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$168+ 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 7/24. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in May or April, booked 65 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 July 3, 2025.

Round-trip from

$311
(Kiwi.com)

One-way from

$168
(Trip.com)

Popular in

November

Cheapest in

May

Average price

$419

Good round-trip deal

$381 or less

Good one-way deal

$220 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. 5% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/1. 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 9/261:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Mon 9/299:15 amMDW - YOW
1 stop6h 19mPorter Airlines
Deal found 7/1$311
This United Airlines deal was found by Cheapflights users on 7/3. 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.
Thu 9/255:25 pmYOW - ORD
Nonstop2h 29mUnited Airlines
Thu 10/91:55 pmORD - YOW
Nonstop2h 11mUnited Airlines
Deal found 7/3$318
This Air Canada deal was found by Cheapflights users on 7/3. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:00 amYOW - ORD
1 stop4h 51mAir Canada
Thu 10/912:00 pmORD - YOW
1 stop4h 04mAir Canada
Deal found 7/3$335
This Kiwi.com deal was found by Cheapflights users on 7/3. 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.
Mon 7/2812:35 pmYOW - MDW
1 stop4h 49mMultiple Airlines
Tue 7/299:40 amMDW - YOW
1 stop13h 42mMultiple Airlines
Deal found 7/3$342
This FlightHub deal was found by Cheapflights users on 7/2. 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 9/196:00 amYOW - ORD
1 stop11h 43mWestJet
Sun 9/211:40 pmORD - YOW
2 stops27h 40mWestJet
Deal found 7/2$359
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 8/23:50 pmYOW - ORD
1 stop9h 03mMultiple Airlines
Sun 8/104:53 pmORD - YOW
1 stop23h 13mMultiple Airlines
Deal found 7/1$375
This FlightHub deal was found by Cheapflights users on 7/2. 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 9/195:55 amYOW - MDW
2 stops16h 41mWestJet
Mon 9/2212:43 pmMDW - YOW
2 stops10h 39mWestJet
Deal found 7/2$481

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 July 3, 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 - MDW

YOWMDW

Ottawa

Fri 9/26

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Mon 9/29

9:15 am-4:34 pm

1 stop6h 19m

$311

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 9/25

5:25 pm-6:54 pm

Nonstop2h 29m

Chicago O'Hare Intl

Thu 10/9

1:55 pm-5:06 pm

Nonstop2h 11m

$318

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 9/25

6:00 am-9:51 am

1 stop4h 51m

Chicago O'Hare Intl

Thu 10/9

12:00 pm-5:04 pm

1 stop4h 04m

$335

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 7/28

12:35 pm-4:24 pm

1 stop4h 49m

Chicago Midway

Tue 7/29

9:40 am-12:22 am

1 stop13h 42m

$342

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 9/19

6:00 am-4:43 pm

1 stop11h 43m

Chicago O'Hare Intl

Sun 9/21

1:40 pm-6:20 pm

2 stops27h 40m

$359

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 8/2

3:50 pm-11:53 pm

1 stop9h 03m

Chicago O'Hare Intl

Sun 8/10

4:53 pm-5:06 pm

1 stop23h 13m

$375

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/19

5:55 am-9:36 pm

2 stops16h 41m

Chicago Midway

Mon 9/22

12:43 pm-12:22 am

2 stops10h 39m

$481

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 8/15

5:55 am-6:37 pm

2 stops13h 42m

Chicago Midway

Fri 8/22

12:43 pm-12:22 am

2 stops10h 39m

$620

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 7/24

5:55 am-4:24 pm

1 stop11h 29m

$168

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sun 9/21

6:00 am-9:51 am

1 stop4h 51m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 16 results
1
2

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 June 27, 2025.

Booking 65 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 July 3, 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 July 3, 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 July 3, 2025.
Peruse reviews from past customers who have flown with ANA, Porter Airlines, and Delta 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.
ANA
8.4
Very good
893 reviews

Comfort

8.2

Boarding

8.5

Entertainment

7.9

Overall

8.4

Crew

8.7

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
ANA
8.4
Very good
893 reviews
ANA
8.4
Very good
893 reviews

Comfort

8.2

Boarding

8.5

Entertainment

7.9

Overall

8.4

Crew

8.7

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
Porter Airlines
8.0
Very good
298 reviews
ANA
8.4
Very good
893 reviews

Comfort

8.2

Boarding

8.5

Entertainment

7.9

Overall

8.4

Crew

8.7

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
Delta
8.0
Very good
7,970 reviews
ANA
8.4
Very good
893 reviews

Comfort

8.2

Boarding

8.5

Entertainment

7.9

Overall

8.4

Crew

8.7

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
United Airlines
7.4
Good
8,845 reviews
ANA
8.4
Very good
893 reviews

Comfort

8.2

Boarding

8.5

Entertainment

7.9

Overall

8.4

Crew

8.7

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.
WestJet
7.2
Good
2,917 reviews
ANA
8.4
Very good
893 reviews

Comfort

8.2

Boarding

8.5

Entertainment

7.9

Overall

8.4

Crew

8.7

Food

7.7

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2025

SEA - HND

The flight with ANA was fantastic. Huge plane but was boarded swiftly and efficiently with a lot of crew members engaged to expedite the process. The onboard crew was polite and considerate and constantly doing things to serve passengers. The plane was new and in great working order-- definitely more spacious than the Alaska plane we took from SLC. Food was solid, not great. Lots of movie options.

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.

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

    Our cheapest airline available from Ottawa to Chicago is Porter Airlines. Our recent data shows that you can find tickets from as low as $311 on this airline. Additional options worth looking into are United Airlines and Air Canada, starting at $318 and $335 round-trip. Porter Airlines is currently priced 25% 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 Air Canada, which is currently one of the cheapest options available, starting at $177. Porter Airlines flights start at $184 while deals on United Airlines start at $221 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: GoJet (93%), Avianca (93%), ANA (93%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $572, our data indicates the cheapest price to be $184. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $338.

  • 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 Ottawa?

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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$394Average$588FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$423Average$551FlexibilityNo cancel feeOn-time67%

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