Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago to San Francisco Bay Area 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 from Chicago to San Francisco Bay Area departing on 5/8. 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
Fri 5/24
Fri 5/31

Search hundreds of travel sites at once for deals on flights to San Francisco Bay Area

In the last 7 days travelers have searched 44,632,927 times on KAYAK, and here is why:

Save 22% 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.

Best San Francisco Bay Area Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

San Francisco
San Franciscononstop$88
San Jose
San Jose1 stop$160

Good to know

Low season

January

High season

July

Cheapest flight

$44
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Chicago Midway Airport to San Francisco

FAQs - booking San Francisco Bay Area flights

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

    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 Chicago to San Francisco Bay Area.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Francisco Bay Area from Chicago 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 Chicago to San Francisco Bay Area?

    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 San Francisco Bay Area with an airline and back to Chicago with another airline.

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

    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 San Francisco Bay Area from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 5 airlines serving from Chicago to San Francisco Bay Area

 
Need help choosing which airline to fly with from Chicago to San Francisco Bay Area? 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.
8.1
Alaska AirlinesOverall score based on 9111 reviews
8.2boarding
7.3food
8.6crew
7.9comfort
7.3entertainment
Airline reviews

It was so easy to board using my boarding pass on my iPhone, and I liked what I was given on the plane for food and drink, and everyone was very friendly.

10.0 ExcellentAnonymous, Apr 2024PDX - OAK
Read more about Alaska Airlines reviews

It was so easy to board using my boarding pass on my iPhone, and I liked what I was given on the plane for food and drink, and everyone was very friendly.

The messaging about the change in flight destination and options for getting to SFO was poor. There should have been frequent updates. When I spoke to the boarding agent moment before we were supposed to board, he was flippant and offered no help before the announcement was made that transportation would be arranged. It was as poor of an experience that I've ever had.

My plane ride down landed 20 min late. Boarding at SFO was strange too. The people at the terminal were nice—but, boarding lacked direction, and was confusing . Coming back was worse—the plane was hours behind—and I barely caught the last Bart train back to San Francisco (3 min more and I would have been in trouble). It was a very stressful trip, and it didn’t need to be.

While the flight and the legroom was good boarding took a long time. The different groups Boarding made no sense as those in the back of the flight boarded last causing delays as people try to find room for their luggage in the upper bins. While there were plenty of seats on the flights We were spaced so that some rows were filled and others were empty. My first flight was very crowded and uncomfortable. On the way back both flights did not have Wi-Fi nor the entertainment package. We were only made aware of this a few hours before the flight. Since the flight was in the morning, I was asleep and was not able to download Books or other media to my phone. This is my first time flying Alaska airlines and I will admit to thinking twice before I do so again.

Our flight was delayed by six hours, our plane never left Portland the night before but the airline didn’t inform anyone till two hours before a six am flight. The plane, our plane never left the west coast! No plane no flight, simply let folks know when you know, not hours and hours later. No one apologized, no one said much of anything, we were just expected to wait quietly and await instructions.

I liked the fast internet and twice serving of snacks and drinks. Paid food options could have included more.

The absolute coldest flight I’ve ever been on, even with a sweater and zip up sweatshirt. Was miserable the entire flight.

the departure got delayed due to SJC situation, but it was a quite good waiting thanks to Alaska airline teams.

The flight attendant in the back of the plane was barely understood as she rushed through instructions to the point of being intelligible. She had a bored demeanor in her delivery.

Good. Quiet. Comfortable. The protests nearly kept me from catching my flight. They waited for me! I made it!

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

Had a broken tray in business class. Crew just shrugged it off.

I didn’t like that I could not select my seat and was assigned a seat when I checked in at LAX

Great experience overall. Check in at Austin was congested as they only have about 6 check in kiosks, one was broken, and there was a lot of Spring Break travelers.

Bag drop off was slow and annoying. Only 2 agents at the entire delta desk, and no one directing traffic for what line to be in, many confused people slowed down the process. Boarding was fine. Seats in Delta comfort plus were fine. Snacks were great! Definitely a bonus. The entertainment system was awful — old, slow, not responsive, and completely unable to play games due to some kind of error. But on the other hand, thank you to Delta for the free WiFi. That made it better.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

Horrible. Flight ORD to CGH was okay, but Paris was a nightmare. Old planes, delays, involuntary downgrades, broken planes, terrible communication. CGH to CPT was my worst flight ever.

Crew was not friendly when I went to request a seat change.

Really impressive staff at airport and on plane, especially given how busy it was

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Everything was good, hard to really comfortable on a flight that long.

Unfortunately our flight was delayed by 45 minutes due to Kate arriving aircraft. Once we stated everything was great.

For some strange reason I was put in zone 5 for boarding even though I had paid premium price for a premium seat right behind business class. This must have been a flaw because everyone else around me in the same zone (row) had been placed in zone 3.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

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

The boarding time. I was in Section 1 the lady in charge just let people in section 3 without see us. Make a line , I have to step out and ask her. We were in the line and she just take my ticket and that’s it, so if I don’t ask her she could leave us at the end! We paid more for that privilege and. She doesn’t care….

