Skyscanner home

198 € Cheap Flights from Chicago Midway to San Diego

Compare Chicago Midway to San Diego flight deals

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

Book the best San Diego fare with no extra fees

Flight deals from Chicago Midway to San Diego

Looking for a cheap last-minute deal or the best return flight from Chicago Midway Airport to San Diego? If you want to travel next month, return fares start from 224 €. Find the lowest prices on one-way and return tickets right here.
San Diego.198 € per passenger.Departing Wed, 30 Sep, returning Mon, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 30 Sep, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 5 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 198 €, select.
San Diego.198 € per passenger.Departing Fri, 2 Oct, returning Mon, 5 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 2 Oct, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 5 Oct, arriving in Chicago Midway.Price includes taxes and charges.From 198 €, select.
San Diego.198 € per passenger.Departing Thu, 12 Nov, returning Mon, 16 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 12 Nov, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 16 Nov, arriving in Chicago Midway.Price includes taxes and charges.From 198 €, select.
San Diego.199 € per passenger.Departing Mon, 21 Sep, returning Sat, 26 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 21 Sep, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sat, 26 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 199 €, select.
San Diego.199 € per passenger.Departing Fri, 30 Oct, returning Wed, 4 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 30 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 199 €, select.
San Diego.224 € per passenger.Departing Mon, 17 Aug, returning Tue, 18 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 17 Aug, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Tue, 18 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 224 €, select.
San Diego.224 € per passenger.Departing Sat, 22 Aug, returning Wed, 2 Sep.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 22 Aug, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Wed, 2 Sep, arriving in Chicago Midway.Price includes taxes and charges.From 224 €, select.
San Diego.225 € per passenger.Departing Tue, 8 Dec, returning Sat, 12 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 Sat, 12 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 225 €, select.
San Diego.254 € per passenger.Departing Thu, 21 Jan, returning Sat, 23 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 Sat, 23 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 254 €, select.
San Diego.269 € per passenger.Departing Tue, 24 Nov, returning Mon, 7 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 24 Nov, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 7 Dec, arriving in Chicago Midway.Price includes taxes and charges.From 269 €, select.
San Diego.291 € per passenger.Departing Wed, 29 Jul, returning Thu, 27 Aug.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 29 Jul, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Thu, 27 Aug, arriving in Chicago Midway.Price includes taxes and charges.From 291 €, select.
San Diego.313 € 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 313 €, select.
San Diego.314 € per passenger.Departing Fri, 29 Jan, returning Mon, 1 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Fri, 29 Jan, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Mon, 1 Feb, arriving in Chicago Midway.Price includes taxes and charges.From 314 €, select.
San Diego.315 € per passenger.Departing Thu, 24 Dec, returning Sun, 10 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 24 Dec, arriving in San Diego International.Inbound direct flight with Southwest Airlines departs from San Diego International on Sun, 10 Jan, arriving in Chicago Midway.Price includes taxes and charges.From 315 €, select.
San Diego.322 € per passenger.Departing Thu, 4 Mar, returning Sun, 7 Mar.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Chicago Midway on Thu, 4 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 322 €, select.
San Diego.331 € per passenger.Departing Fri, 4 Jun, returning Fri, 11 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago Midway on Fri, 4 Jun, arriving in San Diego International.Inbound indirect flight with Delta, departs from San Diego International on Fri, 11 Jun, arriving in Chicago Midway.Price includes taxes and charges.From 331 €, select.

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

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 flights are currently cheapest in October.
Jul
from 356 €
Aug
from 224 €
Sep
from 199 €
Oct
from 198 €
Nov
from 198 €
Dec
from 225 €
Jan
from 254 €
Feb
from 313 €
Mar
from 322 €
Apr
from 335 €
May
from 331 €
Jun
from 331 €

Direct flights from Chicago Midway to San Diego

Alternative Chicago Midway to San Diego routes

Looking for the cheapest, fastest or easiest route from Chicago Midway to San Diego? You could fly into the following airports instead.

San Diego International

4km from central San Diego
ClosestCheapest
from 198 €
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 found198 €
Cheapest month to flyOctober
Average flight time4 hrs, 21 mins
Most popular airlineSouthwest Airlines
Average flights per week26

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

There are 2 airports in San Diego: San Diego International and McClellan-Palomar.
The best price we found for a return flight from Chicago Midway to San Diego is 198 €. 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 21 minutes is the average flight time from Chicago Midway to San Diego.
Southwest Airlines flies direct from Chicago Midway to San Diego.
As of July 2026, there are 26 flights per week flying from Chicago Midway to San Diego.
The cheapest month to fly from Chicago Midway to San Diego is usually October.
If you're flying from Chicago Midway Airport, the cheapest airport near San Diego is San Diego International – which is 4.1 km away from the centre of San Diego. We've found flights into this airport from 198 €.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago Midway Airport to San Diego on Friday, 2 October 2026.
Yes – the average flight time is 4 hours and 21 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 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.

