Find cheap flights from Chicago Midway Airport to Oakland

MDW - OAK

Find cheap flights from Chicago Midway Airport to Oakland

Search hundreds of travel sites at once for deals on flights to Oakland

Round-trip
Economy
Chicago (MDW)
Oakland
Thu 4/15
Thu 4/22
Any month
Compare vs. KAYAK |

Good to know

Low season

DecemberBest time to beat the crowds with an average 39% drop in price.

High season

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

Average price round-trip

$390(avg. price over the last 2 weeks)

Good deal round-trip

$276or less

Good deal one-way

$170or less

Book cheap flights from Chicago Midway Airport to Oakland

When to book flights from Chicago Midway Airport to Oakland

Estimated round-trip price
Average price per month

Top tips for finding a cheap flight

  • Looking for a cheap flight? 25% of our users found flights on this route for $170 or less one-way and $276 or less round-trip.
  • High season is considered to be June, July and August. The cheapest month to fly is December.
  • Morning departure is around 18% cheaper 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 Chicago Midway Airport to Oakland flights

Which airlines have a flexible cancellation policy for flights from Chicago Midway to Oakland due to COVID-19?

Are there Oakland travel restrictions currently due to Coronavirus?

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

How many flights are there between Chicago Midway Airport and Oakland?

Which airlines provide the cheapest flights from Chicago Midway Airport to Oakland?

Do I need a passport to fly between Chicago Midway Airport and Oakland?

Which airlines fly most frequently between Chicago Midway Airport and Oakland?

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

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

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

What is the Hacker Fare option on flights from Chicago Midway Airport to Oakland?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway Airport to Oakland?

Top airlines flying Chicago Midway to Oakland

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 29,160 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Cons: "It was actually quite good, Delta is by far the airline to use compared with the other airlines."

Cons: "I’d prefer more a la carte food options rather than only boxes of stuff that include 3 things I don’t want."

Pros: "Service was great."
Cons: "It was a shortest duration flight of the three so I couldn’t point out here what was lacking. Thank you!"

Pros: "The staff was amazing"
Cons: "I had a very large (over weight person sitting next to me. She occupied about 6 inches of my seat. It was quite uncomfortable. Did my best to be very polite and accommodating but it was terribly uncomfortable and closterphobic."

Cons: "More leg room and seat width. I don’t like having other passengers pressed against me."

Cons: "Comfort plus seats on final leg did not appear to be different than main cabin"

Cons: "Seating was uncomfortable, tight space. Could barely move and i’m Not a large person."

Cons: "The fact the the toilette was kitty cornered in the mid cabin bathroom is a joke on modern society."

Cons: "At least one hour late"

Pros: "Great crew"
Cons: "Wi-Fi not working or hard to get to work. Flight was delayed by an hour and service was very rushed."

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "They ran out of salads so that was a little disappointing."
Cons: "The flight would be more comfortable if we had more leg room."

Pros: "It was very quick! Great service."
Cons: "We need more food options and a little bit more legroom."

Pros: "Crew was friendly, flight ran on time."
Cons: "Can you make the seats any smaller? Cabin space is tight and for people who suffer from claustrophobia it makes it difficult traveling. More cabin space with raising the fares would be great!"

Pros: "El servicios al cliente ala hora de registrarme, fue malísimo, en Santiago república dominicana,"

Cons: "Last seat by bathroom smelled of urine"

Pros: "My upgrade was fabulous!"

Cons: "Left 30 minutes late from SLC."

Pros: "We left and arrived early. Smooth flight overall just a great experience"
Cons: "We couldn’t have peanuts. Not really a negative but"

Pros: "The pilots were communicative of why and what the reasons were of delays as far as the landing and getting the plane to the gate."
Cons: "Attendants that offered drinks and snacks offered me coffee or water but didn’t offer a snack. But asked the girl next to me if she would want one. No consistency"

Pros: "The crew at the airport was very courteous and helpful."
Cons: "No food; not even offered water; I asked a Delta employee about our seats and she was very unprofessional (mind you I'm traveling with kids and my boarding pass said that seats were to be assigned at the gate)."

