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

MDW

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

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

Round-trip
Economy
Boston (BOS)
Chicago Midway
Tue 5/11
Tue 5/18
Any month
Compare vs. KAYAK |

Good to know

Low season

AugustBest time to beat the crowds with an average 5% drop in price.

High season

AprilMost popular time to fly with an average 16% increase in price.

Average price round-trip

$289(avg. price over the last 2 weeks)

Good deal round-trip

$159or less

Good deal one-way

$72or less

FAQs for booking San Francisco Bay Area to Chicago Midway Airport flights

Which airlines have a flexible cancellation policy for flights from San Francisco Bay Area to Chicago Midway due to COVID-19?

How does KAYAK find such low prices 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?

What is the Hacker Fare option on flights from San Francisco Bay Area to Chicago Midway Airport?

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?

Top airlines flying San Francisco Bay Area to Chicago Midway

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,238 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "Yes"
Cons: "Delightful experience except at SFO checkin."

Pros: "Covid safety protocols and people following was excellent."
Cons: "Serve alcohol :)"

Pros: "Crew great....moved passengers around near us for Covid related separation."
Cons: "Cramped.....too many seats in too small of a plane....I'm 6ft / 190 lbs"

Pros: "Good organization, good hygiene, polite crew."

Pros: "On time"

Cons: "Aircraft was too warm. Needed more air!"

Pros: "compared with other airlines they were just OK"
Cons: "everything"

Pros: "The crews were very fast and efficient. The Dinner was good but the breakfast was very basic."
Cons: "The seat was so crammy and disgustingly uncomfortable"

Pros: "Seats are fine. Ordering system is up to date."
Cons: "After the first two hours of my flight (which I sleep through) I couldn’t buy a drink a soda or anything."

Pros: "On time, smooth take off and landing."

Cons: "Better food and more water."

Pros: "My seat didn't recline"

Pros: "Quick boarding process"
Cons: "Wifi stopped working halfway"

Cons: "Great"

Pros: "see above"

Pros: "Nice employees and service"
Cons: "Seat room"

Pros: "Free food. Extra room."
Cons: "Waiting on runway"

Pros: "Delta Comfort om commuter jet"

Pros: "Flew us safely home."
Cons: "We waiting on the runway for over a long period."

Pros: "Cheese plate"
Cons: "TheyCharge me $25 for my bag and I’m at Delta sky Miles older plus the American Express platinum card holder it’s supposed to not be charged"

Cons: "3 hours delay"

Pros: "Had the whole Comfort section to myself!"

Pros: "Quiet, quick, no issues"
Cons: "Slow boarding. Slowest boarding everr. Maybe not enough overhead space, doesn't make sense how there is not enough overhead space while calling zone 2 passengers."

Pros: "The crew are very friendly, positive and have good sense of humor."
Cons: "The flight got delayed badly"

Cons: "Flying into blizzards suck, don’t do it"

Cons: "There is no place to specifically order vegetarian options in booking. Luckily virgin carries extra"

Pros: "Excellent service and upgraded snacks in economy"
Cons: "Nothing"

Pros: "Too many people, no room for carry-ons, departed almost an hour late."
Cons: "Too many people, no room for carry-ons, departed almost an hour late."

Cons: "waiting on the tarmac for 40 minutes"

Pros: "I was bowled over to learn in flight that the lowly steerage (economy) passengers--and everyone else had a selection of 3 complimentary meals! Who does that any more! Unfortunately, the only vegan option ran out just before my seat, but I was still amazed and pleased....and have ordered a vegan meal in advance for my next flight. Incredible! Plus, plenty of room for bags, good video selections, and power at all seats. I love Delta and will fly them more often!"

Pros: "No hassle, no drama, very smooth."
Cons: "The blueberries were rather bland."

Cons: "Food in first class was subpar!"

Pros: "All I need to say."

Pros: "it was great experience"

Cons: "One lavatory didn't work and we had to use the nathroom for first class..couldnt access bathroom half of the flight"

Pros: "Comfort and boarding"
Cons: "Delay and food"

Pros: "It was my husband's birthday and the stewardess (red dress, long brown hair) went out of her way to make him feel special by bringing champagne, cookies and even chocolate once we were getting off the plane. I was very touched."
Cons: "The guy next to me was kind of smelly but was very nice."

