8:00 am - 5:03 pmSAN-MDW
7h 03m1 stop
Frontier Logo
2:44 pm - 9:52 amMDW-SAN
21h 08m1 stop
$143Frontier
Find Deal
Wed, Jul 30 - Tue, Aug 5
Frontier Logo
8:00 am - 5:03 pmSAN-MDW
7h 03m1 stop
Frontier Logo
6:02 pm - 10:54 pmMDW-SAN
6h 52m1 stop
$144Frontier
Find Deal
Tue, Aug 19 - Tue, Aug 26
Southwest Logo
4:05 pm - 10:00 pmSAN-MDW
3h 55mnonstop
Southwest Logo
1:35 pm - 3:45 pmMDW-SAN
4h 10mnonstop
$171Southwest
Find Deal
Wed, Aug 20 - Sun, Aug 24
Southwest Logo
4:05 pm - 10:00 pmSAN-MDW
3h 55mnonstop
Southwest Logo
8:20 am - 10:30 amMDW-SAN
4h 10mnonstop
$204Southwest
Find Deal
Expert advice

Expert advice for your flight from San Diego to Midway

 
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
SAN

Security lines at SAN are generally manageable, even during peak times. Expect waits of 30–35 minutes, with shorter times during off-peak hours.

Read more about SANby Brandon Schultz
MDW

The CTA Orange Line offers a direct route from MDW to downtown Chicago, taking about 25-30 minutes to reach The Loop.

Read more about MDWby Stefanie Waldek
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 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.

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, Tuesday 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 Wednesday, with Sunday 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 $296 (return) on average. On the other hand, the most expensive months are January and June, where the average cost of round-trip tickets is $456 and $407 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 $317, 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonJanuary
High seasonNovember
Cheapest flight$58
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 5% lower on average.
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 $58 for a one-way ticket and $122 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 737-800 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 Delta?

    The two airlines most popular with KAYAK users for flights from San Diego to Chicago are Southwest and Delta. With an average price for the route of $448 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $302 and an overall rating of 8.0.

  • 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 $298 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 3 airlines serving 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 4278 reviews
8.6Crew
8.2Boarding
8.0Comfort
7.6Entertainment
7.0Food
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

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

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

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

Delta flight was on time, seats were comfortable, and crew was nice.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.

Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark

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.

They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

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

Information on your arrival and departure airports

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