$106 Find Cheap Flights from San Francisco Bay Area to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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1 adult, Economy, 0 bags

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Cheap Flights from San Francisco Bay Area to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Francisco Bay Area to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Francisco Bay Area to Chicago

Sat, Jun 27 - Fri, Jul 10
Frontier Logo
8:25 pm - 6:19 am
SJC
-
ORD
7h 54m
1 stop
Frontier Logo
7:15 am - 1:17 pm
ORD
-
SJC
8h 02m
1 stop
$270Frontier
Wed, May 27 - Tue, Jun 9
Alaska Airlines Logo
12:59 pm - 1:14 pm
SJC
-
ORD
22h 15m
1 stop
Alaska Airlines Logo
7:40 am - 1:40 pm
ORD
-
SJC
8h 00m
1 stop
$272Alaska Airlines
Sat, Jul 25 - Sat, Aug 1
American Airlines Logo
11:16 pm - 5:40 am
SFO
-
ORD
4h 24mnonstop
American Airlines Logo
6:45 am - 9:26 am
ORD
-
SFO
4h 41mnonstop
$273American Airlines
Mon, May 18 - Wed, May 27
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
9:00 pm - 11:35 pm
MDW
-
SFO
4h 35mnonstop
$274Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
12:50 pm - 9:25 pm
MDW
-
SFO
10h 35m
2 stops
$275Southwest
Fri, Jun 19 - Tue, Jun 23
Multiple Airlines Logo
8:25 pm - 6:19 am
SJC
-
ORD
7h 54m
1 stop
Multiple Airlines Logo
7:59 pm - 9:26 am
ORD
-
SJC
15h 27m
1 stop
$279Multiple Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
6:00 am - 12:35 pm
SFO
-
ORD
4h 35mnonstop
American Airlines Logo
6:45 am - 9:25 am
ORD
-
SFO
4h 40mnonstop
$282American Airlines
Tue, Jun 9 - Fri, Jun 12
Multiple Airlines Logo
10:22 am - 6:50 pm
SJC
-
ORD
6h 28m
1 stop
Multiple Airlines Logo
9:13 pm - 7:37 pm
ORD
-
SJC
24h 24m
1 stop
$282Multiple Airlines
Tue, Jun 9 - Thu, Jul 2
Delta Logo
12:33 pm - 9:57 pm
OAK
-
ORD
7h 24m
1 stop
Delta Logo
7:45 am - 11:53 am
ORD
-
OAK
6h 08m
1 stop
$306Delta
Tue, May 26 - Wed, Jun 10
Delta Logo
12:28 pm - 9:50 pm
OAK
-
ORD
7h 22m
1 stop
Delta Logo
7:37 pm - 11:54 pm
ORD
-
OAK
6h 17m
1 stop
$308Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from San Jose to Chicago O'Hare Airport

FAQs for booking flights from San Francisco Bay Area to Chicago

  • How does KAYAK find such low prices on flights from San Francisco Bay Area to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Francisco Bay Area to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Francisco Bay Area to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from San Francisco Bay Area is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Francisco Bay Area to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to San Francisco Bay Area with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Francisco Bay Area to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from San Francisco Bay Area up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from San Francisco Bay Area to Chicago

 
Need help choosing which airline to fly with from San Francisco Bay Area to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4315 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

Agent could not provide me a boarding pass for the second leg of my flights - yet with a partner airline. Not understood.

I had to change my flight last minute due to a medical emergency. Their agent was compassionate and extremely helpful. This airlines really cares about making travel, for fun, work, or an emergency a customer-focused experience. Thank you!

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

The flight would have been very good , if not dor the constantly screaming baby in the row behind me. Is there a way to isolate people traveling with infants? This is not the first time this has happened to me.

No headphones provided. No gf food. Only 1 beverage cart run sAN to HNL. Rarely saw crew members

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

They treat me well because of my one world status. Crew is attentive and professional. One of the best airlines out there.

This was my first time flying first class. I was really disappointed with the food option and lack of entertainment. I wasn’t given an option of what to eat. The breakfast was less than desirable. It was a bowl of some type of granola cereal, dried fruit, almond butter and 3 biscuits that we pretty much tasteless. There was so much fiber in that meal I was afraid I would poop myself in the flight. There was absolutely ZERO entertainment available. No tv screen to watch a movie or listen to music. No charging port for my phone. I recently flew Delta Airlines Comfort class and I had a tv screen with numerous options of music to listen to and movies to watch. Also I had a charging port for my phone. I expected more quality from first class. Please understand I am not some prima donna that feels entitled. But the price I paid for first class wasn’t worth what I experienced.

Crew were bad Didn’t help with luggage When asked for a glass of wine, I was told that they will serve later , which they didn’t to Me and didn’t serve anyone else in First class . Didn’t offer any snacks , Chips or Nuts to anyone . Flight was not crowded either. Worst Service/ or No Service !

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

They didn’t offer a water, even after I asked

Remind customers of the need to have passport or new ID for boarding.

The flight never took off and we spent 7 hours at the airport

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

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.

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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Everything you need to know for your flight to Chicago

Cabin class types available on flights to San Francisco Bay Area

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.