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Cheap Flights from Chicago Midway to San Diego International

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

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Flight deals from Chicago Midway to San Diego International

Looking for a cheap last-minute deal or the best return flight from Chicago Midway to San Diego International? Find the lowest prices on one-way and return tickets right here.
San Diego.$219 per passenger.Departing Sat, 18 Apr, returning Sat, 25 Apr.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 18 Apr, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 25 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $219, select.
San Diego.$219 per passenger.Departing Sat, 28 Feb, returning Sat, 7 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 28 Feb, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 7 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $219, select.
San Diego.$232 per passenger.Departing Sat, 25 Apr, returning Sat, 2 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 25 Apr, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 2 May, arriving in Chicago Midway.Price includes taxes and charges.From $232, select.
San Diego.$240 per passenger.Departing Tue, 5 May, returning Sat, 9 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 May, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 9 May, arriving in Chicago Midway.Price includes taxes and charges.From $240, select.
San Diego.$240 per passenger.Departing Tue, 10 Mar, returning Sat, 14 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 10 Mar, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 14 Mar, arriving in Chicago Midway.Price includes taxes and charges.From $240, select.
San Diego.$311 per passenger.Departing Thu, 26 Feb, returning Sat, 28 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 26 Feb, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 28 Feb, arriving in Chicago Midway.Price includes taxes and charges.From $311, select.
San Diego.$344 per passenger.Departing Sun, 1 Mar, returning Wed, 1 Apr.Return flight with Southwest Airlines.Outbound indirect flight with Southwest Airlines, departs from Chicago Midway on Sun, 1 Mar, arriving in San Diego International.Inbound indirect flight with Southwest Airlines, departs from San Diego International on Wed, 1 Apr, arriving in Chicago Midway.Price includes taxes and charges.From $344, select.
San Diego.$473 per passenger.Departing Fri, 3 Jul, returning Mon, 13 Jul.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 3 Jul, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 13 Jul, arriving in Chicago Midway.Price includes taxes and charges.From $473, select.

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 April.
Feb
from $311
Mar
from $240
Apr
from $219
May
from $240
Jun
from $473
Jul
from $473
Aug
from $474
Sep
from $482
Oct
from $568
Nov
from $506
Dec
Find prices
Jan
Find prices

Direct flights from Chicago Midway to San Diego International

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 $219
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$219
Cheapest month to flyFebruary
Average flight time4 hrs, 20 mins
Most popular airlineSouthwest Airlines
Average flights per week19

Check out these San Diego International hotels

Ready to plan your stay? Other travellers rate these San Diego International hotels for cleanliness, service and location.
City24 Hotel Little Italy Mission Hills
1.39 km from San Diego International
$577
Per night
Courtyard by Marriott San Diego Downtown Little Italy
2.36 km from San Diego International
$273
Per night
Carte Hotel San Diego Downtown, Curio Collection By Hilton
2.41 km from San Diego International
$371
Per night
City24 Hotel Little Italy Mission Hills
1.39 km from San Diego International
$577
Per night
Courtyard by Marriott San Diego Downtown Little Italy
2.36 km from San Diego International
$273
Per night
Carte Hotel San Diego Downtown, Curio Collection By Hilton
2.41 km from San Diego International
$371
Per night
Explore top-rated hotels

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 $219. 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 20 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 February 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 February.
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 Saturday, 28 February 2026.
Yes – the average flight time is 4 hours and 20 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 International Airport (MDW) to San Diego International Airport (SAN): what you need to know

  • Take a direct flight from Chicago Midway International Airport to San Diego International Airport and you'll be in the air for an average of 4 hours 20 minutes.

  • San Diego is two hours behind Chicago and is in the UTC-7 timezone.

  • Choose from 16 weekly Chicago Midway International Airport to San Diego International Airport flights. The 05:10 departure with Southwest Airlines is the earliest you can take. Southwest Airlines operates the latest service of the day at 21:20.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This will give you plenty of time to catch your MDW to SAN flight.

  • You can expect bigger queues in popular months like July. Arriving up to four hours in advance for an international flight and two hours for domestic departures will help ensure a smooth travel experience.

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

  • Southwest Airlines is the top choice for travellers on this route.

  • The most punctual carrier that operates MDW to SAN flights is Southwest Airlines. Its services arrive as scheduled 70.07% of the time.

  • Consider adding a stopover when booking your ticket from Chicago Midway International Airport to San Diego International Airport. Simply uncheck 'Direct flights only' to break up your journey, or enjoy a detour to a new and interesting place. Check out these options between MDW and SAN:

    • Phoenix Sky Harbour International Airport

    • Denver International Airport

    • Tucson International Airport

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

  • At the moment, $109 is the cheapest price we've found for a one-way Chicago Midway International Airport to San Diego International Airport flight. The best price for a return plane ticket is $219. Keep in mind that fares could change due to availability at the time of booking.

  • To pick up cheap tickets from MDW to SAN, reserve your journey six months before your planned departure.

  • The cheapest month for flights from Chicago Midway International Airport to San Diego International Airport is May. Use the 'Whole month' tool to find the lowest prices if you have flexible dates.

  • Never miss a deal on cheap flights from MDW to SAN by setting up a Price Alert. You'll get an email or notification on the app when a new discounted fare appears.

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

Handy information about Chicago Midway International Airport (MDW)

  • MDW's address is 5700 South Cicero.

  • Of all flights leaving Chicago Midway International Airport, 77.88% land on time at their destination.

  • To get to Chicago Midway International Airport from central Chicago, it takes around 20 minutes if you're planning to drive. This depends on traffic though. It's approximately 19 kilometres from the airport to the city centre.

  • The journey when using public transport takes roughly 45 minutes.

  • Get your holiday off to a hassle-free start by staying near MDW. Whether you're catching an early flight from Chicago Midway International Airport to San Diego International Airport or want to avoid feeling rushed, these hotels have you covered:

Arriving at San Diego International Airport (SAN)

Getting from San Diego International Airport (SAN) to central San Diego

  • SAN is located at Airport Drive.

  • San Diego International Airport to central San Diego has a drive time of about 10 minutes. It's approximately 5 kilometres away.

  • If you're travelling by public transport, expect a journey of roughly 20 minutes.

When to fly to San Diego International Airport (SAN)

  • July is the most popular month for flights from Chicago Midway International Airport to San Diego International Airport. To avoid the crowds, head to San Diego in May.

  • The warmest month in San Diego is August, with temperatures ranging between 17ºC and 28ºC. Book your flights from Chicago Midway International Airport to San Diego International Airport in this month if you enjoy this type of weather.

  • If you want cooler conditions, look for a cheap ticket from MDW to SAN in February. Temperatures average between 7ºC and 23ºC then.

Explore more of United States

  • San Diego has loads to offer, but there are so many other parts of United States just waiting to be explored. About 177 kilometres north-west of San Diego, a trip to Los Angeles will keep you on the move. Start with leading sights like Griffith Observatory, The Broad and La Brea Tar Pits & Museum.

  • Phoenix is another must-experience destination in United States and is around 483 kilometres east of San Diego. No journey is complete without visiting Desert Botanical Garden, Heard Museum and Papago Park.

More travel options

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.