HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$164+ 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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Ottawa to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$284
(Kiwi.com)

One-way from

$164
(Trip.com)

Popular in

November

Cheapest in

May

Average price

$506

Good round-trip deal

$407 or less

Good one-way deal

$240 or less
Provider with most accurate pricing for Ottawa-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Ottawa-Chicago (CHI) flights.
Search Deals
From Ottawa to Chicago (CHI)
Search Deals
One-way flight from Ottawa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Ottawa to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Ottawa to Chicago (CHI).
Search Deals

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 November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/84:15 pmYOW - ORD
1 stop19h 53mMultiple Airlines
Thu 12/116:15 amORD - YOW
1 stop17h 10mMultiple Airlines
Deal found 11/3$284
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/127:00 amYOW - ORD
1 stop29h 08mMultiple Airlines
Mon 12/152:26 pmORD - YOW
1 stop25h 47mMultiple Airlines
Deal found 11/4$291
This Mytrip deal was found by Cheapflights users on 11/4. 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.
Thu 12/49:30 amYOW - ORD
3 stops26h 38mMultiple Airlines
Sun 12/75:00 amORD - YOW
1 stop18h 25mMultiple Airlines
Deal found 11/4$303
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/24:15 pmYOW - ORD
1 stop18h 02mMultiple Airlines
Tue 12/94:22 pmORD - YOW
2 stops47h 51mMultiple Airlines
Deal found 11/2$305
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/84:15 pmYOW - ORD
1 stop19h 53mMultiple Airlines
Wed 12/177:10 amORD - YOW
1 stop9h 15mMultiple Airlines
Deal found 11/4$310
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:15 pmYOW - ORD
2 stops17h 39mMultiple Airlines
Mon 12/87:10 amORD - YOW
1 stop16h 15mMultiple Airlines
Deal found 11/2$339
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:50 amYOW - MDW
2 stops7h 11mMultiple Airlines
Tue 12/97:44 amMDW - YOW
1 stop8h 41mMultiple Airlines
Deal found 11/2$350
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/45:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Sun 12/77:44 amMDW - YOW
1 stop27h 51mMultiple Airlines
Deal found 11/3$354
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/126:45 amYOW - MDW
2 stops27h 27mMultiple Airlines
Sat 11/1511:36 amMDW - YOW
1 stop11h 22mMultiple Airlines
Deal found 11/2$358
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/55:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Sun 12/76:37 pmMDW - YOW
2 stops21h 14mMultiple Airlines
Deal found 11/2$363
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Fri 12/1212:10 pmYOW - MDW
1 stop4h 10mMultiple Airlines
Mon 12/153:52 pmMDW - YOW
2 stops24h 21mMultiple Airlines
Deal found 11/3$370
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/84:35 pmYOW - MDW
2 stops21h 26mMultiple Airlines
Thu 12/117:44 amMDW - YOW
1 stop8h 41mMultiple Airlines
Deal found 11/3$377

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 November 4, 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

Mon 1/12

9:30 am-9:23 pm

1 stop12h 53m

Chicago O'Hare Intl

Tue 1/13

6:05 am-5:13 pm

1 stop10h 08m

$306

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 12/4

4:15 pm-12:09 am

1 stop8h 54m

Chicago O'Hare Intl

Sun 12/7

2:36 pm-5:13 pm

1 stop25h 37m

$343

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 12/2

6:50 am-1:01 pm

2 stops7h 11m

Chicago Midway

Tue 12/9

7:44 am-5:25 pm

1 stop8h 41m

$350

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 12/4

6:50 am-1:01 pm

2 stops7h 11m

Chicago Midway

Sun 12/7

6:37 pm-5:13 pm

1 stop21h 36m

$357

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sun 11/23

9:30 am-5:11 pm

1 stop8h 41m

Chicago O'Hare Intl

Wed 11/26

6:15 pm-5:13 pm

1 stop21h 58m

$360

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 12/5

5:40 am-3:20 pm

1 stop10h 40m

Chicago Midway

Sun 12/7

6:37 pm-4:51 pm

2 stops21h 14m

$363

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 2/19

7:00 am-7:29 pm

1 stop13h 29m

Chicago O'Hare Intl

Sun 2/22

3:24 pm-5:13 pm

2 stops24h 49m

$364

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 12/12

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Mon 12/15

3:52 pm-5:13 pm

2 stops24h 21m

$370

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 12/8

4:15 pm-1:58 pm

2 stops22h 43m

Chicago O'Hare Intl

Wed 12/17

7:10 am-11:58 pm

2 stops15h 48m

$374

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 12/8

4:35 pm-1:01 pm

2 stops21h 26m

Chicago Midway

Thu 12/11

7:44 am-5:25 pm

1 stop8h 41m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 36 results
1
2
3
4

Compare providers for flights from Ottawa to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Ottawa to Chicago in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Ottawa-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Ottawa-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Ottawa-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Ottawa-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Ottawa-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 31, 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, September is the cheapest month in which you can book a flight from Ottawa to Chicago (average of $131). Flying from Ottawa to Chicago in March is currently the most expensive (average of $256). 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 November 4, 2025.

It’s typically best to fly out from Ottawa to Chicago at noon. Doing so could potentially save you 33% on the flight price compared to flying in the afternoon, 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 November 4, 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 November 4, 2025.
Peruse reviews from past customers who have flown with Porter Airlines and United Airlines 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
387 reviews

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
387 reviews
Porter Airlines
8.0
Very good
387 reviews

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
United Airlines
7.4
Good
9,001 reviews
Porter Airlines
8.0
Very good
387 reviews

Entertainment

7.0

Food

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 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: ANA (90%), GoJet (89%), United Airlines (88%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $682, our data indicates the cheapest price to be $187. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $284.

  • 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, September is the cheapest month in which you can book a flight from Ottawa to Chicago (average of $131). Flying from Ottawa to Chicago in March is currently the most expensive (average of $256). 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
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$324Average$519FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$326Average$544FlexibilityNo cancel feeOn-time67%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.