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$68 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 Midway departing on 6/10. 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 6/29
Sat 7/6

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Good to know

Low season

January

High season

June

Cheapest flight

$68
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 1% 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.

See more FAQs

Prefer to fly non-stop from San Francisco Bay Area to Chicago Midway Airport?

Find which airlines fly direct from San Francisco Bay Area to Midway, which days they fly and book direct flights.

Nonstop departures

San Francisco Bay Area to Chicago Midway

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights

Nonstop returns

Chicago Midway to San Francisco Bay Area

Monday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Tuesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Wednesday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Thursday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Friday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

Saturday

Aeromexico, Air France, Delta, +9 more

Aeromexico, Air France, +10 more

Sunday

Aeromexico, Air France, Allegiant Air, +11 more

Aeromexico, Air France, +12 more

See more direct flights
See more direct flights

Top 4 airlines serving from San Francisco Bay Area to Midway

 
Need help choosing which airline to fly with from San Francisco Bay Area to Midway? 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 9196 reviews
7.3Entertainment
8.2Boarding
7.3Food
8.6Crew
7.9Comfort
Airline reviews

I didn’t know that food needed to be ordered ahead. Please include this in the reservation information. Overall, very good experience.

8.0 ExcellentNorma, May 2024SNA - SEA
Read more about Alaska Airlines reviews

I didn’t know that food needed to be ordered ahead. Please include this in the reservation information. Overall, very good experience.

Plane hit turbulence diverted to Houston. We'll probably get in after 3am

Given incorrect gate upon check-in, corrected by the gate attendant, D6 rather than D5, minor inconvenience. As with the previous flight, passengers were admonished to voluntarily gate-check carry-on luggage with the statement that those in the last boarding group would have no choice but to do so. If the Boeing 737 MAX8/MAX9 doesn't have room for carry-ons it's an interior design flaw on the part of Boeing. Posting an advance warning would be helpful, such as "Boeing 737 MAX planes feature limited carry-on space. Please be aware." SFO's amenities and TSA much better than MCO's. Crew was amazing! Brought my own food because Alaska's onboard selection has soy in everything. Beverage service was excellent. This was the first and last trip with Alaska after the previous flight's issues. It's no reflection on the crew of this flight. They were great.

I had a middle seat in between two large men. It was a redeye so needless to say I didn’t get a minute of sleep. One guy was pouring over into my seat the other kept falling onto my shoulder

Great price on internet. I love that WiFi was so affordable. Got a lot done.

1309 on May had some very bumpy segments that seem to take too long to get to smoother air. My initial flight out of GRR was delayed and missed connections. Sure glad I made a different one in ORD so I could be in Anchorage.

Ground staff at LAX was very helpful. The Alaska lounge food and service is better than most airport lounges. I think the Staff are well trained polite and actually seem happy to work there. Great service Thanks 🙏 Jjk

The flight was very very delayed and arrived much later than planned. There was no communication about why or when our arrival would be. I would expect better and open communication about the flight but there was none. Also just pretzels? How disappointing.

Sat on tarmac for 30 minutes despite staring at three empty gates, one of which we eventually pulled into

It was ok. Alaska was adequate. Efficient and what I paid for it was fair. The boarding area at the gate was a joke. By the time they get past the C boarding group people all line up impatiently and then it’s chaos. We were boarding early then we sat on the tarmac for 30 minutes. I would of rather sat in the airport.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

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

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

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

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.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

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.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

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

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

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

Terrible. Seats are bad and the baggage policy is inconsistent

Better than I expected but I did pay for a seat and carry on bags ahead of time.

I hope to avoid flying with them in the future. First flight got cancelled then got stuck with a 13 hour layover in Denver. The process was long and frustrating to many people.

Flight was delayed on the runway for 40 minutes the crew did not even offer even water to passengers to compensate for the flight delayed. The flight was delayed due to aircraft mechanical issues. Worst customer service ever

The flight was delayed and I had to cancel because I would have missed my connection and there were no other flights for the next two days. They also lost my bag!!

