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Cheap flights from Ottawa to Chicago from C$ 221

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 10/2. 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.
Multiple Airlines Logo
7:00 a.m. - 7:11 p.m.
YOW
-
ORD
13h 11m
1 stop
Multiple Airlines Logo
6:36 p.m. - 12:39 a.m.
ORD
-
YOW
53h 03m
2 stops
C$ 447Multiple Airlines
Wed, 4 Mar - Wed, 11 Mar
Multiple Airlines Logo
7:00 a.m. - 7:11 p.m.
YOW
-
ORD
13h 11m
1 stop
Multiple Airlines Logo
5:22 p.m. - 2:58 p.m.
ORD
-
YOW
20h 36m
1 stop
C$ 449Multiple Airlines
Wed, 4 Mar - Wed, 11 Mar
Multiple Airlines Logo
4:15 p.m. - 11:47 p.m.
YOW
-
ORD
8h 32m
1 stop
Multiple Airlines Logo
5:15 a.m. - 12:25 a.m.
ORD
-
YOW
18h 10m
1 stop
C$ 451Multiple Airlines
Fri, 20 Feb - Tue, 24 Feb
Multiple Airlines Logo
4:15 p.m. - 9:03 p.m.
YOW
-
ORD
29h 48m
1 stop
Multiple Airlines Logo
5:32 p.m. - 12:25 a.m.
ORD
-
YOW
29h 53m
1 stop
C$ 465Multiple Airlines
Fri, 6 Feb - Tue, 10 Feb
Multiple Airlines Logo
4:15 p.m. - 11:47 p.m.
YOW
-
ORD
8h 32m
1 stop
Multiple Airlines Logo
5:15 a.m. - 12:25 a.m.
ORD
-
YOW
18h 10m
1 stop
C$ 467Multiple Airlines
Fri, 20 Feb - Thu, 26 Feb
Porter Airlines Logo
8:40 a.m. - 11:50 a.m.
YOW
-
MDW
4h 10m
1 stop
Porter Airlines Logo
12:45 p.m. - 5:29 p.m.
MDW
-
YOW
3h 44m
1 stop
C$ 534Porter Airlines
Sat, 7 Mar - Sat, 14 Mar
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YOW
-
MDW
4h 20m
1 stop
Porter Airlines Logo
4:15 p.m. - 10:29 p.m.
MDW
-
YOW
5h 14m
1 stop
C$ 541Porter Airlines
Thu, 19 Mar - Sun, 22 Mar
Porter Airlines Logo
6:50 a.m. - 10:10 a.m.
YOW
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:05 a.m. - 3:44 p.m.
MDW
-
YOW
3h 39m
1 stop
C$ 542Porter Airlines
Fri, 20 Feb - Thu, 26 Feb
Porter Airlines Logo
7:00 a.m. - 10:05 a.m.
YOW
-
MDW
4h 05m
1 stop
Porter Airlines Logo
11:00 a.m. - 5:29 p.m.
MDW
-
YOW
5h 29m
1 stop
C$ 548Porter Airlines
Wed, 4 Mar - Wed, 11 Mar
WestJet Logo
5:55 a.m. - 12:30 p.m.
YOW
-
MDW
7h 35m
2 stops
WestJet Logo
1:00 p.m. - 5:35 p.m.
MDW
-
YOW
27h 35m
2 stops
C$ 553WestJet
Fri, 8 May - Mon, 11 May

WestJet flights from Ottawa to Chicago

Our best WestJet deals on Ottawa to Chicago flight tickets
WestJet
8 May
YOW5:55 a.m.Ottawa
7h 35m
2 stops
MDW12:30 p.m.Chicago Midway
11 May
MDW1:00 p.m.Chicago Midway
27h 35m
2 stops
YOW5:35 p.m.Ottawa
C$ 553
WestJet
1 May
YOW6:35 p.m.Ottawa
28h 54m
2 stops
MDW10:29 p.m.Chicago Midway
4 May
MDW6:34 p.m.Chicago Midway
22h 01m
2 stops
YOW5:35 p.m.Ottawa
C$ 586
WestJet
20 Apr
YOW5:40 a.m.Ottawa
13h 14m
2 stops
MDW5:54 p.m.Chicago Midway
25 Apr
MDW1:10 p.m.Chicago Midway
27h 25m
2 stops
YOW5:35 p.m.Ottawa
C$ 589

