MDW

C$ 119 Find Cheap Flights to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

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

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Cheap Flight Deals to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Porter Airlines Logo
4:05 p.m. - 4:54 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
C$ 180Porter Airlines
Find Deal
Fri, 23 May - Mon, 26 May
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:50 p.m. - 8:32 p.m.MDW-YTZ
1h 42mdirect
C$ 181Porter Airlines
Find Deal
Tue, 3 Jun - Sun, 8 Jun
 Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
 Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
C$ 241
Find Deal
Sun, 8 Jun - Sun, 15 Jun
 Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
 Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
C$ 242
Find Deal
Sat, 7 Jun - Sat, 14 Jun
Delta Logo
3:50 p.m. - 6:45 p.m.YYZ-MDW
3h 55m1 stop
Delta Logo
9:16 a.m. - 5:15 p.m.MDW-YYZ
6h 59m1 stop
C$ 292Delta
Find Deal
Thu, 22 May - Mon, 26 May
Delta Logo
3:50 p.m. - 6:45 p.m.YYZ-MDW
3h 55m1 stop
Delta Logo
9:16 a.m. - 5:15 p.m.MDW-YYZ
6h 59m1 stop
C$ 294Delta
Find Deal
Thu, 22 May - Mon, 26 May
Air Transat Logo
4:05 p.m. - 4:54 p.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
5:50 p.m. - 8:32 p.m.MDW-YTZ
1h 42mdirect
C$ 298Air Transat
Find Deal
Wed, 7 May - Sun, 11 May
Air Transat Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
9:40 a.m. - 12:22 p.m.MDW-YTZ
1h 42mdirect
C$ 319Air Transat
Find Deal
Thu, 8 May - Sat, 10 May
WestJet Logo
12:30 p.m. - 5:45 p.m.YYZ-MDW
6h 15m1 stop
WestJet Logo
12:48 p.m. - 9:56 p.m.MDW-YYZ
8h 08m1 stop
C$ 395WestJet
Find Deal
Fri, 30 May - Wed, 4 Jun
WestJet Logo
12:30 p.m. - 5:45 p.m.YYZ-MDW
6h 15m1 stop
WestJet Logo
12:48 p.m. - 11:55 p.m.MDW-YYZ
10h 07m1 stop
C$ 396WestJet
Find Deal
Wed, 21 May - Sat, 24 May

KAYAK's insights & trends for flights to Midway

Get data-powered insights and trends into flights to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as C$ 354. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are C$ 379 on average.

What is the cheapest month to fly to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago Midway Airport is February, where tickets cost C$ 295 on average for return flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from Canada is C$ 446 and C$ 384 respectively. For one-way flights, the best month to travel is May with an average price of C$ 353.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all round-trip flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago Midway Airport is generally in the morning, when round-trip flights cost C$ 252 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is C$ 415.

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Toronto Island Airport C$ 267 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low season

March

High season

December

Cheapest flight

C$ 119
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights to Midway

Are your dates flexible? Find out the best times to travel to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • How far is Chicago Midway Airport from central Chicago?

    The distance between Chicago Midway Airport and downtown Chicago is 14 km.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs C$ 240. The cheapest price found on KAYAK in the last 2 weeks cost C$ 148 and departed from Toronto Island Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find 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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

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

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 13 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Thursday, with 15% of flights taking off on this day.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Toronto Island C$ 216
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Top 3 airlines flying to Midway

 
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 with to Midway? 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
Porter AirlinesOverall score based on 285 reviews
8.1Comfort
8.8Crew
7.0Entertainment
8.2Boarding
7.6Food
Airline reviews

I love the 2 seats per row. More room. The crew were excellent.

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

Over the wing seat at emergency exit only downside people using lavatory have no respect and wait in the space

Flight delayed any hour and couple of big gate changes

The pilot came out and chatted with the passengers. He explained why there was a slight delay. The crew was excellent. Very helpful. I had to buy meals for my whole family and they were in different seats, so the crew had to deal with that. They were very pleasant and accommodating and did a great job!

We were unable to land in Liberia. It was not the airline’s fault, but we had to be diverted to SJO.

We had things stolen from our luggage, we also were refused an upgrade on a flight that was not full.

When we left, it wasn't Great . People were drinking heavily, very disrespectful Extremely loud, the entire trip. I think the crew members, should have get their attention. Coming back was great.

I sat in the club. The seeds were fantastic. The meal was great and Entertainment was good. The crew was fantastic. I recommend it to everybody.

The food was small portions and not fresh. I was seated at the back of the plane so by the time the cart approached me most of the food options were sold out. The cabin crew was fantastic however.

Great flight and crew. Food isn't free and neither are headphones...

We were in economy class but paid for option Plus which offer you an extra snack after take off, free earplugs & blanket. The crew were very attentive. The comfort however wasn’t great, hard to be comfortable in such restraint place. Wasn’t able to sleep through out the 7hrs flight and was exhausted upon arrival.

Internet on both flights was sketchy. Thus in flight entertainment was non- existent on MN - Balrimote leg.

It took 30 minutes to check in with the Westjet rep. They didn’t have enough seats and she needed to make a call… I am always “randomly” selected to be checked at security. Their “randomly “ selection system may need some updating. They treat people like criminals. It is not appropriate behavior.

Will never book through you again. Very disappointed in the notices and action taken or provided when planes are rescheduled, enough to cause missed connections

Lost my luggage. Filed a report and there is no response. Received a phone call from another airline that said they had the bag and they did not know what to do with it

Very good over all , would have been nice to have entertainment on the flight

Absolutely the worst airline I have ever taken. They lost my baggage and told me my bag tags had been cancelled. When my bags arrived days later I had to pick them up at 3:15 am. My return flight was delayed another 6 hours and they broke my bag. Westjet does nothing to try and make it a better customer experience and all the customers services representatives I spoke with were useless and incompetent. Never flying westjet again.

it's all good nothing you can do make better 😌

Very old planes. Seats were not comfortable. Air was not on during the flight leading to incredibly stuffy conditions.

It was so bad experience they wanted just charged passengers for any reason.

Delta was great. West Jet was not. I booked my flight in Sept (well over two months ago), but was told there were 2 reservations and NO tickets for me, my husband and 16mo daughter. We were unable to go ahold of West Jet over the phone and the kiosk was unhelpful so we had to buy completely new tickets in order to get home that day. I’ve called West Jet twice since and sat on the phone for over an hour without speaking to any representatives.

Travelling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Benton Harbor
New Buffalo
Portage
Merrillville
Schererville
Saint Joseph
Valparaiso
Hammond
Munster
Chesterton
Lansing
Monticello
Porter

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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