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CA $1,039 Cheap Flights from Sudbury (YSB) to Chicago (MDW)

View CA $1,039 flight on Sun, Aug 30, 2026Opens in a new window

Popular airlines from Sudbury, ON (YSB-Greater Sudbury) to Chicago Midway Airport (MDW)

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Cheap flights from Sudbury (YSB) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $1,039 for one-way flights and CA $3,719 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, Oct 17 - Wed, Oct 21
YSB
Sudbury
MDW
Chicago
CA $3,719 Roundtrip, found 6 days ago
CA $3,719
Roundtrip
found 6 days ago
Select United flight, departing Sat, Oct 17 from Sudbury to Chicago, returning Wed, Oct 21, priced at CA $3,719 found 6 days ago
United
Sat, Oct 17 - Wed, Oct 21
YSB
Sudbury
MDW
Chicago
CA $3,794 Roundtrip, found 3 hours ago
CA $3,794
Roundtrip
found 3 hours ago
Select United flight, departing Sat, Oct 17 from Sudbury to Chicago, returning Wed, Oct 21, priced at CA $3,794 found 3 hours ago
United
Thu, Aug 13 - Thu, Aug 20
YSB
Sudbury
MDW
Chicago
CA $3,867 Roundtrip, found 5 days ago
CA $3,867
Roundtrip
found 5 days ago
Select United flight, departing Thu, Aug 13 from Sudbury to Chicago, returning Thu, Aug 20, priced at CA $3,867 found 5 days ago
United
Mon, Aug 17 - Mon, Aug 24
YSB
Sudbury
MDW
Chicago
CA $3,884 Roundtrip, found 1 day ago
CA $3,884
Roundtrip
found 1 day ago
Select United flight, departing Mon, Aug 17 from Sudbury to Chicago, returning Mon, Aug 24, priced at CA $3,884 found 1 day ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $989
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $989

Frequently asked questions

How much does a flight from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from YSB to MDW with Expedia. 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 our cheapest fares first, and use the Price Tracking tool to receive alerts when YSB to MDW ticket fares go up or down.
What is the cheapest month to fly from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YSB 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.
Which airlines fly direct from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
Enter YSB to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Sudbury, ON (YSB-Greater Sudbury) 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.
What is the best time to fly from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
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.
How many flights per day from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 1 connecting flight per day from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.). Some common connection points include Calgary Intl. (YYC) and Billy Bishop Toronto City (YTZ).
What is the earliest flight from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
Sort flights by "Departure (earliest)" on Expedia to find the earliest flight from YSB to MDW. To compare more early flights, use the "Early Morning" and "Morning" filters in your search.
How long does it take to fly from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 5 hours 48 minutes. Flights with two or more stops will take significantly longer, typically around 19 hours. The distance covered on this route is approximately 771 kilometers. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.
Can you fly business or first class from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
Select the "Business class" and "First class" filters when looking for YSB to MDW flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.
How do I earn miles on a Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Sudbury, ON (YSB-Greater Sudbury) 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.
Is it cheaper to buy a plane ticket from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Sudbury, ON (YSB-Greater Sudbury) 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.
Is it cheaper to book a Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Sudbury, ON (YSB-Greater Sudbury) 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.
Can I cancel or change the date of my flight from Sudbury, ON (YSB-Greater Sudbury) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Sudbury, ON (YSB-Greater Sudbury) 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.

Travel information

Origin airport
Greater Sudbury
Destination airport
Midway Intl.
Roundtrip price
CA $3,718
Distance
766 km

Book with confidence

Sudbury to Chicago Flights

The easy way to book your flights from Sudbury to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Sudbury whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 14 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Sudbury to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Greater Sudbury, YSB to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Sudbury to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Sudbury currently is just CA $3,719 rising to CA $3,884.  

Here are more money-saving tips: 

  • Fly in October when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Sudbury 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Sudbury to Chicago Flights

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