Find cheap flights from San Diego to Chicago Midway Airport

SAN - MDW

Find cheap flights from San Diego to Chicago Midway Airport

Round-trip
Economy
San Diego (SAN)
Chicago Midway
Wed 11/25
Wed 12/2
Any month
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Good to know

Low season

July Best time to beat the crowds with an average 44% drop in price.

High season

January Most popular time to fly with an average 39% increase in price.

Average price round-trip

$314 (avg. price over the last 2 weeks)

Good deal round-trip

$251 or less

Good deal one-way

$131 or less

When to book flights from San Diego to Chicago Midway

Estimated round-trip price
Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $131 or less one-way and $251 or less round-trip.
  • The cheapest flight from San Diego to Chicago Midway Airport was found 21 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be December, January and February. The cheapest month to fly is July.
  • Morning departure is around 55% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking San Diego to Chicago Midway Airport flights

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How long does a flight from San Diego to Chicago Midway Airport take?

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Top airline flying San Diego to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,789 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Amazing crew very good service ."
Cons: "Chose my seat, instead of leaving it to the airline ."

Pros: "Crew and all folks. I had not flown Delta for a while. Based on this flight, I’ll put Delta as a first option in future plans."

Cons: "Bring ear buds if you want to watch/listen to a movie. Delta changes for ear buds Everything else was fine"

Cons: "Missed flight due to unnecessary delays"

Pros: "Nothing exceptional stands out"
Cons: "Flight was not on time"

Pros: "Crew was great"
Cons: "flight was diverted an hour away for refueling because of weather over SLC. But SLC opened before we even landed at Grand Junction, CO. I had 8 mins to run between concourses to catch the next flight. My bags didn’t make the flight and have perishable food items. But it is what it is."

Pros: "Crew, exit row seat"
Cons: "Bathroom"

Pros: "Great flight"

Pros: "seating, food, service"

Cons: "Delayed 3 hours"

Pros: "That we finally arrived."
Cons: "That we didn't arrive even remotely close to when we were supposed to."

Pros: "Are usually fly international, and I really enjoy it. Flying domestic inside the US is bad because you never know when you will get flight delays, like we got. It wasn’t the fault of Delta, but it sucked."
Cons: "Small seeds, no food, the flight delay"

Pros: "Great crew on board!"

Pros: "on time"

Pros: "Fabulous fight. Attentive staff and I love the free entertainment tv’s."

Pros: "On time boarding in Seattle."
Cons: "Delayed in Los Angeles for about an hour. Checked on flight tracker and this flight is consistently delayed 20-40 minutes. Why hasn't Delta done anything to improve this?"

Pros: "More entertainment options were added. Thank you"
Cons: "It didn't fly fast enough. Jk. Not much to say"

Pros: "The short flight was fine. Crew was friendly."
Cons: "Because we arrived to LAX from SAN so late we had to run to the next gate and barely made the flight. The overhead bins were already very full so we had to stuff our stuff at our feet. Since we arrived so late it would have been better if they had allowed those with a tight connection to disembark first."

Pros: "They kept me fed and hydrated the whole time, they let you watch brand new movies free, the seats are super comfortable. They allow a personal item and carry on at no extra charge."

Pros: "Flight attrndants on delta are mostly ok-- but there are several with bad attitudes who cannot communicate They will just point at things and mumble incoherently with incomplete sentences They will not turn there hips when walking down the aisle to avoid hitting people & they"
Cons: "Flight attendants are miserable"

Pros: "What is the issue?"

Cons: "They delayed the takeoff because of catering, really over a half hour because you wanted to sell more sandwiches. So you make us late and the poor people who had connecting flight, it just does not make sense."

Pros: "Friendly and informative flight attendants kept the passengers in reasonable spirit."
Cons: "Left nearly an hour late after confusion related to oversold seats and upgrades. The gate agent entered the plane multiple times. The landing was rough, the brakes were loud."

Pros: "That my flight was on time"
Cons: "Pretty much everything else about it"

Pros: "Nothing I can think of right away"
Cons: "Late arrival and late departure. Poor service in having my luggage be connected to my flight. Was under the impression that they would do that after I had called the day prior and once I got to airport they didn't do so"

Cons: "The flight was over 20 minutes early"

Pros: "Staff were all polite"
Cons: "The least amount of legroom I've ever had. The most cramped I've ever been and I'm 5'2 and fly a lot. Also for a 5 hour flight, I should not have been as uncomfortable as I was. There's less cushion than before."

