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Cheap flights from Ottawa to Chicago from C$ 187

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 4/12. 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

Enter your travel dates to find the best prices.
Multiple Airlines Logo
4:15 p.m. - 11:08 a.m.YOW-ORD
19h 53m1 stop
Multiple Airlines Logo
6:15 a.m. - 12:25 a.m.ORD-YOW
17h 10m1 stop
C$ 400Multiple Airlines
Find Deal
Mon, 8 Dec - Thu, 11 Dec
Multiple Airlines Logo
7:00 a.m. - 11:08 a.m.YOW-ORD
29h 08m1 stop
Multiple Airlines Logo
2:26 p.m. - 5:13 p.m.ORD-YOW
25h 47m1 stop
C$ 410Multiple Airlines
Find Deal
Fri, 12 Dec - Mon, 15 Dec
Multiple Airlines Logo
9:30 a.m. - 11:08 a.m.YOW-ORD
26h 38m3 stops
Multiple Airlines Logo
5:00 a.m. - 12:25 a.m.ORD-YOW
18h 25m1 stop
C$ 427Multiple Airlines
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Porter Airlines Logo
8:40 a.m. - 3:20 p.m.YOW-MDW
7h 40m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 560Porter Airlines
Find Deal
Fri, 5 Dec - Mon, 8 Dec
WestJet Logo
5:45 p.m. - 1:35 p.m.YOW-ORD
20h 50m1 stop
WestJet Logo
2:20 p.m. - 12:40 a.m.ORD-YOW
9h 20m1 stop
C$ 577WestJet
Find Deal
Thu, 26 Feb - Mon, 2 Mar
Porter Airlines Logo
8:40 a.m. - 11:50 a.m.YOW-MDW
4h 10m1 stop
Porter Airlines Logo
11:00 a.m. - 7:54 p.m.MDW-YOW
7h 54m1 stop
C$ 600Porter Airlines
Find Deal
Sat, 6 Dec - Mon, 8 Dec
WestJet Logo
5:40 a.m. - 1:10 p.m.YOW-MDW
32h 30m2 stops
WestJet Logo
10:49 a.m. - 12:42 a.m.MDW-YOW
12h 53m2 stops
C$ 639WestJet
Find Deal
Sat, 6 Dec - Mon, 8 Dec
Porter Airlines Logo
6:50 a.m. - 10:05 a.m.YOW-MDW
4h 15m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 642Porter Airlines
Find Deal
Tue, 2 Dec - Sun, 7 Dec
WestJet Logo
5:40 a.m. - 9:54 a.m.YOW-MDW
29h 14m2 stops
WestJet Logo
10:49 a.m. - 12:42 a.m.MDW-YOW
12h 53m2 stops
C$ 659WestJet
Find Deal
Tue, 2 Dec - Sun, 7 Dec
Porter Airlines Logo
12:10 p.m. - 3:20 p.m.YOW-MDW
4h 10m1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.MDW-YOW
5h 29m1 stop
C$ 670Porter Airlines
Find Deal
Mon, 8 Dec - Wed, 17 Dec

WestJet flights from Ottawa to Chicago

Our best WestJet deals on Ottawa to Chicago flight tickets
WestJet
26 Feb
YOW5:45 p.m.Ottawa
20h 50m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
2 Mar
ORD2:20 p.m.Chicago O'Hare Intl
9h 20m
1 stop
YOW12:40 a.m.Ottawa
C$ 577
Find similar
WestJet
6 Dec
YOW5:40 a.m.Ottawa
32h 30m
2 stops
MDW1:10 p.m.Chicago Midway
8 Dec
MDW10:49 a.m.Chicago Midway
12h 53m
2 stops
YOW12:42 a.m.Ottawa
C$ 639
Find similar
WestJet
2 Dec
YOW5:40 a.m.Ottawa
29h 14m
2 stops
MDW9:54 a.m.Chicago Midway
7 Dec
MDW10:49 a.m.Chicago Midway
12h 53m
2 stops
YOW12:42 a.m.Ottawa
C$ 659
Find similar

