Cheap flights from San Diego International to Chicago

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Flight deals from San Diego International to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from San Diego International to Chicago? Find the lowest prices on one-way and round-trip tickets right here.

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

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 flights are currently cheapest in June.

Direct flights from San Diego International to Chicago

Alternative San Diego International to Chicago routes

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

San Diego to Chicago: Flight information

The things to know before you go.
Cheapest flight found$158
Cheapest month to flyJune
Average flight time4 hrs, 8 mins
Most popular airlineUnited
Average flights per week346

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

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a round-trip flight from San Diego International to Chicago is $158. 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 7 minutes is the average flight time from San Diego International to Chicago.
United, Southwest Airlines and Alaska Airlines fly direct from San Diego International to Chicago.
There are 346 flights per week flying from San Diego International to Chicago, as of April 2025.
The cheapest month to fly from San Diego International to Chicago is usually April 2025.
If you're flying from San Diego International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the center of Chicago. We've found flights to this airport from $158.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from San Diego International Airport to Chicago on Saturday, June 14, 2025.
Yes – the average flight time is 4 hours and 7 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 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.
In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Frontier Airlines offers the cheapest flight tickets to Chicago.

Traveling from San Diego International Airport (SAN) to Chicago: what you need to know

  • The average time for a direct flight from San Diego International Airport to Chicago is 4 hours 22 minutes.

  • The timezone in Chicago is UTC-5. The city is 2 hours ahead of San Diego, where San Diego International Airport is located.

  • The most popular route is from San Diego International Airport (SAN) to O'Hare International Airport (ORD). Take your pick of 79 weekly services between these two airports. If you want to take off as soon as possible, the earliest flight from SAN to ORD is the 06:15 United option. If you prefer to leave later in the day, the final departure is at 22:59 with American Airlines.

  • To ensure you catch your flight from SAN to Chicago, leave plenty of time to navigate the airport and find your gate. Arriving two hours before international departures and one hour before domestic flights is the standard rule.

  • Going away during a peak time like July? High seasons (like Thanksgiving, Christmas/New Year and spring break) can easily add another hour at check-in and security. Be extra safe and arrive up to four hours before an international flight and two hours before domestic departures.

  • You can catch a direct flight from San Diego International Airport to Chicago that arrives at O'Hare International Airport (ORD).

  • Popular airlines that offer direct flights from San Diego International Airport to Chicago include:

  • You don't need your passport or a visa to travel within United States. You will need a valid identity document though, like an ID card or driver's license. Make sure they're on your packing list after booking your cheap tickets from San Diego International Airport to Chicago.

  • Located around 5 kilometers from the center of San Diego, SAN can be reached in approximately 9 minutes by car, depending on traffic. The journey by public transport takes roughly 20 minutes.

  • Want a handy hotel near SAN? If you're boarding an early flight from San Diego International Airport to Chicago, these accommodation options will put you moments from your departure gate:

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

  • The best price we've found for a one-way ticket from San Diego International Airport to Chicago is $79. The cheapest price for a return flight is $158. Bear in mind fares can change due to availability at the time of booking.

  • Book 9 months before you want to travel. After crunching the numbers on our calendar, this is how far you'll want to book ahead to find cheap tickets from SAN to Chicago.

  • Organize your trip for May. That's the cheapest month for tickets from San Diego International Airport to Chicago. If your travel dates are flexible, use the 'Whole month' tool to find the cheapest price across each month.

  • Snapping up a cheap ticket from SAN to Chicago is easy with Price Alerts. Simply create one of these automatic alerts and we'll let you know as soon as the price has dropped.

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

Airports in Chicago

O'Hare International Airport (ORD)

Chicago Midway International Airport (MDW)

Best time to go to Chicago

  • August is the busiest month to hop on a flight from San Diego International Airport to Chicago while February is the quietest. To work out the best time to visit Chicago, consider whether you like a lively atmosphere or a quieter vibe.

  • The warmest month in Chicago is July, with the temperature ranging between 15ºC and 29ºC. Lock in your flights from San Diego International Airport to Chicago in this month if you enjoy this type of weather.

  • January sees average temperatures of between -12ºC and 3ºC. Look for cheap flights from SAN to Chicago around that time if you like traveling in cooler conditions.

More about Chicago

  • Start your Chicago trip off on the right foot by choosing the ideal place to stay. As soon as you've booked your flight from San Diego International Airport to Chicago, browse our selection of hotels including:

  • There are so many things to discover in this city it can be hard to figure out where to start. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are leading attractions which should be on any good Chicago itinerary.

Complete your Chicago trip with a car rental

  • We use the same magic that helped you find your cheap flight from San Diego International Airport to Chicago to track down incredible deals on car rentals. Search for your ride in seconds and compare offers in one place. Plus you'll find all the info you need to know about car rentals in Chicago, from the most popular car type to the best time to book.

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