CA $211 Cheap Flights from Toronto (YYZ) to Chicago (MDW)

You can find cheap one-way flights from CA $211 and cheap return flights CA $340 YYZ to MDW with Expedia. One-way flights typically cost between CA$278 and CA$1756, and return flights often range between CA$456 and CA$3458. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when YYZ to MDW ticket fares go up or down.

The cheapest months to fly from YYZ to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.

Enter YYZ to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

Delta is one of the cheapest airlines offering connecting return flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$308 for flights that can be booked for departure within the next year. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.

To find a cheap flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

There are approximately 20 connecting flights per day from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW). Some common connection points include Detroit Metropolitan Wayne County (DTW), Liberty International (EWR), and Hartsfield-Jackson Atlanta International (ATL).

The earliest flight from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) typically departs around 6:00 AM. This service is offered by Delta. This is a seasonal service, active in September and October. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

You'll typically find the most flights from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) on a Thursday, with around 31 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Delta, Air Canada, and United.

The most popular departure times for flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) are in the early morning, from 6am to 9am. Many major carriers, including Delta, Air Canada and United, offer flights during this window. Many travellers prefer this time as it allows you to arrive in Chicago early, giving you a full day for business or exploring.

There are no nonstop flights from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 7 hours 30 minutes. If you opt for flights with two or more stops, the travel time increases significantly to about 15 hours. The distance between these two airports is approximately 697 kilometers. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.

You can fly first class between YYZ and MDW. First class cabins are available on Delta.

It's easy to earn miles on a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

If you're planning to travel to Chicago from Pearson Intl. (YYZ), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Liberty Intl. (EWR), Nashville Intl. (BNA), or Washington Dulles Intl. (IAD) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

Typically, booking a last minute flight from Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

Securing a Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

If you booked your Toronto, ON (YYZ-Pearson Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.