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Find First Class Flights to Chicago Midway Airport

1 adult
0 bags
Fri 7/6
Fri 14/6

When to book first class flights to Chicago Midway Airport

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago Midway Airport, so you can find the best time to fly.
Average price per month
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all the values for each month.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.

FAQs for Chicago Midway Airport first class flights

  • How long is a flight to Chicago Midway Airport?

    Flights from Toronto1h 44m
  • What is the most popular airline offering First Class flights to Chicago Midway Airport?

    Among KAYAK users, Delta is the most popular airline offering First Class seats on flights to Chicago Midway Airport.

  • Which airlines offer First Class tickets on flights to Chicago Midway Airport?

    Traveling to Chicago Midway Airport and want to offer yourself a First Class experience? Depending on the origin, the following airlines offer seats in First Class: Delta.

  • How does KAYAK find such good deals on First Class tickets to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport for economy class as well as First Class travelers.

  • What is the best airline for first class flights to Chicago Midway Airport?

    The highest-rated airline by KAYAK users offering first class flights to Chicago Midway Airport is Endeavor Airlines, with an overall rating of 8.8.

See more FAQs

Top 3 airlines flying to Chicago Midway Airport

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly first class to Chicago Midway Airport? 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
DeltaOverall score based on 10789 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

Everything was great. The big planes could still stand to have a bit more leg room. Crew was amazing!!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nice smooth flight with pleasant stewards. Slept most of the flight, they could have slowly turned on the lights to make it more pleasant. Otherwise a good trip.

Great! No food was available during the flight due to the catering service strike but snacks were given throughout the flight which was nice.

Nothing to like about flying in the Dash 8s. With very small seats, little legroom, and a very noisy plane, nothing about such trips is enjoyable.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Difficult to say. Over crowded but that is the fault of the airplane not WestJet

Crew was rude.didn’t even say hi or welcome to board

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Check in was seamless , crew very polite , arrived on time!

Flight arrived early even after leaving late. Bag drop was a zoo, very slow even after using pre-checkin and airport kiosk.

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

Book first class plane tickets to Chicago Midway Airport

Recent round-trip first class deals

 
We’ve provided our cheapest round-trip first class flights to Chicago found on KAYAK in the last 72 hours.
12/7Fri
1 stopDelta
8h 20mYYZ-MDW
14/7Sun
1 stopDelta
6h 35mMDW-YYZ
C$ 783
11/7Thu
1 stopDelta
7h 44mYYC-MDW
14/7Sun
1 stopDelta
9h 52mMDW-YYC
C$ 1,044
30/5Thu
1 stopDelta
8h 21mYUL-MDW
4/6Tue
1 stopDelta
8h 15mMDW-YUL
C$ 1,046
14/8Wed
1 stopDelta
7h 27mYEG-MDW
18/8Sun
1 stopDelta
7h 35mMDW-YEG
C$ 1,061
30/6Sun
1 stopDelta
10h 10mYEG-MDW
10/7Wed
2 stopsDelta
12h 47mMDW-YEG
C$ 1,098
20/9Fri
2 stopsDelta
12h 03mYUL-MDW
23/9Mon
1 stopDelta
8h 52mMDW-YUL
C$ 1,193
10/10Thu
2 stopsDelta
8h 48mYEG-MDW
13/10Sun
2 stopsDelta
10h 18mMDW-YEG
C$ 1,362
17/7Wed
2 stopsDelta
11h 18mYVR-MDW
24/7Wed
2 stopsDelta
10h 37mMDW-YVR
C$ 1,834
10/10Thu
1 stopDelta
7h 35mYEG-MDW
13/10Sun
1 stopDelta
7h 39mMDW-YEG
C$ 1,870
24/5Fri
1 stopDelta
8h 41mYYC-MDW
29/5Wed
1 stopDelta
9h 53mMDW-YYC
C$ 2,003
6/6Thu
2 stopsDelta
11h 08mYVR-MDW
13/6Thu
2 stopsDelta
10h 19mMDW-YVR
C$ 2,006
20/5Mon
2 stopsDelta
11h 07mYVR-MDW
31/5Fri
1 stopDelta
10h 17mMDW-YVR
C$ 2,165
15/8Thu
1 stopDelta
7h 36mYEG-MDW
18/8Sun
1 stopDelta
7h 35mMDW-YEG
C$ 2,409
4/6Tue
2 stopsDelta
10h 55mYEG-MDW
12/6Wed
2 stopsDelta
12h 43mMDW-YEG
C$ 2,582

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Recent one-way first class deals

 
Only flying one-way? Below are some of the best deals for one-way first class flights to Chicago found on KAYAK in the last 72 hours.
26/8Mon
1 stopDelta
6h 18mYYC-MDW
C$ 558
3/7Wed
1 stopDelta
8h 21mYYC-MDW
C$ 559
20/8Tue
1 stopDelta
10h 23mYYC-MDW
C$ 600
7/6Fri
1 stopDelta
8h 21mYYC-MDW
C$ 1,227
20/6Thu
1 stopDelta
8h 21mYYC-MDW
C$ 1,353

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Flights to Chicago Midway Airport

Destination:

Chicago Midway (MDW)United States

Return flight deals:

Chicago Midway - Canada

Cabin classes:

C$ 545
C$ 284

Browse origins: