Find cheap flights from Chicago Midway Airport to Anchorage

MDW - ANC

Find cheap flights from Chicago Midway Airport to Anchorage

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Chicago (MDW)
Anchorage
Sat 1/16
Sat 1/23
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  • Looking for a cheap flight? 25% of our users found flights on this route for $210 or less round-trip.
  • Morning departure is around 174% 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

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Top airline flying Chicago Midway to Anchorage

Scores according to KAYAK customer reviews

7.9
Delta
Overall score based on 28,916 reviews
8.1
Boarding
7.8
Comfort
8.5
Crew
7.8
Entertainment
7.5
Food
Airline reviews

Pros: "When i asked for a window seat at the gate, i was provided one in the comfort zone. Very impressed and pleased. However, the remaining two segments were the opposite. Staff at the gate did not assist in any way for the remaining two flights."
Cons: "The flight from Bend to Seattle was delayed a couple times and caused us to arrive when our connecting flight was already boarding. Luckily we were able to make the main flight on the trip."

Pros: "It suited the time i could travel"
Cons: "I felt although they said the two attendants were great they were at best mediocre especially the man"

Cons: "The website could work for starters"

Pros: "Crew is amazing, seats are pretty good."
Cons: "On time, baggages checked in and were made available on time."

Cons: "Plane was hot and sticky. The air from the vent was not cool."

Pros: "Nice short flight, crew was nice."

Pros: "Use my built up miles for the SEA-ANC leg of our trip, as to physically price it out as one ticket usually increases the fare by 300-600 u$d depending upon time of year. As it was the tail end of an already long journey (OKA-ICN/ICN-SEA), booked the First Class Cabin. Every mile was worth it."
Cons: "N/A"

Cons: "Food really bad on both segments."

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

Pros: "The entertainment was nice."
Cons: "If the screen wasn’t behind the seat. I could hear the tapping of the person behind me."

Pros: "Crew was amazing"
Cons: "If you could figure out how to get online wifi..."

Pros: "The flight was fine"
Cons: "I had twenty minutes to make my connecting flight after my first flight was late to leave. I barely made my connecting flight and my luggage didn’t. It’s very inconvenient to arrive to my destination without clean clothes or a tooth brush."

Cons: "At least one hour late"

Cons: "Delta always has 1 or maybe 2 people checking everyone in, including the baggage drop. So, EVERYONE has to wait for one person to finish checking in the first class passenger with a thousand needs. Very poor service as is their norm."

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."

Cons: "We barely made it through a storm. Super scary. Even the pilot said we "barely made it" over the speaker. I would rather be hours late getting home than feel like my life was possibly gambled with. I have my pilot's license so I am not unfamiliar with having to create an alternate flight plan when inclimate weather strikes. However, this was scary. My boyfriend quietly had a panic attack while we were on board. Would not fly Delta again because of this experience."

Cons: "I understand Mother Nature causes issues tkayakhat no one can control but when I'm receiving updates from the 3rd party travel app that isn't the airline before receiving any information directly from the airline via the gate agent or Deltas travel app and the gate agent not being able to verify the 3rd party travel app something is wrong."

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: "Great airline stewards"
Cons: "Suggestion- Overhead bin should be assigned to the seat the person is seated in."

Pros: "Everything was perfect, everyone was nice, there was lots of room, the crew offered snacks frequently, WiFi had a great connection and there was a wide array of entertainment."
Cons: "There was a problem with the plane that they told us after we boarded that delayed our plane an hour. But hey, better safe than sorry!"

Pros: "Very good flight. Nice staff that seemed to enjoy their jobs. Great smiles and personable. Modern and clean plane with WiFi and charging outlets"
Cons: "There was a mechanical issue that delayed departure. Fortunately I did not have a connection to make. The crew made sure to communicate with everyone onboard frequently so we were aware of the situation and progress. They handled everything well which was reassuring for my peace of mind."

Pros: "Alaska Airlines is way overpriced and way less comfortable than Delta. I’m a Delta loyalist forever now!"
Cons: "Nothing."

Cons: "Alhamdoulillah"

Pros: "Food good, wine OK"
Cons: "Discomfort bad"

Pros: "Courteous crew and smooth flight"
Cons: "Nothing"

Pros: "Flight from SEattle to Atlanta delayed due to mechanical problems for 6 hrs. Once we got to Atlanta there were no flights connecting to Argentina until the following night at 10 pm. Delta did put us up in a hotel but with no food vouchers or any upgrades on delayed flight the next day. Flight attendants and crew were curteous."
Cons: "Fairly small seats and food isn't very good (as seems to be standard these days with most airlines). In flight music is very limited. Movie choices ok. No consideration to upgrade to first class or financial compensation have to be delayed a whole day for a long flight to Argentina."

Pros: "On time departure and arrival"
Cons: "We landed at 2:14 p.m. but did not get our luggage until 3:38 p.m., with "priority" because we were traveling business class. Dozens of bags that were not "priority" preceded ours."

Pros: "Everything is perfect"
Cons: "N/a"

Pros: "Super smooth takeoff and landing. Great plane, more legroom than other airlines."

Pros: "I LOVED the free movies. Great idea and newer movies. Finally was able to watch a movie I'd wanted to see for a long time."
Cons: "Flight was packed which always makes for a more cramped ride. Again, boarding. Flight boarded late and just seems boarding from the back to front would be faster."

