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$78 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 6/11. 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
0 bags
Thu 6/27
Thu 7/4

Search 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
In the last 7 days travelers have searched 42,816,550 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from Midway to San Diego (MDW-SAN)

 
These are the cheapest deals for flights from Midway to San Diego currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 Midway to San Diego

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Midway to San Diego.

Recent one-way flight deals from Midway to San Diego

Only flying one-way? Below are some of the best one-way flight deals from Midway to San Diego found on KAYAK recently.

Recent last minute flight deals from Midway to San Diego

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Midway to San Diego.

Recent direct flight deals from Midway to San Diego

The latest deals for direct flights from Midway to San Diego so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Midway to San Diego

Find recent round-trip train or bus tickets from Midway to San Diego.

All round-trip flight deals to San Diego

The cheapest plane tickets to San Diego found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
2:06 pm - 9:22 pmMDW-SAN
9h 16m1 stop
8:00 am - 9:30 pmSAN-MDW
11h 30m1 stop
$156Frontier
Find Deal
Tue, Jun 11 - Sat, Jun 15
2:06 pm - 6:43 pmMDW-SAN
6h 37m1 stop
8:24 pm - 5:29 amSAN-MDW
7h 05m1 stop
$159Frontier
Find Deal
Tue, Jun 11 - Wed, Jun 12
6:00 am - 3:14 pmMDW-SAN
11h 14m1 stop
8:24 pm - 5:29 amSAN-MDW
7h 05m1 stop
$164Frontier
Find Deal
Wed, Jun 12 - Wed, Jun 12
2:06 pm - 2:00 pmMDW-SAN
25h 54m1 stop
8:24 pm - 5:29 amSAN-MDW
7h 05m1 stop
$165Frontier
Find Deal
Tue, Jun 11 - Wed, Jun 12
1:05 pm - 9:02 pmMDW-SAN
9h 57m1 stop
11:00 pm - 9:17 amSAN-MDW
8h 17m1 stop
$308Delta
Find Deal
Wed, Oct 16 - Tue, Oct 22
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
$328Delta
Find Deal
Thu, Oct 10 - Mon, Oct 14
8:50 pm - 11:00 pmMDW-SAN
4h 10mnonstop
7:00 pm - 12:55 amSAN-MDW
3h 55mnonstop
$452Southwest
Find Deal
Mon, Jul 8 - Thu, Jul 11
8:50 pm - 11:00 pmMDW-SAN
4h 10mnonstop
6:25 pm - 1:40 amSAN-MDW
5h 15m1 stop
$457Southwest
Find Deal
Mon, Jul 8 - Thu, Jul 11
11:05 am - 8:10 amMDW-SAN
23h 05m3 stops
10:41 am - 7:23 pmSAN-MDW
6h 42m1 stop
Tue, Aug 27 - Thu, Aug 29
8:34 pm - 7:24 amMDW-SAN
36h 50m3 stops
5:05 pm - 6:50 pmSAN-MDW
23h 45m2 stops
Mon, Jun 10 - Wed, Jun 12
2:06 pm - 6:43 pmMDW-SAN
6h 37m1 stop
$78Frontier
Find Deal
Tue, Jun 11
2:06 pm - 6:43 pmMDW-SAN
6h 37m1 stop
$80Frontier
Find Deal
Tue, Jun 11
5:55 am - 2:00 pmMDW-SAN
10h 05m1 stop
$84Frontier
Find Deal
Wed, Jun 12
5:00 pm - 11:39 pmMDW-SAN
8h 39m1 stop
$154Delta
Find Deal
Sat, Nov 9
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
$164Delta
Find Deal
Mon, Nov 11
2:14 pm - 11:55 amMDW-SAN
23h 41m3 stops
Mon, Jul 15
8:00 am - 7:24 amMDW-SAN
25h 24m3 stops
Tue, Jun 11
2:24 pm - 10:49 pmMDW-SAN
10h 25m2 stops
$400Alaska Airlines
Find Deal
Tue, Aug 13
9:18 am - 11:48 amMDW-SAN
28h 30m3 stops
$525WestJet
Find Deal
Wed, Jul 10
9:18 am - 11:48 amMDW-SAN
28h 30m3 stops
$625WestJet
Find Deal
Tue, Jul 9
10:22 pm - 7:10 amMDW-SAN
10h 48m1 stop
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
$180Frontier
Find Deal
Thu, May 30 - Sat, Jun 1
5:01 am - 1:08 pmMDW-SAN
10h 07m1 stop
2:08 pm - 5:12 pmSAN-MDW
25h 04m1 stop
$182Frontier
Find Deal
Thu, May 30 - Mon, Jun 3
5:05 am - 7:04 amMDW-SAN
27h 59m1 stop
10:26 am - 12:00 pmSAN-MDW
23h 34m1 stop
$183Frontier
Find Deal
Sat, Jun 1 - Tue, Jun 4
7:40 am - 4:15 pmMDW-SAN
10h 35m1 stop
10:14 pm - 10:31 amSAN-MDW
10h 17m1 stop
$195Frontier
Find Deal
Sun, Jun 2 - Sun, Jun 9
7:40 am - 4:15 pmMDW-SAN
10h 35m1 stop
8:24 pm - 5:29 amSAN-MDW
7h 05m1 stop
$227Frontier
Find Deal
Sun, Jun 2 - Wed, Jun 12
12:08 pm - 11:25 amMDW-SAN
25h 17m2 stops
10:10 am - 6:30 pmSAN-MDW
30h 20m3 stops
$1,036
Find Deal
Fri, May 31 - Fri, Jun 7
12:08 pm - 1:48 pmMDW-SAN
27h 40m3 stops
10:10 am - 6:30 pmSAN-MDW
30h 20m3 stops
$1,118
Find Deal
Fri, May 31 - Fri, Jun 7
9:46 am - 5:29 pmMDW-SAN
9h 43m2 stops
12:51 pm - 10:01 pmSAN-MDW
7h 10m1 stop
$1,214Delta
Find Deal
Thu, May 30 - Mon, Jun 3
2:15 pm - 10:56 pmMDW-SAN
10h 41m2 stops
10:05 pm - 8:48 amSAN-MDW
8h 43m1 stop
$1,254Delta
Find Deal
Wed, May 29 - Fri, Jun 7
9:46 am - 11:45 amMDW-SAN
27h 59m3 stops
1:05 pm - 6:36 pmSAN-MDW
27h 31m3 stops
$2,149WestJet
Find Deal
Sun, Jun 2 - Sun, Jun 9
8:50 pm - 11:00 pmMDW-SAN
4h 10mnonstop
7:00 pm - 12:55 amSAN-MDW
3h 55mnonstop
$452Southwest
Find Deal
Mon, Jul 8 - Thu, Jul 11