Was just ok with over selling I guess. A lot of people in a short space and when we finally arrive i20 minutes, waiting to get out from the plain because we were waiting authorization for out boarding? Something like that.

See my previous comment which is mostly about our flight from Phoenix to SFO

They changed my flight and did not want to accommodate me or try to help me in any way. They do not care about their customers.

The check in at the airport was awful. Told I need to pay for a bag. The item was taken at screening. I went back to get my $ back and they gave me a coupon with a QR code that doesn’t work. Worst costumer service ever!!!!!

4 hour delay because they used our aircraft to fly a different segment (per the captain)

Book cheap flights from Chicago to San Francisco Bay Area

Recent round-trip flight deals

5/8Wed
nonstopFrontier
4h 39mMDW-SFO
5/18Sat
nonstopFrontier
4h 12mSFO-MDW
$88
5/8Wed
nonstopFrontier
4h 39mMDW-SFO
5/15Wed
nonstopFrontier
4h 11mSFO-MDW
$90
7/24Wed
nonstopAlaska Airlines
4h 37mORD-SFO
8/3Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$177
7/31Wed
nonstopAlaska Airlines
4h 40mORD-SFO
8/10Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$179
5/7Tue
nonstopUnited Airlines
4h 51mORD-SFO
5/28Tue
nonstopUnited Airlines
4h 20mSFO-ORD
$205
5/7Tue
1 stopUnited Airlines
6h 36mORD-SFO
5/27Mon
nonstopUnited Airlines
4h 20mSFO-ORD
$211
5/8Wed
nonstopAmerican Airlines
4h 53mORD-SFO
5/15Wed
1 stopAmerican Airlines
7h 03mSFO-ORD
$221
5/4Sat
nonstopAmerican Airlines
4h 52mORD-SFO
5/7Tue
nonstopAmerican Airlines
4h 17mSFO-ORD
$241
7/3Wed
1 stopDelta
8h 09mMDW-SFO
7/8Mon
1 stopDelta
8h 55mSFO-MDW
$257
7/12Fri
1 stopDelta
6h 35mORD-SFO
7/16Tue
1 stopDelta
9h 36mSFO-ORD
$257

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/8Wed
nonstopFrontier
4h 39mMDW-SFO
$44
5/1Wed
nonstopFrontier
4h 39mMDW-SFO
$49
5/14Tue
1 stopAlaska Airlines
7h 34mORD-SFO
$99
7/17Wed
nonstopUnited Airlines
4h 41mORD-SFO
$102
5/8Wed
nonstopAmerican Airlines
4h 53mORD-SFO
$103
5/30Thu
1 stopUnited Airlines
6h 23mORD-SFO
$108
6/8Sat
nonstopAlaska Airlines
4h 37mORD-SFO
$110
6/11Tue
1 stopDelta
9h 48mMDW-SFO
$118
5/30Thu
1 stopDelta
6h 40mORD-SFO
$118
5/17Fri
nonstopAmerican Airlines
4h 53mORD-SFO
$130

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to San Francisco Bay Area

Last minute flight, train and bus deals

4/28Sun
multi-stopFrontier
10h 44mMDW-SFO
5/7Tue
nonstopFrontier
4h 11mSFO-MDW
$166
4/27Sat
nonstopFrontier
4h 39mMDW-SFO
5/7Tue
nonstopFrontier
4h 11mSFO-MDW
$167
4/29Mon
nonstopAlaska Airlines
4h 46mORD-SFO
5/4Sat
nonstopAlaska Airlines
4h 30mSFO-ORD
$319
4/29Mon
nonstopAmerican Airlines
4h 48mORD-SFO
4/30Tue
nonstopAmerican Airlines
4h 17mSFO-ORD
$327
4/29Mon
nonstopAmerican Airlines
4h 52mORD-SFO
4/30Tue
multi-stopAmerican Airlines
8h 11mSFO-ORD
$335
4/29Mon
multi-stopDelta
6h 54mORD-SFO
4/29Mon
multi-stopDelta
8h 40mSFO-ORD
$338
4/29Mon
nonstopAlaska Airlines
4h 46mORD-SFO
5/2Thu
nonstopAlaska Airlines
4h 24mSFO-ORD
$361
4/27Sat
nonstopUnited Airlines
4h 49mORD-SFO
4/30Tue
nonstopUnited Airlines
4h 21mSFO-ORD
$364
4/27Sat
multi-stopUnited Airlines
6h 28mORD-SFO
4/29Mon
nonstopUnited Airlines
4h 21mSFO-ORD
$373
4/29Mon
multi-stopDelta
9h 20mORD-SFO
5/2Thu
multi-stopDelta
6h 40mSFO-ORD
$380

Search by stops

Search by airline

Search by price

Flights to San Francisco Bay Area

Return flight deals:

San Francisco Bay Area - Chicago

Cabin classes:

$311
$328
$277
$32