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Find cheap flights to Chicago Midway Airport from C$ 186

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 1/6. 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
0 bags
Sun 26/5
Sun 2/6

Search 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
In the last 7 days, travellers have searched 44,335,567 times on KAYAK, and here is why:

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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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 313Porter Airlines
Find Deal
Thu, 23 May - Thu, 30 May
3:30 p.m. - 4:17 p.m.YTZ-MDW
1h 47mdirect
8:40 a.m. - 11:22 a.m.MDW-YTZ
1h 42mdirect
C$ 315Porter Airlines
Find Deal
Thu, 23 May - Sun, 26 May
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 316Porter Airlines
Find Deal
Fri, 24 May - Mon, 27 May
12:30 p.m. - 5:06 p.m.YYZ-MDW
5h 36m1 stop
9:32 a.m. - 5:09 p.m.MDW-YYZ
6h 37m1 stop
C$ 353Delta
Find Deal
Thu, 23 May - Thu, 30 May
6:14 a.m. - 11:02 a.m.YUL-MDW
5h 48m1 stop
2:15 p.m. - 11:30 p.m.MDW-YUL
8h 15m1 stop
C$ 365Delta
Find Deal
Sun, 26 May - Tue, 4 Jun
7:00 a.m. - 8:29 p.m.YVR-MDW
11h 29m2 stops
10:59 p.m. - 9:35 p.m.MDW-YVR
24h 36m1 stop
C$ 387
Find Deal
Thu, 9 May - Tue, 14 May
9:15 p.m. - 9:47 p.m.YVR-MDW
22h 32m2 stops
1:42 p.m. - 8:59 p.m.MDW-YVR
9h 17m1 stop
C$ 406
Find Deal
Fri, 7 Jun - Tue, 11 Jun
6:04 a.m. - 12:44 p.m.YYZ-MDW
7h 40m1 stop
9:35 a.m. - 5:10 p.m.MDW-YYZ
6h 35m1 stop
C$ 435KLM
Find Deal
Sun, 4 Aug - Fri, 9 Aug
7:10 p.m. - 11:02 a.m.YYZ-MDW
16h 52m1 stop
6:00 a.m. - 12:10 p.m.MDW-YYZ
5h 10m1 stop
C$ 447WestJet
Find Deal
Fri, 10 May - Sun, 12 May
7:10 p.m. - 11:02 a.m.YYZ-MDW
16h 52m1 stop
6:00 a.m. - 12:10 p.m.MDW-YYZ
5h 10m1 stop
C$ 449WestJet
Find Deal
Fri, 10 May - Sun, 12 May

Flights to Midway - Travel Insights & Trends

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 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 tickets can be as cheap as C$ 388. On the other hand, the most expensive day to fly is Sunday, where prices are C$ 609 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 January, where tickets cost C$ 286 on average for one-way flights. On the other hand, the most expensive months are June and July, where the average cost of tickets from Canada is C$ 635 and C$ 571 respectively. For return trips, the best month to travel is March with an average price of C$ 302.

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

The average price for all 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 afternoon, when flights cost C$ 366 on average. The most expensive time of day to fly to Chicago Midway Airport is generally at night, which is peak travel time and where the average cost of a ticket is C$ 421.

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$ 175 one-way - C$ 311 round-trip.

How far in advance should I book a flight to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 62 days before departure.

Which airline offers the most flights to Chicago Midway Airport?

Of the 5 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 1,444 per week, followed by Frontier with 138 flights per week.

How long is the flight to Chicago Midway Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Montreal, which takes 2h 30m, Toronto, which takes 3h 05m, Calgary, which takes 3h 27m, and Vancouver, which takes 4h 01m.

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

There are around 3 direct flights from within Canada to Chicago Midway Airport every day. Most flights depart in the evening, with 6:00 p.m. the most common departure time and 35% of flights departing in the evening.

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

Each week there are around 20 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Sunday, with 15% of flights taking off on this day.

How many long-haul flights are there to Chicago Midway Airport each week?

There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Chicago Midway Airport. Instead, there are 20 short-haul flights (up to 3 hour flight duration), with the most arriving from Toronto.

How many cities have direct flights to Chicago Midway Airport?

From Canada, there are direct flights to Chicago Midway Airport from 1 city. This city is Toronto and there are 20 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 186
Best time to beat the crowds (3% less expensive on average)
Most popular time to fly (8% more expensive 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 Midway Airport 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$ 276. The cheapest price found on KAYAK in the last 2 weeks cost C$ 173 and departed from Toronto Island Airport.

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

    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 Midway Airport.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport 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 Midway Airport?