Flights from Midway to San Diego - Travel Insights & Trends

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 flights from Chicago Midway Airport to San Diego clicked on KAYAK for each day over the last 12 months.
For Chicago Midway Airport to San Diego, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from San Diego back to Chicago Midway Airport, the best deals are generally found on Monday, with Sunday being the most expensive.

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 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 September, where tickets cost $298 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $481 and $462 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Chicago Midway Airport to San Diego, you should book around 5 days before departure. For the absolute cheapest price, our data suggests you should book 7 days before departure.

Which airlines provide the cheapest flights from Chicago Midway Airport to San Diego?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 3 days, Frontier offered the best one-way deal for that route, at $78. KAYAK users also found Chicago Midway Airport to San Diego round-trip flights on Frontier from $156 and on Delta from $308.

How many flights are there between Chicago Midway Airport and San Diego per day?

Each day, there are between 3 and 4 nonstop flights that take off from Chicago Midway Airport and land in San Diego, with an average flight time of 4h 08m. The most common departure time is 9:00 pm and most flights take off in the morning. Each week, there are 24 flights. The most frequent day of departure is Friday, when 17% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Chicago Midway Airport and San Diego?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There is only one cabin class option available for the route, which is Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Chicago Midway Airport to San Diego take?

Nonstop flights from Chicago Midway Airport generally make it to San Diego in 4h 10m. The flying distance between the two cities is 1,725 miles.

What’s the earliest departure time from Chicago Midway Airport to San Diego?

Early birds can take the earliest flight from Chicago Midway Airport at 5:10 am and will be landing in San Diego at 7:15 am.

What’s the latest departure time from Chicago Midway Airport to San Diego?

If you prefer to fly at night, the latest flight from Chicago Midway Airport to San Diego jets off at 9:20 pm and lands at 11:25 pm.