Pros: "Very smooth"

Cons: "Asked for hot tea but what I got was barely tepid."

Pros: "Excellent trip. Provided ample food snacks and drinks."

Cons: "The attendents only served one round of beverages in Comfort Plus."

Pros: "Individual screen and USB port"
Cons: "No issues that could be controlled I.e. Person in seat in front for mine leaning way ......"

Pros: "Painless"
Cons: "Price of food"

Cons: "Boarding took too long - full plane and double seat booking changed 10 minutes early estimate to 20 minutes late"

Pros: "All restroom floors were wet. I have seen this in others 767's too. Is this a 767 phenomenon"

Pros: "On time"

Cons: "half-broken screen, couldn't access anything on the left side"

Pros: "Plane was a newer one, clean, and the stewards were nice."
Cons: "New seating was terrible. The seats are so jammed together that my knees were pushed up into the seat in front. How can anyone be comfortable with this kind of seating arrangements?"

Pros: "On time"

Pros: "Flight was on time"

Cons: "Covid travel. Had us board an hour before take off and the back half of the plane was 100% full. Every seat including middle seats. 15 min before take off they allowed passengers to take empty seats and spread out."

Cons: "Free beverages"

Cons: "Seats are uncomfortable"

Pros: "Crew was very good and friendly."
Cons: "I would have appreciated a “free snack & cola”."

Pros: "Cost"
Cons: "OMG, miffed and aggravated right now!! Currently on Allegiant Flight 1355. PIE to CVG A non-eating flight. These POSs MFers decide to have a friggen pizza party in the middle of the flight"

Cons: "Seats are uncomfortable after about 40 minutes. Very cramped."

Cons: "Crew unfriendly. Flight attendants and pilots never acknowledged us or said hello or thank you."

Pros: "This flight itself met all expectations and I am very pleased with Allegiant."
Cons: "Communication & Technology @ check-in. I was never able to check in using the Allegiant phone app. Reason never communicated. Unable to check in online. Finally after a long hold over the phone I reached an agent who explained the system was updating. Bad set up. Could have been communicated!"

Pros: "Flight attendants were very kind, attentive and caring. There was a special needs girl in the same row as me that was by herself and they were always making sure she was okay and comfortable as well as the rest of the plane."

Pros: "Crew food. Seat small little leg room."
Cons: "Plane on time. More leg room."

Pros: "We had about a 45 minute weather delay but those things can't be helped. The Captain kept us informed and he flew like superman getting us through all that crazy wind coming into Las Vegas. The plane was new and clean, the crew was great. Love that wide aisle...it eliminates that sardine feeling!!"

Pros: "The crew was the best on any flight I have been on. Love their jokes."

Pros: "Allegiant knows how to get people off and back on the plane ASAP. The last few flights I have taken we left early and arrived earlier than planned because of this. Crew was friendly. I like the fact the flights are direct and no layovers at airports."

Pros: "Great crew and online customer service..."
Cons: "1- Flight Behind Schedule 2- Live customer service agents are truly non-existent until 1.5hrs before ‘departure’"

Pros: "The staff was great"
Cons: "Seats were way to small for tall people with long legs..........."

Pros: "Timing and ease of travel"
Cons: "Nothing"

Pros: "Affordable but no free water or snax"
Cons: "Cheap feeling seat. Thin plastic shells packed tightly together. But hey- its cheap!"

Pros: "The plane was very clean and well lit. The crew was excellent. Very friendly and nice."
Cons: "The seats are pretty uncomfortable. They are so close together and there is no room to store anything. The tray tables are a joke, you can't even fit an iPad on them. The bag check process was trouble at both legs. They have lower weight limits than the major carriers and that really should be highlighted better when you book with Allegiant. Also, bag checkin for the flight I was on started at 7:45am. There were only 2 people at the checkin counter and one of them was busy doing something and ignoring the customers. So that was a little annoying."

Cons: "It was to uncomfortable to sit there in the plane for so long. I also noticed one of the flight attendants with the long brunette hair kept over looking me but would be in all the guys faces instead. Pretty sure it was a jelouse thing. The shorter brunette girl was really pleasant"

Pros: "On time"
Cons: "initially assigned to center seat."