    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 Midway Airport 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 Midway Airport?

    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 Midway Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Chicago Midway Airport

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

Prefer to fly non-stop to Chicago Midway?

Find which airlines fly direct to Midway, which days they fly and book direct flights.

Nonstop departures

Canada to Chicago Midway

Monday

Aeromexico,Air France,Allegiant Air, +11 more

Aeromexico,Air France, +12 more

Tuesday

Aeromexico,Air France,Delta, +9 more

Aeromexico,Air France, +10 more

Wednesday

Aeromexico,Air France,Delta, +9 more

Aeromexico,Air France, +10 more

Thursday

Aeromexico,Air France,Allegiant Air, +10 more

Aeromexico,Air France, +11 more

Friday

Aeromexico,Air France,Allegiant Air, +11 more

Aeromexico,Air France, +12 more

Saturday

Aeromexico,Air France,Delta, +9 more

Aeromexico,Air France, +10 more

Sunday

Aeromexico,Air France,Allegiant Air, +10 more

Aeromexico,Air France, +11 more

See more nonstop flights

Nonstop returns

Chicago Midway to Canada

Monday

Aeromexico,Air France,Allegiant Air, +11 more

Aeromexico,Air France, +12 more

Tuesday

Aeromexico,Air France,Delta, +9 more

Aeromexico,Air France, +10 more

Wednesday

Aeromexico,Air France,Delta, +9 more

Aeromexico,Air France, +10 more

Thursday

Aeromexico,Air France,Allegiant Air, +10 more

Aeromexico,Air France, +11 more

Friday

Aeromexico,Air France,Allegiant Air, +11 more

Aeromexico,Air France, +12 more

Saturday

Aeromexico,Air France,Delta, +9 more

Aeromexico,Air France, +10 more

Sunday

Aeromexico,Air France,Allegiant Air, +10 more

Aeromexico,Air France, +11 more

See more nonstop flights
See more nonstop flights

Top 4 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.
8.8
Endeavor AirlinesOverall score based on 4 reviews
9.5crew
9.5comfort
9.5boarding
7.0entertainment
8.5food
Airline reviews
Pros: "seat space was great and I was lucky enough to have medium size passenger next to me :-)"
Cons: "Can't really think of anything . . . my expectations were exceeded"
8.6 ExcellentIllan, Jun. 2019YYZ - JFK
Read more about Endeavor Airlines reviews
Pros: "seat space was great and I was lucky enough to have medium size passenger next to me :-)"
Cons: "Can't really think of anything . . . my expectations were exceeded"

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.

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

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Plane had a flat tire, delayed boarding and takeoff but one in the air, smooth. Make sure you have downloaded the WJ app before you leave. When on board, you can watch movies or TV shows offered on the app, it passed the time very quickly.

Our recent flight from edmontown to kahalui was excellent. The service staff was very friendly, knowledgeable, funny and attentive. Thanks to all involved that made or travel such a pleasant experience and we hope to fly with west jet again soon

The flight was delayed and I missed boarding my 7 day cruise. I had to book a separate flight home

No real issues just wasnt able to hear / understand any announcements flight attendant was making but everything else was really good- ended up checking my carry on case for free which made deboarding quicker. I would fly West Jet for all my flights.

Seats were comfortable and leg room was good. Slight delay for boarding but nothing too bad. Would fly with them again.

Long lines to board with only two staff checking boarding passes!

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.

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

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

Headphones for the movies have too much bass and can't be adjusted. Almost impossible to hear. Great movie selections but can't really watch them because you can't hear them. Also the system is very slow.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

There was no entertainment at our seats. The flight was comfortable and we had leg room. The snack we had was really good.

Economy seats were surprisingly comfortable, and snacks not too bad. Checked luggage arrived at destination without problems. It was annoying to wait until last to board as lowest-tier seats but understand it’s difficult to gauge when loading a full plane At least checked carryon luggage seemed to come off first. Annoying to have to use app to order food/drink when wifi availability didn’t allow time for it. Advance communication would have helped Food on menu seemed highly processed and unpalatable, overpriced and over packaged. So maybe a good thing to have missed chance to order

