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Find cheap flights from Chicago Midway Airport to San Francisco Bay Area from $49

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to San Francisco Bay Area 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
Sat 6/15
Sat 6/22

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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$98
San Jose
San Jose1 stop$308

Good to know

Low season

February

High season

December

Cheapest flight

$49
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 4% lower on average.
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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport 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 Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport 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 Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to San Francisco Bay Area

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: San Francisco $80 one-way - $138 round-trip

Top 3 airlines serving from Midway to San Francisco Bay Area

 
Need help choosing which airline to fly with from Midway 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.
8.0
DeltaOverall score based on 10673 reviews
7.9Comfort
8.0Entertainment
7.4Food
8.6Crew
8.2Boarding
Airline reviews

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

6.0 GoodEliza, Apr 2024SAN - LAX
Read more about Delta reviews

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

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

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

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

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.

Book cheap flights from Chicago to San Francisco Bay Area

Recent round-trip flight deals

9/18Wed
nonstopFrontier
4h 38mMDW-SFO
9/28Sat
nonstopFrontier
4h 11mSFO-MDW
$98
9/18Wed
nonstopFrontier
4h 38mMDW-SFO
9/21Sat
nonstopFrontier
4h 11mSFO-MDW
$100
9/18Wed
1 stopDelta
6h 52mMDW-SFO
9/20Fri
1 stopDelta
8h 11mSFO-MDW
$236
10/26Sat
1 stopDelta
9h 30mMDW-OAK
10/29Tue
1 stopDelta
8h 32mOAK-MDW
$236
5/31Fri
1 stop
27h 44mMDW-SFO
6/2Sun
1 stop
14h 01mSFO-MDW
$252
6/16Sun
1 stopSouthwest
13h 30mMDW-SJC
6/20Thu
nonstopSouthwest
4h 05mSJC-MDW
$439
6/16Sun
1 stopSouthwest
13h 30mMDW-SJC
6/20Thu
1 stopSouthwest
6h 10mSJC-MDW
$448
8/12Mon
2 stops
23h 30mMDW-SJC
8/18Sun
3 stops
22h 50mSJC-MDW
$495
6/12Wed
1 stopVolaris
14h 12mMDW-SJC
6/19Wed
1 stopVolaris
18h 23mSJC-MDW
$862
6/20Thu
1 stopVolaris
14h 17mMDW-SJC
6/23Sun
1 stopVolaris
21h 15mSJC-MDW
$870

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Recent one-way flight deals

8/24Sat
nonstopFrontier
4h 38mMDW-SFO
$49
7/31Wed
nonstopFrontier
4h 29mMDW-SFO
$50
5/31Fri
1 stop
27h 44mMDW-SFO
$115
7/9Tue
1 stopDelta
8h 02mMDW-SFO
$144
6/28Fri
1 stop
27h 42mMDW-SFO
$147
6/5Wed
1 stopDelta
8h 18mMDW-SJC
$154
6/16Sun
nonstopSouthwest
4h 40mMDW-SFO
$255
6/16Sun
2 stopsSouthwest
13h 20mMDW-SFO
$275
7/2Tue
2 stopsPorter Airlines
17h 12mMDW-SFO
$326
8/23Fri
2 stopsPorter Airlines
14h 07mMDW-SFO
$398

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Last minute flights from Midway to San Francisco Bay Area

Last minute flight, train and bus deals

5/18Sat
nonstopFrontier
4h 29mMDW-SFO
5/22Wed
nonstopFrontier
4h 12mSFO-MDW
$240
5/18Sat
nonstopFrontier
4h 29mMDW-SFO
5/28Tue
multi-stopFrontier
7h 23mSFO-MDW
$255
5/18Sat
multi-stopDelta
7h 32mMDW-SFO
5/25Sat
multi-stopDelta
7h 56mSFO-MDW
$413
5/18Sat
multi-stopDelta
7h 32mMDW-SFO
5/22Wed
multi-stopDelta
7h 56mSFO-MDW
$579
5/19Sun
multi-stop
17h 26mMDW-OAK
5/22Wed
multi-stop
13h 08mOAK-MDW
$932
5/17Fri
multi-stop
17h 32mMDW-OAK
5/21Tue
multi-stop
13h 13mOAK-MDW
$941
5/19Sun
multi-stopVolaris
15h 33mMDW-OAK
5/22Wed
multi-stopVolaris
13h 08mOAK-MDW
$954
5/17Fri
multi-stopVolaris
19h 18mMDW-OAK
5/21Tue
multi-stopVolaris
15h 44mOAK-MDW
$955
5/19Sun
multi-stopWestJet
28h 16mMDW-SFO
5/22Wed
multi-stopWestJet
27h 17mSFO-MDW
$1,125
5/17Fri
multi-stopWestJet
32h 58mMDW-SFO
5/21Tue
multi-stopWestJet
32h 37mSFO-MDW
$1,395

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Chicago Midway Airport - San Francisco Bay Area Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

San Francisco Bay Area - Chicago Midway Airport

Cabin classes:

$636
$598
$477
$27