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Cheap Flights from Chicago Midway to San Diego International

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Chicago Midway to San Diego International flight deals

      Find the cheapest month or even day of the year to fly to San Diego International

      Book the best San Diego International fare with no extra fees

      Flight deals from Chicago Midway to San Diego International

      Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Diego International Airport? If you want to travel next month, return fares start from $453. Find the lowest prices on one-way and return tickets right here.
      San Diego.$452 per passenger.Departing Tue, 20 Oct, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 20 Oct, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Wed, 4 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $452, select.
      San Diego.$452 per passenger.Departing Tue, 20 Oct, returning Tue, 27 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 20 Oct, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 27 Oct, arriving in Chicago Midway.Price includes taxes and charges.From $452, select.
      San Diego.$453 per passenger.Departing Wed, 4 Nov, returning Sat, 7 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 4 Nov, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 7 Nov, arriving in Chicago Midway.Price includes taxes and charges.From $453, select.
      San Diego.$484 per passenger.Departing Tue, 8 Dec, returning Tue, 15 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 8 Dec, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 15 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $484, select.
      San Diego.$485 per passenger.Departing Thu, 17 Dec, returning Sat, 9 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 17 Dec, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 9 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $485, select.
      San Diego.$488 per passenger.Departing Wed, 18 Nov, returning Tue, 1 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 18 Nov, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 1 Dec, arriving in Chicago Midway.Price includes taxes and charges.From $488, select.
      San Diego.$521 per passenger.Departing Mon, 1 Feb, returning Mon, 1 Feb.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Mon, 1 Feb, arriving in San Diego International.Inbound indirect flight with Delta, departs from San Diego International on Mon, 1 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $521, select.
      San Diego.$521 per passenger.Departing Thu, 21 Jan, returning Mon, 25 Jan.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Thu, 21 Jan, arriving in San Diego International.Inbound indirect flight with Delta, departs from San Diego International on Mon, 25 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $521, select.
      San Diego.$524 per passenger.Departing Tue, 2 Feb, returning Sat, 6 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 2 Feb, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 6 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $524, select.
      San Diego.$528 per passenger.Departing Sat, 30 Jan, returning Wed, 3 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 30 Jan, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Wed, 3 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $528, select.
      San Diego.$539 per passenger.Departing Thu, 21 Jan, returning Mon, 25 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 21 Jan, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 25 Jan, arriving in Chicago Midway.Price includes taxes and charges.From $539, select.
      San Diego.$563 per passenger.Departing Wed, 3 Mar, returning Sun, 7 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 3 Mar, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sun, 7 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $563, select.
      San Diego.$564 per passenger.Departing Sat, 27 Feb, returning Thu, 4 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 27 Feb, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Thu, 4 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $564, select.
      San Diego.$690 per passenger.Departing Wed, 7 Apr, returning Wed, 14 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 7 Apr, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Wed, 14 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $690, select.
      San Diego.$692 per passenger.Departing Wed, 12 May, returning Tue, 18 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 12 May, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 18 May, arriving in Chicago Midway.Price includes taxes and charges.From $692, select.
      San Diego.$743 per passenger.Departing Tue, 1 Jun, returning Thu, 1 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Tue, 1 Jun, arriving in San Diego International.Inbound indirect flight with Delta, departs from San Diego International on Thu, 1 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $743, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Chicago Midway to San Diego International found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Chicago Midway to San Diego International

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago Midway to San Diego International flights are currently cheapest in October.
      Oct
      from $452
      Nov
      from $453
      Dec
      from $484
      Jan
      from $521
      Feb
      from $521
      Mar
      from $563
      Apr
      from $690
      May
      from $692
      Jun
      from $885
      Jul
      from $770
      Aug
      from $776
      Sep
      Find prices

      Direct flights from Chicago Midway to San Diego International

      Southwest Airlines

      Chicago Midway to San Diego International: Alternative routes

      Compare routes from Chicago Midway to San Diego below. You may find an airport to fly into that's cheaper, faster, or easier than San Diego International.

      San Diego International

      4km from central San Diego
      ClosestCheapest
      from $452
      Search flights

      McClellan-Palomar

      48km from central San Diego
      Search flights

      Chicago to San Diego: Flight information

      The things to know before you go.
      Cheapest flight found$452
      Cheapest month to flyOctober
      Average flight time4 hrs, 27 mins
      Most popular airlineSouthwest Airlines
      Average flights per week19

      Finding cheap flights from Chicago Midway to San Diego International: Frequently asked questions

      The best price we found for a return flight from Chicago Midway to San Diego International is $452. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      4 hours and 27 minutes is the average flight time from Chicago Midway to San Diego International.
      Southwest Airlines flies direct from Chicago Midway to San Diego International.
      As of October 2026, there are 19 flights per week flying from Chicago Midway to San Diego International.
      The cheapest month to fly from Chicago Midway to San Diego International is usually October.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Diego International Airport on Tuesday, 20 October 2026.
      Yes – the average flight time is 4 hours and 27 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to San Diego International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to San Diego is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Southwest Airlines offers the cheapest flight tickets to San Diego International.