Pros: "Crew was very friendly, very polite unlike the United flights I have taken. I was told the space would be uncomfortable but it was absolutely fine for the short flight."
Cons: "No beverage service. Not even water is offered."

Cons: "5 delays between for a 4:27PM flight that eventually took off at 3:15am. My biggest issue is the unrealistic delay that could have left us in the airport for 11+ hours. Very thankful that they did allow me to change departure locations to another airport at no charge. That flight went well, even arrived early."

Cons: "Long wait due to plane speaker malfunction. Offered free drink pours on flight once we finally took off but it was a very small “2 sip” pour."

Pros: "Passengers were fun"
Cons: "Need entertainment"

Pros: "Pretty empty flight so we were able to change seats. Good thing because my family wasn’t sitting together-$12 to pick or change seats ahead of time. Just be prepared and knowledgeable about this airline and other budget airlines and you will be satisfied. - pay for bags in advance, Try to weigh your checked bags before the airport, Bring snacks or drink on flight - otherwise you have to pay for it. Trenton and punta gorda airports are small, you have to walk to the plane. I love the small airports, no lines , easy parking!"
Cons: "Seats aren’t that comfortable and don’t recline even a bit, tray table is small."

Pros: "Friendly Crew. Staff did expedite our checking bags to make our flight when we asked about our flight that started boarding early and made sure our bags made the flight. Excellent pilots, trip went seamless from wheels up to wheels down."
Cons: "Boarding started 30 minutes earlier than first notified as, Long lines to check bags."

Pros: "Great direct flight to many destinations smaller airports less wait time"
Cons: "seats are crowded"

Pros: "Friendly staff"
Cons: "Last minute delay due to a plane malfunction. Was told very last minute. Seemed like there were no quick resolutions in play. Had to wait over three hours to fly out, doesnt that entail compensation by law?"

Pros: "Ease of getting on and off, direct flight home, free parking in Belleville."
Cons: "seats are ok for 2 hour flight"

Pros: "on time, hepful personnel"
Cons: "my gate checked luggage was lost"

Pros: "Direct flight to my Destination"
Cons: "Rental car I paid for on Allegiant website didn't include $50 in airport and sales taxes making it look like the Allegiant rentals were about the same as renting directly from rental car companies. Problem is that Allegiant didn't include taxes in the quote or amount I paid online. Surprise when I got to my destination and was told it would be $50 more. Alamo agent said I wasn't the first person to have that problem. Then on return my bag was damaged and was told I could place a claim at the ticket counter. It would have been helpful to have an agent there or a way to contact an agent. No such luck. After bag charges, poor service and hidden fees Allegiant isn't really a great deal."

Pros: "Cheap."
Cons: "Both departing and return flights were delayed by just over 5 hours."

Pros: "Flight was cancelled due to Irma in Florida. Customer service agent was fantastic. I was able to rebook die the following week without any hassle."
Cons: "I didn't get to fly to Florida when I first chose."

Pros: "We got the brand new AB 320 on both flights! Nice plane!"
Cons: "Lightning delayed boarding and departure for hours. Not Allegiant's fault but it happened."

Pros: "the pilot"
Cons: "checking in , it seemed like no one knew what they were doing."

Pros: "The plane was clean"
Cons: "You have to pay to choose your seat, to have more than one carry on bag (literally of any size!!), and for any food. Nothing is complimentary. The seats don't lean back at all. No headrest adjustment for any sort of comfort. The seats are hard. We had a 30 min. Delay for some reason we were not made aware of and no apology was made. No Tv's or even a pocket in the seat-back in front of you. Basically if you can fly anything else other than this airline you are probably better off. Delta is basically the exact opposite of this airline and even American does way more. If I can help it I will never use this airline again."

