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$170+ 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 9/12. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$327
(Kiwi.com)

One-way from

$170
(Mytrip)

Popular in

November

Cheapest in

May

Average price

$414

Good round-trip deal

$424 or less

Good one-way deal

$349 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. 6% potential increase in price ($28 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 August 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 August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Fri 9/265:15 pmYOW - ORD
1 stop20h 24mMultiple Airlines
Mon 9/295:30 pmORD - YOW
2 stops18h 33mMultiple Airlines
Deal found 8/18$327
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 9/51:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Mon 9/89:35 amMDW - YOW
1 stop5h 59mPorter Airlines
Deal found 8/17$328
This United deal was found by Cheapflights users on 8/17. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:25 pmYOW - ORD
Nonstop2h 29mMultiple Airlines
Sat 9/68:40 amORD - YOW
1 stop4h 11mMultiple Airlines
Deal found 8/17$328
This FlightHub deal was found by Cheapflights users on 8/18. 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.
Fri 10/175:15 pmYOW - ORD
1 stop20h 24mWestJet
Sat 10/255:30 pmORD - YOW
2 stops30h 12mWestJet
Deal found 8/18$329
This Booking.com deal was found by Cheapflights users on 8/18. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/171:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Sat 10/259:35 amMDW - YOW
1 stop7h 34mPorter Airlines
Deal found 8/18$331
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Fri 9/51:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Sun 9/79:35 amMDW - YOW
1 stop6h 39mPorter Airlines
Deal found 8/19$332
This United Airlines deal was found by Cheapflights users on 8/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/35:25 pmYOW - ORD
Nonstop2h 29mUnited Airlines
Wed 9/39:31 pmORD - YOW
1 stop11h 27mUnited Airlines
Deal found 8/19$332
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/1011:00 amYOW - MDW
1 stop6h 24mPorter Airlines
Fri 9/199:35 amMDW - YOW
1 stop5h 59mPorter Airlines
Deal found 8/19$334
This Mytrip deal was found by Cheapflights users on 8/19. 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.
Wed 9/39:05 amYOW - ORD
1 stop6h 50mAir Canada
Thu 9/42:00 pmORD - YOW
1 stop6h 09mAir Canada
Deal found 8/19$334
This Trip.com deal was found by Cheapflights users on 8/18. 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.
Thu 10/25:25 pmYOW - ORD
Nonstop2h 29mUnited Airlines
Thu 10/99:20 pmORD - YOW
1 stop11h 38mUnited Airlines
Deal found 8/18$336
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/111:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Fri 9/199:35 amMDW - YOW
1 stop7h 34mPorter Airlines
Deal found 8/19$337
This oojo deal was found by Cheapflights users on 8/19. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/195:15 pmYOW - ORD
1 stop20h 24mWestJet
Mon 9/225:30 pmORD - YOW
1 stop30h 10mWestJet
Deal found 8/19$337

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 August 20, 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

Fri 9/26

5:15 pm-12:39 pm

1 stop20h 24m

Chicago O'Hare Intl

Mon 9/29

5:30 pm-1:03 pm

2 stops18h 33m

$327

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 9/4

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Sun 9/7

9:35 am-5:14 pm

1 stop6h 39m

$328

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/5

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Mon 9/8

9:35 am-4:34 pm

1 stop5h 59m

$328

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 9/4

5:25 pm-6:54 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sat 9/6

8:40 am-1:51 pm

1 stop4h 11m

$328

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 9/13

6:33 am-8:00 am

Nonstop2h 27m

Chicago O'Hare Intl

Wed 9/17

8:40 am-1:51 pm

1 stop4h 11m

$328

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 10/18

5:25 pm-6:54 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sun 10/19

8:40 am-1:51 pm

1 stop4h 11m

$328

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 10/17

5:15 pm-12:39 pm

1 stop20h 24m

Chicago O'Hare Intl

Sat 10/25

5:30 pm-12:42 am

2 stops30h 12m

$329

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 10/17

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Sat 10/25

9:35 am-6:09 pm

1 stop7h 34m

$331

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 9/4

5:25 pm-6:54 pm

Nonstop2h 29m

Chicago O'Hare Intl

Sun 9/7

9:31 pm-9:58 am

1 stop11h 27m

$332

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 9/3

6:33 am-8:00 am

Nonstop2h 27m

Chicago O'Hare Intl

Thu 9/4

6:00 am-11:45 am

1 stop4h 45m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 44 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 August 8, 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 August 20, 2025.

It’s typically best to fly out from Ottawa to Chicago in the evening. Doing so could potentially save you 46% 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 August 20, 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).

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 August 20, 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
8.0
Very good
336 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
336 reviews
Porter Airlines
8.0
Very good
336 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,928 reviews
Porter Airlines
8.0
Very good
336 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
8.0
Very good
336 reviews

Overall

8.0

Boarding

8.2

Food

7.6

Entertainment

7.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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?

    Porter Airlines can get you from Ottawa to Chicago in just under 3h 59m. Your travel time can differ by up to . The distance from Ottawa to Chicago is about 651 mi.

  • 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 21% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Ottawa to Chicago one-way?

    To fly one-way, consider booking your trip with Porter Airlines, which is currently one of the cheapest options available, starting at $170. Air Canada flights start at $174 while deals on WestJet start at $176 one-way.

  • 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 (85%), GoJet (80%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $537, our data indicates the cheapest price to be $186. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $323.

  • 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$324Average$519FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$326Average$554FlexibilityNo cancel feeOn-time67%

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