CA $201 Cheap Flights from Ottawa (YOW) to Chicago (MDW)

View CA $201 flight on Sun, May 18, 2025Opens 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 $201 for one-way flights and CA $335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri., May 23 - Mon., May 26
YOW
Ottawa
MDW
Chicago
CA $335 Roundtrip, found 2 hours ago
CA $335
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Fri., May 23 from Ottawa to Chicago, returning Mon., May 26, priced at CA $335 found 2 hours ago
Porter Airlines
Mon., May 12 - Wed., May 14
YOW
Ottawa
MDW
Chicago
CA $361 Roundtrip, just found
CA $361
Roundtrip
just found
Select Porter Airlines flight, departing Mon., May 12 from Ottawa to Chicago, returning Wed., May 14, priced at CA $361 just found
Porter Airlines
Sun., May 18 - Tue., May 20
YOW
Ottawa
MDW
Chicago
CA $385 Roundtrip, found 1 hour ago
CA $385
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Sun., May 18 from Ottawa to Chicago, returning Tue., May 20, priced at CA $385 found 1 hour ago
Porter Airlines
Thu., May 8 - Mon., May 12
YOW
Ottawa
MDW
Chicago
CA $388 Roundtrip, just found
CA $388
Roundtrip
just found
Select Porter Airlines flight, departing Thu., May 8 from Ottawa to Chicago, returning Mon., May 12, priced at CA $388 just found
Porter Airlines
Fri., May 23 - Sun., May 25
YOW
Ottawa
MDW
Chicago
CA $394 Roundtrip, found 1 hour ago
CA $394
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Fri., May 23 from Ottawa to Chicago, returning Sun., May 25, priced at CA $394 found 1 hour ago
Porter Airlines
Thu., Jun. 12 - Fri., Jun. 13
YOW
Ottawa
MDW
Chicago
CA $394 Roundtrip, found 9 hours ago
CA $394
Roundtrip
found 9 hours ago
Select Porter Airlines flight, departing Thu., Jun. 12 from Ottawa to Chicago, returning Fri., Jun. 13, priced at CA $394 found 9 hours ago
Porter Airlines
Mon., May 12 - Wed., May 14
YOW
Ottawa
MDW
Chicago
CA $411 Roundtrip, just found
CA $411
Roundtrip
just found
Select Porter Airlines flight, departing Mon., May 12 from Ottawa to Chicago, returning Wed., May 14, priced at CA $411 just found
Porter Airlines
Sun., May 18 - Tue., May 20
YOW
Ottawa
MDW
Chicago
CA $418 Roundtrip, found 1 hour ago
CA $418
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Sun., May 18 from Ottawa to Chicago, returning Tue., May 20, priced at CA $418 found 1 hour ago
Porter Airlines
Wed., May 7 - Sun., May 11
YOW
Ottawa
MDW
Chicago
CA $424 Roundtrip, found 1 hour ago
CA $424
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Wed., May 7 from Ottawa to Chicago, returning Sun., May 11, priced at CA $424 found 1 hour ago
WestJet
Mon., May 12 - Wed., May 14
YOW
Ottawa
MDW
Chicago
CA $1,240 Roundtrip, just found
CA $1,240
Roundtrip
just found
Select WestJet flight, departing Mon., May 12 from Ottawa to Chicago, returning Wed., May 14, priced at CA $1,240 just found
Flight from Ottawa to Chicago (YOW - MDW) route information
Origin airport
Macdonald-Cartier Intl.
Destination airport
Midway Intl.
Airlines serving
Porter Airlines, WestJet
Roundtrip price
CA $335
Distance
1041 km

Ottawa to Chicago Flights

Ready for an adventure? Thought so! Prepare to see the sights when you book your trip from Ottawa to Chicago with Expedia.ca. Whether you’re visiting for business or pleasure, we know how important it is to bring home travel stories. Maybe your tales will include the best dinner of your life, or the weirdest street art you saw in the city, or the concert that turned you into a fan of a new band. Whatever it is, your new favourite anecdote is right around the corner. Book your trip from YOW to MDW and begin your journey!

Getting a cheap deal on your trip sets the tone for the perfect holiday. And with Expedia.ca, you know you can travel from Ottawa to Chicago on the cheap, with enough money left over for a stellar time in the city. That could mean more tours with the kids, more concerts with the spouse, more dessert amongst co-workers, or even front row seats to a sports game if you’re travelling solo. It’s your holiday! Make it great.

Travelling shouldn’t cost an arm and a leg before you even get to relax on the plane’s armrests. Count on Expedia.ca to get you the best discounts on flights from YOW to MDW. And remember this: You can also save big when you bundle. Add a hotel or car rental deal to your flight and witness those savings add up. Hey, more money for more souvenirs, right? Right! Pack your bags and we’ll see you on the route.

Combine your Chicago flight with a hotel and/or car rental for a package deal designed to save you even more money! Discover additional savings by booking in advance or find a last minute deal. There are tons of ways to save on your flights from with Expedia Canada. Use us as your top travel destination and have the confidence that you’re getting a bargain!

Frequently asked questions

How much is a flight from YOW to Midway Intl. Airport (MDW)?
Round-trip journeys between Ottawa International Airport and Chicago Airport start from CA $335. This figure is based on fares available within the last 7 days on Expedia for flights departing within the next year — book now to avoid missing out. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Macdonald-Cartier Intl. Airport (YOW) to Chicago Airport?
Most flights can be conveniently canceled online, but whether you incur a fee depends on your airline. If you do have to cancel your vacation, follow the instructions in the Customer Service Portal.
How do I find cheap flights from YOW to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for YOW to Midway Intl. Airport (MDW) flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from YOW to Midway Intl. Airport (MDW)?
It’s just 1,050 kilometers between Ottawa and Chicago. It’s quite possible that you’ll spend more time getting to and from the airport than you will actually flying!
Which airlines fly direct from YOW to Midway Airport?
If you want to travel straight from YOW to Midway Airport, you’ll need to book a flight with one or more stops. Unfortunately, there aren’t any airlines that fly directly between these airports.
Are YOW to MDW flight tickets cheaper when they're purchased at the last minute?
Booking last minute from Ottawa International Airport to Chicago Airport can be hit-or-miss. It is possible to find a bargain, but then again, you could miss out! If you’d prefer to play it safe and start your travel planning ahead of time, Expedia compares flight deals up to 12 months in advance. Just remember that not all airlines issue their prices that far in advance. Our advice? Check back often as prices are updated frequently.

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