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MDW - SAN

$92 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 8/2. 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
Tue 7/16
Tue 7/23

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 43,982,894 times on KAYAK, and here is why:

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to San Diego 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 and deals for you by selecting your travel dates.
Choose your dates
10:55 pm - 7:20 pmMDW-SAN
22h 25m1 stop
5:56 pm - 8:50 pmSAN-MDW
24h 54m1 stop
$182Frontier
Find Deal
Thu, Jul 11 - Mon, Jul 15
6:15 am - 6:02 pmMDW-SAN
13h 47m1 stop
8:25 pm - 5:33 amSAN-MDW
7h 08m1 stop
$184Frontier
Find Deal
Wed, Jul 10 - Wed, Jul 17
8:59 pm - 12:23 pmMDW-SAN
17h 24m1 stop
7:27 pm - 4:45 amSAN-MDW
7h 18m1 stop
$186Frontier
Find Deal
Wed, Jul 17 - Sun, Jul 21
8:59 pm - 5:12 pmMDW-SAN
22h 13m1 stop
5:56 pm - 8:50 pmSAN-MDW
24h 54m1 stop
$187Frontier
Find Deal
Fri, Jul 12 - Mon, Jul 15
10:28 am - 3:47 pmMDW-SAN
7h 19m1 stop
6:55 am - 5:04 pmSAN-MDW
8h 09m1 stop
$439Delta
Find Deal
Thu, Sep 5 - Sun, Sep 8
8:50 pm - 11:00 pmMDW-SAN
4h 10mnonstop
7:00 pm - 12:55 amSAN-MDW
3h 55mnonstop
$474Southwest
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
$479Southwest
Find Deal
Mon, Jul 8 - Thu, Jul 11
8:50 pm - 1:17 pmMDW-SAN
18h 27m2 stops
8:58 pm - 6:52 pmSAN-MDW
19h 54m3 stops
Wed, Sep 11 - Wed, Sep 18
12:08 pm - 8:33 pmMDW-SAN
10h 25m2 stops
10:05 pm - 8:38 amSAN-MDW
8h 33m1 stop
$573Delta
Find Deal
Thu, Jul 4 - Thu, Jul 11
8:45 pm - 1:17 pmMDW-SAN
18h 32m2 stops
12:45 pm - 6:52 pmSAN-MDW
28h 07m3 stops
Thu, Sep 12 - Wed, Sep 18

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 $295 on average. On the other hand, the most expensive months are March and June, where the average cost of tickets is $481 and $450 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 $92. KAYAK users also found Chicago Midway Airport to San Diego round-trip flights on Frontier from $182 and on Delta from $439.

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

Each day, there are between 3 and 7 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 7:00 am and most flights take off in the morning. Each week, there are 37 flights. The most frequent day of departure is Wednesday, when 19% 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

$92
Best time to beat the crowds but there is an average 17% increase in price.
Most popular time to fly and prices are also 31% 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 $92 for a one-way ticket and $182 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 10000 reviews
7.9Comfort
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

It was very cold because the air conditioner was on high power, and my son got sick.

4.0 OkayAnonymous, Jun 2024ORD - SEA
Read more about Delta reviews

It was very cold because the air conditioner was on high power, and my son got sick.

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

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.

They never updated the boarding pass on their apps to show their delay

Online check-in was not user-friendly. Too many fees, not cost effective.

They wouldn’t let us on the flight even tho we were an hour early. No refund not even our bags that were prepaid

I brought a ticket and car rental through Travelocity. There was no where to add a KTN. So I thought i’d add it by looking up ticket on frontier website. I tried 3 times with the frontier chat bot to add my KTN it never updated my boarding pass. So then I tried showing up early to do it in person at the airport. The first employee update my ktn in the system and gave me a new boarding pass. I was sent back by tsa to join regular line. Then I was told to add my Ktn. It would cost me $25 extra. Given the length of the cue I did pay. Congratulations! BUT I will NEVER fly frontier again. Plus the plane was very old. It had actual ashtrays and old looking tray backs. Worst travel experience ever. Im warning my friends and family not to use frontier ever.

I did not enjoy the trip home on Frontier for several reasons: there is too much cost besides the flight, which was more than I would normally pay, then having to pay for luggage, and carry-on, seat (if you want to reserve when booking) then you must pay over $3 for a can of soda, and $4 for a snack. A cup of water is free.

Did not realize seats did not recline. Best to travel in an exit row... No question

I strongly dislike Frontier. I find them barebones, the seats not particularly comfortable, the nickel and diming is maddening, the app is TERRIBLE - super confusing to navigate, and the last 4 frontier flights I have flown have been on AVERAGE 2 hours late, one ruining a fancy night out in Vegas with reservations made well in advance, which was nodded to with a measly 5000 miles, which translates to almost nothing. At least credit a free checked bag or something.

8 hr delay. had to buy another ticket with another airline

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

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.
8/2Fri
1 stopFrontier
22h 13mMDW-SAN
$92
8/11Sun
1 stopFrontier
28h 07mMDW-SAN
$94
7/13Sat
1 stopFrontier
7h 15mMDW-SAN
$98
7/11Thu
1 stopFrontier
22h 25mMDW-SAN
$104
7/19Fri
2 stops
23h 07mMDW-SAN
$198
8/12Mon
3 stops
22h 37mMDW-SAN
$248
6/21Fri
1 stopDelta
10h 24mMDW-SAN
$275
6/19Wed
1 stopDelta
6h 36mMDW-SAN
$277
7/18Thu
3 stopsWestJet
28h 30mMDW-SAN
$433
7/20Sat
3 stopsWestJet
25h 39mMDW-SAN
$507

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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.
6/18Tue
multi-stopFrontier
27h 01mMDW-SAN
6/22Sat
multi-stopFrontier
17h 50mSAN-MDW
$245
6/20Thu
multi-stopFrontier
28h 00mMDW-SAN
6/22Sat
multi-stopFrontier
17h 50mSAN-MDW
$288
6/20Thu
multi-stopFrontier
14h 51mMDW-SAN
6/25Tue
multi-stopFrontier
10h 17mSAN-MDW
$291
6/20Thu
multi-stopFrontier
14h 51mMDW-SAN
6/24Mon
multi-stopFrontier
7h 05mSAN-MDW
$293
6/17Mon
multi-stopDelta
6h 51mMDW-SAN
6/20Thu
multi-stopDelta
7h 16mSAN-MDW
$672
6/19Wed
multi-stopDelta
7h 04mMDW-SAN
6/25Tue
multi-stopDelta
8h 43mSAN-MDW
$675
6/17Mon
nonstopSouthwest
4h 10mMDW-SAN
6/20Thu
nonstopSouthwest
4h 00mSAN-MDW
$751
6/17Mon
nonstopSouthwest
4h 10mMDW-SAN
6/20Thu
multi-stopSouthwest
5h 15mSAN-MDW
$756
6/21Fri
multi-stopWestJet
28h 19mMDW-SAN
6/23Sun
multi-stopWestJet
23h 09mSAN-MDW
$1,756
6/21Fri
multi-stopWestJet
28h 19mMDW-SAN
6/25Tue
multi-stopWestJet
23h 09mSAN-MDW
$1,803

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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:

$813