$91 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 1/15. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$264
Overall average: $297
American Airlines
Tue 1/6Wed 1/21
SFO - ORD • Non-stop
Cheapest one-way
$91
Typical prices: $220-$312
Frontier
Thu 1/15
SJC - ORD • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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

Tue, Jan 6 - Wed, Jan 21
American Airlines Logo
6:00 am - 12:25 pm
SFO
-
ORD
4h 25mnonstop
American Airlines Logo
11:46 am - 2:37 pm
ORD
-
SFO
4h 51mnonstop
$264American Airlines
Sat, Feb 21 - Tue, Feb 24
Southwest Logo
6:55 am - 12:55 pm
SFO
-
MDW
4h 00mnonstop
Southwest Logo
1:55 pm - 9:50 pm
MDW
-
SFO
9h 55m1 stop
$265Southwest
Tue, Jan 6 - Thu, Jan 8
United Airlines Logo
11:56 pm - 6:25 am
SFO
-
ORD
4h 29mnonstop
United Airlines Logo
4:16 pm - 7:09 pm
ORD
-
SFO
4h 53mnonstop
$265United Airlines
Thu, Jan 22 - Tue, Jan 27
Southwest Logo
11:10 am - 5:15 pm
OAK
-
MDW
4h 05mnonstop
Southwest Logo
11:10 am - 2:05 pm
MDW
-
OAK
4h 55mnonstop
$265Southwest
Tue, Mar 17 - Tue, Mar 24
Alaska Airlines Logo
6:30 am - 4:33 pm
SFO
-
ORD
8h 03m1 stop
Alaska Airlines Logo
2:05 pm - 7:19 pm
ORD
-
SFO
7h 14m1 stop
$266Alaska Airlines
Wed, Jan 7 - Fri, Jan 9
American Airlines Logo
6:00 am - 12:25 pm
SFO
-
ORD
4h 25mnonstop
American Airlines Logo
11:46 am - 2:37 pm
ORD
-
SFO
4h 51mnonstop
$267American Airlines
Sun, Jan 4 - Thu, Jan 8
Frontier Logo
11:20 pm - 1:21 pm
SFO
-
MDW
12h 01m1 stop
Frontier Logo
6:10 am - 1:18 pm
MDW
-
SFO
9h 08m1 stop
$268Frontier
Thu, Mar 12 - Wed, Mar 18
United Airlines Logo
11:59 pm - 6:19 am
SFO
-
ORD
4h 20mnonstop
United Airlines Logo
9:15 pm - 12:16 am
ORD
-
SFO
5h 01mnonstop
$269United Airlines
Sat, Feb 14 - Tue, Feb 17
Alaska Airlines Logo
6:15 am - 4:33 pm
OAK
-
ORD
8h 18m1 stop
Alaska Airlines Logo
5:29 pm - 9:14 am
ORD
-
OAK
17h 45m1 stop
$269Alaska Airlines
Fri, Jan 9 - Sun, Jan 11
Frontier Logo
6:05 am - 2:05 pm
SFO
-
MDW
6h 00m1 stop
Frontier Logo
6:10 am - 1:18 pm
MDW
-
SFO
9h 08m1 stop
$272Frontier
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$91
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 2% increase in price.
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 11465 reviews
7.0Entertainment
8.1Boarding
7.1Food
8.5Crew
7.8Comfort
Airline reviews

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

8.0 ExcellentEvie, Dec 2025
SAN - HNL
Read more Alaska Airlines reviews

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

The flight attendants were excellent and I was in the back of the plane. Much much better than recent JetBlue experiences on that route and better than Delta on that route.

I’m not sure there is anything that can be improved, even the cost was fantastic.

Poor. They should have given me a row with more room and instead they put me in a middle seat with two strangers next to me

They were so kind to us! The entire staff were so good to us when we had our service dog join our trip and we couldn't be more grateful!

Larger seats and more room would elevate the experience. Otherwise, it was good!

Flight crew and flight were good. But it departed two hours late.

They changed our flight from a one stop 3 hour layover to a non-stop. Saved us hours and got us there sooner.

The ground crew did not supply drink or snacks during the layover in SFO. So there weren't many options. Otherwise, it was all great.

No accommodation or credit offered for cancelled layover flight to Eugene from portland

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

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

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 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.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

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.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

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.

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

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.