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C$99 Cheap Flights from San Diego (SANA) to Chicago Midway (MDW)

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Flight deals from San Diego to Chicago Midway Airport

Looking for a cheap last-minute deal or the best return flight from San Diego to Chicago Midway Airport? If you want to travel next month, return fares start from C$270. Find the lowest prices on one-way and return tickets right here.
Chicago.C$99 per passenger.Departing Thu., Apr. 23.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Thu., Apr. 23, arriving in Chicago Midway.Price includes taxes and charges.From C$99, select.
Chicago.C$111 per passenger.Departing Tue., May 5.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue., May 5, arriving in Chicago Midway.Price includes taxes and charges.From C$111, select.
Chicago.C$134 per passenger.Departing Tue., May 19.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue., May 19, arriving in Chicago Midway.Price includes taxes and charges.From C$134, select.
Chicago.C$135 per passenger.Departing Sat., Apr. 25.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Sat., Apr. 25, arriving in Chicago Midway.Price includes taxes and charges.From C$135, select.
Chicago.C$190 per passenger.Departing Tue., Jun. 23.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue., Jun. 23, arriving in Chicago Midway.Price includes taxes and charges.From C$190, select.
Chicago.C$191 per passenger.Departing Mon., Jul. 20.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Mon., Jul. 20, arriving in Chicago Midway.Price includes taxes and charges.From C$191, select.
Chicago.C$205 per passenger.Departing Tue., Aug. 4.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Tue., Aug. 4, arriving in Chicago Midway.Price includes taxes and charges.From C$205, select.
Chicago.C$221 per passenger.Departing Tue., Jul. 21.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue., Jul. 21, arriving in Chicago Midway.Price includes taxes and charges.From C$221, select.
Chicago.C$221 per passenger.Departing Sun., Jun. 7.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Sun., Jun. 7, arriving in Chicago Midway.Price includes taxes and charges.From C$221, select.
Chicago.C$222 per passenger.Departing Tue., Oct. 20.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Tue., Oct. 20, arriving in Chicago Midway.Price includes taxes and charges.From C$222, select.
Chicago.C$222 per passenger.Departing Wed., Aug. 12.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Wed., Aug. 12, arriving in Chicago Midway.Price includes taxes and charges.From C$222, select.
Chicago.C$223 per passenger.Departing Thu., Sep. 17.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Thu., Sep. 17, arriving in Chicago Midway.Price includes taxes and charges.From C$223, select.
Chicago.C$249 per passenger.Departing Sat., Dec. 26.One-way flight with Delta.Outbound indirect flight with Delta, departs from San Diego International on Sat., Dec. 26, arriving in Chicago Midway.Price includes taxes and charges.From C$249, select.
Chicago.C$281 per passenger.Departing Mon., Mar. 30.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from San Diego International on Mon., Mar. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$281, select.
Chicago.C$361 per passenger.Departing Mon., Mar. 30.One-way flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from San Diego International on Mon., Mar. 30, arriving in Chicago Midway.Price includes taxes and charges.From C$361, select.

Find the cheapest month to fly from San Diego 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 to Chicago Midway flights are currently cheapest in April.
Mar.
from C$281
Apr.
from C$99
May
from C$111
Jun.
from C$190
Jul.
from C$191
Aug.
from C$205
Sep.
from C$223
Oct.
from C$222
Nov.
Find prices
Dec.
from C$249
Jan.
Find prices
Feb.
Find prices

Which airlines fly from San Diego to Chicago Midway?

San Diego to Chicago Midway: Alternative routes

Compare routes from San Diego 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
ClosestCheapest
from C$99
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from C$99
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
from C$164
Search flights

San Diego to Chicago: Flight information

The things to know before you go.
Cheapest flight foundC$99
Cheapest month to flyApril
Average flight time3 hrs, 58 mins
Most popular airlineSouthwest Airlines
Average flights per week26

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

The best price we found for a return flight from San Diego to Chicago Midway is C$227. 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 58 minutes is the average flight time from San Diego to Chicago Midway.
Southwest Airlines flies direct from San Diego to Chicago Midway.
As of March 2026, there are 26 flights per week flying from San Diego to Chicago Midway.
The cheapest month to fly from San Diego to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from San Diego to Chicago Midway Airport on Tuesday, May 12, 2026.
Yes – the average flight time is 3 hours and 58 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.