United Airlines flights from Ottawa to Chicago

Our best United Airlines deals on Ottawa to Chicago flight tickets
United Airlines
2 Feb
YOW5:11 p.m.Ottawa
2h 44m
ORD6:55 p.m.Chicago O'Hare Intl
6 Feb
ORD3:35 p.m.Chicago O'Hare Intl
5h 21m
1 stop
YOW9:56 p.m.Ottawa
C$ 1,464
United Airlines
22 Jan
YOW6:20 a.m.Ottawa
2h 45m
ORD8:05 a.m.Chicago O'Hare Intl
26 Jan
ORD2:27 p.m.Chicago O'Hare Intl
6h 29m
1 stop
YOW9:56 p.m.Ottawa
C$ 1,474
United Airlines
22 Jan
YOW6:20 a.m.Ottawa
2h 45m
ORD8:05 a.m.Chicago O'Hare Intl
26 Jan
ORD1:55 p.m.Chicago O'Hare Intl
2h 17m
YOW5:12 p.m.Ottawa
C$ 1,478

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 21 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 - ORD

YOWORD

Ottawa

Wed 4/3

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

1 stop13h 11m

Chicago O'Hare Intl

Wed 11/3

6:36 p.m.-12:39 a.m.

2 stops53h 03m

C$ 447

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 4/3

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

1 stop13h 11m

Chicago O'Hare Intl

Wed 11/3

5:22 p.m.-2:58 p.m.

1 stop20h 36m

C$ 449

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 20/2

4:15 p.m.-11:47 p.m.

1 stop8h 32m

Chicago O'Hare Intl

Tue 24/2

5:15 a.m.-12:25 a.m.

1 stop18h 10m

C$ 451

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 6/2

4:15 p.m.-9:03 p.m.

1 stop29h 48m

Chicago O'Hare Intl

Tue 10/2

5:32 p.m.-12:25 a.m.

1 stop29h 53m

C$ 465

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 20/2

4:15 p.m.-11:47 p.m.

1 stop8h 32m

Chicago O'Hare Intl

Thu 26/2

5:15 a.m.-12:25 a.m.

1 stop18h 10m

C$ 467

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 7/3

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

1 stop4h 10m

Chicago Midway

Sat 14/3

12:45 p.m.-5:29 p.m.

1 stop3h 44m

C$ 534

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 19/3

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

1 stop4h 20m

Chicago Midway

Sun 22/3

4:15 p.m.-10:29 p.m.

1 stop5h 14m

C$ 541

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 20/2

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

1 stop4h 20m

Chicago Midway

Thu 26/2

11:05 a.m.-3:44 p.m.

1 stop3h 39m

C$ 542

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 4/3

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Wed 11/3

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

1 stop5h 29m

C$ 548

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 8/5

5:55 a.m.-12:30 p.m.

2 stops7h 35m

Chicago Midway

Mon 11/5

1:00 p.m.-5:35 p.m.

2 stops27h 35m

C$ 553

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$ 495.

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$ 702. 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$ 889. 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$ 708. 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$ 843 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 16% 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$ 279

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$ 279. The best round-trip flight deal from Ottawa to Chicago found on momondo in the last 72 hours is C$ 528.
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$ 320Free CancellationRating
7.9
412 reviews
Search Porter Airlines flights
United AirlinesPriceFrom C$ 464Free CancellationRating
7.4
9,191 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 504Free CancellationRating
7.1
10,646 reviews
Search Air Canada flights

  • United Airlines Flights From Ottawa to Chicago

    Across 14 United Airlines flights from Ottawa to Chicago this week, the average price was C$ 676, with the best United Airlines deals starting from C$ 464 round-trip. 9,191 users have rated United Airlines on momondo, with an average score of 7.4/10.

  • Air Canada Flights From Ottawa to Chicago

    Across 10,646 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$ 504 to C$ 678. 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