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$138+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
abr. 20 — abr. 271
dom. 4/20
dom. 4/27
1 adult, Economy
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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 May or April, booked 65 days in advance, depart on a Saturday or Friday and return on a Friday

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 abril 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$260
(Booking.com)

One-way from

$138
(Mytrip)

Popular in

November

Cheapest in

May

Average price

$395

Good round-trip deal

$390 or less

Good one-way deal

$239 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)
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One-way flight from Ottawa to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in April 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).
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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 abril 15, 2025.

This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/2312:35 pmYOW - MDW
1 stop5h 19mPorter Airlines
vie. 5/309:40 amMDW - YOW
1 stop5h 53mPorter Airlines
Deal found 4/15$260
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.
sáb. 5/243:50 pmYOW - ORD
1 stop9h 15mMultiple Airlines
jue. 5/295:51 amORD - YOW
1 stop8h 05mMultiple Airlines
Deal found 4/15$320
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/227:00 amYOW - MDW
2 stops14h 17mMultiple Airlines
lun. 5/269:40 amMDW - YOW
1 stop5h 53mMultiple Airlines
Deal found 4/15$375
This Flightnetwork 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/225:25 pmYOW - ORD
Nonstop2h 28mAir Canada
dom. 5/251:56 pmORD - YOW
Nonstop2h 10mAir Canada
Deal found 4/15$435
This FlightHub 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/145:55 amYOW - ORD
2 stops17h 46mWestJet
lun. 5/265:30 pmORD - YOW
1 stop30h 12mWestJet
Deal found 4/14$455
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/25:25 pmYOW - ORD
Nonstop2h 28mUnited Airlines
mié. 8/68:00 amORD - YOW
1 stop5h 27mUnited Airlines
Deal found 4/15$456
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/3010:15 amYOW - ORD
3 stops14h 43mPorter Airlines
vie. 6/67:00 amORD - YOW
1 stop9h 18mPorter Airlines
Deal found 4/15$498
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/256:10 amYOW - ORD
2 stops18h 49mDelta
sáb. 5/316:59 pmORD - YOW
2 stops22h 22mDelta
Deal found 4/15$636
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/305:55 amYOW - MDW
2 stops13h 50mDelta
lun. 6/26:25 pmMDW - YOW
2 stops28h 57mDelta
Deal found 4/14$772
This WestJet 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/612:20 pmYOW - MDW
2 stops30h 25mWestJet
jue. 5/812:48 pmMDW - YOW
2 stops10h 34mWestJet
Deal found 4/15$853

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 abril 15, 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

vie. 5/23

12:35 pm-4:54 pm

1 stop5h 19m

Chicago Midway

vie. 5/30

9:40 am-4:33 pm

1 stop5h 53m

$260

OttawaChicago

YOW - ORD

YOWORD

Ottawa

sáb. 5/24

3:50 pm-12:05 am

1 stop9h 15m

Chicago O'Hare Intl

jue. 5/29

5:51 am-2:56 pm

1 stop8h 05m

$320

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

jue. 5/22

7:00 am-8:17 pm

2 stops14h 17m

Chicago Midway

lun. 5/26

9:40 am-4:33 pm

1 stop5h 53m

$375

OttawaChicago

YOW - ORD

YOWORD

Ottawa

jue. 5/22

5:25 pm-6:53 pm

Nonstop2h 28m

Chicago O'Hare Intl

dom. 5/25

1:56 pm-5:06 pm

Nonstop2h 10m

$435

OttawaChicago

YOW - ORD

YOWORD

Ottawa

mié. 5/14

5:55 am-10:41 pm

2 stops17h 46m

Chicago O'Hare Intl

lun. 5/26

5:30 pm-12:42 am

1 stop30h 12m

$455

OttawaChicago

YOW - ORD

YOWORD

Ottawa

sáb. 8/2

5:25 pm-6:53 pm

Nonstop2h 28m

Chicago O'Hare Intl

mié. 8/6

8:00 am-2:27 pm

1 stop5h 27m

$456

OttawaChicago

YOW - ORD

YOWORD

Ottawa

vie. 5/30

10:15 am-11:58 pm

3 stops14h 43m

Chicago O'Hare Intl

vie. 6/6

7:00 am-5:18 pm

1 stop9h 18m

$498

OttawaChicago

YOW - ORD

YOWORD

Ottawa

dom. 5/25

6:10 am-11:59 pm

2 stops18h 49m

Chicago O'Hare Intl

sáb. 5/31

6:59 pm-6:21 pm

2 stops22h 22m

$636

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

vie. 5/30

5:55 am-6:45 pm

2 stops13h 50m

Chicago Midway

lun. 6/2

6:25 pm-12:22 am

2 stops28h 57m

$772

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

mar. 5/6

12:20 pm-5:45 pm

2 stops30h 25m

Chicago Midway

jue. 5/8

12:48 pm-12:22 am

2 stops10h 34m

$853

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

Showing 1-10 of 17 results
1
2

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*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice 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 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 April 11, 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 abril 15, 2025.

It’s typically best to fly out from Ottawa to Chicago in the evening. Doing so could potentially save you 49% 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 abril 15, 2025.

The most flights from YOW to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (7 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 abril 15, 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
281 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Entertainment

7.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Entertainment

7.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,917 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Entertainment

7.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
United Airlines
7.4
Good
8,658 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Entertainment

7.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
WestJet
7.2
Good
2,805 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Entertainment

7.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Air Canada
7.0
Good
9,127 reviews
Porter Airlines
8.0
Very good
281 reviews

Comfort

8.0

Overall

8.0

Boarding

8.2

Food

7.6

Crew

8.7

Entertainment

7.0

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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 11 daily outbound flights to Chicago from 3 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 $260 on this airline. Additional options worth looking into are Air Canada and WestJet, starting at $435 and $455 round-trip. Porter Airlines is currently priced 38% 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 $138. Air Canada flights start at $239 while deals on United Airlines start at $266 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 (84%), ANA (80%), Republic Airways (79%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking for the cheapest flight from Ottawa to Chicago? While on average our users pay $450, our data indicates the cheapest price to be $129. The most popular route (Ottawa - Chicago O'Hare Intl), is priced around $343.

  • 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
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 3 airlines flying from Ottawa to Chicago

Discover the top 3 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 abril 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$291Average$433FlexibilityNo cancel feeOn-time52%
United AirlinesCheapest$410Average$606FlexibilityNo cancel feeOn-time69%
Air CanadaCheapest$423Average$554FlexibilityNo cancel feeOn-time67%

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