Cheap Flights from Ottawa to Chicago

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Flight deals from Ottawa to Chicago

Looking for a cheap last-minute deal or the best return flight from Ottawa to Chicago? Find the lowest prices on one-way and return tickets right here.

Chicago.$422 per passenger.Departing Wed, 15 Apr, returning Wed, 15 Apr.Return flight with United.Outbound indirect flight with United, departs from Ottawa International on Wed, 15 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 15 Apr, arriving in Ottawa International.Price includes taxes and charges.From $422, select.

Chicago.$619 per passenger.Departing Tue, 31 Mar, returning Wed, 1 Apr.Return flight with United.Outbound indirect flight with United, departs from Ottawa International on Tue, 31 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 1 Apr, arriving in Ottawa International.Price includes taxes and charges.From $619, select.

Chicago.$640 per passenger.Departing Sat, 18 Apr, returning Sun, 3 May.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Sat, 18 Apr, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sun, 3 May, arriving in Ottawa International.Price includes taxes and charges.From $640, select.

Chicago.$685 per passenger.Departing Fri, 6 Mar, returning Sun, 8 Mar.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Fri, 6 Mar, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sun, 8 Mar, arriving in Ottawa International.Price includes taxes and charges.From $685, select.

Chicago.$716 per passenger.Departing Mon, 1 Jun, returning Sat, 6 Jun.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Mon, 1 Jun, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sat, 6 Jun, arriving in Ottawa International.Price includes taxes and charges.From $716, select.

Chicago.$730 per passenger.Departing Sun, 17 May, returning Sat, 6 Jun.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Sun, 17 May, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sat, 6 Jun, arriving in Ottawa International.Price includes taxes and charges.From $730, select.

Chicago.$754 per passenger.Departing Fri, 1 May, returning Sun, 3 May.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Fri, 1 May, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sun, 3 May, arriving in Ottawa International.Price includes taxes and charges.From $754, select.

Chicago.$789 per passenger.Departing Mon, 15 Jun, returning Mon, 6 Jul.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Ottawa International on Mon, 15 Jun, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Mon, 6 Jul, arriving in Ottawa International.Price includes taxes and charges.From $789, select.

Find the cheapest month to fly from Ottawa to Chicago

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

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Direct flights from Ottawa to Chicago

Alternative Ottawa to Chicago routes

Looking for the cheapest, fastest or easiest route from Ottawa to Chicago? You could fly into the following airports instead.

Ottawa to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$422
Cheapest month to fly	April
Average flight time	2 hrs, 28 mins
Most popular airline	United
Average flights per week	109

Finding cheap flights from Ottawa to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Ottawa to Chicago?

The best price we found for a return flight from Ottawa to Chicago is $422. 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.

How long does it take to fly from Ottawa to Chicago?

2 hours and 28 minutes is the average flight time from Ottawa to Chicago.

Which airlines fly direct from Ottawa to Chicago?

United, Air New Zealand and Air Canada fly direct from Ottawa to Chicago.

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

As of February 2026, there are 109 flights per week flying from Ottawa to Chicago.

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

The cheapest month to fly from Ottawa to Chicago is usually April.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Ottawa, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $422.

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

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Ottawa to Chicago on Wednesday, 15 April 2026.

Can I get a direct flight from Ottawa to Chicago?

Yes – the average flight time is 2 hours and 28 minutes.

How can I get the best flight deal from Ottawa to Chicago?

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 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.

What’s the weather like in Chicago?

In February, the average temperature is usually around -2°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

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

The cheapest airline that flies to Chicago is United .

Flying from Ottawa to Chicago: what you need to know

Planning your getaway begins with figuring out where you'll fly out of in Ottawa. Ottawa/Macdonald-Cartier International Airport (YOW) is the city's main airport, so explore your options for reserving a flight from Ottawa to Chicago taking off from here.
When choosing where to land in Chicago, O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW) are the major entry points.
The average duration of a direct Ottawa to Chicago flight is 2 hours 20 minutes.
Give yourself enough time to catch your Ottawa to Chicago flight. As a general rule, turn up two hours before international departures and an hour ahead for domestic flights.
If you're jetting off during a major holiday or other peak period, give yourself extra time. A good general rule is two hours ahead of domestic flights and up to four hours before international departures. Lines at security and check-in will be longer.