Pros: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos, please reimburse on the credit card"
Cons: "I can’t make it in mexico city on tuesday, wednesday’s performance had to be cancelled and we need to pay the cancellation fee 11500 mexican pesos of the studio and musicians"

Pros: "Like the fact I could watch 2-3 movies. Love the gluten free options for snacks."
Cons: "All of the couples were not assigned seats together. I've never seen anything so stupid. So before the plane took off, about four of us ladies from all over the back of the plane stood up and each jumbled a bunch of seats like a rubix cube so the men could then get up and go sit with their wives."

Cons: "Delta’s computer system was down. Long wait at the counter even though I did web check-in."

Pros: "Nothing"
Cons: "Lost baggage. No one told us anything till after an hour"

Cons: "The monitors kept on freezing"

Pros: "food was pretty good."
Cons: "a bit squashy in the seat. Inability to go online and select my seat without having to ring Delta and they do it."

Pros: "Seating and boarding were fine. That process was relatively quick/straightforward"
Cons: "I have never had an on time Delta flight, and hopefully, it will happen one day"

Pros: "Nice flight attendant. The woman who checked in my dog and my bag was really nice too. On time, efficient, and clean."

Cons: "Due to the earthquakes, the film festival I was going to was cancelled. Ten days prior to the flight I called AeroMexico to cancel and they said there would be a cancellation penalty, which was fine. When I tried to redeem my credit, they said there was also an additional "No-show fee" even though I called to cancel 10 days prior, which left a total of $70 credit after all their penalties. I called and emailed to complain but they did nothing but pass me to someone else who was equally unhelpful. I will never fly AeroMexico for any reason in the future."

Pros: "Compared to previous flight - this was so much better with upgrade to first class and extra space."

Cons: "Courtesy, on time and good communication."

Pros: "For a short flight, they gave it drinks and snacks."

Pros: "Plane was clean, attendants were friendly, and food was fine."
Cons: "I had a flight from Detroit to Montreal. Tried to check in and DTW was not a choice on the westjet website and so I physically could not check in. I realized the flight was technically operated not by WestJet, but Gojet. Went to Gojet's website and was told that Delta took care of all of their ticketing and such. Went to Delta's website, entered my ticket number and card number but I was not in the system as I was given all WestJet info (not Delta's). Luckily the baggage check in people figured it all out."

Pros: "Crew was courtesy"
Cons: "1hour delay from departing LAX runway - not good"

Pros: "Crew and being able to watch movies."
Cons: "Cost of flight"

Pros: "Ease of it all!"
Cons: "The jerk behind me who kept kicking my seat and kept coughing obnoxiously like he had never been on a plane"

Pros: "Flight was delayed for over 6 hours. Not an ideal way to spend the day."

Pros: "Delta was so accommodating"
Cons: "N/a"

Pros: "Enjoyed food and movies.Woul"
Cons: "Would like more comedy or romance movies. Becky"

Cons: "Efficient and comfortable all I ask for"

Pros: "The crews were very friendly and everything went as planned. It was a nice flight."

Pros: "Short eas6 trio"
Cons: "Lack if parking at airport"

Pros: "Enjoy able"
Cons: "Noise"

Pros: "We barely got on the flight."
Cons: "The boarding "red shirt" saved us. We are a band on tour and thanks to her we made the gig"

Pros: "Left reasonably on time, arrived a bit early, able to find overhead storage for my roll-on, even boarding in Zone 3"
Cons: "Very tightly packed; minimal comfort for the flight."

Pros: "Very early"

Pros: "We arrived in Las Vegas"
Cons: "Even in first class, it appeared to me that the legroom has been decreased."

Pros: "The crew was nice"
Cons: "I didn't like the fact that I didn't get my luggage with me when I arrived to casablanca as I lived 4 hours away from the casablanca. I have to come back the next day to get my luggage. I was very mad about it.plus I noticed one of my luggage has been damaged so now I have to buy another one because I can t use it. It was disgusting."