Pros: "Boarding was easy"
Cons: "Arrived 15 mins late and then taxied for another 5-10 mins."

Cons: "Undersized overhead bins so ALL carry-on rollerbags had to be checked."

Pros: "Boarding was quick and easy. Woot! For food on the SAN to JFK flight!"
Cons: "I hate that I booked and checked in early, but still had my seat assignment changed twice before boarding, and when I got to my seat, it was in front of the exit row, and my seat wouldn't recline. It was terribly uncomfortable"

Pros: "Service. Sweet attendant."

Pros: "Everything was excellent."
Cons: "Cant get used to cookies and drink service on long haul flight. Do not care for salable food choices so packed a sandwich."

Pros: "The crew was friendly and accommodating, and service was good"
Cons: "I purchased a basic economy ticket and upon checking in, my Delta app said my seat was unassigned and I had to get my boarding pass at the airport. I checked back later and the app had me as number 7 on the standby list. I called Delta (wait time 3+ hours... my flight was in 3), and then the Delta app support where I was able to get through to someone. She told me that the ticket I purchased over a month in advance did not guarantee me a seat on the plane (???). She said that if I was bumped from the flight they would reschedule me for the next morning. She was pretty rude and made it seem like I had a 50/50 shot of getting on this plane. I rushed to the airport in hopes that I would be the first from Standby there, and the gate agent told me that I was fine and would board right after first class and be assigned a seat then. Great. Once I got my seat assignment, I board to find out there is someone else sitting in my seat...... They eventually called the desk and had her moved, but it was the weirdest boarding experience I've had.. and I've flown Spirit. These planes that Delta fly's are SO OLD. Both times I have flown Delta the "turbulence" has been so bad and cold air was blowing right on my the whole flight with no option to turn it off (it wasn't from one of the vents, but from the side). Someone close to me works for Delta and I know for a fact that some of their engines blow mid-flight.. and they tell the passengers that it's turbulence.. so that doesn't make me feel very safe. I won't fly Delta again if there is another comparable option."

Cons: "Extreme delays"

Cons: "Flight attendants were a little snobby and didn't treat all passengers equally, in my humble opinion (note: I was sitting in 1st class)."

Cons: "no legroom in a first class and expensive seat"

Pros: "Very easy flight & process"

Pros: "Always have great experience with Delta flight attendants and staff. The entertainment on mobile phone was a really nice add-on, I had never seen before."
Cons: "Flight was delayed in taking off, waiting for connecting passengers. Plane was old, which is most Delta planes, but this one showed it. The tray table looked like it was from the 70s or 80s. Flying into Midway instead of O'hare was anticlimactic."

Pros: "Excellent crew"
Cons: "Leg room"

Pros: "Liked the entertainment option. I was able to watch most of a movie on the first flight, then pick up the end on the second. B737-900 ER is a nice plane"
Cons: "Boarding sequence seems inefficient"

Cons: "The plane temperature was too hot from boarding to landing"

Pros: "The crew, and boarding quickly"
Cons: "The flight was packed. It was hot as we boarded. The seat was tight and uncomfortable"

Pros: "Nice staff"
Cons: "No leg room, tight squeeze, charge for checked bags, no room for carryon luggage, bin compartments are too small"

Pros: "Good flight, on time, uneventful. The best kind"
Cons: "No free beer :)"

Pros: "We were given snacks and sandwiches for the delay."
Cons: "Paid for an upgrade but the seat was not what I had asked for. The agent said I would get a refund but I was not clear on how that works. Our plane experienced a mechanical issue. We were told after we boarded. Had to wait 1 1/2 hours in a stuffy hot plane. The bathrooms were very dirty and stinky. The bathroom door did not close properly. We finally deplaned and waited for a new plane. Got to Kona at 2:00am. The air temp was warm the entire flight. Had to endure a grumpy crew. Not the best flying experience. I know you can do better. Maybe look at how Hawaiian airlines does it and you might get some inspiration on how to improve."

