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SAN - MDW

$72 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 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
Tue 7/2
Tue 7/9

Search 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
In the last 7 days travelers have searched 42,335,261 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 San Diego to Midway (SAN-MDW)

 
These are the cheapest deals for flights from San Diego to Midway 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 San Diego to Midway

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

Recent one-way flight deals from San Diego to Midway

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

Recent last minute flight deals from San Diego to Midway

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

Recent direct flight deals from San Diego to Midway

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

Cheap bus & train deals from San Diego to Midway

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

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
10:15 am - 11:52 amSAN-MDW
23h 37m1 stop
10:00 pm - 8:05 pmMDW-SAN
24h 05m1 stop
$136Frontier
Find Deal
Tue, Sep 10 - Wed, Sep 18
9:30 pm - 10:42 amSAN-MDW
11h 12m1 stop
6:00 am - 1:54 pmMDW-SAN
9h 54m1 stop
$140Frontier
Find Deal
Tue, Aug 20 - Sat, Aug 24
9:06 pm - 6:33 amSAN-MDW
7h 27m1 stop
10:00 pm - 10:14 amMDW-SAN
14h 14m1 stop
$150Frontier
Find Deal
Thu, Sep 19 - Mon, Sep 23
8:24 pm - 5:29 amSAN-MDW
7h 05m1 stop
5:40 am - 7:23 pmMDW-SAN
15h 43m2 stops
$154Frontier
Find Deal
Wed, Jun 12 - Sat, Jun 15
10:14 pm - 10:31 amSAN-MDW
10h 17m1 stop
5:40 am - 7:23 pmMDW-SAN
15h 43m2 stops
$155Frontier
Find Deal
Thu, Jun 13 - Sat, Jun 15
8:36 am - 9:02 pmSAN-MDW
10h 26m1 stop
6:00 am - 1:54 pmMDW-SAN
9h 54m1 stop
$164Frontier
Find Deal
Tue, Aug 13 - Sat, Aug 17
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
3:45 pm - 9:02 pmMDW-SAN
7h 17m1 stop
$318Delta
Find Deal
Fri, Oct 18 - Tue, Oct 22
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
$353Delta
Find Deal
Wed, Oct 16 - Mon, Oct 21
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
9:35 am - 2:05 pmMDW-SAN
6h 30m1 stop
$377Delta
Find Deal
Thu, Oct 24 - Mon, Oct 28
1:38 pm - 7:00 pmSAN-MDW
27h 22m3 stops
9:08 pm - 7:24 amMDW-SAN
36h 16m3 stops
Thu, Jun 27 - Mon, Jul 1
8:24 pm - 5:21 amSAN-MDW
6h 57m1 stop
$72Frontier
Find Deal
Sat, Jun 8
8:41 pm - 6:33 amSAN-MDW
7h 52m1 stop
$74Frontier
Find Deal
Mon, Sep 2
8:40 pm - 6:33 amSAN-MDW
7h 53m1 stop
$75Frontier
Find Deal
Tue, Sep 3
10:14 pm - 10:31 amSAN-MDW
10h 17m1 stop
$76Frontier
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Thu, Jun 13
10:05 pm - 8:38 amSAN-MDW
8h 33m1 stop
$164Delta
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Fri, Aug 30
4:22 pm - 11:18 amSAN-MDW
16h 56m3 stops
Thu, Jul 11
5:50 pm - 8:17 pmSAN-MDW
24h 27m2 stops
Sun, Jul 7
7:20 pm - 8:42 amSAN-MDW
11h 22m2 stops
$307Delta
Find Deal
Thu, Sep 5
12:35 pm - 6:38 pmSAN-MDW
28h 03m3 stops
$614WestJet
Find Deal
Fri, Aug 30
12:35 pm - 1:44 pmSAN-MDW
23h 09m3 stops
$1,286WestJet
Find Deal
Sat, Jun 8
8:21 pm - 5:29 amSAN-MDW
7h 08m1 stop
8:58 pm - 7:20 amMDW-SAN
12h 22m1 stop
$160Frontier
Find Deal
Wed, Jun 5 - Wed, Jun 12
8:21 pm - 4:40 amSAN-MDW
6h 19m1 stop
8:58 pm - 7:20 amMDW-SAN
12h 22m1 stop
$162Frontier
Find Deal
Tue, Jun 4 - Wed, Jun 12
8:21 pm - 5:29 amSAN-MDW
7h 08m1 stop
6:00 am - 6:43 pmMDW-SAN
14h 43m1 stop
$168Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
8:21 pm - 5:29 amSAN-MDW
7h 08m1 stop
6:00 am - 7:24 pmMDW-SAN
15h 24m2 stops
$174Frontier
Find Deal
Wed, Jun 5 - Tue, Jun 11
8:21 pm - 4:40 amSAN-MDW
6h 19m1 stop
6:35 am - 3:50 pmMDW-SAN
11h 15m1 stop
$188Frontier
Find Deal
Tue, Jun 4 - Thu, Jun 6
5:56 pm - 9:30 pmSAN-MDW
25h 34m1 stop
8:58 pm - 7:20 amMDW-SAN
12h 22m1 stop
$199Frontier
Find Deal
Fri, Jun 7 - Wed, Jun 12
10:50 pm - 7:55 amSAN-MDW
7h 05m1 stop
6:00 am - 11:05 amMDW-SAN
7h 05m1 stop
$634Delta
Find Deal
Tue, Jun 4 - Tue, Jun 11
10:50 pm - 7:55 amSAN-MDW
7h 05m1 stop
1:24 pm - 6:15 pmMDW-SAN
6h 51m1 stop
$673Delta
Find Deal
Mon, Jun 3 - Mon, Jun 10
5:10 pm - 6:50 pmSAN-MDW
23h 40m2 stops
9:08 pm - 4:09 pmMDW-SAN
21h 01m3 stops
Wed, Jun 5 - Fri, Jun 14
10:05 pm - 8:48 amSAN-MDW
8h 43m1 stop
12:45 pm - 7:29 pmMDW-SAN
8h 44m1 stop
$895Delta
Find Deal
Fri, Jun 7 - Mon, Jun 10