Pros: "amazing crew"
Cons: "more padding in seats"

Cons: "Volaris has no social distancing in flight"

Cons: "Have electric outlets, seats too tight, have beverage service"

Pros: "Quick boarding and ease with carry-on"
Cons: "We didn't get the safety announcement in full. The friendliness of the staff -"

Cons: "Everything needs to change! Worst airline worst service rude people. Horrific experience wish I got my money back."

Cons: "Flight was over sold and lost my seat"

Cons: "The flights took off over an hour late. The seats were incredibly uncomfortable and didn’t recline., even ven a little bit. I am 5’6” and my knees touched the seat in front of me."

Pros: "Affordability, that's about all that is good with Volaris. Everything else is either bad or mediocre."
Cons: "Don't board passengers onto the aircraft until it is ready for passengers. Both direction (OAK to MEX and MEX to OAK), we were boarded onto a hot (not aconditioned) aircraft for at least 15 minutes before the A/C is turned on. In addition, boarding were completed and all passengers were sitting in the aircraft for over an hour before it started the taxis to the run way....why board passengers so early? At least turn on the A/C and let the cabin cool down before boarding passengers."

Pros: "On-time flight"
Cons: "- Worst seats ever. I felt that I was sitting on stones. Limites recline, limited legs space.No entertainment, no water. Worst boarding system EVER!!! ,No flight again, Do not fly this airline!!"

Pros: "It was ok."
Cons: "It was ok."

Pros: "It was ok."
Cons: "The prices for the flights are deceptive. You pay extra for EVERYTHING! Seat assignment, drinks, luggage, additional weight for luggage I’ve 22 lbs. a real ripoff compared to other airlines. Plus, they wouldn’t give us boarding passes for the leg from Guadalajara to Oaxaca in Oakland so we missed that flight and had to buy tickets on another airline."

Cons: "Free snacks and beverages"

Pros: "The crew were absolutely amazing. They offered to tag my carry on free of charge as baggage. No issues whatsoever with stroller or car seat. Very friendly staff."
Cons: "The plane itself was uncomfortable and would prefer complimentary snack or beverages."

Cons: "El equipaje tardó mucho en salir"

Cons: "The flight did not exist!"

Cons: "Late and slow boarding, last minute gate change"

Pros: "The crew was very knowledgeable and assertive in their commands."
Cons: "Planes are too small. There weren’t any TVs on them and all 4 of my flights ran late."

Pros: "volaris charged me 20 usd more only because I had 11 kg of luggage , the limit was 10 kg"
Cons: "The airplane wasn’t clean, spaces very reduced, bad service... that’s the problem with cheap companies but Volaris can do better"

Pros: "Ok"
Cons: "This fly was pretty good!"

Pros: "The crew was friendly and helpful"
Cons: "The seats were very uncomfortable, the boarding was confusing and took a long time."

Pros: "Good basic airline ALWAYS reserve your seat ahead of time"
Cons: "Softer seats more like cement"

Cons: "Everything they over charge on everything and they forgot to send our luggage so I had to wait till the next flight to get my luggage to get are boarding tickets the wanted to charge us $7 dollars for each person and for each luggage they charge us $50 dollars per when it should of been $26 dollars"

Pros: "Nothing to like. Crew was unprofessional, rude, and no comfort in the flight."
Cons: "Everything could be better. At least offer compliments coffee/sodas instead of charging for every little thing."

Pros: "Efficient"
Cons: "Not much else for a bare bones carrier"

Pros: "The price is good. The punctuality is good"
Cons: "The luggage fee is too high"

Pros: "On time, clean and fairly new aircraft"
Cons: "Entertainment, food choices on board, boarding staff"

Pros: "Friendly crew"
Cons: "Boarding pass options and instructions confusing, I finally decided to get the boarding pass at Volaris airport counter instead.... I was charged another fee for the process."

Pros: "crew was friendly"
Cons: "no entertainment choices offered - RADIO OR VIDEO."

Pros: "It was on time. Crew was fine."
Cons: "Cramped seating, uncomfortably hot the whole way, they Michel and dime you for every single thing so the “low fare” became more expensive than other options."