Good to know

Low season

August

High season

April

Cheapest flight

$78
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 32% 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 $78 for a one-way ticket and $156 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, and Alaska Airlines 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from Chicago to San Diego are Delta and Frontier. With an average price for the route of $459 and an overall rating of 8.0, Delta is the most popular choice. Frontier is also a great choice for the route, with an average price of $203 and an overall rating of 6.2.

  • 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.

See more FAQs

Prefer to fly non-stop from Chicago Midway Airport to San Diego?

Find which airlines fly direct from Midway to San Diego, which days they fly and book direct flights.

Nonstop 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

Nonstop 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
See more direct flights

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
DeltaOverall score based on 10502 reviews
8.2Boarding
7.4Food
8.0Entertainment
7.9Comfort
8.6Crew
Airline reviews

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

8.0 ExcellentLiam, May 2024SLC - SJC
Read more about Delta reviews

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

There was a loud squeaky sound the whole time we were flying.

Had a broken tray in business class. Crew just shrugged it off.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

Bag drop off was slow and annoying. Only 2 agents at the entire delta desk, and no one directing traffic for what line to be in, many confused people slowed down the process. Boarding was fine. Seats in Delta comfort plus were fine. Snacks were great! Definitely a bonus. The entertainment system was awful — old, slow, not responsive, and completely unable to play games due to some kind of error. But on the other hand, thank you to Delta for the free WiFi. That made it better.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

See my previous comment which is mostly about our flight from Phoenix to SFO

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

Book cheap flights from Chicago to San Diego

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to San Diego found on KAYAK in the last 72 hours.
6/11Tue
1 stopFrontier
6h 37mMDW-SAN
$78
6/11Tue
1 stopFrontier
6h 37mMDW-SAN
$80
6/12Wed
1 stopFrontier
10h 05mMDW-SAN
$84
11/9Sat
1 stopDelta
8h 39mMDW-SAN
$154
11/11Mon
1 stopDelta
6h 54mMDW-SAN
$164
7/15Mon
3 stops
23h 41mMDW-SAN
$271
6/11Tue
3 stops
25h 24mMDW-SAN
$291
8/13Tue
2 stopsAlaska Airlines
10h 25mMDW-SAN
$400
7/10Wed
3 stopsWestJet
28h 30mMDW-SAN
$525
7/9Tue
3 stopsWestJet
28h 30mMDW-SAN
$625

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Last minute flights from Midway to San Diego

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to San Diego that are departing in the next 10 days.
5/30Thu
multi-stopFrontier
10h 48mMDW-SAN
6/1Sat
multi-stopFrontier
7h 29mSAN-MDW
$180
5/30Thu
multi-stopFrontier
10h 07mMDW-SAN
6/3Mon
multi-stopFrontier
25h 04mSAN-MDW
$182
6/1Sat
multi-stopFrontier
27h 59mMDW-SAN
6/4Tue
multi-stopFrontier
23h 34mSAN-MDW
$183
6/2Sun
multi-stopFrontier
10h 35mMDW-SAN
6/9Sun
multi-stopFrontier
10h 17mSAN-MDW
$195
6/2Sun
multi-stopFrontier
10h 35mMDW-SAN
6/12Wed
multi-stopFrontier
7h 05mSAN-MDW
$227
5/31Fri
multi-stop
25h 17mMDW-SAN
6/7Fri
multi-stop
30h 20mSAN-MDW
$1,036
5/31Fri
multi-stop
27h 40mMDW-SAN
6/7Fri
multi-stop
30h 20mSAN-MDW
$1,118
5/30Thu
multi-stopDelta
9h 43mMDW-SAN
6/3Mon
multi-stopDelta
7h 10mSAN-MDW
$1,214
5/29Wed
multi-stopDelta
10h 41mMDW-SAN
6/7Fri
multi-stopDelta
8h 43mSAN-MDW
$1,254
6/2Sun
multi-stopWestJet
27h 59mMDW-SAN
6/9Sun
multi-stopWestJet
27h 31mSAN-MDW
$2,149

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Chicago Midway Airport - San Diego Flights

Departure:

Chicago Midway Airport (MDW)United States

Destination:

San Diego (SAN)United States

Return flight deals:

San Diego - Chicago Midway Airport

Cabin classes:

$670