Main Cabin Extra offers early boarding and complimentary drinks, ideal for longer flights.
Download the American Airlines app for in-flight entertainment access on your device.

Planning a trip from Chicago to San Diego? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.
| Low season | September |
|---|---|
| High season | December |
| Cheapest flight | $79 |
Direct departures
Chicago to San Diego
Monday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Tuesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Wednesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Thursday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Friday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Saturday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Sunday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Direct returns
San Diego to Chicago
Monday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Tuesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Wednesday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Thursday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Friday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Saturday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Sunday
Alaska Airlines, American Airlines, Southwest, +1 more
Alaska Airlines, American Airlines, +2 more
1
Did not like that every price option offered, even the more expensive one, required I pay for my seat. My seat was changed without my consent My TSA did not show in Boarding Pass
Did not like that every price option offered, even the more expensive one, required I pay for my seat. My seat was changed without my consent My TSA did not show in Boarding Pass
Boarding passes could not be received online, even after online check-in. While they appeared on the Alaska.com app, they did not transfer to inbox or messages and were not available at all on the Alaska.com app following the check-in process. There was no choice other than to get boarding passes at the airport counter.
Poor, the last leg of our trip was cancelled and we didn't know about it until we arrived at the airport. Another flight on the same airline was not available until three days later which would have ruined our vacation. Luckily we were able to get re-blooked on another airline after spending hours at the airport.
The flight was fine. The connecting flight was a nightmare. Gate change without text or email notification was super frustrating and I ended up missing my connecting flight. Return flight was delayed and had I not quadruple checked flight time, gate and refreshed the Alaska Airlines app every 5 minutes, I would have taken a flight that would not arrive in time for my connecting flight. Ended up flying Delta home.
The flight was delayed so we didn’t get into San Diego until almost 1 AM. Otherwise, it was lovely.
I always like flying with Alaska, great service and leg room
They changed our flight from a one stop 3 hour layover to a non-stop. Saved us hours and got us there sooner.
A very good experience - all staff was friendly and helpful.
My mother suffers from Lupus and has challenges walking. I specifically called Alaska airlines, stated her condition and made sure my mother’s had wheel char assistance towards gate and into the gate hall so she just had to get into the plane and walk a couple of steps. It was assured by Alaska team that the service was granted in both airports , DEN and SAN . In Denver , the wheelchair assistance never arrived. I had to personally grab another airline wheelchair sit my mom.Then I had to go to Alaska Airlines front desk twice to let them know my mother was waiting at the wheelchair service station. Upon arrival to SD Airport , there was no wheelchair service waiting for her in the hall before deplaning. She had to walk her way out in pain. Absolutely inconsiderate and unacceptable by the airline! Never again flying with Alaska Airlines.
Waiting 2 hours after landing to arrive at a gate was ridiculous.
The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.
The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.
Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.
San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.
Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.
Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.
All was good. I just had a hard time getting connected to the WiFi/internet during the flight
Delays delays delays. Late taking off, late landing, wait for a gate, etc.
Connecting flight is on time and boarding was a breeze!
Better and more food and drinks. Put msnbc and free speech tv on the news channel selection list.
Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.
I liked the snacks and the flight attendants were friendly.
After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.
Very thoughtful flight attendant offered me water immediately since I had run to make my connection.
Always wish for more healthy, gluten free options. We have to bring our own.
Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.
Other than a way way too cold cabinets for the entire flight, all was great
One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.
Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.
I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion
The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.
The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.
We loved the steward on the plane. He made the night enjoyable
We are too tired and frustrated to comment politely at this point
The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.
My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.
3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!
After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"
After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.
Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan
I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.
Not clean and was told I would get a great seat and it was not great at all
Flight got delayed for 5 hours no good explanation was offered ;(
Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.
Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.
When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.
Better than expected. Staff were friendly and nice on both flights.
Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.
i was unable to check in the flight. refund requested
Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.