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Cheap flights from Ottawa to Chicago from C$ 237

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Ottawa to Chicago departing on 7/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Ottawa to Chicago

Cheap round-trip flights

Logo
4:25 p.m. - 10:21 a.m.YOW-MDW
18h 56m1 stop
Logo
8:05 a.m. - 5:20 p.m.MDW-YOW
32h 15m2 stops
C$ 471
Find Deal
Fri, 3 Oct - Wed, 15 Oct
United Airlines Logo
6:33 a.m. - 8:00 a.m.YOW-ORD
2h 27mdirect
United Airlines Logo
10:50 a.m. - 2:04 p.m.ORD-YOW
2h 14mdirect
C$ 472United Airlines
Find Deal
Fri, 3 Oct - Wed, 15 Oct
Logo
1:25 p.m. - 4:24 p.m.YOW-MDW
3h 59m1 stop
Logo
9:35 a.m. - 12:22 a.m.MDW-YOW
13h 47m1 stop
C$ 473
Find Deal
Wed, 1 Oct - Sat, 11 Oct
Logo
4:25 p.m. - 3:17 p.m.YOW-ORD
23h 52m1 stop
Logo
5:05 a.m. - 5:20 p.m.ORD-YOW
11h 15m1 stop
C$ 476
Find Deal
Fri, 26 Sep - Sun, 28 Sep
United Airlines Logo
5:50 p.m. - 11:30 p.m.YOW-ORD
6h 40m1 stop
United Airlines Logo
9:20 p.m. - 9:58 a.m.ORD-YOW
11h 38m1 stop
C$ 479United Airlines
Find Deal
Fri, 26 Sep - Mon, 29 Sep
Porter Airlines Logo
1:25 p.m. - 4:24 p.m.YOW-MDW
3h 59m1 stop
Porter Airlines Logo
11:00 a.m. - 6:39 p.m.MDW-YOW
6h 39m1 stop
C$ 512Porter Airlines
Find Deal
Thu, 23 Oct - Sun, 26 Oct
WestJet Logo
12:20 p.m. - 12:39 p.m.YOW-ORD
25h 19m2 stops
WestJet Logo
5:30 p.m. - 4:19 p.m.ORD-YOW
21h 49m2 stops
C$ 516WestJet
Find Deal
Fri, 3 Oct - Mon, 6 Oct
Porter Airlines Logo
9:35 a.m. - 4:24 p.m.YOW-MDW
7h 49m1 stop
Porter Airlines Logo
9:35 a.m. - 4:34 p.m.MDW-YOW
5h 59m1 stop
C$ 532Porter Airlines
Find Deal
Thu, 9 Oct - Sun, 12 Oct
WestJet Logo
5:40 a.m. - 4:11 p.m.YOW-ORD
11h 31m2 stops
WestJet Logo
11:14 a.m. - 12:42 a.m.ORD-YOW
12h 28m2 stops
C$ 552WestJet
Find Deal
Fri, 7 Nov - Mon, 10 Nov
Delta Logo
5:55 a.m. - 6:35 p.m.YOW-MDW
13h 40m2 stops
Delta Logo
9:35 a.m. - 12:22 a.m.MDW-YOW
13h 47m2 stops
C$ 1,554Delta
Find Deal
Thu, 2 Oct - Mon, 6 Oct

United Airlines flights from Ottawa to Chicago

Our best United Airlines deals on Ottawa to Chicago flight tickets
United Airlines
3 Oct
YOW6:33 a.m.Ottawa
2h 27m
ORD8:00 a.m.Chicago O'Hare Intl
15 Oct
ORD10:50 a.m.Chicago O'Hare Intl
2h 14m
YOW2:04 p.m.Ottawa
C$ 472
Find similar
United Airlines
26 Sep
YOW5:50 p.m.Ottawa
6h 40m
1 stop
ORD11:30 p.m.Chicago O'Hare Intl
29 Sep
ORD9:20 p.m.Chicago O'Hare Intl
11h 38m
1 stop
YOW9:58 a.m.Ottawa
C$ 479
Find similar
United Airlines
3 Oct
YOW7:29 p.m.Ottawa
4h 46m
1 stop
ORD11:15 p.m.Chicago O'Hare Intl
15 Oct
ORD8:50 a.m.Chicago O'Hare Intl
4h 23m
1 stop
YOW2:13 p.m.Ottawa
C$ 480
Find similar

WestJet flights from Ottawa to Chicago

Our best WestJet deals on Ottawa to Chicago flight tickets
WestJet
3 Oct
YOW12:20 p.m.Ottawa
25h 19m
2 stops
ORD12:39 p.m.Chicago O'Hare Intl
6 Oct
ORD5:30 p.m.Chicago O'Hare Intl
21h 49m
2 stops
YOW4:19 p.m.Ottawa
C$ 516
Find similar
WestJet
7 Nov
YOW5:40 a.m.Ottawa
11h 31m
2 stops
ORD4:11 p.m.Chicago O'Hare Intl
10 Nov
ORD11:14 a.m.Chicago O'Hare Intl
12h 28m
2 stops
YOW12:42 a.m.Ottawa
C$ 552
Find similar
WestJet
2 Dec
YOW5:40 a.m.Ottawa
11h 38m
2 stops
ORD4:18 p.m.Chicago O'Hare Intl
4 Dec
ORD11:15 a.m.Chicago O'Hare Intl
12h 27m
2 stops
YOW12:42 a.m.Ottawa
C$ 570
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Ottawa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 15 September 2025.
Use the filters below to find and compare flights from Ottawa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/10

4:25 p.m.-10:21 a.m.

