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$76 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 6/8. 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
Sat 6/15
Sat 6/22

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 42,211,976 times on KAYAK, and here is why:

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

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

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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
5:55 am - 7:01 amMDW-SAN
27h 06m1 stop
8:01 am - 12:00 pmSAN-MDW
25h 59m1 stop
$137Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
6:00 am - 9:25 pmMDW-SAN
17h 25m1 stop
2:34 pm - 4:33 amSAN-MDW
11h 59m1 stop
$139Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
10:22 pm - 7:10 amMDW-SAN
10h 48m1 stop
8:04 am - 9:54 pmSAN-MDW
11h 50m1 stop
$140Frontier
Find Deal
Thu, May 30 - Sun, Jun 2
9:10 pm - 12:42 pmMDW-SAN
17h 32m1 stop
8:04 am - 11:09 amSAN-MDW
25h 05m1 stop
$141Frontier
Find Deal
Tue, May 28 - Sun, Jun 2
5:01 am - 7:14 amMDW-SAN
28h 13m1 stop
8:04 am - 9:54 pmSAN-MDW
11h 50m1 stop
$142Frontier
Find Deal
Fri, May 31 - Sun, Jun 2
9:10 pm - 7:20 pmMDW-SAN
24h 10m1 stop
8:01 am - 10:27 pmSAN-MDW
12h 26m2 stops
$144Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
10:59 pm - 8:22 amMDW-SAN
11h 23m1 stop
8:01 am - 10:27 pmSAN-MDW
12h 26m2 stops
$145Frontier
Find Deal
Sat, Jun 8 - Tue, Jun 11
9:10 pm - 7:19 pmMDW-SAN
24h 09m1 stop
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
$146Frontier
Find Deal
Wed, May 29 - Fri, May 31
2:05 pm - 9:02 pmMDW-SAN
8h 57m1 stop
6:15 am - 5:16 pmSAN-MDW
9h 01m1 stop
$308Delta
Find Deal
Sat, Oct 12 - Sat, Oct 19
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 - 7:45 amMDW-SAN
12h 55m1 stop
$76Frontier
Find Deal
Sat, Jun 8
5:01 am - 7:10 amMDW-SAN
28h 09m1 stop
$77Frontier
Find Deal
Thu, May 30
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
$164Delta
Find Deal
Sun, Nov 10
2:22 pm - 12:30 pmMDW-SAN
24h 08m3 stops
Fri, May 31
6:40 am - 12:20 pmMDW-SAN
7h 40m1 stop
$251Southwest
Find Deal
Wed, May 22
1:35 pm - 9:10 pmMDW-SAN
9h 35m2 stops
$256Southwest
Find Deal
Wed, May 22
12:08 pm - 1:40 pmMDW-SAN
27h 32m3 stops
Mon, Jul 22
9:32 am - 2:24 pmMDW-SAN
6h 52m1 stop
$287Delta
Find Deal
Tue, May 28
9:18 am - 12:18 pmMDW-SAN
29h 00m3 stops
$564WestJet
Find Deal
Sun, Jul 14
9:29 am - 11:45 amMDW-SAN
28h 16m3 stops
$569WestJet
Find Deal
Sun, Jun 9
9:10 pm - 7:21 pmMDW-SAN
24h 11m1 stop
9:33 am - 7:55 pmSAN-MDW
8h 22m1 stop
$137Frontier
Find Deal
Tue, May 21 - Tue, May 28
6:00 am - 7:04 amMDW-SAN
27h 04m1 stop
2:29 pm - 11:52 amSAN-MDW
19h 23m1 stop
$147Frontier
Find Deal
Tue, May 21 - Tue, Aug 27
7:05 am - 3:01 pmMDW-SAN
9h 56m1 stop
9:30 pm - 10:42 amSAN-MDW
11h 12m1 stop
$156Frontier
Find Deal
Tue, May 21 - Tue, Aug 27
5:01 am - 7:04 amMDW-SAN
28h 03m1 stop
2:55 pm - 11:09 amSAN-MDW
18h 14m1 stop
$157Frontier
Find Deal
Sun, May 19 - Sat, May 25
5:11 am - 9:25 pmMDW-SAN
18h 14m1 stop
10:26 am - 11:09 amSAN-MDW
22h 43m1 stop
$159Frontier
Find Deal
Mon, May 20 - Tue, May 28
10:04 am - 12:04 pmMDW-SAN
28h 00m3 stops
10:41 am - 7:23 pmSAN-MDW
6h 42m1 stop
Mon, May 20 - Sun, Aug 25
10:04 am - 12:04 pmMDW-SAN
28h 00m3 stops
10:41 am - 7:23 pmSAN-MDW
6h 42m1 stop
Mon, May 20 - Thu, Aug 22
9:46 am - 5:29 pmMDW-SAN
9h 43m2 stops
10:20 pm - 8:51 amSAN-MDW
8h 31m1 stop
$1,152Delta
Find Deal
Fri, May 17 - Fri, May 17
11:59 am - 8:32 pmMDW-SAN
10h 33m2 stops
11:15 am - 10:01 pmSAN-MDW
8h 46m1 stop
$1,164Delta
Find Deal
Sat, May 18 - Tue, May 21
9:46 am - 11:45 amMDW-SAN
27h 59m3 stops
12:35 pm - 4:55 pmSAN-MDW
26h 20m3 stops
$2,052WestJet
Find Deal
Fri, May 17 - Sat, May 25
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 $465 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 $76. KAYAK users also found Chicago Midway Airport to San Diego round-trip flights on Frontier from $137 and on Delta from $308.