Pros: "I did not like anything about it. The Departure flight was two hours late. They made us board then unboard the plane, change gates. Then the return flight was posponed from 9pm to 3am departure. They didn't have any refreshments in the gare area other than stale unhealthy pizza, no water. The seats on the plane were the most uncomfortable. I even purchased the extI did not like anything about it. The Departure flight was two hours late. They made us board then unboard the plane, change gates. Then the return flight was posponed from 9pm to 3am departure. They didn't have any refreshments in the gare area other than stale unhealthy pizza, no water. The seats on the plane were the most uncomfortable. I even purchased the extra legroom. No recline, no room. Horrible flight"
Cons: "I did not like anything about it. The Departure flight was two hours late. They made us board then unboard the plane, change gates. Then the return flight was posponed from 9pm to 3am departure. They didn't have any refreshments in the gare area other than stale unhealthy pizza, no water. The seats on the plane were the most uncomfortable. I even purchased the extI did not like anything about it. The Departure flight was two hours late. They made us board then unboard the plane, change gates. Then the return flight was posponed from 9pm to 3am departure. They didn't have any refreshments in the gare area other than stale unhealthy pizza, no water. The seats on the plane were the most uncomfortable. I even purchased the extra legroom. No recline, no room. Horrible flight"

Pros: "Considering the fare was advertised between $350 and $700 with other carriers on Kayak, I took this one for $179, roundtrip, direct from LAX to Grand Junction."
Cons: "When the crew runs to get coffee in the terminal, make sure to do the same. I brought some snacks, but wish I had brought coffee. The man next to me kept creeping into my space which was incredibly annoying, but it was a relatively quick flight. Beats the two day drive from L.A. to Colorado."

Pros: "Fast flight"
Cons: "Charge for carry on and in flight snacks and drinks (sodas,juices,water)"

Pros: "Their flights are always delayed. They have some pretty old flights and they always get broke before the take off and they have to do some maintenance before take off. Not going to fly again with them."
Cons: "Entire flight experience."

Pros: "The price of the flight was cheap, but i know why. You ended up paying for your carry on luggage, ypu pay for seat assignment if you want to guarentee sitting with you party, you pay for soda. My flight was 1.5 hours late, due to mechanical problem. Plane was janky and it felt like it STILL needed repairs."
Cons: "Low airfare."

Cons: "Delayed 5 hours!"

Pros: "Flight attendants were very respectful and courteous."
Cons: "Last 10 minutes of landing the plane was very very rough. A few people had to pull out the barf bags Lots of speeding up and slowing down. Ups and downs. It wasn't turbulence but it felt like it."

Pros: "We eventually got to Las Vegas."
Cons: "Everything. Spend an it make and book with someone else."

Pros: "The flight attendants were very nice and helpful."

Pros: "The outbound leg went well except for the very uncomfortable seats that are thinly padded and do not recline. We left on time and arrived on time."
Cons: "The return trip left five hours late due to a faulty plane. I appreciate not using a plane that was mechanically not working. I also appreciate that we did finally leave on the same day we were to leave. The replacement plane was as uncomfortable as the plane used in the first leg of my round trip."

Pros: "The crew was good and had customer service"
Cons: "After an 36 hour delay and only $8 meal voucher in Las Vegas, highly disappointed!!! The next flight was late arrival and Late boarding. everything to include water and sodas are extra fees. not impressed and will never fly Allegiant again"

Pros: "The price range is far for travelers"
Cons: "They should give free snacks and water juice to the customers that travel with this airline. The other airlines off complimentary snacks and drinks other wise it was a good experience"

Pros: "The direct flight"
Cons: "The seats were a bit hard"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from San Francisco Bay Area to Chicago Midway Airport

Airlines flying from San Francisco Bay Area to Chicago Midway Airport have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from San Francisco Bay Area to Chicago Midway Airport

Mandatory masks

Masks required on board, masks provided on flights from San Francisco Bay Area to Chicago Midway Airport

Social distancing seating

Middle seats unavailable to book on flights from San Francisco Bay Area to Chicago Midway Airport

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from San Francisco Bay Area to Chicago Midway Airport

