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$217+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
Jun 5 — Jun 121
Fri 6/5
Fri 6/12
1 adult, Economy
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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”

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Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in February or May, booked 29 days in advance, depart on a Saturday or Tuesday and return on a Saturday

Cheap 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 May 6, 2026.

This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 5/237:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Wed 5/275:30 pm
ORD
-
YOW
1 stop11h 05m
WestJet
Deal found 5/2$349
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/267:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Wed 5/275:30 pm
ORD
-
YOW
1 stop11h 05m
WestJet
Deal found 5/2$351
This FlightHub deal was found by Cheapflights users on 5/2. 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.
Mon 5/257:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Sun 5/315:30 pm
ORD
-
YOW
1 stop11h 05m
WestJet
Deal found 5/2$362
This FlightHub deal was found by Cheapflights users on 5/2. 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.
Tue 5/267:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Sun 5/315:30 pm
ORD
-
YOW
1 stop11h 05m
WestJet
Deal found 5/2$363
This FlightHub deal was found by Cheapflights users on 5/2. 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.
Mon 5/257:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Sat 5/305:30 pm
ORD
-
YOW
2 stops17h 05m
WestJet
Deal found 5/2$372
This FlightHub deal was found by Cheapflights users on 5/2. 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.
Tue 5/267:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Sat 5/305:30 pm
ORD
-
YOW
2 stops17h 05m
WestJet
Deal found 5/2$373
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 5/292:20 pm
YOW
-
ORD
2 stops18h 35m
Multiple Airlines
Thu 6/45:11 pm
ORD
-
YOW
1 stop20h 22m
Multiple Airlines
Deal found 5/3$374
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sat 5/237:20 am
YOW
-
ORD
1 stop10h 20m
WestJet
Sun 5/315:30 pm
ORD
-
YOW
1 stop11h 05m
WestJet
Deal found 5/2$382
This Kiwi.com deal was found by Cheapflights users on 5/2. 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 5/268:00 am
YOW
-
MDW
1 stop7h 35m
Porter Airlines
Sat 5/3010:30 am
MDW
-
YOW
1 stop7h 44m
Porter Airlines
Deal found 5/2$386
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Sun 5/2411:00 am
YOW
-
MDW
1 stop4h 35m
Porter Airlines
Sat 5/3010:30 am
MDW
-
YOW
1 stop7h 44m
Porter Airlines
Deal found 5/2$388
This Kiwi.com deal was found by Cheapflights users on 5/2. 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.
Thu 6/48:00 am
YOW
-
MDW
1 stop7h 35m
Porter Airlines
Mon 6/810:15 am
MDW
-
YOW
1 stop3h 39m
Porter Airlines
Deal found 5/2$392
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Thu 6/48:00 am
YOW
-
MDW
1 stop7h 35m
Porter Airlines
Sun 6/710:15 am
MDW
-
YOW
1 stop3h 39m
Porter Airlines
Deal found 5/1$393

Find 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 May 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$349
(Kiwi.com)

One-way from

$217
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$381

Good round-trip deal

$437 or less

Good one-way deal

$295 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. 13% potential increase in price ($69 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($31 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
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

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 May 6, 2026.
Use the filters below to find and compare flights from Ottawa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 5/28

8:45 pm-2:35 pm

1 stop18h 50m

Chicago Midway

Fri 6/5

10:15 am-10:14 am

1 stop22h 59m

$410

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 5/26

8:00 am-2:35 pm

1 stop7h 35m

Chicago Midway

Fri 5/29

10:30 am-9:44 pm

1 stop10h 14m

$413

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/6

7:00 am-10:02 pm

2 stops16h 02m

Chicago Midway

Sun 6/7

10:15 am-2:54 pm

1 stop3h 39m

$432

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/6

7:15 pm-9:35 am

1 stop15h 20m

Chicago Midway

Sun 6/7

3:20 pm-12:25 am

1 stop8h 05m

$474

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/3

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Sat 7/11

10:25 am-7:09 pm

1 stop7h 44m

$478

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 5/25

8:00 am-2:35 pm

1 stop7h 35m

Chicago Midway

Thu 5/28

10:30 am-9:44 pm

1 stop10h 14m

$482

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 5/22

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Sat 5/23

10:30 am-7:14 pm

1 stop7h 44m

$508

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/24

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Sun 7/26

10:25 am-5:54 pm

1 stop6h 29m

$542

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 5/20

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Fri 5/22

10:30 am-8:04 pm

1 stop8h 34m

$544

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 5/21

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Fri 5/22

10:30 am-8:04 pm

1 stop8h 34m

$544

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/1

Showing 1-10 of 42 resultsSorted by cheapest first
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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 May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
ExpediaPrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Ottawa-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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?

Booking 29 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 $131). Flying from Ottawa to Chicago in January is currently the most expensive (average of $539). 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 May 6, 2026.

When flying from Ottawa to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 May 6, 2026.

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 May 6, 2026.
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
436 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
436 reviews
Porter Airlines
8.0
Very good
436 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,684 reviews
Porter Airlines
8.0
Very good
436 reviews

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 1 airline.

  • How long is the flight from Ottawa to Chicago?

    Porter Airlines, Air Canada, and United Airlines can get you from Ottawa to Chicago in just under 7h 16m. Your travel time can differ by up to 11h 34m. The distance from Ottawa to Chicago is about 653 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What is the cheapest airline to fly 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. United Airlines is currently priced 28% 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: Republic Airways (73%), ANA (71%), Air Canada (66%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $444, our data indicates the cheapest price to be $215. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $427.

  • 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 $131). Flying from Ottawa to Chicago in January is currently the most expensive (average of $539). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Ottawa to Chicago

Discover the top airline 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 May 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$324Average$580FlexibilityNo cancel feeOn-time69%

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