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

Each day, there are between 5 and 7 nonstop flights that take off from Chicago Midway Airport and land in San Diego, with an average flight time of 4h 11m. The most common departure time is 8:00 pm and most flights take off in the morning. Each week, there are 42 flights. The most frequent day of departure is Friday, when 17% of all weekly flights depart. The fewest flights depart on a Wednesday.

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

$76
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 33% 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 $76 for a one-way ticket and $137 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 $464 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 $204 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 10673 reviews
7.4Food
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
Airline reviews

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

6.0 GoodEliza, Apr 2024SAN - LAX
Read more about Delta reviews

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

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Crew was not friendly when I went to request a seat change.

Really impressive staff at airport and on plane, especially given how busy it was

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

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.
6/8Sat
1 stopFrontier
12h 55mMDW-SAN
$76
5/30Thu
1 stopFrontier
28h 09mMDW-SAN
$77
11/10Sun
1 stopDelta
6h 54mMDW-SAN
$164
5/31Fri
3 stops
24h 08mMDW-SAN
$241
5/22Wed
1 stopSouthwest
7h 40mMDW-SAN
$251
5/22Wed
2 stopsSouthwest
9h 35mMDW-SAN
$256
7/22Mon
3 stops
27h 32mMDW-SAN
$260
5/28Tue
1 stopDelta
6h 52mMDW-SAN
$287
7/14Sun
3 stopsWestJet
29h 00mMDW-SAN
$564
6/9Sun
3 stopsWestJet
28h 16mMDW-SAN
$569

Search by stops

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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.
5/21Tue
multi-stopFrontier
24h 11mMDW-SAN
5/28Tue
multi-stopFrontier
8h 22mSAN-MDW
$137
5/21Tue
multi-stopFrontier
27h 04mMDW-SAN
8/27Tue
multi-stopFrontier
19h 23mSAN-MDW
$147
5/21Tue
multi-stopFrontier
9h 56mMDW-SAN
8/27Tue
multi-stopFrontier
11h 12mSAN-MDW
$156
5/19Sun
multi-stopFrontier
28h 03mMDW-SAN
5/25Sat
multi-stopFrontier
18h 14mSAN-MDW
$157
5/20Mon
multi-stopFrontier
18h 14mMDW-SAN
5/28Tue
multi-stopFrontier
22h 43mSAN-MDW
$159
5/20Mon
multi-stop
28h 00mMDW-SAN
8/25Sun
multi-stop
6h 42mSAN-MDW
$454
5/20Mon
multi-stop
28h 00mMDW-SAN
8/22Thu
multi-stop
6h 42mSAN-MDW
$458
5/17Fri
multi-stopDelta
9h 43mMDW-SAN
5/17Fri
multi-stopDelta
8h 31mSAN-MDW
$1,152
5/18Sat
multi-stopDelta
10h 33mMDW-SAN
5/21Tue
multi-stopDelta
8h 46mSAN-MDW
$1,164
5/17Fri
multi-stopWestJet
27h 59mMDW-SAN
5/25Sat
multi-stopWestJet
26h 20mSAN-MDW
$2,052

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Chicago Midway Airport - San Diego Flights

Departure:

Chicago Midway Airport (undefined)United States

Destination:

San Diego (SAN)United States

Return flight deals:

San Diego - Chicago Midway Airport

Cabin classes:

$662