Pros: "The pilot did a good job flying considering the conditions."
Cons: "Delta and Midway airport did not handle the weather conditions as well as they could have. Communications we terrible and no one adapted quickly to handle things properly. Of course the winter weather alert was mostly to blame, but what could be done to smooth things out didn't happen."

Pros: "Very easy going"

Pros: "I like the service"
Cons: "The plane landed with very Chwica I of aviation lovers"

Pros: "They provided a lot of entertainment options. They also kept the lights dimmed so it was easier to relax."
Cons: "It was extremely uncomfortable. I couldn't sleep a wink due to how uncomfortable I was. My knees just ached so bad I couldn't sleep without waking up in pain.I wish the seats could lower for shorter people like myself."

Read more about Delta

Book cheap flights from San Diego to Chicago Midway Airport

Recent round-trip flight deals

12/10
Thu
1 stop
Delta
7h 53m
SAN - MDW
12/15
Tue
1 stop
Delta
8h 10m
MDW - SAN
12/29
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7h 15m
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1/6
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8h 44m
MDW - SAN
3/9
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1 stop
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9h 38m
SAN - MDW
3/16
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1 stop
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7h 40m
MDW - SAN
12/11
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1 stop
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7h 53m
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12/13
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8h 10m
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1/12
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1 stop
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7h 18m
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4/1
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1 stop
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7h 40m
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12/22
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8h 39m
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12/30
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8h 46m
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12/23
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10h 08m
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1/1
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1 stop
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8h 46m
MDW - SAN
12/23
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1 stop
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8h 39m
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12/29
Tue
1 stop
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8h 46m
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12/20
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3 stops
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33h 15m
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1/2
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35h 34m
MDW - SAN
12/21
Mon
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50h 59m
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12/27
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21h 01m
MDW - SAN
3/24
Wed
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Delta
9h 12m
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3/28
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6h 28m
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12/3
Thu
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8h 43m
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12/6
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8h 39m
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12/22
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8h 39m
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12/29
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8h 46m
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6h 37m
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6h 33m
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12/23
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28h 21m
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1/2
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35h 34m
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12/23
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24h 56m
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1/2
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51h 08m
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12/23
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Delta
10h 08m
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12/26
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8h 50m
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12/23
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28h 21m
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32h 23m
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12/23
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24h 56m
SAN - MDW
1/2
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32h 23m
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3/9
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Multiple Airlines
26h 03m
SAN - MDW
3/16
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Multiple Airlines
15h 26m
MDW - SAN
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Recent one-way flight deals

12/3
Thu
1 stop
Delta
9h 48m
SAN - MDW
11/30
Mon
1 stop
Delta
9h 52m
SAN - MDW
12/12
Sat
3 stops
Multiple Airlines
48h 43m
SAN - MDW
12/23
Wed
2 stops
Multiple Airlines
28h 21m
SAN - MDW
12/21
Mon
1 stop
Delta
7h 15m
SAN - MDW
12/23
Wed
2 stops
Multiple Airlines
28h 21m
SAN - MDW
12/27
Sun
1 stop
Delta
10h 08m
SAN - MDW
12/17
Thu
3 stops
Multiple Airlines
31h 37m
SAN - MDW
12/20
Sun
3 stops
Multiple Airlines
45h 34m
SAN - MDW
12/17
Thu
3 stops
Multiple Airlines
57h 15m
SAN - MDW
12/23
Wed
3 stops
Multiple Airlines
24h 56m
SAN - MDW
12/18
Fri
3 stops
Multiple Airlines
33h 56m
SAN - MDW
12/20
Sun
3 stops
Multiple Airlines
33h 15m
SAN - MDW
12/20
Sun
3 stops
Multiple Airlines
33h 15m
SAN - MDW
12/22
Tue
3 stops
Multiple Airlines
45h 47m
SAN - MDW
12/22
Tue
2 stops
Multiple Airlines
38h 39m
SAN - MDW
12/17
Thu
1 stop
Delta
8h 43m
SAN - MDW
12/27
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1 stop
Delta
10h 08m
SAN - MDW
11/29
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8h 32m
SAN - MDW
11/29
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1 stop
Delta
7h 50m
SAN - MDW
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