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Cheap Flights from San Diego International to Chicago Midway

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      Travellers and cabin class, 1 Adult, Economy

      Compare San Diego International to Chicago Midway flight deals

      Find the cheapest month or even day of the year to fly to Chicago Midway

      Book the best Chicago Midway fare with no extra fees

      Flight deals from San Diego International to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from San Diego International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from R 3,712. Find the lowest prices on one-way and return tickets right here.
      Chicago.R 1,852 per passenger.Departing Sat, 29 Aug.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Sat, 29 Aug, arriving in Chicago Midway.Price includes taxes and charges.From R 1,852, select.
      Chicago.R 1,852 per passenger.Departing Wed, 18 Nov.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Wed, 18 Nov, arriving in Chicago Midway.Price includes taxes and charges.From R 1,852, select.
      Chicago.R 1,852 per passenger.Departing Tue, 6 Oct.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 6 Oct, arriving in Chicago Midway.Price includes taxes and charges.From R 1,852, select.
      Chicago.R 1,856 per passenger.Departing Tue, 8 Sep.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 8 Sep, arriving in Chicago Midway.Price includes taxes and charges.From R 1,856, select.
      Chicago.R 2,102 per passenger.Departing Mon, 14 Dec.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Mon, 14 Dec, arriving in Chicago Midway.Price includes taxes and charges.From R 2,102, select.
      Chicago.R 2,284 per passenger.Departing Tue, 28 Jul.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue, 28 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 2,284, select.
      Chicago.R 2,930 per passenger.Departing Tue, 26 Jan.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 26 Jan, arriving in Chicago Midway.Price includes taxes and charges.From R 2,930, select.
      Chicago.R 3,090 per passenger.Departing Wed, 24 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Diego International on Wed, 24 Mar, arriving in Chicago Midway.Price includes taxes and charges.From R 3,090, select.
      Chicago.R 3,095 per passenger.Departing Wed, 21 Apr.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Diego International on Wed, 21 Apr, arriving in Chicago Midway.Price includes taxes and charges.From R 3,095, select.
      Chicago.R 3,318 per passenger.Departing Tue, 28 Jul.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue, 28 Jul, arriving in Chicago Midway.Price includes taxes and charges.From R 3,318, select.
      Chicago.R 3,415 per passenger.Departing Sun, 28 Feb.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Diego International on Sun, 28 Feb, arriving in Chicago Midway.Price includes taxes and charges.From R 3,415, select.
      Chicago.R 4,349 per passenger.Departing Sun, 28 Feb.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Sun, 28 Feb, arriving in Chicago Midway.Price includes taxes and charges.From R 4,349, select.

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

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like San Diego International to Chicago Midway flights are currently cheapest in August.
      Jul
      from R 2,284
      Aug
      from R 1,852
      Sep
      from R 1,856
      Oct
      from R 1,852
      Nov
      from R 1,852
      Dec
      from R 2,102
      Jan
      from R 2,930
      Feb
      from R 3,415
      Mar
      from R 3,090
      Apr
      from R 3,095
      May
      Find prices
      Jun
      Find prices

      Direct flights from San Diego International to Chicago Midway

      San Diego International to Chicago Midway: Alternative routes

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

      Chicago Midway

      14km from central Chicago
      Closest
      from R 1,854
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from R 1,130
      Search flights

      Chicago Rockford

      127km from central Chicago
      from R 1,359
      Search flights

      San Diego to Chicago: Flight information

      The things to know before you go.
      Cheapest flight foundR 1,852
      Cheapest month to flyNovember
      Average flight time3 hrs, 55 mins
      Most popular airlineSouthwest Airlines
      Average flights per week25

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

      The best price we found for a return flight from San Diego International to Chicago Midway is R 3,704. 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.
      3 hours and 55 minutes is the average flight time from San Diego International to Chicago Midway.
      Southwest Airlines flies direct from San Diego International to Chicago Midway.
      As of July 2026, there are 25 flights per week flying from San Diego International to Chicago Midway.
      The cheapest month to fly from San Diego International to Chicago Midway is usually October.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Diego International Airport to Chicago Midway Airport on Wednesday, 28 October 2026.
      Yes – the average flight time is 3 hours and 55 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 Chicago Midway 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 Chicago 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 Chicago Midway.

