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 | July |
Cheapest flight | $111 |
Direct departures
San Francisco to Chicago
Monday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Tuesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Wednesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Thursday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Friday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Saturday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Sunday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Direct returns
Chicago to San Francisco
Monday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Tuesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Wednesday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Thursday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Friday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Saturday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Sunday
American Airlines, Southwest, United Airlines
American Airlines, Southwest, +1 more
Flight was delayed 14 hours! We missed an entire day of our vacation and had to pay for hotel that we didn’t use
Flight was delayed 14 hours! We missed an entire day of our vacation and had to pay for hotel that we didn’t use
Could not check in online. Called airline twice, thinking Hawaiian Airlines could check me in during phone call. NO. In 2nd phone call, Customer Service explained that due to “transition period” of Hawaiian Airlines/Alaska Airlines merger, I could only check in at the airport. In addition, flight to Kahului was late at arrival gate; I made connection to Lihue but my bag did not, so I had to return to Lihue airport a couple hours after my arrival to retrieve the bag.
I still in San Francisco😡the flight has delay and lm not sure l can back to Seattle or not😡lm here from 7.30pm and still waiting😡 l never will use of Kayak.
On time boarding, take off and landing. Will fly again with Alaska Airlines.
Flight was smooth, pleasant passengers and crew. Enjoyed the experience
Flight attendant was awful, I felt second hand embarrassment with every one of her interactions with people onboard. She was so incredibly rude every chance she got
Great flight - efficient and cheerful team on board, at SFO gate. Also, PAE (Paine Field, Everett, WA) is a great little airport to fly out or in to!
I was sitting towards back of plane and the flight attendants I thought spoke unusually loud for an evening flight. They chatted and chatted all night long and it seemed odd to me that they didn’t try to lower their voices. It is annoying as a passenger to hear all their conversations.
Had to pay $8 for internet wasnt cool, no tv’s, had to use phone to watch movies, no food choices seemed available unless u ordered in advance maybe I'm wrong about that but seemed that way, no snacks were served. Seemed a very bare bones flight. But it was on time and safe so that was good
We were singled out, greeted and helped with check-in at the busy airport. They offered to take our bags there and gave no fuss when we said they were carry-on. With United just last week I had to put up a fight just to get onto the flight with my one authorized carry-on.
Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.
Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience
As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.
The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.
The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.
Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.
It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.
Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.
No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.
Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch
Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!
I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.
Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely
Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.
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.
Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.
It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.
After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.
Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.
This was the best 2 flights I have had with American out of SGF. Great crew both flights.
It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.
Very crowded flight but what can you expect these days?? Crew was accommodating.
Excellent - explanations were clear staff was nice and flight was comfortable
The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.
Lost bag and 2 days no word leaving for cruise no clothes or stuff
The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company
Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.
This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.
Severe turbulence. Captain never came on to reassure passengers after things settled down.
We were delayed three times ,and that destroyed my plans, and reservations
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….
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