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Find cheap flights from Canada to Chicago Midway Airport from $117

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 3/18. 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
Wed 3/27
Wed 4/3

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 travelers have searched 50,103,318 times on KAYAK, and here is why:

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Flights to Midway - Travel Insights & Trends

Get data-powered insights and trends for 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 Sunday where tickets can be as cheap as $305. On the other hand, the most expensive day to fly is Monday, where prices are $537 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 $209 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 $464 and $417 respectively. For return trips, the best month to travel is March with an average price of $221.

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 $244 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the morning, which is peak travel time and where the average cost of a ticket is $316.

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 $128 one-way - $211 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 4 airlines that fly to Chicago Midway Airport, Southwest offers the most flights, with around 1,742 per week, followed by Frontier with 112 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 31m, Calgary, which takes 3h 27m, Toronto, which takes 3h 35m, and Vancouver, which takes 4h 00m.

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

There are around 283 direct flights from within Canada to Chicago Midway Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 42% of flights departing in the morning.

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

Each week there are around 1,975 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Wednesday, with 20% of flights taking off on this day.

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

Each week, there are 62 medium-haul flights (3-6 hour flight duration) and 1,988 short-haul flights (up to 3 hour flight duration) to Chicago Midway Airport. There aren't any long-haul flights (6-12 hour flight duration).

How many cities have direct flights to Chicago Midway Airport?

From Canada, there are direct flights to Chicago Midway Airport from 69 cities. The city with the most direct flights is Orlando, with 91 direct flights each week.

Good to know

Low season

January

High season

August

Cheapest flight

$117
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Toronto Island to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    You’ll need to travel 9 miles to reach the Chicago city center from Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $226. The cheapest price found on KAYAK in the last 2 weeks cost $121 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 travelers 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

  • 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 $128 one-way - $170 round-trip
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be August, September and October. The cheapest month to fly from Canada is January.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.
See more tips

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, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 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 direct flights

Nonstop returns

Chicago Midway to Canada

Monday

Aeromexico, Air France, Allegiant Air, +10 more

Aeromexico, Air France, +11 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, +10 more

Aeromexico, Air France, +11 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 direct flights
See more direct flights

Top airline flying from Canada to Midway

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 KAYAK reviews.
7.4
Porter AirlinesOverall score based on 491 reviews
76boarding
75food
75comfort
74overall
82crew
66entertainment
Airline reviews

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?

Read more about Porter Airlines

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.

New jet. Lots of leg room. On time departure. Early arrival. Reasonable airfare. Excellent online experience.

I had checked in online the day before but was instructed to collect our boarding passes when we arrived. I am not completely comfortable using the automated Kiosks and always enjoy the nostalgia of speaking with someone when checking in for a flight. Upon doing so however, we were immediately asked,"did you check in online already?" To which I replied, "yes, but we were asked to retrieve our boarding passes upon arrival." She then said, "that's what those machines over there are for. We really encourage people to use those." That unfortunately sparked a series of shortness and overall poor behavior in my opinion from the woman who checked us in. I understand it was early in the morning but I am always excited to experience flying and that interaction has unfortunately left a bitter taste in my mouth to the point I will forever now hesitate to book with Porter again. Thank you for taking the time to read this. Cheers, JD

Everything was fantastic, by far the best airline experience in Canada 🇨🇦!

Flights to Chicago Midway Airport