How to find the cheapest flights from Ottawa to Chicago

At the moment, $257 is the best price we've seen for a one-way ticket from Ottawa to Chicago. The cheapest price for a return flight is $422. Remember fares may change due to demand at the time of booking.
Score cheap Ottawa to Chicago flights by booking two months ahead. Based on our research, that's the ideal time frame for bagging a bargain.
The best month for finding cheap plane tickets from Ottawa to Chicago is May. Use the 'Whole month' tool to compare prices, then choose the dates that offer the lowest fares.
Locking in a cheap flight from Ottawa to Chicago couldn't be easier with Price Alerts. All you need to do is set up one of these automatic alerts and we'll let you know when the price has dropped.
Save money on your Ottawa to Chicago flight with the help of our filters. Select your ideal departure time, duration and airlines, then sort the results by 'Cheapest' to see the best deals.

Flying from Ottawa

Ottawa/Macdonald-Cartier International Airport (YOW)

Set off from Ottawa/Macdonald-Cartier International Airport (YOW) on a nonstop flight from Ottawa to Chicago. From YOW, you can fly directly into O'Hare International Airport (ORD).
United Airlines is a leading airline that offers direct Ottawa to Chicago plane tickets leaving from YOW.
YOW is about 11 kilometres from central Ottawa. If you're ride-sharing, driving or catching a cab from the centre, it'll take you 20 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the trip time to be around 45 minutes.
Want a relaxed start to your travels? Stay near Ottawa/Macdonald-Cartier International Airport. Whether you have an early flight from Ottawa to Chicago or just don't want to be rushed, these hotels are ideal:
58.21% of flights that take off from Ottawa/Macdonald-Cartier International Airport make it to their destination on time.
You'll find YOW at 50 Airport Road.

Arriving in Chicago

O'Hare International Airport (ORD)

O'Hare International Airport (ORD) to central Chicago takes around 35 minutes by car. The centre is roughly 26 kilometres away.
It usually takes 55 minutes to get there on public transport.
Book a hotel close to ORD if you have a late flight from Ottawa to Chicago. Settle into one of these accommodation options and skip the long transfer:
Follow your own route with an O'Hare International Airport rental car. Pick up your wheels from Routes Car Rentals, Dollar or Budget and find adventure across Chicago and beyond.
To lock in the lowest price, reserve your ride from O'Hare International Airport about four weeks in advance of your Ottawa to Chicago flight.
The street address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Chicago Midway International Airport (MDW) is about 14 kilometres from central Chicago. Once you've hopped off your flight from Ottawa to Chicago, it takes approximately 20 minutes to get to the heart of the city in a ride-share or cab.
If you hop on public transport, the ride to the centre takes 45 minutes or so.
After your flight from Ottawa to Chicago, tuck yourself in at a hotel close to MDW. These are some comfortable accommodation options that'll help you sink into relaxation mode:
Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car simple. These trusted companies are located around or in the terminal and will have you on the road before long.
Avoid last-minute price surges. Securing your ride four weeks ahead of your arrival at MDW will save you money.
Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Chicago Rockford International Airport (RFD) is roughly 129 kilometres from central Chicago. It takes about 1 hour 25 minutes to reach the city centre in a car once you've stepped off your flight from Ottawa to Chicago.
The journey takes roughly 4 hours 15 minutes on public transport.
Start your trip without stressing over how to get to your destination with a Chicago Rockford International Airport rental car. You can book with trusted names here like Budget, Alamo and National.
Booking at least a few weeks in advance of your flight from Ottawa to Chicago is smart. In addition to better deals, you'll be able to choose the vehicle make and model you prefer at RFD.
Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

August is the most popular month for flights from Ottawa to Chicago. To escape the crowds, visit Chicago in January.
The warmest month in Chicago is July, with temperatures ranging between 15ºC and 29ºC. Book your Ottawa to Chicago ticket then if that's your definition of good weather.
If you like cooler conditions, search for a cheap flight from Ottawa to Chicago in January when temperatures average between -12ºC and 3ºC.

More about Chicago

Start your Chicago trip off on the right foot by choosing the ideal place to stay. Once you've booked your flight from Ottawa to Chicago, explore our range of hotels including:
All great adventures should include a little sightseeing. Millennium Park, Art Institute of Chicago and LandShark Beer Garden at Navy Pier are essential stops on your Chicago itinerary.

Explore more of United States

Chicago has loads to offer, but there are so many other corners of United States you'll want to see. Around 451 kilometres south-east of Chicago, a trip to Columbus will keep you on the move. Start with leading attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.
Indianapolis is another essential stop in United States and is around 257 kilometres south-east of Chicago. No trip is complete without seeing The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.