In July, the average temperature is usually around 22°C. August is typically the warmest month in San Diego, when it usually averages around 28°C. You can expect the least rain in June. The coldest month is December, with temperatures averaging 10°C. The rainiest month is February.
Currently, Southwest Airlines offers the cheapest flight tickets to San Diego.

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

  • Expect to be travelling for 3 hours 55 minutes. That's the average time for a direct flight from Chicago Midway International Airport to San Diego.

  • The timezone in San Diego is UTC-8. The city is two hours behind Chicago, where Chicago Midway International Airport is located.

  • Chicago Midway International Airport (MDW) to San Diego International Airport (SAN) is the most traveled route, with 17 flights a week to choose from. If you prefer a later start to the day, the last flight from MDW to SAN is with Southwest Airlines at 21:00. Choose the first departure with Southwest Airlines at 07:10 if you want to fly out earlier.

  • For a smooth journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your MDW to San Diego flight.

  • Travelling during a peak time like July? Major public holidays and other popular seasons can lead to longer lines at security. Play it safe and arrive up to four hours before international flights and two hours before domestic departures.

  • Start your journey at MDW and travel straight to San Diego International Airport (SAN). That will be your arrival point when searching for Chicago Midway International Airport to San Diego tickets.

  • Southwest Airlines is a popular carrier that offers direct flights from Chicago Midway International Airport to San Diego.

  • MDW is about 14 kilometres from central Chicago. If you're driving, catching a taxi or ride-sharing from the centre, it'll take 25 minutes or so to get there, depending on traffic conditions. If you're taking public transport, expect the trip time to be around 30 minutes.

  • Want a leisurely start to your travels? Stay near MDW. Whether you're taking an early flight from Chicago Midway International Airport to San Diego or just don't like being rushed, these hotels put convenience first:

  • 76% of flights departing from Chicago Midway International Airport land at their destination on time.

  • MDW is located at 5700 South Cicero.

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

  • The best price we've found for a one-way Chicago Midway International Airport to San Diego flight is 99 €. The cheapest price for a return flight is 198 €. Keep in mind fares can change due to availability at the time of booking.

  • Don't wait until the last minute. You're more likely to pick up cheap flights from MDW to San Diego if you book early. Airlines often have some excellent early bird deals.

  • If you have flexibility with your travel dates, make the most of the 'Whole month' tool. It'll give you the cheapest price across each month when looking for a Chicago Midway International Airport to San Diego ticket.

  • Picking up a cheap flight from MDW to San Diego is a breeze with Price Alerts. Simply set up one of these automatic notifications and we'll get in touch when a new discount appears.

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

Airports in San Diego

San Diego International Airport (SAN)

  • The distance from San Diego International Airport (SAN) to central San Diego is roughly 5 kilometres. It'll take you about 15 minutes to reach the centre driving.

  • It takes around 25 minutes if you're using public transport.

  • Look into staying at a hotel close to SAN if you have a late flight from Chicago Midway International Airport to San Diego. Settle into one of these options and make your first night all about rest:

  • Lock in the best deal by reserving your ride from San Diego International Airport around two weeks in advance of your flight from MDW to San Diego.

  • The address for SAN is N Harbour Dr.

McClellan-Palomar Airport (CLD)

  • McClellan-Palomar Airport (CLD) is around 48 kilometres from the centre of San Diego. Explore your options for heading into town after your flight from Chicago Midway International Airport to San Diego has touched down.

  • Hang the 'Do not disturb' sign on your door and relax at a hotel near CLD. Here are a few options where you can check in after your MDW to San Diego flight:

  • Save time at the rental desk by completing your booking beforehand. Secure your ride from CLD ahead of time so you can just grab the keys and get going.

Best time to go to San Diego

  • It's time to pick your trip dates for your flight from Chicago Midway International Airport to San Diego. July is the busiest month to travel to San Diego. If you prefer a more relaxed vibe, go in December.

  • The warmest month in San Diego is August, with temperatures ranging between 16ºC (61ºF) and 27ºC (81ºF). Book your Chicago Midway International Airport to San Diego plane ticket then if that's your idea of comfortable weather.

  • February has average temperatures of between 8ºC (46ºF) and 22ºC (72ºF). Search for a cheap ticket from MDW to San Diego around that time if you want to travel when it's cooler.

More about San Diego

  • After booking your flight from Chicago Midway International Airport to San Diego, choose a hotel that puts you right where the action is. Make one of these options your base for exploring San Diego:

  • There are so many things to see and do in this city it can be hard to know where to begin. San Diego Balboa Park, San Diego Zoo and USS Midway Museum are major attractions which should be on any well-planned San Diego itinerary.

Explore more of the United States

  • Los Angeles is just one of the many cities in the United States waiting to be discovered once you've seen San Diego. Around 177 kilometres away to the northwest, its top attractions include Hollywood Sign, Universal Studios Hollywood and Hollywood Bowl.

  • Around 483 kilometres east of San Diego, Phoenix is another essential stop in the United States. No visit is complete without checking out Camelback Mountain, Yayoi Kusama Fireflies Infinity Mirror Room and Heard Museum.

Plan the rest of your trip from Chicago to San Diego

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