      Travelling from Chicago Midway Airport (MDW) to San Diego International Airport (SAN): what you need to know

      • Hop on a direct flight from Chicago Midway Airport to San Diego International Airport and you'll be travelling for an average of 4 hours 15 minutes.

      • San Diego's timezone is UTC-8, which makes San Diego two hours behind Chicago.

      • Every week, there are 14 Chicago Midway Airport to San Diego International Airport flights. If you prefer to get going as soon as possible, opt for the 07:10 Southwest Airlines flight. If you're eager to make the most of your day before flying, the latest flight is at 21:00 with Southwest Airlines.

      • Give yourself enough time to make your MDW to SAN flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.

      • During popular months such as July, you'll want to get to the airport well in advance. Arrive two hours before domestic departures and four hours ahead for an international flight when you travel during a peak period in general.

      • Southwest Airlines offers direct flights from Chicago Midway Airport to San Diego International Airport. Book with this popular carrier, then get ready to see the sights in San Diego — and maybe even more of the United States if time allows.

      • Most travellers choose to travel with Southwest Airlines on this route.

      • The most punctual carrier operating MDW to SAN flights is Southwest Airlines. Its services land without delay 73.55% of the time.

      • We make it a piece of cake to book a flight with a stopover. To see all your options for tickets from Chicago Midway Airport to San Diego International Airport, uncheck 'Direct flights only.' Then, choose a flight that has a stop long enough to visit your chosen city. Popular stopovers between MDW and SAN include:

        • Denver International Airport

        • Phoenix Sky Harbour Airport

        • Harry Reid International Airport

      How to find the cheapest flights from Chicago Midway Airport (MDW) to San Diego International Airport (SAN)

      • At the moment, $226 is the lowest price we've seen for a one-way Chicago Midway Airport to San Diego International Airport flight. The best price for a return ticket is $452. Bear in mind that fares may change due to demand at the time of booking.

      • Don't wait until the last minute. You're more likely to get cheap tickets from MDW to SAN if you book in advance. Airlines often have some great early bird discounts.

      • The cheapest month for flights from Chicago Midway Airport to San Diego International Airport is May. Use the 'Whole month' tool to see the lowest airfares if you have a flexible schedule.

      • Save time searching for cheap flights from MDW to SAN by creating a Price Alert. We'll send you an email or notification through the app when a lower fare becomes available.

      • Tailor your flights with filters. Choose your departure and arrival times, total journey duration and airlines. You can also sort the results by 'Best,' 'Fastest' or 'Cheapest' flights from Chicago Midway Airport to San Diego International Airport.

      Handy information about Chicago Midway Airport (MDW)

      • The address for MDW is 5700 South Cicero.

      • When it comes to the on-time performance of Chicago Midway Airport, data shows 76% of flights arrive within the scheduled timeframe.

      • To get to Chicago Midway Airport from central Chicago, it'll take about 25 minutes by car. This depends on traffic though. It's approximately 16 kilometres from the airport to the city centre.

      • Planning to take public transport? Expect a journey time of around 30 minutes.

      • Booked an early flight from Chicago Midway Airport to San Diego International Airport? Avoid the last-minute rush to the airport (and sneak in some extra snooze time) by picking one of these stays close to MDW:

      Arriving at San Diego International Airport (SAN)

      When to fly to San Diego International Airport (SAN)

      • The quietest month for a flight from Chicago Midway Airport to San Diego International Airport is March, while August is the busiest. Pick the ideal time to visit San Diego based on whether you prefer a bustling atmosphere or a more laid-back vibe.

      • Before locking in your flight from Chicago Midway Airport to San Diego International Airport, consider the kind of weather you enjoy. August is the warmest month in San Diego, with temperatures ranging from 16ºC to 27ºC.

      • February sees average temperatures of between 8ºC and 22ºC. Look for cheap tickets from MDW to SAN sometime around then if you like travelling in cooler conditions.

      Explore more of the United States

      • Los Angeles is just one of the many places in the United States waiting to be explored after you've experienced San Diego. Around 177 kilometres away to the north-west, check out popular attractions including Hollywood Sign, Universal Studios Hollywood and Hollywood Bowl.

      • Phoenix is another must-experience destination in the United States and is around 483 kilometres east of San Diego. No trip is complete without visiting Camelback Mountain, Yayoi Kusama Fireflies Infinity Mirror Room and Heard Museum.

      More travel options

      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.