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Cheap flights from Ottawa to Chicago from C$ 202

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 19/2. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
12:10 p.m. - 3:20 p.m.
YOW
-
MDW
4h 10m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.
MDW
-
YOW
5h 29m
1 stop
C$ 373Porter Airlines
Mon, 27 Apr - Thu, 30 Apr
Multiple Airlines Logo
3:40 p.m. - 12:40 a.m.
YOW
-
ORD
10h 00m
2 stops
Multiple Airlines Logo
8:16 p.m. - 5:25 p.m.
ORD
-
YOW
20h 09m
1 stop
C$ 376Multiple Airlines
Tue, 24 Feb - Tue, 3 Mar
Multiple Airlines Logo
3:55 p.m. - 12:40 a.m.
YOW
-
ORD
9h 45m
1 stop
Multiple Airlines Logo
8:16 p.m. - 5:25 p.m.
ORD
-
YOW
20h 09m
1 stop
C$ 377Multiple Airlines
Tue, 24 Feb - Tue, 3 Mar
Multiple Airlines Logo
4:15 p.m. - 10:36 a.m.
YOW
-
ORD
19h 21m
1 stop
Multiple Airlines Logo
7:17 a.m. - 12:25 a.m.
ORD
-
YOW
16h 08m
1 stop
C$ 383Multiple Airlines
Mon, 23 Mar - Wed, 25 Mar
Multiple Airlines Logo
6:45 a.m. - 10:05 a.m.
YOW
-
MDW
4h 20m
1 stop
Multiple Airlines Logo
11:00 a.m. - 12:39 a.m.
MDW
-
YOW
12h 39m
1 stop
C$ 384Multiple Airlines
Thu, 12 Mar - Fri, 20 Mar
Multiple Airlines Logo
4:15 p.m. - 10:36 a.m.
YOW
-
ORD
19h 21m
1 stop
Multiple Airlines Logo
8:41 p.m. - 12:25 a.m.
ORD
-
YOW
26h 44m
1 stop
C$ 388Multiple Airlines
Mon, 23 Mar - Wed, 25 Mar
Multiple Airlines Logo
9:30 a.m. - 4:55 p.m.
YOW
-
ORD
8h 25m
1 stop
Multiple Airlines Logo
6:36 p.m. - 12:25 a.m.
ORD
-
YOW
28h 49m
1 stop
C$ 400Multiple Airlines
Mon, 23 Mar - Tue, 24 Mar
Multiple Airlines Logo
4:15 p.m. - 10:36 a.m.
YOW
-
ORD
19h 21m
1 stop
Multiple Airlines Logo
9:28 a.m. - 12:25 a.m.
ORD
-
YOW
13h 57m
2 stops
C$ 409Multiple Airlines
Mon, 23 Mar - Wed, 25 Mar
Multiple Airlines Logo
5:00 p.m. - 12:40 a.m.
YOW
-
ORD
8h 40m
2 stops
Multiple Airlines Logo
6:51 p.m. - 5:25 p.m.
ORD
-
YOW
21h 34m
1 stop
C$ 418Multiple Airlines
Fri, 27 Feb - Sun, 1 Mar
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YOW
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.
MDW
-
YOW
5h 29m
1 stop
C$ 437Porter Airlines
Mon, 23 Mar - Wed, 25 Mar

WestJet flights from Ottawa to Chicago

Our best WestJet deals on Ottawa to Chicago flight tickets
WestJet
27 Apr
YOW7:30 a.m.Ottawa
10h 10m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
30 Apr
ORD5:30 p.m.Chicago O'Hare Intl
11h 10m
1 stop
YOW5:40 a.m.Ottawa
C$ 443
WestJet
7 May
YOW7:30 a.m.Ottawa
10h 10m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
11 May
ORD5:30 p.m.Chicago O'Hare Intl
22h 50m
1 stop
YOW5:20 p.m.Ottawa
C$ 464
WestJet
7 May
YOW7:30 a.m.Ottawa
10h 10m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
11 May
ORD5:30 p.m.Chicago O'Hare Intl
18h 00m
2 stops
YOW12:30 p.m.Ottawa
C$ 466

