Cheap Flights from Ottawa International to Chicago Midway

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Compare Ottawa International to Chicago Midway flight deals

Find the cheapest month or even day of the year to fly to Chicago Midway

Book the best Chicago Midway fare with no extra fees

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Flight deals from Ottawa International to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Ottawa International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $708. Find the lowest prices on one-way and return tickets right here.

Chicago.$681 per passenger.Departing Sun, 20 Sep, returning Mon, 21 Sep.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Sun, 20 Sep, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Mon, 21 Sep, arriving in Ottawa International.Price includes taxes and charges.From $681, select.

Chicago.$692 per passenger.Departing Wed, 23 Sep, returning Sun, 4 Oct.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Wed, 23 Sep, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sun, 4 Oct, arriving in Ottawa International.Price includes taxes and charges.From $692, select.

Chicago.$708 per passenger.Departing Mon, 19 Oct, returning Fri, 23 Oct.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Mon, 19 Oct, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Fri, 23 Oct, arriving in Ottawa International.Price includes taxes and charges.From $708, select.

Chicago.$1,160 per passenger.Departing Mon, 5 Jul, returning Fri, 9 Jul.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Mon, 5 Jul, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Fri, 9 Jul, arriving in Ottawa International.Price includes taxes and charges.From $1,160, select.

Chicago.$1,972 per passenger.Departing Thu, 19 Nov, returning Thu, 26 Nov.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Thu, 19 Nov, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Thu, 26 Nov, arriving in Ottawa International.Price includes taxes and charges.From $1,972, select.

Chicago.$2,025 per passenger.Departing Wed, 19 May, returning Fri, 21 May.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Wed, 19 May, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Fri, 21 May, arriving in Ottawa International.Price includes taxes and charges.From $2,025, select.

Chicago.$2,029 per passenger.Departing Thu, 10 Dec, returning Thu, 7 Jan.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Thu, 10 Dec, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Thu, 7 Jan, arriving in Ottawa International.Price includes taxes and charges.From $2,029, select.

Chicago.$2,033 per passenger.Departing Thu, 3 Dec, returning Sun, 6 Dec.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Thu, 3 Dec, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Sun, 6 Dec, arriving in Ottawa International.Price includes taxes and charges.From $2,033, select.

Chicago.$2,035 per passenger.Departing Sat, 31 Oct, returning Sun, 1 Nov.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Sat, 31 Oct, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Sun, 1 Nov, arriving in Ottawa International.Price includes taxes and charges.From $2,035, select.

Chicago.$2,203 per passenger.Departing Mon, 4 Jan, returning Fri, 15 Jan.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Mon, 4 Jan, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Fri, 15 Jan, arriving in Ottawa International.Price includes taxes and charges.From $2,203, select.

Chicago.$2,436 per passenger.Departing Sun, 29 Nov, returning Wed, 2 Dec.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Ottawa International on Sun, 29 Nov, arriving in Chicago Midway.Inbound indirect flight with WestJet, departs from Chicago Midway on Wed, 2 Dec, arriving in Ottawa International.Price includes taxes and charges.From $2,436, select.

Find the cheapest month to fly from Ottawa International to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Ottawa International to Chicago Midway flights are currently cheapest in September.

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Ottawa International to Chicago Midway: Alternative routes

Compare routes from Ottawa International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

Ottawa to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$681
Cheapest month to fly	September

Finding cheap flights from Ottawa International to Chicago Midway: Frequently asked questions

How much are return flights from Ottawa International to Chicago Midway?

The best price we found for a return flight from Ottawa International to Chicago Midway is $681. 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.

Which airlines fly direct from Ottawa International to Chicago Midway?

Currently, there are no airlines that fly direct from Ottawa International to Chicago Midway. But we found flights with one or more stops from $681.

How many flights are there a week from Ottawa International to Chicago Midway?

As of September 2026, there are no flights flying from Ottawa International to Chicago Midway.

When is the cheapest time to fly from Ottawa International to Chicago Midway?

The cheapest month to fly from Ottawa International to Chicago Midway is usually September.