Book cheap flights from San Francisco Bay Area to Chicago Midway Airport

Recent round-trip flight deals

9/13
Mon
1 stop
Delta
6h 23m
SFO - MDW
9/18
Sat
1 stop
Delta
8h 09m
MDW - SFO
9/14
Tue
2 stops
Delta
9h 17m
OAK - MDW
9/21
Tue
2 stops
Delta
10h 03m
MDW - OAK
8/30
Mon
1 stop
Delta
6h 23m
SFO - MDW
9/8
Wed
1 stop
Delta
8h 09m
MDW - SFO
8/18
Wed
1 stop
Delta
7h 34m
SFO - MDW
8/19
Thu
1 stop
Delta
7h 37m
MDW - SFO
8/18
Wed
1 stop
Delta
6h 25m
SJC - MDW
9/1
Wed
1 stop
Delta
8h 49m
MDW - SJC
9/13
Mon
1 stop
Delta
6h 23m
SFO - MDW
9/23
Thu
1 stop
Delta
7h 37m
MDW - SFO
8/23
Mon
1 stop
Delta
8h 47m
SJC - MDW
9/1
Wed
2 stops
Delta
9h 02m
MDW - SJC
9/11
Sat
2 stops
Delta
14h 20m
OAK - MDW
9/15
Wed
2 stops
Delta
10h 03m
MDW - OAK
8/16
Mon
1 stop
Delta
9h 20m
SFO - MDW
8/20
Fri
1 stop
Delta
8h 09m
MDW - SFO
8/22
Sun
1 stop
Delta
6h 25m
SJC - MDW
8/30
Mon
1 stop
Delta
6h 38m
MDW - SJC
8/22
Sun
1 stop
Delta
6h 25m
SJC - MDW
8/31
Tue
2 stops
Delta
9h 50m
MDW - SJC
9/11
Sat
2 stops
Delta
14h 35m
OAK - MDW
9/15
Wed
2 stops
Delta
10h 03m
MDW - OAK
8/24
Tue
2 stops
Delta
9h 17m
OAK - MDW
8/28
Sat
2 stops
Delta
12h 38m
MDW - OAK
10/12
Tue
1 stop
Delta
6h 25m
SJC - MDW
10/13
Wed
2 stops
Delta
22h 35m
MDW - SJC
8/22
Sun
1 stop
Delta
6h 25m
SJC - MDW
8/27
Fri
1 stop
Delta
6h 38m
MDW - SJC
9/11
Sat
1 stop
Delta
8h 18m
SFO - MDW
10/13
Wed
1 stop
Delta
11h 01m
MDW - SFO
9/17
Fri
2 stops
Delta
9h 39m
OAK - MDW
9/18
Sat
2 stops
Delta
12h 38m
MDW - OAK
5/16
Sun
2 stops
Multiple Airlines
30h 25m
OAK - MDW
5/24
Mon
3 stops
Multiple Airlines
40h 02m
MDW - OAK
5/20
Thu
2 stops
Multiple Airlines
30h 25m
OAK - MDW
5/23
Sun
3 stops
Multiple Airlines
44h 48m
MDW - OAK
6/16
Wed
3 stops
Multiple Airlines
26h 55m
OAK - MDW
6/21
Mon
3 stops
Multiple Airlines
39h 37m
MDW - OAK
Show more results

Recent one-way flight deals

8/18
Wed
1 stop
Delta
8h 47m
SJC - MDW
8/22
Sun
1 stop
Delta
6h 25m
SJC - MDW
5/18
Tue
2 stops
Multiple Airlines
34h 07m
SFO - MDW
5/24
Mon
2 stops
Delta
12h 53m
SJC - MDW
5/24
Mon
2 stops
Delta
12h 52m
OAK - MDW
6/27
Sun
2 stops
Multiple Airlines
29h 08m
OAK - MDW
7/6
Tue
1 stop
Delta
7h 20m
SFO - MDW
6/27
Sun
2 stops
Multiple Airlines
27h 31m
OAK - MDW
6/27
Sun
2 stops
Multiple Airlines
27h 31m
OAK - MDW
5/16
Sun
2 stops
Multiple Airlines
26h 19m
SJC - MDW
6/22
Tue
2 stops
Delta
11h 57m
OAK - MDW
6/3
Thu
3 stops
Multiple Airlines
30h 29m
OAK - MDW
8/11
Wed
1 stop
Delta
6h 37m
SJC - MDW
6/8
Tue
2 stops
Delta
12h 00m
SJC - MDW
5/18
Tue
3 stops
Multiple Airlines
45h 44m
OAK - MDW
6/11
Fri
3 stops
Allegiant Air
47h 56m
OAK - MDW
6/3
Thu
2 stops
Allegiant Air
23h 28m
OAK - MDW
5/23
Sun
2 stops
Allegiant Air
18h 07m
OAK - MDW
6/25
Fri
3 stops
Allegiant Air
44h 49m
OAK - MDW
6/4
Fri
3 stops
Allegiant Air
47h 26m
OAK - MDW
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First