Book cheap flights from San Francisco Bay Area to Chicago

Recent round-trip flight deals

9/7Sat
nonstopFrontier
4h 11mSFO-MDW
9/11Wed
nonstopFrontier
4h 38mMDW-SFO
$138
9/7Sat
nonstopFrontier
4h 11mSFO-MDW
9/14Sat
nonstopFrontier
4h 38mMDW-SFO
$139
7/10Wed
nonstopFrontier
4h 10mSFO-MDW
7/24Wed
nonstopFrontier
4h 29mMDW-SFO
$140
9/4Wed
nonstopFrontier
4h 11mSFO-MDW
9/7Sat
nonstopFrontier
4h 38mMDW-SFO
$141
8/9Fri
1 stopDelta
8h 43mSFO-MDW
8/16Fri
1 stopDelta
7h 36mMDW-SFO
$262
8/16Fri
1 stopDelta
9h 47mSFO-MDW
8/18Sun
1 stopDelta
7h 36mMDW-SFO
$317
8/11Sun
2 stops
17h 50mOAK-MDW
8/18Sun
2 stops
18h 04mMDW-OAK
$393
8/11Sun
2 stops
17h 50mOAK-MDW
8/18Sun
3 stops
29h 06mMDW-OAK
$445
6/13Thu
1 stopVolaris
17h 33mSJC-MDW
6/18Tue
1 stopVolaris
17h 06mMDW-SJC
$786
6/12Wed
1 stopVolaris
18h 23mSJC-MDW
6/15Sat
1 stopVolaris
14h 17mMDW-SJC
$844

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Recent one-way flight deals

6/10Mon
nonstopFrontier
4h 11mSFO-MDW
$68
7/10Wed
nonstopFrontier
4h 10mSFO-MDW
$69
8/2Fri
1 stopDelta
8h 43mSFO-MDW
$118
9/30Mon
2 stopsDelta
11h 46mOAK-MDW
$123
7/18Thu
1 stop
13h 59mSFO-MDW
$142
6/9Sun
2 stops
13h 26mSJC-MDW
$161
6/9Sun
1 stopSouthwest
17h 10mSFO-MDW
$295
6/4Tue
nonstopSouthwest
4h 00mSFO-MDW
$309
7/24Wed
2 stopsPorter Airlines
13h 22mSFO-MDW
$357
7/8Mon
2 stopsPorter Airlines
13h 22mSFO-MDW
$365

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Last minute flights from San Francisco Bay Area to Midway

Last minute flight, train and bus deals

6/3Mon
nonstopFrontier
4h 12mSFO-MDW
6/7Fri
nonstopFrontier
4h 28mMDW-SFO
$141
6/3Mon
nonstopFrontier
4h 12mSFO-MDW
6/7Fri
nonstopFrontier
4h 28mMDW-SFO
$163
6/3Mon
nonstopFrontier
4h 12mSFO-MDW
7/5Fri
nonstopFrontier
4h 29mMDW-SFO
$179
6/4Tue
multi-stopDelta
6h 07mSFO-MDW
6/19Wed
multi-stopDelta
8h 06mMDW-SFO
$646
6/1Sat
multi-stopDelta
8h 23mOAK-MDW
6/4Tue
multi-stopDelta
8h 35mMDW-OAK
$714
6/1Sat
multi-stop
13h 08mOAK-MDW
6/4Tue
multi-stop
26h 55mMDW-OAK
$820
5/31Fri
multi-stopVolaris
17h 33mSJC-MDW
6/2Sun
multi-stopVolaris
14h 17mMDW-SJC
$858
5/31Fri
multi-stop
17h 33mSJC-MDW
6/3Mon
multi-stop
37h 51mMDW-SJC
$861
5/31Fri
multi-stopVolaris
17h 33mSJC-MDW
6/4Tue
multi-stopVolaris
14h 17mMDW-SJC
$891
5/31Fri
multi-stopWestJet
25h 32mSFO-MDW
6/2Sun
multi-stopWestJet
29h 03mMDW-SFO
$1,616

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Flights to Chicago Midway Airport

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - San Francisco Bay Area

Cabin classes:

$360
$433
$246
$43