$52 Find Cheap Flights from Chicago Midway Airport to California

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 California departing on 8/26. 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

KAYAK searches hundreds of travel sites at once for deals on flights to California

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to California, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to California, as well as popular online travel agencies
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Flights Deals

Best California Flight Deals from Midway

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Los Angeles
Los Angelesnonstop$163
San Francisco
San Franciscononstop$105
San Diego
San Diegononstop$104
San Jose
San Jose1 stop$185
Palm Springs
Palm Springs1 stop$151
Fresno
Fresno1 stop$170
Reno
Renononstop$175
Sacramento
Sacramento1 stop$173
Los Angeles
Los Angelesnonstop$163
San Francisco
San Franciscononstop$105
San Diego
San Diegononstop$104
San Jose
San Jose1 stop$185
Palm Springs
Palm Springs1 stop$151
Fresno
Fresno1 stop$170
Reno
Renononstop$175
Sacramento
Sacramento1 stop$173

Cheap Flights from Midway to California

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to California 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 Midway to California

Tue, Oct 7 - Wed, Oct 15
Southwest Logo
7:10 am - 9:30 amMDW-SAN
4h 20mnonstop
Southwest Logo
6:25 pm - 12:25 amSAN-MDW
4h 00mnonstop
$104Southwest
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Sat, Sep 27 - Sat, Oct 4
Southwest Logo
8:15 am - 10:50 amMDW-SFO
4h 35mnonstop
Southwest Logo
10:40 am - 4:45 pmSFO-MDW
4h 05mnonstop
$105Southwest
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Mon, Aug 18 - Tue, Aug 26
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
4:05 pm - 10:00 pmSAN-MDW
3h 55mnonstop
$109Southwest
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Thu, Aug 14 - Thu, Aug 21
Southwest Logo
8:50 pm - 11:05 pmMDW-SAN
4h 15mnonstop
Southwest Logo
1:40 pm - 7:40 pmSAN-MDW
4h 00mnonstop
$114Southwest
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Sat, Aug 2 - Fri, Aug 8
Frontier Logo
8:05 am - 4:19 pmMDW-LAS
10h 14m1 stop
Frontier Logo
12:59 am - 1:50 pmLAS-MDW
10h 51m1 stop
$129Frontier
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Sat, Sep 27 - Sun, Sep 28
Frontier Logo
11:23 am - 6:24 pmMDW-LAS
9h 01m1 stop
Frontier Logo
12:55 am - 1:11 pmLAS-MDW
10h 16m1 stop
$138Frontier
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Tue, Aug 5 - Sat, Aug 9
Frontier Logo
6:02 pm - 9:25 amMDW-LAS
17h 23m1 stop
Frontier Logo
6:43 pm - 1:29 pmLAS-MDW
16h 46m1 stop
$152Frontier
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Wed, Sep 3 - Sat, Sep 13
Delta Logo
1:08 pm - 8:42 pmMDW-SJC
9h 34m1 stop
Delta Logo
11:35 am - 8:53 amSJC-MDW
19h 18m2 stops
$239Delta
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Sun, Aug 31 - Sat, Sep 13
Delta Logo
6:00 am - 5:04 pmMDW-SJC
13h 04m2 stops
Delta Logo
2:25 pm - 8:53 amSJC-MDW
16h 28m2 stops
$244Delta
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Tue, Aug 26 - Fri, Sep 5
Delta Logo
9:15 am - 8:14 pmMDW-RNO
12h 59m1 stop
Delta Logo
10:59 pm - 9:36 amRNO-MDW
8h 37m1 stop
$247Delta
Find Deal
Useful Info

KAYAK's insights & trends for Midway to California flights

Get data-powered insights and trends into flights from Midway to California to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to California flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to California.

The cheapest ticket to California from Chicago Midway Airport found in the last 72 hours was to San Francisco, at $122 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Los Angeles (LAX), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $213.

Can I save money by flying with a layover from Chicago Midway Airport to California?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $432, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago Midway Airport to California?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to California, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago Midway Airport to California is September, when tickets cost $250 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $391 and $359 respectively.

What’s the cheapest day of the week to fly from Chicago Midway Airport to California?

The average price of all round-trip flights from Chicago Midway Airport to California clicked on KAYAK for each day over the last 12 months.

For Chicago Midway Airport to California, Tuesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from California back to Chicago Midway Airport, the best deals are generally found on Tuesday, with Sunday being the most expensive.

How far in advance should I book a flight from Chicago Midway Airport to California?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago Midway Airport to California, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago Midway Airport to California, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.


Good to know

Low seasonFebruary
High seasonApril
Cheapest flight$52
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Chicago Midway Airport to San Diego

FAQs - booking California flights

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to California?

    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 California.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to California?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to California 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 California?

    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 from Chicago Midway Airport to California with an airline and back 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 California?

    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 from Chicago Midway Airport to California up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to California?

    The cheapest time of day to fly to California is generally in the evening, when round-trip flights cost $327 on average. Morning departures are around 11% more expensive than evening flights, on average. The most expensive time of day to fly to California is generally in the morning, which is peak travel time and where the average cost of a ticket is $363.

Top tips for finding cheap flights to California

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Las Vegas $119 one-way - $207 round-trip; Los Angeles $134 one-way - $229 round-trip

Reviews of the top 5 airlines serving from Midway to California

 
See real verified KAYAK customer reviews for airlines flying from Chicago to California. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Midway to California? 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 4252 reviews
7.0Food
8.6Crew
7.6Entertainment
8.1Boarding
8.0Comfort
Airline reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

4.0 OkayAnonymous, Jun 2025MDW - LGA
Read more Southwest reviews

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

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

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

My flight to Chicago left and landed early. My return flight left two minutes late and arrived 2 minutes late. My seat selections were ideal! There were no snacks going to Chicago and no snacks on the return trip. There are no charging outlets on board.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Seats are much much more comfortable than United, which is what I usually fly

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

It was very bad it got delayed by 2 hours.Never going to travel with spirit airlines in future.

The flight times got delayed multiple times due to weather which is understandable, but later the time got prepared 30min. Made to the flight barely but got stressed too much.

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Very good. Nothing more or less than expected. No complaints.

My experience with the spirit as a first time it was OK, but the seats need a little cushion, the problem I had the most impacted me was when checking in the scales were so off and wrong. It will tell that you would have more weight, which was not true. The scale was say that it had Thirty Eight Pounds, when get in the labels when we send the luggage into the band. It says that it was overweight. I really really dislike that because the scales are not accurate. If I use Spirit and I have that issue again. That will be my last time flying with the spirit, even though I like so much to service the planes, and everything else

hahaha we are delayed for one hour plus.. but thx we arrived San Diego safe

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Very dissatisfied with spirit airlines after buying my ticket's they cancelled our flights with no reasoning.

Unclear pricing; ended up being charged an extra $52 just to get onboard

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

Very bad! No good service delayed my second connection flight

They canceled flight. Hard to believe there was even a plane incoming for us to get on

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Horrendous. I do not recommend Frontier. The passengers lack manners and decency, and the flight attendants lack professionalism. If I wasn’t in a bind to fly with 48 hours notice for a job interview, I would not have selected a flight with Frontier and I never plan to fly with them in the future.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

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