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 |
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High season | May |
Cheapest flight | $88 |
Find which airlines fly direct from San Francisco Airport to Chicago, which days they fly and book direct flights.
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
No non-alcoholic drinks available except water and small apple juice cans.
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
Flight delay was inconvenient and exhausting getting in at 1 am. However the crew and lounge was very comfortable.
No complaints. Great service. A first class entry lane at boarding wouldn’t hurt.
I appreciate the priority for safety. I did not enjoy how the delays were handled.
Awful . Extra charge on my bags even after it was confirmed it wasn’t overweight.
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.
Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.
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.
It was good. Just that the seats could not be reclined. The people behind were not ready to let the chairs be reclined
Plane left & arrived early- 5 Crew great. Wi fi - paid for 2, only 1 worked - so so. Waste of $. Coolie was good
There was no USB plug in my section of the plane. So I could not charge my phone. Also, there was no screen to watch movie or anything like that. Wish I had known that in advance, I would’ve brought my iPad.
Made all groups except 2 check despite ample bin space. Inflight WiFi and entertainment didn’t work most of the time.
Not enough room between rows and food was gross. $160 baggage charge?! Never again.
Excellent staff helping my 96 year old senior promptly with her oxygen needs
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
The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.
Amazingly comfy flight - I had upgraded for a reasonable price and it was worth it. The food also was good.
Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?
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.
After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.
I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.
It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.
Average price | Average duration | |
---|---|---|
Flights | $581 | 4h 16m |
Trains | $448 | 0h 00m |
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