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SAN - MDW

$59 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 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
Wed 6/5
Wed 6/12

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 42,830,901 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

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

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Diego to Midway 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
8:34 am - 5:50 amSAN-MDW
19h 16m1 stop
5:01 am - 7:04 amMDW-SAN
28h 03m1 stop
$127Frontier
Find Deal
Wed, May 15 - Wed, May 22
11:04 am - 4:40 amSAN-MDW
15h 36m1 stop
6:00 am - 6:43 pmMDW-SAN
14h 43m1 stop
$138Frontier
Find Deal
Tue, Jun 4 - Tue, Jun 11
2:39 pm - 11:09 amSAN-MDW
18h 30m1 stop
9:10 pm - 2:40 pmMDW-SAN
19h 30m1 stop
$139Frontier
Find Deal
Tue, May 21 - Wed, May 29
8:21 pm - 5:50 amSAN-MDW
7h 29m1 stop
10:01 pm - 7:04 amMDW-SAN
11h 03m1 stop
$140Frontier
Find Deal
Wed, May 29 - Sat, Jun 1
10:15 pm - 8:45 amSAN-MDW
8h 30m1 stop
6:45 pm - 11:39 pmMDW-SAN
6h 54m1 stop
$408Delta
Find Deal
Fri, Oct 18 - Tue, Oct 22
3:15 pm - 11:45 pmSAN-MDW
6h 30m1 stop
6:55 am - 9:15 amMDW-SAN
4h 20mnonstop
$431Southwest
Find Deal
Sun, May 26 - Sun, Jun 2
6:30 pm - 12:20 amSAN-MDW
3h 50mnonstop
12:15 pm - 2:30 pmMDW-SAN
4h 15mnonstop
$524Southwest
Find Deal
Mon, May 20 - Wed, May 22
7:20 pm - 8:37 amSAN-MDW
11h 17m2 stops
9:35 am - 1:56 pmMDW-SAN
6h 21m1 stop
$540Delta
Find Deal
Sun, Sep 1 - Fri, Sep 6
5:05 pm - 6:50 pmSAN-MDW
23h 45m2 stops
8:45 pm - 5:07 pmMDW-SAN
22h 22m2 stops
Wed, Jun 12 - Sun, Jun 23
9:25 am - 6:50 pmSAN-MDW
31h 25m3 stops
10:41 pm - 9:50 pmMDW-SAN
25h 09m2 stops
Wed, Jun 12 - Sun, Jun 23

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 Tuesday, 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 $442 and $343 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure 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 average of all the values for each month.
To get a below average price on the flight from San Diego to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 54 days before departure.

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 $59. KAYAK users also found San Diego to Chicago Midway Airport round-trip flights on Frontier from $127 and on Delta from $408.

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

Each day, there are between 2 and 7 nonstop flights that take off from San Diego and land in Chicago Midway Airport, with an average flight time of 3h 56m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 38 flights. The most frequent day of departure is Thursday, when 18% of all weekly flights depart. The fewest flights depart on a Saturday.

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

Nonstop flights from San Diego generally make it to Chicago Midway Airport in 3h 50m. The flying distance between the two cities is 1,725 miles.

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 12:30 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

$59
Best time to beat the crowds with an average 44% drop in price.
Most popular time to fly and prices are also 20% 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 $59 for a one-way ticket and $127 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 $525 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 10826 reviews
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
7.9Comfort
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.

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).

You need to be a hacker to get the (Free) WiFi

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

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

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.
5/21Tue
1 stopFrontier
7h 08mSAN-MDW
$59
5/18Sat
1 stopFrontier
7h 29mSAN-MDW
$70
5/31Fri
1 stopFrontier
7h 29mSAN-MDW
$73
5/29Wed
1 stopFrontier
7h 29mSAN-MDW
$75
5/14Tue
1 stopFrontier
12h 05mSAN-MDW
$76
6/8Sat
1 stopFrontier
17h 50mSAN-MDW
$80
6/12Wed
2 stops
23h 45mSAN-MDW
$224
6/29Sat
1 stopDelta
8h 43mSAN-MDW
$430
6/30Sun
1 stopDelta
8h 44mSAN-MDW
$458
7/31Wed
2 stopsDelta
10h 11mSAN-MDW
$532

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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.
5/7Tue
multi-stopFrontier
11h 31mSAN-MDW
5/18Sat
multi-stopFrontier
12h 25mMDW-SAN
$228
5/11Sat
multi-stopFrontier
9h 06mSAN-MDW
5/14Tue
multi-stopFrontier
11h 29mMDW-SAN
$229
5/11Sat
multi-stopFrontier
12h 16mSAN-MDW
5/29Wed
multi-stopFrontier
13h 03mMDW-SAN
$232
5/10Fri
multi-stopFrontier
12h 04mSAN-MDW
5/25Sat
multi-stopFrontier
11h 03mMDW-SAN
$239
5/10Fri
multi-stopFrontier
12h 04mSAN-MDW
5/29Wed
multi-stopFrontier
13h 03mMDW-SAN
$242
5/9Thu
multi-stopFrontier
11h 00mSAN-MDW
5/13Mon
multi-stopFrontier
9h 29mMDW-SAN
$244
5/7Tue
multi-stopDelta
8h 46mSAN-MDW
5/9Thu
multi-stopDelta
6h 52mMDW-SAN
$655
5/7Tue
multi-stopDelta
7h 05mSAN-MDW
5/10Fri
multi-stopDelta
7h 22mMDW-SAN
$659
5/8Wed
multi-stop
27h 55mSAN-MDW
5/12Sun
multi-stop
17h 02mMDW-SAN
$770
5/7Tue
multi-stopDelta
8h 06mSAN-MDW
5/8Wed
multi-stopDelta
26h 06mMDW-SAN
$999

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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: