MDW

C$ 108 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 5/9. 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
1 adult, Economy

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 Flights 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Midway

Thu, 11 Sep - Thu, 18 Sep
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 161Porter Airlines
Find Deal
Thu, 28 Aug - Sun, 31 Aug
Porter Airlines Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
10:40 a.m. - 1:20 p.m.MDW-YTZ
1h 40mdirect
C$ 162Porter Airlines
Find Deal
Sat, 27 Sep - Tue, 30 Sep
 Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
 Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 206
Find Deal
Fri, 5 Sep - Sun, 7 Sep
 Logo
7:30 a.m. - 8:19 a.m.YTZ-MDW
1h 49mdirect
 Logo
9:15 a.m. - 11:57 a.m.MDW-YTZ
1h 42mdirect
C$ 207
Find Deal
Mon, 25 Aug - Tue, 26 Aug
Air Transat Logo
7:55 a.m. - 8:45 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 211Air Transat
Find Deal
Fri, 24 Oct - Sun, 26 Oct
Air Transat Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 222Air Transat
Find Deal
Wed, 10 Sep - Wed, 17 Sep
Delta Logo
2:50 p.m. - 6:37 p.m.YYZ-MDW
4h 47m1 stop
Delta Logo
9:20 a.m. - 6:28 p.m.MDW-YYZ
8h 08m1 stop
C$ 292Delta
Find Deal
Sat, 30 Aug - Wed, 3 Sep
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
4:25 p.m. - 11:53 p.m.MDW-YUL
6h 28m1 stop
C$ 296Delta
Find Deal
Sat, 27 Sep - Tue, 30 Sep
WestJet Logo
6:00 a.m. - 5:35 p.m.YYZ-MDW
12h 35m1 stop
WestJet Logo
9:20 a.m. - 6:28 p.m.MDW-YYZ
8h 08m1 stop
C$ 379WestJet
Find Deal
Thu, 21 Aug - Tue, 26 Aug
WestJet Logo
1:20 p.m. - 9:44 p.m.YYZ-MDW
9h 24m1 stop
WestJet Logo
10:31 a.m. - 4:57 p.m.MDW-YYZ
5h 26m1 stop
C$ 383WestJet
Find Deal
Booking Insights

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 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 May, where tickets cost C$ 283 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$ 442 and C$ 380 respectively. For one-way flights, the best month to travel is September with an average price of C$ 254.

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$ 198 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low seasonFebruary
Cheapest flightC$ 108
Best time to beat the crowds (13% less expensive on average)
Most popular time to fly and prices are also 5% 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$ 192. The cheapest price found on KAYAK in the last 2 weeks cost C$ 122 and departed from Toronto Island Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Tuesday where round-trip tickets can be as cheap as C$ 341. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are C$ 362 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago Midway Airport is generally in the morning, when round-trip flights cost C$ 235 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.

  • 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 Tuesday, with 15% of flights taking off on this day.

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$ 163
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the 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 317 reviews
8.2Boarding
8.7Crew
7.6Food
8.0Comfort
7.0Entertainment
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

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

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

The plane was pretty full, and we dis not have any includes meal for our 4h30 flight? And on-board entertainment wasn't available, there was no TV or plugging to charger your device on the plane. They told us to download an app if we wanted to watch movies but it never connected, that was a disappointment, the r we st was very good though and the crew were really nice!

Seats were very tight especially for first leg of trip.

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Price was good. Entertainment and food could have been better

Staff was nice, helpful, and did all they could. I understand economy seats are bottom of the barrel, but we're crammed in there with others in our row.

Our flight info was lost as the original booking was with westjet... almost missed our outbound flight trying to get it corrected. Inbound we had to reschedule completely as they didn't have our information and resold our seats ending up getting home much later than planned. The confirmation numbers we received from justfly for westjet didn't help anything with delta as they said we needed a delta confirmation which we never received. I talked with justfly and they said it's the airlines problem and with westjet and they said it is the 3rd party bookers issue.... so, not fun

They kept making changes to the itinerary. I actually wasn't able to go and i tried to get flight credit in exchange for the ticket, but the customer service chat was taking way too much time.

WestJet canceled my booking, replaced it with a booking that didn't work (departing from cruise ship), and didn't offer any flights that did work. Their only option was for me to cancel and go to another airline for more money. Which I did.

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

Travelling to a place near Midway?

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