United's Economy Plus offers up to six inches more legroom than standard economy seats.
United's Priority Boarding can be purchased to ensure overhead bin space for carry-ons.
Planning a trip from San Francisco to Chicago? 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.
When planning a flight from San Francisco to Chicago, it's important to consider a few key factors to ensure you're getting the best deal. Generally, the cheapest day to fly is Saturday, and the most affordable month is September.
Day Choice: Opt for flights on Saturdays for the best rates.
Month Choice: September generally offers the cheapest flights.
Booking Advance: Book your flight at least 120 days in advance to get the best price.
Airline Choice: Frontier Airlines typically offers the cheapest fares for this route.
Route Selection: Flying from San Francisco to Chicago Midway (SFO - MDW) is usually the cheapest route.
Flight Type: Flights with one stop are generally cheaper than direct flights.
This feature is powered by ChatGPT: an OpenAI-developed artificial intelligence model trained with KAYAK proprietary data and third-party data not verified by KAYAK.
Low season | January |
---|---|
High season | August |
Cheapest flight | $90 |
Direct departures
San Francisco 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
Direct returns
Chicago to San Francisco
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
Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.
Flying on Hawaiian Airlines was good. But, getting a boarding pass was a hassle. I booked what I thought was an Alaska Airlines flight that was actually a Hawaiian Airlines flight. I couldn't check in online. I had to wait for the Hawaiian Airlines counter to open so I could get my boarding pass which was a requirement for me to get in The Club or the Centurion Lounge. (I had no check in luggage so I didn't expect to have to physically check in.) The Alaska Airlines staff blamed the FAA for the problem.
Great, overall. Thicker seat cushion would be nice. My butt hurt the whole flight.
Thicker seat cushion would be nice. My butt hurt the whole flight.
All good! No entertainment on this new plane yet but ok for this short flight. Great on time flight! Thanks
No non-alcoholic drinks available except water and small apple juice cans.
The flight was delayed over two and a half hours thus causing me to miss my best friend’s funeral. All because the flight crew had to get more rest. That was the reason stated. I understand however very unfortunate. Glad everyone is well rested and resting in peace.
All good except both the outbound and return flights were delayed about 1 1/2 hrs.
Not great. My flight was canceled due to a mechanical problem and I could not get rebooked for the same day. I needed to get to my destination yesterday, not today. I was able to book with another airline but it was a layover and ultimately a 1 hour flight took me 12 hours. Normally I like Alaska much more than Southwest, but Southwest came through with a not terrible price for same day.
The plane was late arriving. The Alaska people did a great job of turning it around quickly and getting us off. We took off about 35 minutes after it reached the gate.
I liked the flight attendant named Tyler. He was charismatic and genuine. I like the pilot in my second flight, he was considerate to everyone’s feelings. I liked the people I sat beside. I like the plane size. I like Alaska airlines
Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.
It was a perfect flight in all aspects! Both legs!
Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.
I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.
Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.
Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.
Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.
I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.
We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.
Service was great, boarding and exiting went smoothly, and the flight was very pleasant.
Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.
Boarding seemed to be organized bedlam. For what ever reason, preboarding took longer than 20 minutes. Made the plane 20 minutes late taking off. Luckily we arrived on time. Flight crew seemed very friendly. Only slight turbulence.
The personnel were professional and friendly. The Boeing 737 Max 9 is too claustrophobic and was very warm at both airport gates, and still warm in the air.
While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.
get E+, a must for 5 hours flight if you are tall
The first flight was better in terms of the aircraft.
Compared with other carriers business class for an overnight was not worth the extra expense.
Easy to board. Flight was super crowded though so I didn't sleep well on that cross country red-eye flight. The aisles seem ot have gotten narrower and the seat smaller whn luggage and people are getting bigger so it would be AWESOME to have more space and breathing room in general ;)
Pilot Erika DeLong made us feel safe and at ease in a frankly scary time to be flying. Her warm smile and greeting and excellent command of the aircraft in foggy bumpy weather helped us all to calm our nerves and get us home safely.
Wish movie and music choices changed more often. Mostly same from a month or two ago when I last flew.
Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.
The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!
Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows
British Airways staff are very polite and willing to help.
To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.
The plane was late and then sat on the runway for almost 45 minutes before taking off.
We kept being told that the flight was full and that all overhead compartments were full and therefore had to check in our hand luggage. We were some of the last people to board and noticed that there was still sufficient space in the overhead compartments. We were obliged to check in hand luggage when there was space and so had to wait at luggage retrieval which took a while to then noticed damage to our luggage - not a great experience!
Crew professional. Easy bag drop off. On time. Good entertainment.
Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.
Per usual, flight status, staff courtesy and professionalism were excellent
Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.
I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.
The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew
The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.
It was a short flight so no food or entertainment….
Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.
Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark
The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.
They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous
No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.
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