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

  • Start planning your trip by checking out the ideal departure point for your flight from San Diego to Chicago Midway International Airport (MDW). Explore the options for setting off from San Diego International Airport (SAN) or McClellan-Palomar Airport (CLD), two of the city's main airports.

  • Expect to be in the air for 3 hours 57 minutes. On average, that's the time it takes for a direct flight from San Diego to Chicago Midway International Airport.

  • Chicago is 2 hours ahead of San Diego. Chicago Midway International Airport is located in Chicago, which operates on the UTC-5 timezone.

  • San Diego International Airport (SAN) to Chicago Midway International Airport (MDW) is the most popular route. There are 15 direct departures a week to choose from. If you prefer starting your day later, hop on the last flight with Southwest Airlines at 19:05. Opt for the first SAN to MDW departure operated by Southwest Airlines at 06:20 if you want to get going earlier.

  • Get to the airport on time so you don't miss your flight from San Diego to MDW. Be there at least two hours ahead for international flights and an hour early for domestic departures to avoid sprinting to your gate.

  • With more people on the move during busy periods like July, get to the terminal earlier than usual. Two hours for domestic flights and up to four for international journeys will allow extra time for delays. Remember things also get busy during major holidays like Thanksgiving.

Airports in San Diego

San Diego International Airport (SAN)

  • San Diego International Airport (SAN) provides a hassle-free way to reach your destination. Nonstop flights from San Diego to Chicago Midway International Airport (MDW) leave from this terminal.

  • Southwest Airlines is a popular airline that operates direct flights from San Diego to Chicago Midway International Airport taking off from SAN.

  • From central San Diego, SAN is approximately 5 kilometres away. Use navigation apps or check the official airport website to find the best way to reach the terminal.

  • Need a handy hotel near San Diego International Airport? If you're catching an early flight from San Diego to Chicago Midway International Airport, these stays will put you moments from check-in:

About Chicago Midway International Airport (MDW)

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • From Chicago Midway International Airport, Chicago is approximately 19 kilometres away. It takes around 21 minutes to get to the centre driving.

  • It takes roughly 46 minutes if you're travelling by public transport.

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

  • For a one-way ticket from San Diego to Chicago Midway International Airport, C$99 is the best price we've seen. You can also book a return flight starting from C$227. These are currently the lowest fares but could change based on availability.

  • Get flight tickets from San Diego to MDW by booking 9 months ahead. According to flight price data, that's the sweet spot for finding a bargain.

  • The cheapest month for tickets from San Diego to Chicago Midway International Airport is June. Use the 'Whole month' search feature to find the most affordable day to fly if you're flexible with your departure dates.

  • Create a Price Alert for flight tickets from San Diego to MDW. You don't need to check every day to see if prices have dropped. We'll notify you when the price changes.

  • Use the filters to tailor your flights from San Diego to Chicago Midway International Airport. Simply select your ideal arrival and departure times, number of stops and airlines. You can also sort your results by 'Cheapest' to get the best deals.

The best time to fly from San Diego to Chicago Midway International Airport (MDW)

  • July is the most popular month for flights from San Diego to Chicago Midway International Airport. To escape the crowds, plan your trip to Chicago in May when things are quieter.

  • Before booking a flight from San Diego to MDW, think about the type of weather you enjoy. July is the warmest month in Chicago, with the temperature ranging from 15ºC to 29ºC.

  • Look for cheap flights from San Diego to Chicago Midway International Airport in January if you like cooler conditions. Temperatures are at their lowest around then, ranging between -12ºC and 3ºC on average.

More about Chicago

Complete your Chicago trip with a car rental

  • Finding you a cheap flight from San Diego to Chicago Midway International Airport isn't the only thing we're good at. Browse our car rentals in Chicago and explore on your own terms. We search for deals from trusted car rental providers and put them all in one place. You can instantly compare offers and then book with no fees.

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 45 days.