Pros: "Nothing"
Cons: "Never ever am fliying with volaris airlines they charge for everything for seats for food and service horrible they didnt let me carry my little ourse i had on the side like really bad experience"

Cons: "Left 22 minutes late, there was a bomb scare, we made a emergency landing and after one hour we are still on the plane with no ens in sight."

Pros: "Web check in was super easy, the flight was on time and all the crew was really nice."
Cons: "No complimentary drinks or food, no entertainment on board."

Pros: "nothing of the flying company I liked the bags have cost, the snaks also have terrible cost company I do not return to travel by volaris"
Cons: "nothing of the flying company I liked the bags have cost, the snaks also have terrible cost company I do not return to travel by volaris"

Pros: "Very nice crew"
Cons: "Departure 35 minutes late."

Pros: "Everything but the seats were fine."
Cons: "Seats were terrible! Bumpy, uncomfortable to sit on even for the hour flight."

Pros: "The flight was on-time. The plane was clean, the toilets were clean."
Cons: "The Food service was very slow, we didn't have enough time to eat. We got seats with no window, it was uncomfortable. Not enough space to strech the legs."

Pros: "The food and the place"
Cons: "The weather to hot"

Cons: "Super mala, organización, aviones pequeños"

Cons: "Only snack options during my flight, was hoping to buy a meal."

Cons: "Delayed and they del even the wather"

Pros: "Ticket agents we're respectful"
Cons: "Never received email boarding pass. No kiosks. Charged for boarding pass even though they could see my reservation/confirmation# Website States checked bags15kgs/carry on 7kgs. At check-in stated only 10 klgs total so we had to pay again due to overage. Only water free on flight. I fly every week for work."

Pros: "La posibilidad de viajar a Chicag sin escalas"
Cons: "La línea Volaris o por lo menos el avión en el que viajamos es muy viejo. Y el mantenimiento deficiente."

Pros: "Nothing"
Cons: "It was extremely delayed and the personal was terrible goving information or any solution"

Cons: "El abordaje en La Paz, fue eterno, súper lento ."

Pros: "The crew was very nice and attentive."
Cons: "The flight was 2 hours late. It took too long to board once it started. We had to take a shuttle to another building and stand and wait for 20 minutes in a line on a ramp. No option to purchase a sandwich on the plane, nor real food options in the terminal"

Cons: "The seats are super tight. They made me oay for my carry on. The wouldn't recline and we had to take shuttles to get to the airport."

Pros: "Nothing"
Cons: "Tiny seating space. Don't be fooled by the low starting price they have a bunch of hidden fees. Cero interest in helping costimers. There are openly after people's money. I never review anything unless is alarming. Go with interjet or Jetblue or anything else. Please listen, not BIAS on this one, fam."

Pros: "the timing"
Cons: "baggage limits"

Cons: "Overbooked and Cancelled. Never booking through KIWI again!"

Cons: "Rude crew worker's"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway Airport to Oakland

Airlines flying from Chicago Midway Airport to Oakland 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 Chicago Midway Airport to Oakland

Mandatory masks

Masks required on board, masks provided on flights from Chicago Midway Airport to Oakland