1 stop18h 56m

Chicago Midway

Wed 15/10

8:05 a.m.-5:20 p.m.

2 stops32h 15m

C$ 471

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 3/10

6:33 a.m.-8:00 a.m.

Nonstop2h 27m

Chicago O'Hare Intl

Wed 15/10

10:50 a.m.-2:04 p.m.

Nonstop2h 14m

C$ 472

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 1/10

1:25 p.m.-4:24 p.m.

1 stop3h 59m

Chicago Midway

Sat 11/10

9:35 a.m.-12:22 a.m.

1 stop13h 47m

C$ 473

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 26/9

4:25 p.m.-3:17 p.m.

1 stop23h 52m

Chicago O'Hare Intl

Sun 28/9

5:05 a.m.-5:20 p.m.

1 stop11h 15m

C$ 476

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 26/9

5:50 p.m.-11:30 p.m.

1 stop6h 40m

Chicago O'Hare Intl

Mon 29/9

9:20 p.m.-9:58 a.m.

1 stop11h 38m

C$ 479

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 23/10

1:25 p.m.-4:24 p.m.

1 stop3h 59m

Chicago Midway

Sun 26/10

11:00 a.m.-6:39 p.m.

1 stop6h 39m

C$ 512

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 3/10

12:20 p.m.-12:39 p.m.

2 stops25h 19m

Chicago O'Hare Intl

Mon 6/10

5:30 p.m.-4:19 p.m.

2 stops21h 49m

C$ 516

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 9/10

9:35 a.m.-4:24 p.m.

1 stop7h 49m

Chicago Midway

Sun 12/10

9:35 a.m.-4:34 p.m.

1 stop5h 59m

C$ 532

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 7/11

5:40 a.m.-4:11 p.m.

2 stops11h 31m

Chicago O'Hare Intl

Mon 10/11

11:14 a.m.-12:42 a.m.

2 stops12h 28m

C$ 552

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 2/10

5:55 a.m.-6:35 p.m.

2 stops13h 40m

Chicago Midway

Mon 6/10

9:35 a.m.-12:22 a.m.

2 stops13h 47m

C$ 1,554

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Ottawa to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of June is another great option to travel to Chicago, with average flight prices from Ottawa averaging around C$ 496.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 807. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around C$ 938. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

At noon is the cheapest time of day to fly from Ottawa to Chicago when you can find flight prices for as low as C$ 507. Flying to Chicago at noon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 917 per ticket.

What is the cheapest Ottawa to Chicago flight route?

Fly from Ottawa to Chicago O'Hare Intl for the best Ottawa - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Ottawa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 715 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Ottawa for as low as C$ 321 on momondo.

What cabin class options are available on Ottawa to Chicago flights?

There are 4 cabin classes available to choose from on Ottawa to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Ottawa to Chicago flights?

No. A direct flight is the cheapest option for a flight between Ottawa to Chicago.

How have Ottawa to Chicago flight prices changed over time?

As of September 2025, prices for Ottawa to Chicago flights are approximately 9% more expensive when compared to flights at the same time last year.

When to book flights from Ottawa to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Ottawa to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Ottawa to Chicago (YOW to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Ottawa to Chicago

Best price found

C$ 320

Fastest flight time

2h 24m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Ottawa in the past 72 hours is C$ 320. The best round-trip flight deal from Ottawa to Chicago found on momondo in the last 72 hours is C$ 597.
The fastest flight from Ottawa to Chicago takes 2h 24m
Direct flights go from Ottawa to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • How far is Ottawa to Chicago by plane?

    A flight from Ottawa to Chicago will travel around 1035.5 km. In terms of flight time, this usually takes a little over 2h 27m.

  • When did momondo last update prices for flights from Ottawa Airport to Chicago?

    Prices for flights from Ottawa Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Ottawa Airport to Chicago?

  • How old do you have to be to fly from Ottawa Airport to Chicago?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Ottawa Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Ottawa to Chicago?

  • What is the most popular airline from Ottawa to Chicago?

Best airlines flying from Ottawa to Chicago

Compare and see reviews for airlines that fly from Ottawa to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 372Free CancellationRating
7.9
363 reviews
Search Porter Airlines flights
United AirlinesPriceFrom C$ 466Free CancellationRating
7.4
8,931 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 504Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights

  • United Airlines Flights From Ottawa to Chicago

    Across 21 United Airlines flights from Ottawa to Chicago this week, the average price was C$ 497, with the best United Airlines deals starting from C$ 336 round-trip. 8,931 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • Air Canada Flights From Ottawa to Chicago

    Across 10,000 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Ottawa to Chicago about 21 times each week, with ticket deals ranging from C$ 364 to C$ 471. Price data is based on momondo searches in the last 72 hours.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

Why use momondo?

Why should I use momondo to find a flight deal from Ottawa to Chicago?

Finding the right flight to Chicago from Ottawa is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Ottawa to Chicago with flexible booking policies on momondo?

All flight searches from Ottawa to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Ottawa to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Ottawa.

I’m not ready to book a flight from Ottawa to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Ottawa to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport