$68 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 3/9. 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.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$166
Overall average: $415
Frontier
Mon 3/9Wed 3/11
SJC - ORD • 1 stop
Cheapest non-stop
$217
Typical prices: $548-$950
Southwest
Wed 3/18Sat 3/21
OAK - MDW • Non-stop
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Flight Deals
Useful Info
Flight Deals

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

Mon, Mar 9 - Wed, Mar 11
Frontier Logo
8:20 pm - 6:08 am
SJC
-
ORD
7h 48m
1 stop
Frontier Logo
4:28 pm - 6:07 pm
ORD
-
SJC
27h 39m
2 stops
$166Frontier
Mon, Mar 9 - Wed, Mar 11
Frontier Logo
8:20 pm - 6:08 am
SJC
-
ORD
7h 48m
1 stop
Frontier Logo
8:55 pm - 6:07 pm
ORD
-
SJC
23h 12m
1 stop
$198Frontier
Wed, Mar 18 - Sat, Mar 21
Southwest Logo
11:55 pm - 5:55 am
OAK
-
MDW
4h 00mnonstop
Southwest Logo
9:40 pm - 12:20 am
MDW
-
OAK
4h 40mnonstop
$217Southwest
Tue, Mar 3 - Tue, Mar 10
Southwest Logo
7:30 am - 4:05 pm
OAK
-
MDW
6h 35m
1 stop
Southwest Logo
9:00 pm - 11:40 pm
MDW
-
OAK
4h 40mnonstop
$227Southwest
Wed, Feb 25 - Wed, Mar 4
Alaska Airlines Logo
10:26 am - 11:59 pm
SJC
-
ORD
11h 33m
1 stop
Alaska Airlines Logo
8:20 am - 5:33 pm
ORD
-
SJC
11h 13m
1 stop
$237Alaska Airlines
Tue, May 5 - Wed, May 13
Delta Logo
12:34 pm - 9:18 pm
OAK
-
ORD
6h 44m
1 stop
Delta Logo
6:59 pm - 11:49 pm
ORD
-
OAK
6h 50m
1 stop
$237Delta
Tue, May 12 - Wed, May 20
Alaska Airlines Logo
2:09 pm - 11:59 pm
OAK
-
ORD
7h 50m
1 stop
Alaska Airlines Logo
3:43 pm - 11:37 pm
ORD
-
OAK
9h 54m
1 stop
$240Alaska Airlines
Sat, Feb 28 - Wed, Mar 4
Delta Logo
12:40 pm - 9:52 pm
OAK
-
ORD
7h 12m
1 stop
Delta Logo
2:05 pm - 11:51 pm
ORD
-
OAK
11h 46m
2 stops
$242Delta
Fri, Feb 20 - Tue, Feb 24
United Airlines Logo
11:59 pm - 6:19 am
SFO
-
ORD
4h 20mnonstop
United Airlines Logo
6:17 pm - 9:20 pm
ORD
-
SFO
5h 03mnonstop
$250United Airlines
Sat, Feb 21 - Tue, Feb 24
United Airlines Logo
10:50 pm - 5:12 am
SFO
-
ORD
4h 22mnonstop
United Airlines Logo
12:46 pm - 3:51 pm
ORD
-
SFO
5h 05mnonstop
$253United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$68
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 2% 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
Alaska AirlinesOverall score based on 11808 reviews
8.1Boarding
7.0Entertainment
7.8Comfort
7.1Food
8.5Crew
Airline reviews

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

4.0 OkayStephanie, Jan 2026
SFO - SNA
Read more Alaska Airlines reviews

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

The stewardess are very nice and pleasant, Someone onboard had a medical attention, and they attended that person non-stop all throughout the flight, and yet, did not forget to serve and help other passengers.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

My TSA pre check was left Off my boarding pass which was a large inconvenience.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

Overall it was fine, however one of my two checked bags did not arrive and I was told it was left in Palm Springs. I don't understand how one of the two bags made it through fine but the other got lost .

The Alaska Airlines app made it very difficult to find my boarding pass. It was very frustrating to use! The flight itself was flawless.

It wasn’t great. Your app is not user friendly unless you sign up for those points. It tries to force you and won’t show you flight/trip info until you sign up. You have to somehow get into get your boarding pass because your kiosks don’t offer boarding pass information only bag check. It was not helpful or user friendly. The app is useless unless you sign up for your rewards program. My daughters info was missing even though I checked us in we had to get out of security and go back to a ticket window the woman told us that it sometimes populates incorrectly so it didn’t have her information. It populated incorrect birth date. She said this is common. Luckily we were at Palm Springs and not JFK where leaving the giant security line would have been a much bigger problem. I will avoid your airline in the future if it’s possible. Also no food availability except dry snack boxes.

The whole experience went smoothly with no hitches along the way.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

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.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

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.

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.

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.

Traveling to a place near Chicago?

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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.