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Find cheap flights from San Francisco Bay Area to Chicago Midway Airport from $44

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 8/21. 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
Thu 6/6
Thu 6/13

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In the last 7 days travelers have searched 42,573,820 times on KAYAK, and here is why:

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Good to know

Low season

January

High season

October

Cheapest flight

$44
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 16% 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, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 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 9137 reviews
8.6Crew
7.3Entertainment
8.2Boarding
7.9Comfort
7.3Food
Airline reviews

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

4.0 OkayRandy, May 2024SFO - SEA
Read more about Alaska Airlines reviews

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

The space for legs in coach is better than other Airlines you can even cross your legs!!

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

Honestly, there was not much they could do. Due to wind, the flight was delayed for several hours because we had to be diverted to San Jose where we needed to refuel before departing to Hawaii. Wish they had offered some snacks during the delays/diversion because we had to wait such a long time to finally get our food served during the flight after leaving California.

They canceled the flight 30 minutes prior to departure without any heads up.

All parts were excellent, especially staff at bag tag printing and inflight crew. Just the normal differences from past air travel could be improved but we’ve learned to accept those—cramped seats, minimal food/beverage, etc.

Better organizing of entry and exit onto the plane regarding all of the baggage people haul on. There should be a better system so those with no baggage can get in and out more quickly. The baggage haul-on situation is absurd.

Attentive crew. Best of all was the empty seat between me and my rowmate.

We had a very scary attempted landing in Palm Springs and were redirected to Ontario. It was a stressful flight.

Every thing means , crew, service, timing, boarding is very good.

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).

You need to be a hacker to get the (Free) WiFi

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.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

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

8/24Sat
nonstopFrontier
4h 11mSFO-MDW
8/26Mon
nonstopFrontier
4h 38mMDW-SFO
$108
5/20Mon
nonstopFrontier
4h 12mSFO-MDW
6/1Sat
nonstopFrontier
4h 29mMDW-SFO
$123
9/9Mon
nonstopFrontier
4h 11mSFO-MDW
9/16Mon
nonstopFrontier
4h 38mMDW-SFO
$128
9/16Mon
nonstopFrontier
4h 11mSFO-MDW
9/20Fri
nonstopFrontier
4h 38mMDW-SFO
$130
9/20Fri
1 stopDelta
8h 11mSFO-MDW
9/25Wed
1 stopDelta
7h 40mMDW-SFO
$236
9/28Sat
1 stopDelta
8h 30mSFO-MDW
10/2Wed
1 stopDelta
7h 40mMDW-SFO
$265
6/1Sat
2 stops
22h 32mSJC-MDW
6/7Fri
2 stops
27h 06mMDW-SJC
$364
6/1Sat
3 stops
26h 51mSJC-MDW
6/7Fri
2 stops
27h 06mMDW-SJC
$386
6/4Tue
1 stopVolaris
18h 18mSJC-MDW
6/10Mon
1 stopVolaris
14h 17mMDW-SJC
$715
5/30Thu
1 stopVolaris
18h 13mSJC-MDW
6/3Mon
1 stopVolaris
14h 17mMDW-SJC
$718

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Recent one-way flight deals

8/21Wed
nonstopFrontier
4h 11mSFO-MDW
$44
9/28Sat
nonstopFrontier
4h 11mSFO-MDW
$46
7/9Tue
1 stopDelta
8h 55mSFO-MDW
$120
5/22Wed
2 stopsDelta
9h 16mOAK-MDW
$123
5/16Thu
1 stop
14h 09mSFO-MDW
$138
6/23Sun
1 stop
14h 03mSFO-MDW
$166
5/29Wed
1 stopSouthwest
8h 10mSFO-MDW
$171
5/29Wed
2 stopsSouthwest
10h 50mSFO-MDW
$176
10/3Thu
1 stopVolaris
13h 08mOAK-MDW
$313
10/13Sun
1 stopVolaris
13h 08mOAK-MDW
$314

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Last minute flights from San Francisco Bay Area to Midway

Last minute flight, train and bus deals

5/11Sat
nonstopFrontier
4h 11mSFO-MDW
5/14Tue
nonstopFrontier
4h 39mMDW-SFO
$154
5/11Sat
multi-stopFrontier
9h 25mSFO-MDW
5/14Tue
nonstopFrontier
4h 39mMDW-SFO
$167
5/10Fri
multi-stopFrontier
17h 41mSFO-MDW
5/14Tue
nonstopFrontier
4h 39mMDW-SFO
$175
5/11Sat
nonstopFrontier
4h 11mSFO-MDW
5/15Wed
nonstopFrontier
4h 39mMDW-SFO
$204
5/10Fri
multi-stopDelta
8h 22mSFO-MDW
5/15Wed
multi-stopDelta
9h 02mMDW-SFO
$459
5/7Tue
multi-stopDelta
8h 11mSFO-MDW
5/8Wed
multi-stopDelta
9h 31mMDW-SFO
$520
5/11Sat
multi-stop
22h 42mSJC-MDW
5/13Mon
multi-stop
37h 56mMDW-SJC
$788
5/10Fri
multi-stopVolaris
14h 20mSJC-MDW
5/13Mon
multi-stopVolaris
14h 17mMDW-SJC
$816
5/9Thu
multi-stop
13h 08mOAK-MDW
5/12Sun
multi-stop
19h 00mMDW-OAK
$899
5/7Tue
multi-stopVolaris
15h 44mOAK-MDW
5/9Thu
multi-stopVolaris
15h 33mMDW-OAK
$1,040

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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:

$408
$513
$219
$38