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

      • Around 3 hours 55 minutes is how long you can expect to be travelling on a direct flight from San Diego International Airport to Chicago Midway Airport.

      • Chicago's timezone is UTC-6, which makes Chicago two hours ahead of San Diego.

      • Flights from SAN to MDW start at 06:30 — the first with Southwest Airlines. The last service of the day is at 19:55 with Southwest Airlines. Overall, there are 14 weekly San Diego International Airport to Chicago Midway Airport flights.

      • Your SAN to MDW flight won't wait if you're running late, so show up at the airport on time. Arrive up to one hour in advance for domestic flights and two hours ahead when you're flying internationally.

      • You can expect longer queues during popular months such as August. Arriving up to four hours in advance for an international flight and two hours for domestic departures is a wise move.

      • Southwest Airlines is your ticket to exploring Chicago (and maybe even some other exciting parts of the United States!). Browse the direct flights from San Diego International Airport to Chicago Midway Airport offered by this airline.

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

      • With 75.73% of its services arriving as scheduled, Southwest Airlines is the most punctual carrier operating SAN to MDW flights.

      • Consider adding a stopover when booking your ticket from San Diego International Airport to Chicago Midway Airport. Just deselect 'Direct flights only' to break up your journey, or enjoy a detour to a new and interesting place. Here's where you can stop between SAN and MDW:

        • Denver International Airport

        • Phoenix Sky Harbour Airport

        • Harry Reid International Airport

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

      • The lowest price we've seen for a one-way San Diego International Airport to Chicago Midway Airport flight is R 1,852. A round-trip plane ticket is currently R 3,704. Depending on the availability when you book, these fares can change.

      • Book one month before you want to fly. After looking at the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from SAN to MDW.

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

      • Getting your hands on cheap flights from SAN to MDW is a breeze with Price Alerts. Simply create one of these automatic alerts and we'll get in touch as soon as a new discounted fare appears.

      • Discover the right flight for you by using the filters. To see the 'Best,' 'Cheapest' or 'Fastest' flights from San Diego International Airport to Chicago Midway Airport, use the 'Sort by' function. You can also filter results by departure and arrival times, airline, and journey duration.

      Handy information about San Diego International Airport (SAN)

      • SAN's address is N Harbour Dr.

      • When it comes to the on-time performance of San Diego International Airport, data shows 74% of flights complete their journey on time.

      • Central San Diego to San Diego International Airport is around 5 kilometres. Depending on traffic, it'll take about 15 minutes to get there if you're catching a taxi, ride-sharing or driving.

      • The journey when using public transport takes roughly 25 minutes.

      • Catching an early flight from San Diego International Airport to Chicago Midway Airport? Avoid the last-minute rush to the terminal (and sneak in some extra precious sleep) by picking one of these stays near SAN:

      Arriving at Chicago Midway Airport (MDW)

      • If you're arriving on a late San Diego International Airport to Chicago Midway Airport flight, nothing beats the convenience of staying close to the terminal. Grab your bags from the carousel and then be showered and snoozing shortly after at one of these options near MDW:

      • Pick up a Chicago Midway Airport rental car and explore Chicago and beyond with your own set of wheels. Dollar, Hertz and Budget are top providers you can book with here.

      • For the best deal, book your vehicle from Chicago Midway Airport about four weeks in advance.

      When to fly to Chicago Midway Airport (MDW)

      • July is the busiest month for flights from San Diego International Airport to Chicago Midway Airport. To avoid the crowds, visit Chicago in December.

      • The warmest month in Chicago is July, with temperatures ranging between 16ºC (61ºF) and 28ºC (82ºF). Book your flights from San Diego International Airport to Chicago Midway Airport in this month if you enjoy this type of weather.

      • Look for cheap tickets from SAN to MDW in January if you'd rather travel during cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

      Explore more of the United States

      • You've visited Chicago, now it's time to explore other parts of the United States. Journey around 451 kilometres south-east to Columbus to check off its leading sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you've got a jam-packed schedule ahead.

      • Indianapolis is another favourite destination in the United States and is around 257 kilometres south-east of Chicago. No trip is complete without visiting Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

      Plan the rest of your trip from San Diego to Chicago

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