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$174+ Cheap flights from Ottawa (YOW) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in May or June, booked 22 days in advance, depart on a Saturday or Friday and return on a Thursday

Cheap flight deals from Ottawa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Ottawa (YOW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$299
(Kiwi.com)

One-way from

$174
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$392

Good round-trip deal

$523 or less

Good one-way deal

$340 or less
From Ottawa to Chicago (CHI)
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One-way flight from Ottawa to Chicago (CHI)
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Highest demand for flights based on searches. 7% potential increase in price ($33 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Ottawa to Chicago (CHI).
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Price to beat on a one-way flight from Ottawa to Chicago (CHI).
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Find flight deals from Ottawa to Chicago

Cheapest flights from Ottawa to Chicago
Explore the most affordable flight options available from Ottawa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/126:00 amYOW - ORD
1 stop11h 43mWestJet
Sun 10/195:30 pmORD - YOW
1 stop12h 15mWestJet
Deal found 9/16$299
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/121:15 pmYOW - MDW
1 stop4h 09mPorter Airlines
Sun 10/199:35 amMDW - YOW
1 stop5h 59mPorter Airlines
Deal found 9/16$300
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:55 pmYOW - ORD
1 stop20h 40mMultiple Airlines
Tue 11/47:43 pmORD - YOW
1 stop20h 42mMultiple Airlines
Deal found 9/16$313
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:00 amYOW - MDW
1 stop6h 24mMultiple Airlines
Tue 10/219:35 amMDW - YOW
1 stop13h 47mMultiple Airlines
Deal found 9/16$314
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/53:50 pmYOW - ORD
1 stop20h 00mMultiple Airlines
Thu 10/912:53 pmORD - YOW
2 stops10h 29mMultiple Airlines
Deal found 9/16$314
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/143:50 pmYOW - ORD
1 stop8h 55mMultiple Airlines
Tue 10/215:05 amORD - YOW
1 stop11h 15mMultiple Airlines
Deal found 9/16$321
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/141:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Tue 10/219:35 amMDW - YOW
1 stop7h 34mPorter Airlines
Deal found 9/16$323
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/153:50 pmYOW - ORD
1 stop8h 55mMultiple Airlines
Wed 10/225:05 amORD - YOW
1 stop11h 15mMultiple Airlines
Deal found 9/17$335
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/164:25 pmYOW - ORD
1 stop16h 09mMultiple Airlines
Fri 10/245:05 amORD - YOW
1 stop11h 15mMultiple Airlines
Deal found 9/16$337
This FlightHub deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:00 amYOW - ORD
1 stop11h 43mWestJet
Fri 10/245:30 pmORD - YOW
1 stop23h 50mWestJet
Deal found 9/17$343
This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1810:00 amYOW - ORD
1 stop4h 14mAir Canada
Sun 10/198:25 pmORD - YOW
1 stop4h 09mAir Canada
Deal found 9/16$344
This Mytrip deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:50 pmYOW - ORD
2 stops26h 00mMultiple Airlines
Mon 10/65:05 amORD - YOW
1 stop11h 15mMultiple Airlines
Deal found 9/15$345

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Ottawa to Chicago that are best for you.

