MDW

$94 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 5/13. 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.
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Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from San Francisco Bay Area to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from San Francisco Bay Area to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
11:50 pm - 1:34 pmSFO-MDW
11h 44m1 stop
Frontier Logo
2:12 pm - 10:22 pmMDW-SFO
10h 10m1 stop
$198Frontier
Find Deal
Sat, May 10 - Wed, May 14
Frontier Logo
2:03 pm - 2:48 pmSFO-MDW
22h 45m1 stop
Frontier Logo
2:44 pm - 12:09 amMDW-SFO
11h 25m1 stop
$200Frontier
Find Deal
Sat, May 17 - Sat, May 24
Frontier Logo
2:03 pm - 2:48 pmSFO-MDW
22h 45m1 stop
Frontier Logo
2:44 pm - 12:09 amMDW-SFO
11h 25m1 stop
$201Frontier
Find Deal
Sat, May 17 - Sat, May 24
Frontier Logo
2:03 pm - 2:48 pmSFO-MDW
22h 45m1 stop
Frontier Logo
2:44 pm - 12:09 amMDW-SFO
11h 25m1 stop
$202Frontier
Find Deal
Sat, May 17 - Sat, May 24
Southwest Logo
7:45 pm - 5:00 amSFO-MDW
7h 15m1 stop
Southwest Logo
7:00 pm - 11:10 pmMDW-SFO
6h 10m1 stop
$216Southwest
Find Deal
Tue, Jun 10 - Sat, Jun 28
Southwest Logo
6:35 pm - 5:20 amSFO-MDW
8h 45m1 stop
Southwest Logo
1:35 pm - 4:05 pmMDW-SFO
4h 30mnonstop
$217Southwest
Find Deal
Tue, Jun 3 - Thu, Jun 5
Delta Logo
12:52 am - 8:45 amSFO-MDW
5h 53m1 stop
Delta Logo
7:21 pm - 11:39 pmMDW-SFO
6h 18m1 stop
$257Delta
Find Deal
Mon, Jul 28 - Fri, Aug 1
Delta Logo
6:00 am - 5:45 pmOAK-MDW
9h 45m2 stops
Delta Logo
9:21 am - 4:16 pmMDW-OAK
8h 55m2 stops
$267Delta
Find Deal
Tue, Jun 3 - Wed, Jun 11
 Logo
6:00 am - 8:53 pmSJC-MDW
36h 53m2 stops
 Logo
6:25 am - 1:40 pmMDW-SJC
9h 15m1 stop
Fri, May 30 - Mon, Jun 2
 Logo
11:00 am - 8:53 pmSJC-MDW
31h 53m2 stops
 Logo
6:25 am - 1:43 pmMDW-SJC
9h 18m1 stop
Fri, May 23 - Sun, May 25
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Good to know

Low seasonJanuary
High seasonMay
Cheapest flight$94
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from San Francisco 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.

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 9968 reviews
7.9Comfort
8.2Boarding
7.1Entertainment
7.1Food
8.5Crew
Airline reviews

My youngest didn't have a assigned seat until we biard6the plane.

2.0 MediocreStephanie, Apr 2025SAN - SLC
Read more Alaska Airlines reviews

My youngest didn't have a assigned seat until we biard6the plane.

I got the last seat on the plane, in the back in the corner against the window, and I paid a competitive price for my ticket several weeks before the flight.

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

There was no seating at the gate, no where to charge your devices, super crowded. Boarding in group F meant all luggage space was taken when it was time for me to board. The boarding crew was short with everyone and seemed irritated. The luggage space was insufficient, the seat was too small for me (6'4") and very uncomfortable trip. I was in a middle seat between a person snoring the whole trip and a person with very strong body odor. The flight crew was terse and unfriendly, seemed irritated and impatient. Yelled a lot at people with earbuds in, understandable. Finally, we arrived 10 minutes early, only to sit on the tarmac for 20 minutes and wait for a gate. Worst flight experience I've had in years.

Check your emails that you sent me. 9 emails were sent telling me that my flight is Delayed. Each one with a different time 7:10, 7:55, 9:31, 9:09, 9:29, 9:44, 10:00, 9:49, and 10:10. That was how my experience went.

It was my first time flying Alaska Airlines and first time flying from Santa Rosa airport. The staff was very professional and friendly. Their instructions were clear and any question was answered satisfactorily. My seat was comfortable and the in-flight beverage service very adequate for the duration of the flight. We arrived ahead of the scheduled landing time and deplaning was simple. I look forward to flying with Alaska again.

Personal demeanor not good on flight returning to LAX..Great and superb on the way to Portland

No non-alcoholic drinks available except water and small apple juice cans.

Flight attendant took my carefully folded coat and flung it across the aisle to the bin across the way. Where one of the passengers rescued it for me, because that just wasn’t right!!

First time flying with any airline that has decent seating. Great experience crew was friendly and the pilot was as well.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Delta flight was on time, seats were comfortable, and crew was nice.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

Horrible. Grateful to be alive but spent 13 hours at airport only to return back to my familys house and flight changed to next day. They tried to fix a part on plane, had no back up plane and after 10 hours , reattempted the flight and it STILL wasn't fixed. We got a meal voucher and rescheduled flight but there should be some other compensation for the 15 hours spent in airport

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

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Frontier had yet another flight cancellation. Have never made a complete round trip with this airline without at least one leg getting cancelled. Miserable flights - dirty, uncomfortable planes that apparently always have issues since I've had multiple delays and cancellations with them.

Flight was delayed 3 times, would have been nice to have received text message instead of email notifications. Frontier app wasn’t even updated accordingly, no gate number disclosed. No agent at front desk of gate to inform of delay. Very confused and left if the dark

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

They changed the timing , first delayed by 4 hours then went back to 40 mins late, we had to run back to airport to not miss our flight. This is ridiculous

No frills for sure. No gate announcements about flight delay, not even water to drink on the flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.

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