Air Canada flights from Ottawa to Chicago

Our best Air Canada deals on Ottawa to Chicago flight tickets
Air Canada
11 Nov
YOW6:20 a.m.Ottawa
2h 41m
ORD8:01 a.m.Chicago O'Hare Intl
18 Nov
ORD2:00 p.m.Chicago O'Hare Intl
4h 18m
1 stop
YOW7:18 p.m.Ottawa
C$ 1,239
Find similar
Air Canada
14 Nov
YOW5:14 p.m.Ottawa
2h 41m
ORD6:55 p.m.Chicago O'Hare Intl
23 Nov
ORD8:00 a.m.Chicago O'Hare Intl
4h 18m
1 stop
YOW1:18 p.m.Ottawa
C$ 1,330
Find similar
Air Canada
10 Nov
YOW5:14 p.m.Ottawa
2h 41m
ORD6:55 p.m.Chicago O'Hare Intl
14 Nov
ORD6:28 p.m.Chicago O'Hare Intl
6h 10m
1 stop
YOW1:38 a.m.Ottawa
C$ 1,405
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 5 November 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 - ORD

YOWORD

Ottawa

Mon 8/12

4:15 p.m.-11:08 a.m.

1 stop19h 53m

Chicago O'Hare Intl

Thu 11/12

6:15 a.m.-12:25 a.m.

1 stop17h 10m

C$ 400

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 12/12

7:00 a.m.-11:08 a.m.

1 stop29h 08m

Chicago O'Hare Intl

Mon 15/12

2:26 p.m.-5:13 p.m.

1 stop25h 47m

C$ 410

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 4/12

9:30 a.m.-11:08 a.m.

3 stops26h 38m

Chicago O'Hare Intl

Sun 7/12

5:00 a.m.-12:25 a.m.

1 stop18h 25m

C$ 427

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 5/12

8:40 a.m.-3:20 p.m.

1 stop7h 40m

Chicago Midway

Mon 8/12

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 560

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 26/2

5:45 p.m.-1:35 p.m.

1 stop20h 50m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-12:40 a.m.

1 stop9h 20m

C$ 577

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/12

8:40 a.m.-11:50 a.m.

1 stop4h 10m

Chicago Midway

Mon 8/12

11:00 a.m.-7:54 p.m.

1 stop7h 54m

C$ 600

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/12

5:40 a.m.-1:10 p.m.

2 stops32h 30m

Chicago Midway

Mon 8/12

10:49 a.m.-12:42 a.m.

2 stops12h 53m

C$ 639

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 2/12

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Sun 7/12

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 642

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 2/12

5:40 a.m.-9:54 a.m.

2 stops29h 14m

Chicago Midway

Sun 7/12

10:49 a.m.-12:42 a.m.

2 stops12h 53m

C$ 659

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 8/12

12:10 p.m.-3:20 p.m.

1 stop4h 10m

Chicago Midway

Wed 17/12

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 670

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$ 504.

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 Saturday when prices can be found for as low as C$ 782. 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 Sunday because tickets tend to average around C$ 939. 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$ 515. 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$ 903 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$ 734 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$ 500 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?

You could potentially save up to 37% on your flight if you consider stops on a Ottawa to Chicago flight.

How have Ottawa to Chicago flight prices changed over time?

As of November 2025, prices for Ottawa to Chicago flights are approximately 23% cheaper 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$ 335

Fastest flight time

2h 08m

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$ 335. The best round-trip flight deal from Ottawa to Chicago found on momondo in the last 72 hours is C$ 565.
The fastest flight from Ottawa to Chicago takes 2h 08m
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 4h 05m.

  • 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$ 378Free CancellationRating
8.0
387 reviews
Search Porter Airlines flights
United AirlinesPriceFrom C$ 474Free CancellationRating
7.4
9,001 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 501Free CancellationRating
7.1
10,404 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$ 681, with the best United Airlines deals starting from C$ 474 round-trip. 9,001 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • Air Canada Flights From Ottawa to Chicago

    Across 10,404 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$ 501 to C$ 649. 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