Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from San Diego to Chicago (O'Hare) now!
Whether you're traveling for business or pleasure, solo, or with the whole family, you'll enjoy the flexibility of flying Southwest®.
Find your next flight from San Diego to Chicago (O'Hare) now!
San Diego, CA to Chicago (O'Hare), IL
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 35 travel days available.
Southwest seats are first come, first served based on check-in order. But there are ways to board the plane earlier!
We make bag-checking a breeze with our flexible baggage policy. Here’s how to make your journey even smoother:
Take advantage of inflight entertainment with free movies4, free live TV5, free texting6, and $8 inflight Internet7.
We also offer free sodas, coffee, and snacks8—learn more about the inflight food and beverage experience.
Have a change of travel plans? We offer free same-day standby for all fare types. This means that you can retain your current flight while listing for standby on an earlier flight. If a seat becomes available, it’s yours at no charge!
Rapid Rewards Members can redeem their points for flights, hotel stays, rental cars, gift cards, and more. And your points never expire!
| Departing from | San Diego International Airport (SAN) |
|---|---|
| Arriving at | Chicago O'Hare International Airport (ORD) |
| Average flight time | Unavailable |
| Distance | 1723 miles |
| 73† | Weekly flights |
|---|---|
| 0 | Nonstop flight per day Monday through Friday |
| 0 | Nonstop flight on Saturday |
| 0 | Nonstop flight on Sunday |
Other popular flights from San Diego:
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 5/1/2024 and 5/31/2024. Note: route may not operate every day of the week.
Year-round, Chicago is a wonderful place to visit. Midwesterners have a keen way to adapt to the long winters. In Chicago, that means eating lots of deep-dish pizza and other delicious foods available around the city as well as enjoying brewery tours and live shows. Summertime in Chicago makes the cold winters worth it: outdoor festivals and block parties fill up nearly every week and weekend in every neighborhood in the city. Consider one of the neighborhood festivals where local restaurants can share their delicious cuisine, artisans share jewelry and other works of art, and musicians come from around the world to spread happiness to Chicagoans and its visitors. Some of the most famous music festivals occur during the warmer months, including the Chicago Jazz Festival, which takes place in Millennium Park and features world-renown musicians from around the globe.
In addition to music festivals, Chicago is home to a number of famous music venues. The city is the birthplace of its own form of Blues, thanks to musicians like Muddy Waters who emigrated from the South and brought the Delta Blues to the City of Big Shoulders. Today, you can find a few great Blues clubs in the city where local and national musicians play. There are great opportunities to find a range of other genres of music, too, at places like the Vic Theatre, the Aragon Ballroom, the Riviera Theatre, and the Chicago Theatre, to name a few.
Having a good sense of humor is imperative to visiting Chicago, especially in the depths of winter. The city is known for its excellent improv comedy and stand-up comedy scenes. Visit a comedy club to see improv students from the recent classes master their art or enjoy national talent as they fill the auditoriums with laughter. Attend a show at the clubs where some of your favorite comedians got their start. You might even want to test your own chops at an open mic night. Just be sure to get there early to put your name on the list!
1EarlyBird Check-In® pricing starts at $15 one-way, and is subject to availability. Pricing may vary based on the popularity and length of each (one-way) flight. Please see optional travel charges for more details.
2Upgraded boarding prices and benefits are per eligible segment. Flights must be within 24 hours of departure to be eligible for upgraded boarding.
3First and second checked bags. Weight and size limits apply.
4Where available. Available only on WiFi-enabled aircraft. Limited-time offer.
5Due to licensing restrictions, on WiFi-enabled international flights, free live TV and iHeartRadio may not be available for the full duration of flight.
6Texting only allows access to iMessage and WhatsApp (which must be downloaded and activated before connecting to SouthwestWiFi).
7Internet access for $8 per device from takeoff to landing. Price is subject to change. May not be available for the full duration of flight. In order to provide a top-notch Internet experience, we prohibit access to certain high-bandwidth applications and websites. We also prohibit access to certain obscene or offensive content.
8Flights traveling 175 miles or less will have only water available. Complimentary snacks are served on flights over 175 miles. If you’re flying between Hawaii and the continental U.S., you’ll have even more snacks to choose from.
9Free same-day standby: You can list for same-day standby for an earlier flight via a Southwest Customer Service Agent at the airport or the Southwest app or mobile web. You must request to be added to the same-day standby list at least 10 minutes prior to the scheduled departure of your original flight or the no-show policy will apply. If using the app or mobile web, you must list your name 30 minutes ahead of scheduled departure. You will receive a message based on the contact preference selected during booking if you are cleared on the flight. Group bookings and Unaccompanied Minors are not eligible for same-day standby. You will be required to pay any government taxes and fees associated with these itinerary changes but refunds will be provided. Your original boarding position is not guaranteed on your standby flight. Southwest Business Customers booked through travel agencies may need to see a Southwest agent at the airport for a standby listing. See Southwest.com/standby for more details.
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