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$62 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 5/21. 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 6/8
Sat 6/15

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 43,968,530 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
8:55 pm - 10:14 amMDW-SAN
15h 19m1 stop
5:06 pm - 11:09 amSAN-MDW
16h 03m1 stop
$133Frontier
Find Deal
Thu, May 23 - Wed, May 29
5:01 am - 7:04 amMDW-SAN
28h 03m1 stop
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
$134Frontier
Find Deal
Wed, May 22 - Sat, May 25
10:33 pm - 8:58 amMDW-SAN
12h 25m1 stop
8:54 am - 7:55 pmSAN-MDW
9h 01m1 stop
$135Frontier
Find Deal
Sat, May 18 - Tue, May 21
10:01 pm - 7:04 amMDW-SAN
11h 03m1 stop
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
$136Frontier
Find Deal
Sat, May 18 - Wed, May 22
5:01 am - 1:08 pmMDW-SAN
10h 07m1 stop
6:34 pm - 5:50 amSAN-MDW
9h 16m1 stop
$139Frontier
Find Deal
Thu, May 30 - Sun, Jun 2
10:33 pm - 8:58 amMDW-SAN
12h 25m1 stop
10:11 am - 9:06 pmSAN-MDW
8h 55m1 stop
$140Frontier
Find Deal
Sat, May 18 - Sat, Jun 1
10:33 pm - 8:58 amMDW-SAN
12h 25m1 stop
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
$143Frontier
Find Deal
Sat, May 18 - Fri, May 31
6:00 am - 6:24 amMDW-SAN
26h 24m1 stop
8:40 pm - 6:33 amSAN-MDW
7h 53m1 stop
$144Frontier
Find Deal
Tue, Aug 20 - Tue, Aug 27
10:22 pm - 7:10 amMDW-SAN
10h 48m1 stop
2:04 pm - 9:54 pmSAN-MDW
5h 50m1 stop
$146Frontier
Find Deal
Thu, May 30 - Sun, Jun 2
10:01 pm - 7:04 amMDW-SAN
11h 03m1 stop
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
$147Frontier
Find Deal
Sat, May 25 - Wed, May 29

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 Tuesday, 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 $468 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 5 days before departure.

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 12m. The most common departure time is 6:00 am and most flights take off in the morning. Each week, there are 42 flights. The most frequent day of departure is Thursday, 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

$62
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 $62 for a one-way ticket and $133 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 10789 reviews
8.6Crew
8.2Boarding
7.9Comfort
8.0Entertainment
7.4Food
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

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

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.

The check in at the airport was awful. Told I need to pay for a bag. The item was taken at screening. I went back to get my $ back and they gave me a coupon with a QR code that doesn’t work. Worst costumer service ever!!!!!

4 hour delay because they used our aircraft to fly a different segment (per the captain)

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.
5/21Tue
1 stopFrontier
9h 56mMDW-SAN
$62
5/22Wed
1 stopFrontier
28h 03mMDW-SAN
$66
6/15Sat
1 stopFrontier
8h 37mMDW-SAN
$67
6/15Sat
1 stopFrontier
8h 37mMDW-SAN
$70
6/11Tue
2 stopsFrontier
15h 24mMDW-SAN
$73
5/18Sat
1 stopFrontier
12h 25mMDW-SAN
$76
5/27Mon
1 stopDelta
6h 34mMDW-SAN
$271
6/13Thu
3 stops
25h 08mMDW-SAN
$387
6/2Sun
1 stopDelta
7h 24mMDW-SAN
$449
7/21Sun
1 stopDelta
7h 19mMDW-SAN
$484

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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.
5/14Tue
multi-stopFrontier
11h 29mMDW-SAN
5/15Wed
multi-stopFrontier
6h 18mSAN-MDW
$140
5/14Tue
multi-stopFrontier
11h 29mMDW-SAN
5/21Tue
multi-stopFrontier
7h 08mSAN-MDW
$154
5/14Tue
multi-stopFrontier
28h 54mMDW-SAN
5/16Thu
multi-stopFrontier
10h 21mSAN-MDW
$172
5/11Sat
multi-stopFrontier
13h 27mMDW-SAN
5/22Wed
multi-stopFrontier
7h 29mSAN-MDW
$218
5/13Mon
multi-stopFrontier
9h 29mMDW-SAN
5/15Wed
multi-stopFrontier
19h 16mSAN-MDW
$223
5/12Sun
multi-stopFrontier
11h 56mMDW-SAN
5/22Wed
multi-stopFrontier
7h 29mSAN-MDW
$228
5/13Mon
multi-stop
22h 33mMDW-SAN
5/23Thu
multi-stop
23h 21mSAN-MDW
$455
5/14Tue
multi-stopDelta
8h 57mMDW-SAN
5/15Wed
multi-stopDelta
12h 37mSAN-MDW
$927
5/14Tue
multi-stopDelta
9h 43mMDW-SAN
5/15Wed
multi-stopDelta
12h 37mSAN-MDW
$949
5/14Tue
multi-stopDelta
16h 42mMDW-SAN
5/15Wed
multi-stopDelta
12h 37mSAN-MDW
$1,178

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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