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway Airport to Oakland

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway Airport to Oakland

Book cheap flights from Chicago Midway Airport to Oakland

Recent round-trip flight deals

5/6
Thu
2 stops
Delta
12h 20m
MDW - OAK
5/11
Tue
2 stops
Delta
14h 00m
OAK - MDW
5/25
Tue
2 stops
Delta
9h 38m
MDW - OAK
6/2
Wed
2 stops
Delta
13h 30m
OAK - MDW
5/12
Wed
2 stops
Delta
9h 38m
MDW - OAK
5/15
Sat
2 stops
Delta
10h 03m
OAK - MDW
5/9
Sun
2 stops
Delta
9h 38m
MDW - OAK
5/21
Fri
2 stops
Delta
8h 57m
OAK - MDW
5/6
Thu
2 stops
Delta
12h 18m
MDW - OAK
5/8
Sat
2 stops
Delta
13h 44m
OAK - MDW
5/21
Fri
2 stops
Delta
12h 18m
MDW - OAK
5/28
Fri
2 stops
Delta
13h 30m
OAK - MDW
5/20
Thu
2 stops
Delta
9h 38m
MDW - OAK
5/24
Mon
2 stops
Delta
14h 00m
OAK - MDW
5/20
Thu
2 stops
Delta
9h 38m
MDW - OAK
5/24
Mon
2 stops
Delta
14h 00m
OAK - MDW
5/8
Sat
2 stops
Delta
10h 38m
MDW - OAK
5/23
Sun
2 stops
Delta
11h 43m
OAK - MDW
4/29
Thu
2 stops
Delta
12h 11m
MDW - OAK
5/4
Tue
2 stops
Delta
12h 36m
OAK - MDW
4/29
Thu
2 stops
Delta
12h 11m
MDW - OAK
5/3
Mon
2 stops
Delta
12h 31m
OAK - MDW
9/22
Wed
2 stops
Delta
10h 03m
MDW - OAK
9/26
Sun
2 stops
Delta
10h 38m
OAK - MDW
5/15
Sat
2 stops
Delta
11h 01m
MDW - OAK
5/23
Sun
2 stops
Delta
11h 43m
OAK - MDW
4/30
Fri
2 stops
Delta
9h 47m
MDW - OAK
5/2
Sun
2 stops
Delta
11h 17m
OAK - MDW
4/30
Fri
2 stops
Delta
10h 40m
MDW - OAK
5/2
Sun
2 stops
Delta
12h 31m
OAK - MDW
5/20
Thu
2 stops
Delta
9h 38m
MDW - OAK
5/23
Sun
2 stops
Delta
14h 00m
OAK - MDW
5/13
Thu
3 stops
Multiple Airlines
44h 48m
MDW - OAK
5/16
Sun
2 stops
Multiple Airlines
30h 25m
OAK - MDW
5/28
Fri
2 stops
Delta
12h 20m
MDW - OAK
6/1
Tue
2 stops
Delta
13h 30m
OAK - MDW
6/3
Thu
2 stops
Delta
10h 38m
MDW - OAK
6/8
Tue
2 stops
Delta
9h 17m
OAK - MDW
5/9
Sun
2 stops
Delta
9h 38m
MDW - OAK
5/24
Mon
2 stops
Delta
14h 00m
OAK - MDW
Show more results

Recent one-way flight deals

5/11
Tue
2 stops
Delta
9h 38m
MDW - OAK
5/6
Thu
2 stops
Delta
12h 18m
MDW - OAK
4/30
Fri
2 stops
Delta
10h 40m
MDW - OAK
5/10
Mon
3 stops
Multiple Airlines
41h 05m
MDW - OAK
4/27
Tue
2 stops
Delta
10h 40m
MDW - OAK
5/13
Thu
3 stops
Multiple Airlines
44h 48m
MDW - OAK
5/9
Sun
2 stops
Delta
9h 38m
MDW - OAK
6/2
Wed
2 stops
Delta
10h 38m
MDW - OAK
5/28
Fri
2 stops
Delta
12h 20m
MDW - OAK
5/16
Sun
2 stops
Delta
9h 38m
MDW - OAK
4/28
Wed
2 stops
Delta
11h 39m
MDW - OAK
8/21
Sat
2 stops
Delta
10h 42m
MDW - OAK
7/3
Sat
2 stops
Delta
12h 38m
MDW - OAK
5/14
Fri
3 stops
Multiple Airlines
44h 49m
MDW - OAK
5/28
Fri
3 stops
Multiple Airlines
42h 08m
MDW - OAK
5/11
Tue
3 stops
Multiple Airlines
29h 18m
MDW - OAK
6/2
Wed
1 stop
Volaris
30h 18m
MDW - OAK
5/18
Tue
1 stop
Volaris
23h 02m
MDW - OAK
5/11
Tue
1 stop
Volaris
23h 02m
MDW - OAK
5/19
Wed
1 stop
Volaris
30h 18m
MDW - OAK
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