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$175+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
May 18 — May 251
Mon 5/18
Mon 5/25
1 adult, Economy
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1. Tell us where you want to go

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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 April 18, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/15. 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 5/307:00 am
YOW
-
ORD
1 stop17h 13m
Multiple Airlines
Sat 6/68:05 am
ORD
-
YOW
2 stops15h 15m
Multiple Airlines
Deal found 4/15$335
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 4/217:00 am
YOW
-
ORD
1 stop15h 17m
Multiple Airlines
Tue 4/287:15 pm
ORD
-
YOW
1 stop21h 10m
Multiple Airlines
Deal found 4/14$343
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 5/66:55 am
YOW
-
MDW
1 stop8h 40m
Multiple Airlines
Mon 5/114:52 pm
MDW
-
YOW
2 stops30h 28m
Multiple Airlines
Deal found 4/13$354
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/304:15 pm
YOW
-
ORD
1 stop9h 09m
Multiple Airlines
Mon 5/41:49 pm
ORD
-
YOW
1 stop21h 26m
Multiple Airlines
Deal found 4/13$361
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/68:00 am
YOW
-
ORD
2 stops13h 11m
Multiple Airlines
Thu 5/145:30 pm
ORD
-
YOW
1 stop20h 03m
Multiple Airlines
Deal found 4/14$366
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/27:00 am
YOW
-
ORD
2 stops15h 17m
Multiple Airlines
Mon 5/412:59 pm
ORD
-
YOW
1 stop22h 16m
Multiple Airlines
Deal found 4/14$371
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/58:00 am
YOW
-
ORD
2 stops13h 11m
Multiple Airlines
Thu 5/71:49 pm
ORD
-
YOW
1 stop21h 26m
Multiple Airlines
Deal found 4/14$375
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/58:00 am
YOW
-
ORD
2 stops13h 11m
Multiple Airlines
Fri 5/81:49 pm
ORD
-
YOW
1 stop26h 46m
Multiple Airlines
Deal found 4/14$377
This Kiwi.com deal was found by Cheapflights users on 4/15. 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 7/29:05 am
YOW
-
ORD
1 stop8h 06m
Multiple Airlines
Mon 8/317:55 am
ORD
-
YOW
2 stops15h 25m
Multiple Airlines
Deal found 4/15$382
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 5/52:20 pm
YOW
-
MDW
2 stops21h 49m
Multiple Airlines
Fri 5/293:20 pm
MDW
-
YOW
1 stop3h 44m
Multiple Airlines
Deal found 4/14$386
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 6/46:55 am
YOW
-
MDW
1 stop8h 40m
Multiple Airlines
Sun 6/710:25 am
MDW
-
YOW
1 stop12h 55m
Multiple Airlines
Deal found 4/13$389
This Kiwi.com deal was found by Cheapflights users on 4/13. 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 4/307:00 am
YOW
-
MDW
2 stops13h 31m
Multiple Airlines
Mon 5/43:20 pm
MDW
-
YOW
1 stop25h 34m
Multiple Airlines
Deal found 4/13$415

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 April 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$335
(Kiwi.com)

One-way from

$175
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$425

Good round-trip deal

$416 or less

Good one-way deal

$215 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. 16% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($33 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 18, 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

Fri 6/26

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Thu 7/2

3:20 pm-8:04 pm

1 stop3h 44m

$438

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/24

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Sun 7/26

3:20 pm-8:04 pm

1 stop3h 44m

$440

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/30

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Mon 5/4

3:20 pm-5:54 pm

1 stop25h 34m

$447

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/30

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Thu 5/7

10:30 am-5:54 pm

1 stop6h 24m

$456

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/26

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Sun 6/28

10:25 am-5:54 pm

1 stop6h 29m

$464

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 6/29

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Mon 7/6

3:20 pm-8:04 pm

1 stop3h 44m

$469

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 6/29

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Sun 7/5

3:20 pm-8:04 pm

1 stop3h 44m

$469

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 6/24

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Tue 6/30

3:20 pm-8:04 pm

1 stop3h 44m

$474

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 7/29

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Wed 8/5

3:20 pm-8:04 pm

1 stop3h 44m

$492

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 6/29

11:00 am-2:35 pm

1 stop4h 35m

Chicago Midway

Mon 8/31

3:20 pm-8:04 pm

1 stop3h 44m

$493

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

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 April.
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?

Use this chart to determine the optimal time to book a round-trip flight from Ottawa to Chicago. Price data was last updated on April 10, 2026.

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 April 18, 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 April 18, 2026.

The most flights from YOW to CHI are scheduled on a Monday (13 on average). You will have fewer flight options on Thursday, 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 April 18, 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
435 reviews

Crew

8.6

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

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
435 reviews
Porter Airlines
8.0
Very good
435 reviews

Crew

8.6

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

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
9,604 reviews
Porter Airlines
8.0
Very good
435 reviews

Crew

8.6

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

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, WestJet, and United Airlines can get you from Ottawa to Chicago in just under 2h 08m. Your travel time can differ by up to 10h 38m. 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 25% 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 (72%), ANA (70%), 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 $425, our data indicates the cheapest price to be $173. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $393.

  • 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 April 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$324Average$580FlexibilityNo cancel feeOn-time69%

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