MDW

$107 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 4/28. 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

Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$237Southwest
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
5:50 am - 11:55 am
OAK
-
MDW
4h 05mnonstop
Southwest Logo
3:55 pm - 8:20 pm
MDW
-
OAK
6h 25m
1 stop
$243Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
5:25 am - 11:35 am
SFO
-
MDW
4h 10mnonstop
Southwest Logo
3:00 pm - 8:55 pm
MDW
-
SFO
7h 55m
1 stop
$247Southwest
Tue, May 5 - Tue, May 12
Southwest Logo
6:00 am - 2:00 pm
OAK
-
MDW
6h 00m
1 stop
Southwest Logo
8:50 pm - 11:25 pm
MDW
-
OAK
4h 35mnonstop
$247Southwest
Thu, May 28 - Tue, Jun 2
Frontier Logo
11:59 pm - 2:12 pm
SFO
-
MDW
12h 13m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$250Frontier
Tue, Apr 14 - Tue, Apr 21
Delta Logo
10:55 pm - 8:47 am
SFO
-
MDW
7h 52m
1 stop
Delta Logo
1:24 pm - 7:03 pm
MDW
-
SFO
7h 39m
1 stop
$257Delta
Sat, May 16 - Wed, May 20
Frontier Logo
10:15 pm - 11:12 am
SFO
-
MDW
10h 57m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$258Frontier
Sat, May 9 - Tue, May 12
Frontier Logo
10:15 pm - 11:12 am
SFO
-
MDW
10h 57m
1 stop
Frontier Logo
3:07 pm - 11:04 pm
MDW
-
SFO
9h 57m
1 stop
$260Frontier
Mon, Apr 13 - Tue, Apr 21
Delta Logo
8:20 pm - 8:46 am
SJC
-
MDW
10h 26m
2 stops
Delta Logo
6:00 am - 12:21 pm
MDW
-
SJC
8h 21m
1 stop
$276Delta
Tue, Apr 14 - Sat, Apr 18
Delta Logo
8:20 pm - 8:47 am
SJC
-
MDW
10h 27m
2 stops
Delta Logo
9:27 am - 4:59 pm
MDW
-
SJC
9h 32m
2 stops
$281Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$107
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 2% 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 4 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 4324 reviews
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

10.0 ExcellentMartie, Mar 2026
LGB - BNA
Read more Southwest reviews

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

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.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

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!

Economy plus was so cramped I could not use my laptop. It was beyond bad.

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.

Remind customers of the need to have passport or new ID for boarding.

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.

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