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$157+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$261
(FlightHub)

One-way from

$157
(FlightHub)

Popular in

November

Cheapest in

May

Average price

$451

Good round-trip deal

$351 or less

Good one-way deal

$232 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 ($23 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 June 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 June 12, 2025.

This FlightHub deal was found by Cheapflights users on 6/10. 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.
Wed 7/308:35 amYOW - MDW
1 stop8h 49mPorter Airlines
Tue 8/59:40 amMDW - YOW
1 stop8h 13mPorter Airlines
Deal found 6/10$261
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 7/255:55 amYOW - MDW
1 stop11h 29mMultiple Airlines
Sun 7/279:40 amMDW - YOW
1 stop8h 58mMultiple Airlines
Deal found 6/10$327
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 6/233:50 pmYOW - ORD
1 stop18h 00mMultiple Airlines
Wed 6/255:51 amORD - YOW
1 stop8h 05mMultiple Airlines
Deal found 6/10$361
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 7/45:25 pmYOW - ORD
Nonstop2h 28mUnited Airlines
Sun 7/66:15 pmORD - YOW
Nonstop2h 20mUnited Airlines
Deal found 6/11$376
This Air Canada deal was found by Cheapflights users on 6/10. 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.
Tue 7/16:00 amYOW - ORD
1 stop4h 52mAir Canada
Sun 7/68:40 amORD - YOW
1 stop4h 04mAir Canada
Deal found 6/10$386
This FlightHub deal was found by Cheapflights users on 6/12. 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 8/296:00 amYOW - ORD
1 stop11h 44mWestJet
Tue 9/25:30 pmORD - YOW
2 stops21h 49mWestJet
Deal found 6/12$473
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/165:55 amYOW - ORD
2 stops8h 47mDelta
Mon 8/181:30 pmORD - YOW
2 stops9h 52mDelta
Deal found 6/11$575
This FlightHub deal was found by Cheapflights users on 6/11. 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 6/275:55 amYOW - MDW
2 stops16h 50mWestJet
Tue 7/112:44 pmMDW - YOW
2 stops10h 38mWestJet
Deal found 6/11$595
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/85:55 amYOW - MDW
2 stops12h 44mDelta
Tue 7/159:25 amMDW - YOW
2 stops13h 57mDelta
Deal found 6/10$604

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 June 12, 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

Wed 7/30

8:35 am-4:24 pm

1 stop8h 49m

Chicago Midway

Tue 8/5

9:40 am-6:53 pm

1 stop8h 13m

$261

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/25

5:55 am-4:24 pm

1 stop11h 29m

Chicago Midway

Sun 7/27

9:40 am-7:38 pm

1 stop8h 58m

$327

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 6/23

3:50 pm-8:50 am

1 stop18h 00m

Chicago O'Hare Intl

Wed 6/25

5:51 am-2:56 pm

1 stop8h 05m

$361

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 7/4

5:25 pm-6:53 pm

Nonstop2h 28m

Chicago O'Hare Intl

Sun 7/6

6:15 pm-9:35 pm

Nonstop2h 20m

$376

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Tue 7/1

6:00 am-9:52 am

1 stop4h 52m

Chicago O'Hare Intl

Sun 7/6

8:40 am-1:44 pm

1 stop4h 04m

$386

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 8/29

6:00 am-4:44 pm

1 stop11h 44m

Chicago O'Hare Intl

Tue 9/2

5:30 pm-4:19 pm

2 stops21h 49m

$473

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 8/16

5:55 am-1:42 pm

2 stops8h 47m

Chicago O'Hare Intl

Mon 8/18

1:30 pm-12:22 am

2 stops9h 52m

$575

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/27

5:55 am-9:45 pm

2 stops16h 50m

Chicago Midway

Tue 7/1

12:44 pm-12:22 am

2 stops10h 38m

$595

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 7/8

5:55 am-5:39 pm

2 stops12h 44m

Chicago Midway

Tue 7/15

9:25 am-12:22 am

2 stops13h 57m

$604

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 7/21

8:35 am-4:24 pm

1 stop8h 49m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 17 results
1
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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 June 9, 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 June 12, 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 June 12, 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).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Get a feel of what it's like to fly with Porter Airlines, Delta and United Airlines from Ottawa to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Air Canada
7.1
Good
9,537 reviews
Porter Airlines
8.0
Very good
288 reviews

Overall

8.0

Entertainment

7.0

Comfort

8.1

Food

7.6

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 $261 on this airline. Additional options worth looking into are United Airlines and Air Canada, starting at $376 and $386 round-trip. Porter Airlines is currently priced 37% 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 $157. WestJet flights start at $207 while deals on United Airlines start at $213 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 (89%), ANA (85%), GoJet (82%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $499, our data indicates the cheapest price to be $155. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $361.

  • 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

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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$410Average$606FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$423Average$550FlexibilityNo cancel feeOn-time67%

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