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

Book Cheap Chicago Plane Tickets

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
23/5Thu
directPorter Airlines
1h 47mYTZ-MDW
30/5Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 313
23/5Thu
directPorter Airlines
1h 47mYTZ-MDW
26/5Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 315
24/5Fri
directPorter Airlines
1h 47mYTZ-MDW
27/5Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 316
23/5Thu
1 stopDelta
5h 36mYYZ-MDW
30/5Thu
1 stopDelta
6h 37mMDW-YYZ
C$ 353
26/5Sun
1 stopDelta
5h 48mYUL-MDW
4/6Tue
1 stopDelta
8h 15mMDW-YUL
C$ 365
9/5Thu
2 stops
11h 29mYVR-MDW
14/5Tue
1 stop
24h 36mMDW-YVR
C$ 387
7/6Fri
2 stops
22h 32mYVR-MDW
11/6Tue
1 stop
9h 17mMDW-YVR
C$ 406
4/8Sun
1 stopKLM
7h 40mYYZ-MDW
9/8Fri
1 stopKLM
6h 35mMDW-YYZ
C$ 435
10/5Fri
1 stopWestJet
16h 52mYYZ-MDW
12/5Sun
1 stopWestJet
5h 10mMDW-YYZ
C$ 447
10/5Fri
1 stopWestJet
16h 52mYYZ-MDW
12/5Sun
1 stopWestJet
5h 10mMDW-YYZ
C$ 449

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
1/6Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 186
21/5Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 187
7/5Tue
1 stop
16h 16mYYZ-MDW
C$ 189
15/5Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 192
7/5Tue
1 stop
16h 16mYYZ-MDW
C$ 205
8/5Wed
1 stopDelta
9h 12mYYC-MDW
C$ 207
18/6Tue
1 stopDelta
3h 44mYYZ-MDW
C$ 212
25/6Tue
1 stopKLM
3h 44mYYZ-MDW
C$ 227
28/5Tue
1 stopWestJet
6h 37mYYZ-MDW
C$ 246
1/6Sat
1 stopWestJet
5h 25mYYZ-MDW
C$ 250

Search by stops

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Search by price

Recent domestic flight deals

17/7Wed
directFrontier
1h 55mATL-MDW
28/7Sun
directFrontier
1h 56mMDW-ATL
C$ 171
6/5Mon
multi-stopFrontier
12h 36mSEA-MDW
14/5Tue
multi-stopFrontier
12h 21mMDW-SEA
C$ 230
19/9Thu
multi-stopFrontier
10h 36mSEA-MDW
23/9Mon
multi-stopFrontier
11h 16mMDW-SEA
C$ 234
27/5Mon
multi-stopDelta
8h 21mEWR-MDW
1/6Sat
multi-stopDelta
5h 37mMDW-EWR
C$ 237
17/5Fri
multi-stopFrontier
20h 42mSEA-MDW
21/5Tue
multi-stopFrontier
27h 04mMDW-SEA
C$ 241
17/7Wed
directFrontier
1h 55mATL-MDW
28/7Sun
multi-stopFrontier
29h 41mMDW-ATL
C$ 241
4/6Tue
multi-stopDelta
7h 17mEWR-MDW
11/6Tue
multi-stopDelta
5h 52mMDW-EWR
C$ 244
3/6Mon
directSouthwest
2h 25mLGA-MDW
5/6Wed
multi-stopSouthwest
4h 40mMDW-LGA
C$ 248
16/6Sun
directSouthwest
2h 35mBOS-MDW
22/6Sat
directSouthwest
2h 15mMDW-BOS
C$ 272
17/5Fri
multi-stop
22h 12mSEA-MDW
19/5Sun
multi-stop
12h 34mMDW-SEA
C$ 2,056

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Last minute flights to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
27/4Sat
directPorter Airlines
1h 47mYTZ-MDW
8/5Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 479
29/4Mon
directPorter Airlines
1h 47mYTZ-MDW
10/5Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 480
30/4Tue
directPorter Airlines
1h 47mYTZ-MDW
11/5Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 482
29/4Mon
directPorter Airlines
1h 47mYTZ-MDW
11/5Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 493
30/4Tue
multi-stop
5h 42mYHZ-MDW
12/5Sun
multi-stop
9h 26mMDW-YHZ
C$ 565
30/4Tue
multi-stop
8h 37mYHZ-MDW
12/5Sun
multi-stop
9h 26mMDW-YHZ
C$ 572
1/5Wed
multi-stopWestJet
5h 10mYYZ-MDW
2/5Thu
multi-stopWestJet
5h 10mMDW-YYZ
C$ 598
30/4Tue
multi-stopDelta
3h 35mYYZ-MDW
6/5Mon
multi-stopDelta
8h 21mMDW-YYZ
C$ 602
30/4Tue
multi-stopWestJet
5h 10mYYZ-MDW
21/5Tue
multi-stopWestJet
5h 10mMDW-YYZ
C$ 605
29/4Mon
multi-stopDelta
13h 30mYVR-MDW
3/5Fri
multi-stopDelta
11h 59mMDW-YVR
C$ 869

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