Flights from San Diego to Midway - Travel Insights & Trends

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 flights from San Diego to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from San Diego to Chicago Midway Airport. For your return ticket, we recommend flying on a Saturday and avoiding Sundays for the best deals.

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 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 February, where tickets cost $152 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $423 and $341 respectively.

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

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 $72. KAYAK users also found San Diego to Chicago Midway Airport round-trip flights on Frontier from $136 and on Delta from $318.

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

Each day, there are between 3 and 6 nonstop flights that take off from San Diego and land in Chicago Midway Airport, with an average flight time of 3h 57m. The most common departure time is 7:00 am and most flights take off in the afternoon. Each week, there are 29 flights. The most frequent day of departure is Monday, when 21% of all weekly flights depart. The fewest flights depart on a Sunday.

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

Early birds can take the earliest flight from San Diego at 6:30 am and will be landing in Chicago Midway Airport at 12:35 pm.

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

If you prefer to fly at night, the latest flight from San Diego to Chicago Midway Airport jets off at 7:05 pm and lands at 1:00 am.

Good to know

Low season

February

High season

November

Cheapest flight

$72
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 19% 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 $72 for a one-way ticket and $136 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, and Alaska Airlines 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, Delta or Frontier?

    The two airlines most popular with KAYAK users for flights from San Diego to Chicago 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 $219 and an overall rating of 6.2.

  • 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.

See more FAQs

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

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

Nonstop 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

Nonstop 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 airlines flying 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
DeltaOverall score based on 10410 reviews
8.0Entertainment
8.2Boarding
7.4Food
7.9Comfort
8.6Crew
Airline reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

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

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

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

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

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

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

Book cheap flights from San Diego to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from San Diego to Chicago found on KAYAK in the last 72 hours.
6/8Sat
1 stopFrontier
6h 57mSAN-MDW
$72
9/2Mon
1 stopFrontier
7h 52mSAN-MDW
$74
9/3Tue
1 stopFrontier
7h 53mSAN-MDW
$75
6/13Thu
1 stopFrontier
10h 17mSAN-MDW
$76
8/30Fri
1 stopDelta
8h 33mSAN-MDW
$164
7/11Thu
3 stops
16h 56mSAN-MDW
$276
7/7Sun
2 stops
24h 27mSAN-MDW
$295
9/5Thu
2 stopsDelta
11h 22mSAN-MDW
$307
8/30Fri
3 stopsWestJet
28h 03mSAN-MDW
$614
6/8Sat
3 stopsWestJet
23h 09mSAN-MDW
$1,286

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Last minute flights from San Diego to Midway

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 San Diego to Chicago that are departing in the next 10 days.
6/5Wed
multi-stopFrontier
7h 08mSAN-MDW
6/12Wed
multi-stopFrontier
12h 22mMDW-SAN
$160
6/4Tue
multi-stopFrontier
6h 19mSAN-MDW
6/12Wed
multi-stopFrontier
12h 22mMDW-SAN
$162
6/5Wed
multi-stopFrontier
7h 08mSAN-MDW
6/11Tue
multi-stopFrontier
14h 43mMDW-SAN
$168
6/5Wed
multi-stopFrontier
7h 08mSAN-MDW
6/11Tue
multi-stopFrontier
15h 24mMDW-SAN
$174
6/4Tue
multi-stopFrontier
6h 19mSAN-MDW
6/6Thu
multi-stopFrontier
11h 15mMDW-SAN
$188
6/7Fri
multi-stopFrontier
25h 34mSAN-MDW
6/12Wed
multi-stopFrontier
12h 22mMDW-SAN
$199
6/4Tue
multi-stopDelta
7h 05mSAN-MDW
6/11Tue
multi-stopDelta
7h 05mMDW-SAN
$634
6/3Mon
multi-stopDelta
7h 05mSAN-MDW
6/10Mon
multi-stopDelta
6h 51mMDW-SAN
$673
6/5Wed
multi-stop
23h 40mSAN-MDW
6/14Fri
multi-stop
21h 01mMDW-SAN
$834
6/7Fri
multi-stopDelta
8h 43mSAN-MDW
6/10Mon
multi-stopDelta
8h 44mMDW-SAN
$895

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San Diego - Chicago Midway Airport Flights

Departure:

San Diego (SAN)United States

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Diego

Cabin classes: