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Find cheap flights from San Francisco Bay Area to Chicago from $44

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 8/24. 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
週六 6/8
週六 6/15

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Good to know

Low season

February

High season

July

Cheapest flight

$44
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 14% 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, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Nonstop returns

Chicago to San Francisco Bay Area

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +79 more

ANA, Aer Lingus, +80 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 9141 reviews
7.3Entertainment
7.9Comfort
8.2Boarding
8.6Crew
7.3Food
Airline reviews

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

4.0 OkayRandy, May 2024SFO - SEA
Read more about Alaska Airlines reviews

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

The space for legs in coach is better than other Airlines you can even cross your legs!!

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

They canceled the flight 30 minutes prior to departure without any heads up.

All parts were excellent, especially staff at bag tag printing and inflight crew. Just the normal differences from past air travel could be improved but we’ve learned to accept those—cramped seats, minimal food/beverage, etc.

Better organizing of entry and exit onto the plane regarding all of the baggage people haul on. There should be a better system so those with no baggage can get in and out more quickly. The baggage haul-on situation is absurd.

Attentive crew. Best of all was the empty seat between me and my rowmate.

We had a very scary attempted landing in Palm Springs and were redirected to Ontario. It was a stressful flight.

Every thing means , crew, service, timing, boarding is very good.

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

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

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.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

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.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

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

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

Book cheap flights from San Francisco Bay Area to Chicago

Recent round-trip flight deals

9/21週六
nonstopFrontier
4h 11mSFO-MDW
9/25週三
nonstopFrontier
4h 38mMDW-SFO
$88
8/21週三
nonstopFrontier
4h 11mSFO-MDW
8/28週三
nonstopFrontier
4h 38mMDW-SFO
$90
8/14週三
nonstopAlaska Airlines
4h 21mSFO-ORD
8/21週三
nonstopAlaska Airlines
4h 44mORD-SFO
$179
9/28週六
nonstopAlaska Airlines
4h 20mSFO-ORD
10/2週三
1 stopAlaska Airlines
9h 38mORD-SFO
$188
7/13週六
nonstopAmerican Airlines
4h 13mSFO-ORD
7/17週三
nonstopAmerican Airlines
4h 45mORD-SFO
$209
8/7週三
nonstopUnited Airlines
4h 18mSFO-ORD
8/12週一
nonstopUnited Airlines
4h 40mORD-SFO
$240
6/26週三
1 stopDelta
8h 28mSFO-ORD
6/29週六
1 stopDelta
6h 44mORD-SFO
$252
6/10週一
nonstopUnited Airlines
4h 20mSFO-ORD
6/17週一
1 stopUnited Airlines
6h 23mORD-SFO
$253
6/15週六
nonstopAmerican Airlines
4h 18mSFO-ORD
6/18週二
nonstopAmerican Airlines
4h 48mORD-SFO
$254
8/9週五
1 stopDelta
8h 59mSFO-MDW
8/14週三
1 stopDelta
6h 48mMDW-SFO
$272

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Recent one-way flight deals

8/24週六
nonstopFrontier
4h 11mSFO-MDW
$44
6/4週二
1 stopSpirit Airlines
7h 07mOAK-ORD
$53
5/28週二
nonstopAmerican Airlines
4h 17mSFO-ORD
$95
8/17週六
nonstopAlaska Airlines
4h 21mSFO-ORD
$97
8/6週二
1 stopAlaska Airlines
7h 20mSFO-ORD
$99
5/31週五
nonstopUnited Airlines
4h 20mSFO-ORD
$116
6/1週六
nonstopAmerican Airlines
4h 22mSFO-ORD
$117
5/26週日
1 stopDelta
8h 47mSFO-ORD
$118
7/16週二
1 stopDelta
9h 45mSFO-MDW
$123
6/8週六
nonstopUnited Airlines
4h 20mSFO-ORD
$137

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Last minute flights from San Francisco Bay Area to Chicago

Last minute flight, train and bus deals

5/13週一
nonstopFrontier
4h 11mSFO-MDW
6/12週三
nonstopFrontier
4h 28mMDW-SFO
$202
5/13週一
nonstopFrontier
4h 11mSFO-MDW
5/14週二
nonstopFrontier
4h 39mMDW-SFO
$204
5/13週一
multi-stopDelta
5h 59mSFO-ORD
5/21週二
multi-stopDelta
6h 40mORD-SFO
$312
5/13週一
multi-stopDelta
5h 59mSFO-ORD
5/14週二
multi-stopDelta
6h 40mORD-SFO
$316
5/13週一
nonstopUnited Airlines
4h 21mSFO-ORD
5/16週四
nonstopUnited Airlines
4h 53mORD-SFO
$337
5/13週一
nonstopUnited Airlines
4h 21mSFO-ORD
5/16週四
multi-stopUnited Airlines
6h 37mORD-SFO
$346
5/11週六
multi-stopAlaska Airlines
8h 47mSFO-ORD
5/18週六
nonstopAlaska Airlines
4h 37mORD-SFO
$403
5/11週六
multi-stopAlaska Airlines
7h 39mSFO-ORD
5/21週二
nonstopAlaska Airlines
4h 37mORD-SFO
$448
5/13週一
nonstopAmerican Airlines
4h 17mSFO-ORD
5/16週四
nonstopAmerican Airlines
4h 45mORD-SFO
$494
5/11週六
nonstopAmerican Airlines
4h 20mSFO-ORD
5/14週二
nonstopAmerican Airlines
4h 45mORD-SFO
$501

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Flights to Chicago

Return flight deals:

Chicago - San Francisco Bay Area

Cabin classes:

$333
$301
$219
$38