MDW

$101 Find Cheap Flights from San Francisco Bay Area to Chicago Midway Airport

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 5/16. 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

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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

Wed, Apr 15 - Sat, Apr 18
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
$223Southwest
Sat, Apr 25 - Tue, Apr 28
Frontier Logo
10:38 pm - 9:58 am
SFO
-
MDW
9h 20m
1 stop
Frontier Logo
6:10 am - 5:34 pm
MDW
-
SFO
13h 24m
1 stop
$232Frontier
Wed, Apr 22 - Sat, Apr 25
Southwest Logo
7:40 pm - 4:35 am
SFO
-
MDW
6h 55m
1 stop
Southwest Logo
10:00 am - 12:35 pm
MDW
-
SFO
4h 35mnonstop
$233Southwest
Wed, Apr 15 - Sat, Apr 18
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:30 pm - 9:45 pm
MDW
-
OAK
6h 15m
1 stop
$233Southwest
Sat, May 2 - Sat, May 9
Southwest Logo
11:25 pm - 5:40 am
SFO
-
MDW
4h 15mnonstop
Southwest Logo
6:10 pm - 8:45 pm
MDW
-
SFO
4h 35mnonstop
$234Southwest
Thu, Apr 16 - Sat, Apr 18
Southwest Logo
11:55 pm - 6:00 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
5:55 pm - 8:30 pm
MDW
-
OAK
4h 35mnonstop
$234Southwest
Tue, Apr 14 - Tue, Apr 21
Frontier Logo
6:00 am - 10:14 pm
SFO
-
MDW
14h 14m
2 stops
Frontier Logo
6:10 am - 5:34 pm
MDW
-
SFO
13h 24m
1 stop
$236Frontier
Fri, Apr 10 - Sat, Apr 18
Delta Logo
12:10 am - 8:50 am
SFO
-
MDW
6h 40m
1 stop
Delta Logo
9:27 am - 2:55 pm
MDW
-
SFO
7h 28m
1 stop
$237Delta
Mon, Mar 30 - Sat, Apr 4
Delta Logo
10:40 pm - 8:53 am
SFO
-
MDW
8h 13m
1 stop
Delta Logo
1:10 pm - 7:28 pm
MDW
-
SFO
8h 18m
1 stop
$242Delta
Mon, May 18 - Tue, May 26
Delta Logo
10:55 pm - 8:43 am
SJC
-
MDW
7h 48m
1 stop
Delta Logo
1:59 pm - 8:38 pm
MDW
-
SJC
8h 39m
1 stop
$287Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Oakland to Chicago Midway Airport

FAQs for booking San Francisco Bay Area to Chicago Midway Airport flights

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway 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 Midway 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 Midway 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 Midway 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 Midway 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.
8.0
SouthwestOverall score based on 4313 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

10.0 ExcellentMarty, Mar 2026
SJC - LGB
Read more Southwest reviews

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

The seats were comfortable, and the boarding process was pretty smooth.

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

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

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

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Got on the plane and sat there for an hour before departure.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

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

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

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.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

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

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

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

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.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

The flight never took off and we spent 7 hours at the airport

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.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

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.

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

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