Porter Airlines flights from Ottawa to Chicago

Our best Porter Airlines deals on Ottawa to Chicago flight tickets
Porter Airlines
27 Apr
YOW12:10 p.m.Ottawa
4h 10m
1 stop
MDW3:20 p.m.Chicago Midway
30 Apr
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 373
Porter Airlines
23 Mar
YOW6:45 a.m.Ottawa
4h 20m
1 stop
MDW10:05 a.m.Chicago Midway
25 Mar
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 437
Porter Airlines
23 Feb
YOW6:50 a.m.Ottawa
4h 20m
1 stop
MDW10:10 a.m.Chicago Midway
2 Mar
MDW11:00 a.m.Chicago Midway
5h 29m
1 stop
YOW5:29 p.m.Ottawa
C$ 443

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 29 January 2026.
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

Mon 27/4

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

1 stop4h 10m

Chicago Midway

Thu 30/4

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

1 stop5h 29m

C$ 373

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Tue 24/2

3:40 p.m.-12:40 a.m.

2 stops10h 00m

Chicago O'Hare Intl

Tue 3/3

8:16 p.m.-5:25 p.m.

1 stop20h 09m

C$ 376

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Tue 24/2

3:55 p.m.-12:40 a.m.

1 stop9h 45m

Chicago O'Hare Intl

Tue 3/3

8:16 p.m.-5:25 p.m.

1 stop20h 09m

C$ 377

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 23/3

4:15 p.m.-10:36 a.m.

1 stop19h 21m

Chicago O'Hare Intl

Wed 25/3

7:17 a.m.-12:25 a.m.

1 stop16h 08m

C$ 383

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 12/3

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Fri 20/3

11:00 a.m.-12:39 a.m.

1 stop12h 39m

C$ 384

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 23/3

4:15 p.m.-10:36 a.m.

1 stop19h 21m

Chicago O'Hare Intl

Wed 25/3

8:41 p.m.-12:25 a.m.

1 stop26h 44m

C$ 388

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 23/3

9:30 a.m.-4:55 p.m.

1 stop8h 25m

Chicago O'Hare Intl

Tue 24/3

6:36 p.m.-12:25 a.m.

1 stop28h 49m

C$ 400

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 23/3

4:15 p.m.-10:36 a.m.

1 stop19h 21m

Chicago O'Hare Intl

Wed 25/3

9:28 a.m.-12:25 a.m.

2 stops13h 57m

C$ 409

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 27/2

5:00 p.m.-12:40 a.m.

2 stops8h 40m

Chicago O'Hare Intl

Sun 1/3

6:51 p.m.-5:25 p.m.

1 stop21h 34m

C$ 418

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 23/3

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Wed 25/3

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

1 stop5h 29m

C$ 437

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 typical price of a round-trip flight between Ottawa and Chicago?

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$ 486.

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$ 689. 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$ 875. 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?

In the afternoon is the cheapest time of day to fly from Ottawa to Chicago when you can find flight prices for as low as C$ 692. Flying to Chicago in the afternoon 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$ 834 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

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 74% 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 January 2026, prices for Ottawa to Chicago flights are approximately 15% 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$ 281

Fastest flight time

2h 08m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Ottawa in the past 72 hours is C$ 281. The best round-trip flight deal from Ottawa to Chicago found on momondo in the last 72 hours is C$ 510.
The fastest flight from Ottawa to Chicago takes 2h 08m
Direct flights go from Ottawa to Chicago every day.
There are 3 airports in Chicago. From Ottawa there are direct flights to 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 08m.

  • 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$ 315Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
United AirlinesPriceFrom C$ 456Free CancellationRating
7.4
9,215 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 495Free CancellationRating
7.1
10,667 reviews
Search Air Canada flights

  • United Airlines Flights From Ottawa to Chicago

    Across 9 United Airlines flights from Ottawa to Chicago this week, the average price was C$ 645, with the best United Airlines deals starting from C$ 456 round-trip. 9,215 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • Air Canada Flights From Ottawa to Chicago

    Across 10,667 Air Canada reviews on momondo, the average score is 7.1/10. Air Canada flies from Ottawa to Chicago about 14 times each week, with ticket deals ranging from C$ 495 to C$ 665. 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