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Cheap Flights from San Francisco Bay Area to Chicago

 
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, Sep 28 - Thu, Oct 1
Frontier Logo
10:17 am - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
17h 21m1 stop Las Vegas Harry Reid Intl
Frontier Logo
8:55 pm - 9:22 amORD  Chicago O'Hare Intl-OAK Oakland
14h 27m1 stop Las Vegas Harry Reid Intl
$198Frontier
Thu, Sep 24 - Tue, Sep 29
Frontier Logo
6:51 pm - 5:38 amOAK  Oakland-ORD Chicago O'Hare Intl
8h 47m1 stop Las Vegas Harry Reid Intl
Frontier Logo
1:21 pm - 11:51 amORD  Chicago O'Hare Intl-OAK Oakland
24h 30m1 stop Las Vegas Harry Reid Intl
$208Frontier
Sat, Oct 31 - Mon, Nov 9
Multiple Airlines Logo
12:20 pm - 12:21 amSFO  San Francisco-ORD Chicago O'Hare Intl
10h 01m1 stop Denver Intl
Multiple Airlines Logo
2:15 pm - 8:16 pmORD  Chicago O'Hare Intl-SFO San Francisco
8h 01m1 stop San Diego
$251Multiple Airlines
Fri, Sep 25 - Sat, Sep 26
Multiple Airlines Logo
8:25 am - 7:21 pmSFO  San Francisco-ORD Chicago O'Hare Intl
8h 56m1 stop San Diego
Multiple Airlines Logo
4:35 pm - 10:28 pmORD  Chicago O'Hare Intl-SFO San Francisco
7h 53m1 stop Dallas/Fort Worth
$251Multiple Airlines
Mon, Sep 21 - Mon, Sep 28
American Airlines Logo
7:00 am - 1:34 pmSFO  San Francisco-ORD Chicago O'Hare Intl
4h 34mnonstop
American Airlines Logo
9:06 pm - 11:56 pmORD  Chicago O'Hare Intl-SFO San Francisco
4h 50mnonstop
$255American Airlines
Sat, Sep 19 - Fri, Sep 25
American Airlines Logo
2:58 pm - 9:35 pmSFO  San Francisco-ORD Chicago O'Hare Intl
4h 37mnonstop
American Airlines Logo
6:45 am - 9:34 amORD  Chicago O'Hare Intl-SFO San Francisco
4h 49mnonstop
$256American Airlines
Fri, Oct 2 - Mon, Oct 5
United Airlines Logo
11:30 pm - 5:59 amSFO  San Francisco-ORD Chicago O'Hare Intl
4h 29mnonstop
United Airlines Logo
9:40 pm - 12:30 amORD  Chicago O'Hare Intl-SFO San Francisco
4h 50mnonstop
$257United Airlines
Sat, Sep 26 - Sat, Sep 26
United Airlines Logo
5:00 am - 11:25 amSFO  San Francisco-ORD Chicago O'Hare Intl
4h 25mnonstop
United Airlines Logo
3:35 pm - 6:24 pmORD  Chicago O'Hare Intl-SFO San Francisco
4h 49mnonstop
$257United Airlines
Wed, Sep 23 - Thu, Sep 24
Delta Logo
12:05 am - 8:30 amSFO  San Francisco-ORD Chicago O'Hare Intl
6h 25m1 stop Minneapolis St Paul
Delta Logo
6:59 pm - 11:40 pmORD  Chicago O'Hare Intl-SFO San Francisco
6h 41m1 stop Los Angeles
$257Delta
Mon, Sep 21 - Wed, Sep 23
Delta Logo
2:30 pm - 11:31 pmSFO  San Francisco-ORD Chicago O'Hare Intl
7h 01m1 stop Los Angeles
Delta Logo
8:25 am - 1:06 pmORD  Chicago O'Hare Intl-SFO San Francisco
6h 41m1 stop Minneapolis St Paul
$257Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$99
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Oakland to Chicago O'Hare Airport

FAQs for booking San Francisco Bay Area to Chicago O'Hare Airport flights

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

    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 O'Hare Airport.

  • 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 O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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 O'Hare Airport?

    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 O'Hare Airport 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.
7.9
Alaska AirlinesOverall score based on 12864 reviews
7.0Entertainment
7.8Comfort
7.0Food
8.1Boarding
8.5Crew
Airline reviews

The plane smelled like an aquarium. Many passengers noted it smelled like fish. We then sat on the plane for over 2 hours before taking off

4.0 OkayKelsey, Aug 2026
Read more Alaska Airlines reviews

The plane smelled like an aquarium. Many passengers noted it smelled like fish. We then sat on the plane for over 2 hours before taking off

Only issue is that when you board last they make you check your carry on due to lack of space. Did not care for that.

My flight was several times rescheduled and then finally canceled.

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.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

There was no coffee on the flight. I was very surprised. I know it is a small thing, but they seemed to have run out of other drinks.

If Alaska Air is going to partner with other airlines, then it has to make the transition to the connecting flight better, especially if Alaska Air is the one that is running late. When I realized our 30 minutes of lateness due to weather was going to make getting to my connecting flight home more difficult ,I would have expected more from the crew than blank stares and "sorry". My son and I had 20 minutes to get from Gate E to the end of Gate K in the Chicago airport. My 50+ year-old body had to sprint and yell to get through the throngs and have any chance of arriving to the gate on time. In addition, the seats I had chosen when I purchased the connecting flight were changed so that my son and I placed in the last rows next to the bathrooms and were separated. There needs to be better communication between the airlines if one is going to be late. The thought of not making it home on time (we still had an 1.5 hour drive to get there) was stressful and unnecessary.

Delta was fine though my flight was delayed 4 hours into LGA and my return into ORD involved a taxi of 1+ hour to the gate

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was very warm the entire time, despite my vents being open. Additionally, we didn't have internet on our personal devices

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

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

long flights are never truly comfortable but the airline did their best. crew was great and the flight was safe.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

The staff did not do a good job of getting everyone boarded quickly, so we missed our take off window and had to sit on the tarmac for 20+ min waiting for our turn. The plan was old. Pockets on the back of seats were torn and tearing off. One of the attendants was rude-she would ask a question but he walking away before you finished answering so she kept getting our drink orders wrong.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

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.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

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

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.

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.

Wifi did not work. Cut off on and off every 10 min

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

The flight from LA to Chicago was smooth and service was very good overall.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Was not able to watch most shows on the entertainment site. They would not load

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

The flight was uneventful. What was a problem was I was delayed getting home one entire day because the flight from Sacramento was delayed. That made getting to my connecting flight impossible. I had to stay another night at the hotel and incur that expense as a result.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

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.

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.

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.

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

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

Flying Frontier was a nightmare. From the booking through Kayak, checking in, departing and arriving, I will never recommend Kayak or Frontier.

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