SAN - MDW

$89 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 5/9. 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

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

 
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.

Recent round-trip flight deals from San Diego to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Diego to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
7:16 pm - 3:00 pmSAN-MDW
17h 44m1 stop
Frontier Logo
6:25 am - 6:16 pmMDW-SAN
13h 51m1 stop
$181Frontier
Find Deal
Thu, May 29 - Mon, Jun 2
Frontier Logo
1:23 pm - 7:08 pmSAN-MDW
27h 45m1 stop
Frontier Logo
6:15 am - 11:58 pmMDW-SAN
19h 43m1 stop
$191Frontier
Find Deal
Wed, May 14 - Mon, May 19
Frontier Logo
6:25 am - 7:08 pmSAN-MDW
10h 43m1 stop
Frontier Logo
8:03 pm - 12:13 amMDW-SAN
6h 10m1 stop
$198Frontier
Find Deal
Mon, May 12 - Thu, May 15
Southwest Logo
5:55 pm - 11:55 pmSAN-MDW
4h 00mnonstop
Southwest Logo
7:25 am - 9:40 amMDW-SAN
4h 15mnonstop
$237Southwest
Find Deal
Wed, Jun 4 - Sat, Jun 7
Southwest Logo
8:50 pm - 5:20 amSAN-MDW
6h 30m1 stop
Southwest Logo
7:25 am - 9:40 amMDW-SAN
4h 15mnonstop
$247Southwest
Find Deal
Wed, Jun 4 - Sat, Jun 7
Southwest Logo
5:55 pm - 11:55 pmSAN-MDW
4h 00mnonstop
Southwest Logo
8:40 pm - 10:55 pmMDW-SAN
4h 15mnonstop
$257Southwest
Find Deal
Tue, Jun 3 - Fri, Jun 6
Southwest Logo
5:55 pm - 11:55 pmSAN-MDW
4h 00mnonstop
Southwest Logo
5:40 pm - 9:40 pmMDW-SAN
6h 00m1 stop
$267Southwest
Find Deal
Tue, Jun 3 - Fri, Jun 6
Delta Logo
8:50 am - 6:03 pmSAN-MDW
7h 13m1 stop
Delta Logo
2:00 pm - 8:26 pmMDW-SAN
8h 26m1 stop
$328Delta
Find Deal
Wed, Aug 20 - Sat, Oct 4
Delta Logo
10:15 pm - 8:41 amSAN-MDW
8h 26m1 stop
Delta Logo
7:21 pm - 11:20 pmMDW-SAN
5h 59m1 stop
$334Delta
Find Deal
Wed, Jun 25 - Tue, Jul 1
Delta Logo
10:30 pm - 9:41 amSAN-MDW
9h 11m1 stop
Delta Logo
7:21 pm - 11:18 pmMDW-SAN
5h 57m1 stop
$337Delta
Find Deal
Fri, Jul 4 - Tue, Jul 8
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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 February, where the average cost of round-trip tickets is $456 and $384 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 $271 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 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$89
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 0% 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 $89 for a one-way ticket and $181 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, and Delta 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 $471 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 $376 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 $213 or less one-way and $377 or less round-trip.

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

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
See more direct flights

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 4294 reviews
8.0Comfort
7.1Food
8.2Boarding
7.6Entertainment
8.6Crew
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

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.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

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!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

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.

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.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.

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

Information on your arrival and departure airports

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