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CA $399 Cheap Flights from Ottawa (YOW) to Chicago (MDW)

View CA $399 flight on Fri, Aug 7, 2026Opens in a new window

Popular airlines from Ottawa International Airport (YOW) to Chicago Midway Airport (MDW)

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Cheap flights from Ottawa (YOW) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $399 for one-way flights and CA $723 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, Sep 24 - Mon, Sep 28
YOW
Ottawa
MDW
Chicago
CA $723 Roundtrip, found 5 hours ago
CA $723
Roundtrip
found 5 hours ago
Select Porter Airlines flight, departing Thu, Sep 24 from Ottawa to Chicago, returning Mon, Sep 28, priced at CA $723 found 5 hours ago
Porter Airlines
Wed, Jul 29 - Wed, Aug 5
YOW
Ottawa
MDW
Chicago
CA $736 Roundtrip, found 6 days ago
CA $736
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Wed, Jul 29 from Ottawa to Chicago, returning Wed, Aug 5, priced at CA $736 found 6 days ago
Porter Airlines
Wed, Jul 29 - Wed, Aug 5
YOW
Ottawa
MDW
Chicago
CA $745 Roundtrip, found 6 days ago
CA $745
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Wed, Jul 29 from Ottawa to Chicago, returning Wed, Aug 5, priced at CA $745 found 6 days ago
Porter Airlines
Thu, Sep 24 - Mon, Sep 28
YOW
Ottawa
MDW
Chicago
CA $755 Roundtrip, found 5 hours ago
CA $755
Roundtrip
found 5 hours ago
Select Porter Airlines flight, departing Thu, Sep 24 from Ottawa to Chicago, returning Mon, Sep 28, priced at CA $755 found 5 hours ago
Porter Airlines
Mon, Aug 24 - Fri, Aug 28
YOW
Ottawa
MDW
Chicago
CA $757 Roundtrip, found 1 day ago
CA $757
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Mon, Aug 24 from Ottawa to Chicago, returning Fri, Aug 28, priced at CA $757 found 1 day ago
Porter Airlines
Wed, Aug 5 - Fri, Aug 7
YOW
Ottawa
MDW
Chicago
CA $762 Roundtrip, found 8 hours ago
CA $762
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Wed, Aug 5 from Ottawa to Chicago, returning Fri, Aug 7, priced at CA $762 found 8 hours ago
Porter Airlines
Sat, Dec 12 - Sun, Dec 13
YOW
Ottawa
MDW
Chicago
CA $765 Roundtrip, found 8 hours ago
CA $765
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Sat, Dec 12 from Ottawa to Chicago, returning Sun, Dec 13, priced at CA $765 found 8 hours ago
Porter Airlines
Tue, Jul 21 - Tue, Jul 28
YOW
Ottawa
MDW
Chicago
CA $767 Roundtrip, found 16 hours ago
CA $767
Roundtrip
found 16 hours ago
Select Porter Airlines flight, departing Tue, Jul 21 from Ottawa to Chicago, returning Tue, Jul 28, priced at CA $767 found 16 hours ago
Porter Airlines
Wed, Aug 5 - Fri, Aug 7
YOW
Ottawa
MDW
Chicago
CA $767 Roundtrip, found 8 hours ago
CA $767
Roundtrip
found 8 hours ago
Select Porter Airlines flight, departing Wed, Aug 5 from Ottawa to Chicago, returning Fri, Aug 7, priced at CA $767 found 8 hours ago
WestJet
Tue, Sep 1 - Sun, Sep 6
YOW
Ottawa
MDW
Chicago
CA $1,519 Roundtrip, found 2 days ago
CA $1,519
Roundtrip
found 2 days ago
Select WestJet flight, departing Tue, Sep 1 from Ottawa to Chicago, returning Sun, Sep 6, priced at CA $1,519 found 2 days 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 $597
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $597

Frequently asked questions

How much does a flight from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $399 and cheap return flights from CA $723 YOW to MDW with Expedia. Return flights often range between CA$1058 and CA$3794. 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 YOW to MDW ticket fares go up or down.
What is the cheapest month to fly from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YOW 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 Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YOW to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
Porter Airlines is one of the cheapest airlines offering connecting return flights from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.), with prices starting from around CA$751 for flights that can be booked for departure within the next year. These flights typically include a layover in Toronto (YYZ-Pearson Intl.). Prices are per adult, economy/coach class. 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.
How do I find cheap flights from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Ottawa, ON (YOW-Macdonald-Cartier 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.
What is the best time to fly from Ottawa, ON (YOW-Macdonald-Cartier Intl.) 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 Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 8 connecting flights per day from Ottawa Macdonald-Cartier Intl. (YOW) to Chicago Midway Intl. (MDW). Some common connection points include Pearson Intl. (YYZ), Washington Dulles Intl. (IAD), and Liberty Intl. (EWR).
What is the earliest flight from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 5:00 AM. This service is seasonal, active only in April, and is operated by airlines such as Air Canada and Delta. An early departure like this can be great if you want to maximize your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Ottawa Macdonald-Cartier International Airport (YOW) to Chicago Midway International Airport (MDW) on a Thursday, with around 13 flights available. This gives you a good selection for your travel plans. Major airlines on this route include United, Air Canada, and Porter Airlines. Compared to other days, Thursdays offer notably more flight options, making it a convenient day to travel.
What are the most popular departure times for flights from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.) are in the early morning, from 6am to 9am. Many major carriers, including United, Porter Airlines and Air Canada, offer flights during this window. Many travellers prefer this time as it allows you to arrive at your destination early, giving you more time to enjoy your trip.
How long does it take to fly from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 4 hours 18 minutes. These flights cover a distance of approximately 1,048 kilometers. If you opt for flights with two or more stops, your travel time will be significantly longer, typically around 13 hours 30 minutes. 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 Ottawa, ON (YOW) to Chicago, IL (MDW)?
Select the "Business class" and "First class" filters when looking for Ottawa, ON (YOW) to Chicago, IL (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 Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Ottawa, ON (YOW-Macdonald-Cartier 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.
What airports do you fly into for Chicago, IL (MDW) from Ottawa, ON (YOW)?
From Macdonald-Cartier Intl. (YOW), you can fly directly into Midway Intl. (MDW) in Chicago. Some flights may connect through major hubs like Pearson Intl. (YYZ), Liberty Intl. (EWR), or Washington Dulles Intl. (IAD) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Ottawa, ON (YOW-Macdonald-Cartier 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.
Is it cheaper to book a Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Ottawa, ON (YOW-Macdonald-Cartier 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.
Can I cancel or change the date of my flight from Ottawa, ON (YOW-Macdonald-Cartier Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Ottawa, ON (YOW-Macdonald-Cartier 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.

Travel information

Origin airport
Macdonald-Cartier Intl.
Destination airport
Midway Intl.
Airlines serving
Porter Airlines, WestJet
Roundtrip price
CA $722
Distance
1041 km

Book with confidence

Ottawa to Chicago Flights

The easy way to book your flights from Ottawa to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Ottawa whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 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 Ottawa to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Macdonald-Cartier Intl., YOW to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Ottawa to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Ottawa currently is just CA $723 rising to CA $1,519.  

Here are more money-saving tips: 

  • Fly in September 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 Ottawa 

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.

Ottawa to Chicago Flights

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