Pros: "The staff and crew were great help all along the route and the planes were well kept and clean."
Cons: "One of the legs did not have the free wifi available, but they mentioned that before takeoff and were very apologetic that it had not been added to that plane yet."

Cons: "When they called for passengers with infants and those who needed more time they also called for anyone who wanted to check their luggage. So of course people cut right in front of me as I was about to scan my pass. What is the point of asking us to come up if they are just going to let people jump in front of me."

Cons: "The air conditioning was broken so it was sweltering the whole time. Staff didn't even mention it or apologize. No leg room. Bags took longer than 20 minutes to arrive but we didn't make a fuss since we were just glad to be finished with Delta. I'll never fly Delta again even if it costs me more."

Pros: "Got grounded for five hours stuck on the plane."

Cons: "Didn't stick to zones when boarding customers. Gate agent basically let anyone board during pre boarding and priority boarding, why even offer it if you aren't going to make people adhere to the rules."

Pros: "Friendly staff/ comfortable seating."

Pros: "Service, seats, food and pilot were all good."
Cons: "There ought to be a better way to go from an international flight to a connecting domestic flight. Security and Customs should be combined to expedite the process for passengers and crew members. I'm not suggesting not going through security, buy why couldn't we do it at the same place as customs? Too often Delta flights are delayed and I don't understand why Delta wouldn't do everything it could to expedite every part of the process for its crew and passengers. I went through TSA pre-check with Delta crew members. My connecting flight was delayed. We were waiting on the pilot..."

Cons: "It's just a really small plane so the comfort isn't great but only a half hour flight"

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: "Great helpful​ happy staff, made you feel welcome. Good atmosphere and peaceful. Food excellent."
Cons: "On transatlantic flight , seats comfortable but inadequate recline for a night flight and no footrest."

Pros: "Direct flight to JFK using Delta. Was not aware that I was NOT flying on West Jet therefore encountered problems searching for a way to check in online. Ground crew airport check in at the Delta counter and at the Boarding gate was helpful and efficient. However request for Special Assistance in Toronto was poorly handled. We did not accept the conditions offered to us as one wheel chair operator had to push 3 passengers and I had to wait for him to return to me after two people were brought to their gates. My Husband had to wheel me in to my gate."

Pros: "Low price."
Cons: "Delta provided no information as to why the flight was late. No earlier flights on other airlines were offered."

Pros: "Seated my husband I together (finally) at very back of plane next to window (not our preference)."
Cons: "My husband and I although booked together were seated in middle seats 9 rows apart. We atrempted to change our seats online at KLM (not possible), online at Delta (didn't recognize our KLM purchased flight), in person at KLM counter in SVG, in person with THE Delta rep at the check-in gate in AMS...no one could help us due to different systems used for seating for each company that the other one doesn't have access to. Flights booked by one company and operated by another seem common enough that this system needs to be improved. - Silver KLM travelers Also WAY too hot on plane."

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."

Cons: "Enforce your baggage size and number limits. A significant number of passengers take bags onboard that are oversized."

Pros: "The flight crew was nice and polite. They served drinks and snacks in a timely manner while on the flight."
Cons: "Flight was scheduled to leave early, the plane arrived, but they couldn't turn the plane around fast enough. We left the gat late, then pilot said we would still be arriving half an hour early. We arrived about 45 minutes late, and that was a problem because our connecting flight was due to depart now in 15 minutes. Lightning forced the airport to shutdown, which was great, we had a chance to catch our flight, but we were stuck in the airplane, and we couldn't get to our gate until the all-clear. I know this is not Delta's fault, but they did arrive quite late on a flight that, according to them, would be early. They also never communicated to the other flight that there were several passengers catching that connection. So by the time we had ran to catch our connection they had closed the ramp. Lightning hit again, and they shutdown the airport once again, so the airplane was still at the gate for about an hour, and they did not allow the 20+ passengers to board that plane, which was right there. So frustrating. The only thing that saved it was that our new flight was the new airbus, and although it left an hour and a half later, the comfort level was phenomenal."

Pros: "After the extremely long wait to check bags which made us miss the flight, the date crew got us in another flight...it wasn't direct which is what I paid for, but they did get us out, but i missed an interview because of the lack of crew and a missing luggage."
Cons: "Checking a bag, delta did not have enough crew to get everyone thru to their flights. We waited for 80 minutes inline to check a bag. Then we ran to the gate inky to find the gate was closed less than 2 minutes before we arrived. At least 20 others also missed the plane because of the lack of crew and long lines checking bags. It was frustrating, irritating, uncaring crew checking in, and a bit rude. Then on of my checked luggage was lost enroute - which made getting off the flights even later which made me miss a meeting that I was scheduled to be at. All because you didn't have the crew needed to check in."

Pros: "Finally, a free movie! Now, whoever picks the movie needs to do a better job, but atleast it was something! Service was Excellent, first pass with snack and drink carts, then they came through with coffee, and again with water! Now, that's service! Great job! Very friendly staff."
Cons: "Bathrooms, once again... disgusting. Urine on the floor, smelled awful. Tiny bathrooms, only 1 up front"

Read more about Delta
COVID-19 information

Safety measures for airlines flying from Chicago Midway to Anchorage

Airlines flying from Chicago Midway to Anchorage 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 to Anchorage

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Chicago Midway to Anchorage

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Chicago Midway to Anchorage

Book cheap flights from Chicago Midway Airport to Anchorage

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