Fly from

Ottawa

Fly to

Chicago

Route

Depart

Return

Price

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sun 10/12

6:00 am-4:43 pm

1 stop11h 43m

Chicago O'Hare Intl

Sun 10/19

5:30 pm-6:45 am

1 stop12h 15m

$299

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 10/12

1:15 pm-4:24 pm

1 stop4h 09m

Chicago Midway

Sun 10/19

9:35 am-4:34 pm

1 stop5h 59m

$300

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 10/15

11:00 am-4:24 pm

1 stop6h 24m

Chicago Midway

Wed 10/22

9:35 am-4:34 pm

1 stop5h 59m

$300

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 11/1

6:55 pm-2:35 pm

1 stop20h 40m

Chicago O'Hare Intl

Tue 11/4

7:43 pm-5:25 pm

1 stop20h 42m

$313

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 10/14

11:00 am-4:24 pm

1 stop6h 24m

Chicago Midway

Tue 10/21

9:35 am-12:22 am

1 stop13h 47m

$314

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sun 10/5

3:50 pm-10:50 am

1 stop20h 00m

Chicago O'Hare Intl

Thu 10/9

12:53 pm-12:22 am

2 stops10h 29m

$314

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 10/15

3:50 pm-11:45 pm

1 stop8h 55m

Chicago O'Hare Intl

Wed 10/22

5:05 am-5:20 pm

1 stop11h 15m

$335

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 10/16

6:00 am-4:43 pm

1 stop11h 43m

Chicago O'Hare Intl

Fri 10/24

5:30 pm-6:20 pm

1 stop23h 50m

$343

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 10/16

5:25 pm-6:54 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sun 10/19

6:06 pm-9:35 pm

Nonstop2h 29m

$346

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 10/16

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Fri 10/24

9:35 am-6:09 pm

1 stop7h 34m

$347

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 34 results
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Best time to book a flight from Ottawa to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Ottawa with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Ottawa to Chicago

How far ahead should I book a flight from Ottawa to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Ottawa to Chicago. Price data was last updated on September 12, 2025.

Booking 22 days in advance of your planned departure date is, on average, the best time to get cheap flights from Ottawa to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Ottawa to Chicago?

Currently, August is the cheapest month in which you can book a flight from Ottawa to Chicago (average of $245). Flying from Ottawa to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YOW to CHI?

Find hourly flight availability from Ottawa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

It’s typically best to fly out from Ottawa to Chicago in the evening. Doing so could potentially save you 47% on the flight price compared to flying in the morning, which is usually more expensive.

Weekly flight availability from Ottawa to Chicago

Explore weekly flight availability from Ottawa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 17, 2025.

The most flights from YOW to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (12 on average).

How much does it cost to fly round-trip from Ottawa to Chicago?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 17, 2025.
Peruse reviews from past customers who have flown with Porter Airlines, United Airlines, and Air Canada from Ottawa to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,926 reviews
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
365 reviews

Entertainment

7.0

Food

7.6

Overall

7.9

Comfort

7.9

Crew

8.6

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Ottawa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Ottawa to Chicago?

    Located just 6.6 mi from the city center, Ottawa is the airport most travelers will use when flying to Chicago from Ottawa. Booking flights from Ottawa (YOW) to Chicago should be relatively easy as there are 12 daily outbound flights to Chicago from 2 different airlines.

  • How long is the flight from Ottawa to Chicago?

    WestJet and Porter Airlines can get you from Ottawa to Chicago in just under 4h 09m. Your travel time can differ by up to 7h 34m. The distance from Ottawa to Chicago is about 651 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Ottawa to Chicago round-trip?

    Our cheapest airline available from Ottawa to Chicago is United Airlines. Our recent data shows that you can find tickets from as low as $324 on this airline. An additional option worth looking into is Air Canada, starting at $326. United Airlines is currently priced 20% below the average price you’ll pay for this route.

  • What are the most reliable airlines from Ottawa to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Ottawa to Chicago on time: Avianca (90%), ANA (88%), GoJet (85%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $845, our data indicates the cheapest price to be $201. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $299.

  • Can I find deals for flights from Ottawa to Chicago that include hotel bookings?

    Yes. In addition to deals on Ottawa to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Ottawa to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Ottawa to Chicago.

  • Can I find deals for business class flights from Ottawa to Chicago?

    Yes. Cheapflights offers flight deals from Ottawa to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Ottawa to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Ottawa to Chicago (average of $245). Flying from Ottawa to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Ottawa to Chicago

Discover the top 2 airlines that operate flights from Ottawa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$324Average$519FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$326Average$550FlexibilityNo cancel feeOn-time67%

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