Which upcoming date is cheapest to fly from Ottawa International Airport to Chicago Midway Airport on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Ottawa International Airport to Chicago Midway Airport on Sunday, 20 September 2026.

Can I get a direct flight from Ottawa International Airport to Chicago Midway Airport?

No airlines currently offer direct flights between Ottawa International Airport and Chicago Midway Airport. Most routes have one or more stops.

How can I find the best flight deal to Chicago Midway?

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.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

Which is the cheapest airline to fly from Ottawa International Airport to Chicago Midway with?

Currently, Porter Airlines offers the cheapest flight tickets to Chicago Midway.

Flying from Ottawa/Macdonald-Cartier International Airport (YOW) to Chicago Midway International Airport (MDW): what you need to know

Chicago's timezone is UTC-5, making Chicago one hour behind Ottawa.
Give yourself plenty of time to make your YOW to MDW flight. Generally, it's best to arrive at least two hours before international departures and an hour ahead for domestic flights.
During popular months such as July, it's best to get to the airport well in advance. Plan to arrive two hours before domestic departures and four hours ahead of international flights when you travel during peak periods in general.

How to find the cheapest flights from Ottawa/Macdonald-Cartier International Airport (YOW) to Chicago Midway International Airport (MDW)

Currently, $391 is the lowest price we've found for a one-way Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport flight. The best price for a return plane ticket is $681. Remember that fares can change due to availability when booking.
Don't leave things to the last moment. You're more likely to get cheap tickets from YOW to MDW if you book in advance. Airlines often have some terrific early bird discounts.
The 'Whole month' tool shows you the cheapest flights from Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport across every month. It's a good way to find a bargain if your travel dates aren't set in stone.
Finding cheap flights from YOW to MDW couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll notify you when fares go down.
Select your preferred departure and arrival times, airlines and number of stops with the filters. Alternatively, sort your results by 'Cheapest' to get the best deals on flights from Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport.

Handy information about Ottawa/Macdonald-Cartier International Airport (YOW)

The address for YOW is 50 Airport Road.
58.21% of flights departing from Ottawa/Macdonald-Cartier International Airport reach their destination on schedule.
Ottawa/Macdonald-Cartier International Airport is around 13 kilometres from central Ottawa. If you're catching a cab, ride-sharing or driving from the centre, it'll take you 20 minutes or so to arrive, depending on the traffic.
Expect a journey time of roughly 45 minutes on public transport.
Taking an early flight from Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport? Avoid the stress of rushing to the terminal (and get some extra shut-eye) by picking one of these stays close to YOW:

Arriving at Chicago Midway International Airport (MDW)

The last thing you want is a long trip to your hotel if you're landing late on an Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport flight. Stay at one of these accommodation options near MDW instead:
Grab a Chicago Midway International Airport rental car and explore Chicago and beyond with your own wheels. Dollar, Hertz and Budget are top outlets to choose from here.
Lock in the lowest price by booking your vehicle from Chicago Midway International Airport about four weeks before your departure date.

Getting from Chicago Midway International Airport (MDW) to central Chicago

The address for MDW is 5700 South Cicero.
Chicago Midway International Airport to central Chicago has a drive time of about 20 minutes. It's approximately 19 kilometres away.
If you're using public transport, expect a journey time of roughly 45 minutes.

When to fly to Chicago Midway International Airport (MDW)

It's time to choose your dates for your flight from Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport. July is the busiest month to visit Chicago. If you'd like a more low-key vibe, go in May.
Book your flight from Ottawa/Macdonald-Cartier International Airport to Chicago Midway International Airport for July if you want to go to Chicago during its warmest month. You can expect temperatures of between 15ºC and 29ºC.
If you want to travel in cooler conditions, search for a cheap ticket from YOW to MDW in January. Temperatures average between -12ºC and 3ºC then.

Explore more of United States

Columbus is just one of the many places in United States waiting to be discovered once you've seen the sights of Chicago. Around 451 kilometres away to the south-east, its best attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in United States. Experience this destination's highlights firsthand at The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.