Find flights
When to book
FAQs & Tips
Direct Flights
Airlines
Deals

$39 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 8/21. 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
0 bags
Sat 7/6
Sat 7/13

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

In the last 7 days travelers have searched 44,060,346 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

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

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

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

Good to know

Low season

February

High season

June

Cheapest flight

$39
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from San Francisco to Chicago Midway 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.

See more FAQs

Prefer to fly non-stop from San Francisco Bay Area to Chicago?

Find which airlines fly direct from San Francisco Bay Area to Chicago, which days they fly and book direct flights.

Nonstop departures

San Francisco Bay Area to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights

Nonstop returns

Chicago to San Francisco Bay Area

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights
See more direct flights

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 9216 reviews
7.3Entertainment
8.6Crew
8.2Boarding
7.9Comfort
7.3Food
Airline reviews

Seats are uncomfortable but let room was adequate. The snack is pretty weak and the staff not particularly friendly.

10.0 ExcellentAnonymous, Jun 2024SJC - SAN
Read more about Alaska Airlines reviews

Seats are uncomfortable but let room was adequate. The snack is pretty weak and the staff not particularly friendly.

Flight was cancelled just before we boarded. I had to stayed an extra night in SF and arrived one day late. Also I had to flight back JFK and not Newark since they didn't have flight to Newark until very late the following day. A real bad experience on this flight. It took me 2 days to get back home.

Plane was very cold, but other than that, it was a perfect flight

We landed in San Diego from Fresno 10 min late and our gate was occupied. We waited OVER AN HOUR to get to the gate and didnt get any updates about what was happening until I asked. Then we were told it would be another 5 minutes....which turned into 25. My wife was waiting in cell phone lot over an hour and finally had to leave. It cost me $40 cab ride and a fight with my wife. THanks for nothing Alaska Air.

The flight was delayed by more than two hours. A notification ahead of time would be most helpful.

The flight was delayed for 2 hours and the last delay was not communicated and had to check manually.

Loved the airport. The announcements for boarding were too loud & echoing in the large waiting area, so hard to follow. Other than that, we had a great experience.

First time traveling with them and they were great leaving on time arriving on time very clean planes 😊

Staff was very friendly. Flight was on time and arrived early. Flight was comfortable.

The airline itself was extremely comfortable and the staff were wonderful. The communication was excellent amongst the pilots and flight attendants and the passengers. I was throughly impressed by the cleaning crew that came on the plane immediately to ready it for the next flight. I have flown a bunch of times post Covid pandemic and have never seen this! I gave the “okay” rating for the food and entertainment because I didn’t order food and there wasn’t entertainment offered through the plane (only your personal devices).

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

There was a loud squeaky sound the whole time we were flying.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

Book cheap flights from San Francisco Bay Area to Chicago

Recent round-trip flight deals

9/4Wed
nonstopFrontier
4h 11mSFO-MDW
9/7Sat
nonstopFrontier
4h 38mMDW-SFO
$78
9/14Sat
nonstopFrontier
4h 11mSFO-MDW
9/28Sat
nonstopFrontier
4h 38mMDW-SFO
$80
9/4Wed
nonstopAlaska Airlines
4h 20mSFO-ORD
9/7Sat
nonstopAlaska Airlines
4h 44mORD-SFO
$144
8/17Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
8/22Thu
nonstopAlaska Airlines
4h 44mORD-SFO
$151
9/3Tue
1 stopUnited Airlines
6h 32mSFO-ORD
9/7Sat
nonstopUnited Airlines
4h 39mORD-SFO
$185
8/3Sat
nonstopUnited Airlines
4h 13mSFO-ORD
8/10Sat
nonstopUnited Airlines
4h 40mORD-SFO
$187
9/6Fri
1 stopDelta
8h 38mSFO-MDW
9/11Wed
1 stopDelta
7h 23mMDW-SFO
$236
8/16Fri
1 stopDelta
5h 43mSFO-ORD
8/19Mon
1 stopDelta
9h 51mORD-SFO
$236
7/9Tue
nonstopAmerican Airlines
4h 14mSFO-ORD
7/23Tue
nonstopAmerican Airlines
4h 38mORD-SFO
$248
8/14Wed
nonstopAmerican Airlines
4h 17mSFO-ORD
8/18Sun
1 stopAmerican Airlines
7h 04mORD-SFO
$292

Search by stops

Search by airline

Search by price

Recent one-way flight deals

8/21Wed
nonstopFrontier
4h 11mSFO-MDW
$39
8/7Wed
nonstopFrontier
4h 10mSFO-MDW
$41
7/10Wed
nonstopUnited Airlines
4h 13mSFO-ORD
$90
7/9Tue
1 stopAlaska Airlines
7h 20mSFO-ORD
$99
8/5Mon
nonstopAlaska Airlines
4h 21mSFO-ORD
$100
7/15Mon
nonstopUnited Airlines
4h 18mSFO-ORD
$104
7/9Tue
nonstopAmerican Airlines
4h 14mSFO-ORD
$109
7/13Sat
nonstopAmerican Airlines
4h 13mSFO-ORD
$115
8/2Fri
1 stopDelta
8h 43mSFO-MDW
$118
7/12Fri
1 stopDelta
5h 58mSFO-ORD
$118

Search by stops

Search by airline

Search by price

Last minute flights from San Francisco Bay Area to Chicago

Last minute flight, train and bus deals

6/10Mon
multi-stopFrontier
21h 41mSFO-ORD
6/21Fri
multi-stopFrontier
19h 13mORD-SFO
$252
6/11Tue
multi-stopSpirit Airlines
34h 21mOAK-ORD
6/13Thu
multi-stopSpirit Airlines
8h 22mORD-OAK
$263
6/10Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
6/19Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$519
6/9Sun
multi-stopAlaska Airlines
9h 45mSFO-ORD
6/19Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$528
6/8Sat
multi-stopDelta
8h 56mOAK-MDW
6/12Wed
multi-stopDelta
16h 26mMDW-OAK
$573
6/7Fri
multi-stopDelta
8h 20mSFO-ORD
6/19Wed
multi-stopDelta
9h 32mORD-SFO
$583
6/8Sat
multi-stopUnited Airlines
22h 16mSFO-ORD
6/9Sun
nonstopUnited Airlines
4h 44mORD-SFO
$609
6/8Sat
multi-stopAmerican Airlines
9h 09mSFO-ORD
6/19Wed
multi-stopAmerican Airlines
9h 06mORD-SFO
$633
6/8Sat
multi-stopAmerican Airlines
9h 53mSFO-ORD
6/19Wed
multi-stopAmerican Airlines
9h 06mORD-SFO
$638
6/9Sun
nonstopUnited Airlines
4h 20mSFO-ORD
6/17Mon
multi-stopUnited Airlines
12h 12mORD-SFO
$652

Search by stops

Search by airline

Search by price

Flights to Chicago

Return flight deals:

Chicago - San Francisco Bay Area

Cabin classes:

$357
$232
$245
$44