Cheap flights to Chicago Midway airport

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Flight deals to Chicago Midway

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Airports near Chicago

Looking for an alternative route to Chicago? There are 3 more airports nearby. Compare them below to find the cheapest or fastest.

Direct flights to Chicago Midway

Frequently asked questions

Porter Airlines (Canada) Ltd, Porter Airlines Inc, flyGTA Airlines and United all fly non-stop to Chicago Midway.
The cheapest month to fly to Chicago Midway is usually May.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
Yes – the average flight time is 1 hour and 45 minutes.
The best price we found for a round-trip flight to Chicago Midway is C$317. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
We found flights to Chicago O'Hare International Airport, which is 25.4 km from Chicago, from C$266.
After crunching the numbers on our flight calendar, we found that the cheapest date to fly to Chicago Midway Airport is Saturday, May 25, 2024.
We crunched all the numbers in our flight calendar, and it looks like the cheapest time to book a flight to Chicago Midway is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Porter Airlines (Canada) Ltd offers the cheapest flight tickets to Chicago Midway.

Flying to Chicago Midway

The things to know before you go.
Cheapest flight foundC$188
Cheapest month to flyMay
Average flight time1 hr, 46 mins
Most popular airlinePorter Airlines (Canada) Ltd
Average flights per week35

Discover Chicago Midway

Known for its upscale shopping boutiques, architecturally significant buildings, and, of course, its delicious deep-dish pizza, Chicago is a city that should be on every Canadian's travel bucket list. And since it's just a short flight away from major Canadian cities like Toronto and Ottawa, it's a great spot to visit for a weekend trip or a longer vacation. Chicago Midway International Airport (MDW) is one of the top international airports in the city, with over 22 million passengers served per year. To book a cheap flight to Chicago from anywhere in the world, simply enter your home city and travel dates with MDW as the final destination. Skyscanner will search all flight possibilities so you can compare and book the best option for you.

Best Time to Book a Flight to Chicago

Chicago residents generally experience hot, humid summers and cold, snowy winters. Thunderstorms, high winds, and even tornadoes are possible in the summers as well. Despite the possible weather issues, tourists flock to Chicago from June to August for festivals like the Pitchfork Music Festival and the Taste of Chicago food festival. Other smaller festivals and events also take place during these months. However, many tourists do choose to skip the hot and humid weather and visit during the spring or fall when temperatures are generally more comfortable.

Airlines that Fly to Chicago Midway International Airport

Chicago Midway Airport is served by six airlines:

Most of the available flight routes are to and from major U.S. cities like Detroit, Atlanta, and New York. There are also many direct flight paths to Mexican cities. Currently, the only direct flight route from Canada to Chicago Midway Airport is via Porter Airlines and leaves from Billy Bishop Toronto City Airport (YTZ) on Toronto Island.

Arriving at the Airport

MDW consists of one passenger terminal split into three Concourses. Taxi stands are available just outside of each concourse and are operated by over a dozen licensed taxi companies. Fares are based on metered rates and can vary depending on the daily traffic. Generally, a ride to downtown Chicago shouldn't cost more than $40 CAD.

Public transportation busses and trains are also available at Midway Airport. To board a train or bus, head east from the passenger terminal to the Midway Transportation Center. An enclosed walkway connects the two buildings. Rental car services are also available in a building separate from the airport. Midway's Rental Car Facility can be reached by boarding a free shuttle bus that picks up at arrivals every 15 minutes.

Chicago Midway International Airport Facilities

Midway Airport has many amenities to aid after a long flight, including coffee shops and restaurants, device charging stations, and ATMs and banks. Free Wi-Fi is also accessible throughout the terminal. If you need to relax after a long flight, stop by the Yoga Room to meditate and practice yoga. You can also unwind by touring the terminal and viewing the beautiful paintings and sculptures on display as part of the airport's art program. If you'd rather just head straight to a hotel, there are a dozen great hotels in the Midway area which you can compare and book free through Skyscanner to ensure availability.

What to See and Do in Chicago

If you've never been to Chicago before, there are a few things that all first-time tourists must do, like take a picture of the Cloud Gate sculpture. This stainless steel sculpture is better known as The Bean for its unique shape. The shiny, reflective surface is great for photo-ops. Visiting the Art Institute of Chicago is another activity that should be on every Chicago tourist's to-do list. The Institute was founded in the late 1800s and is one of the largest art museums in the country. It is home to pieces by world-famous artists like Picasso as well as thousands of other paintings, sculptures, prints, and photographs.


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Prices shown on this page are estimated lowest prices only. Found in the last 45 days.