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Cheap flights from Ottawa to Chicago from C$ 184

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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
22 Jan — 29 Jan1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in May or June, booked 51 days in advance, depart on a Saturday or Friday and return on a Tuesday

Cheap flight deals from Ottawa to Chicago

Enter your travel dates to find the best prices.

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 23 December 2025.

Thu 25/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Sat 27/124:15 p.m.MDW - YOW
1 stop5h 14mPorter Airlines
Deal found 22/12C$ 742
Fri 26/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Sat 27/1211:00 a.m.MDW - YOW
1 stop7h 54mPorter Airlines
Deal found 22/12C$ 775
Wed 24/1212:05 p.m.YOW - ORD
1 stop6h 43mAir Canada
Mon 29/122:00 p.m.ORD - YOW
1 stop6h 18mAir Canada
Deal found 22/12C$ 858
Mon 29/125:40 a.m.YOW - ORD
2 stops34h 13mMultiple Airlines
Sun 4/19:34 a.m.ORD - YOW
1 stop26h 06mMultiple Airlines
Deal found 20/12C$ 876
Mon 29/128:55 p.m.YOW - MDW
1 stop14h 10mMultiple Airlines
Sun 4/17:44 a.m.MDW - YOW
1 stop27h 56mMultiple Airlines
Deal found 20/12C$ 889
Wed 24/124:15 p.m.YOW - ORD
1 stop23h 47mMultiple Airlines
Mon 29/1212:39 p.m.ORD - YOW
2 stops27h 34mMultiple Airlines
Deal found 22/12C$ 932
Wed 24/124:15 p.m.YOW - ORD
1 stop23h 47mMultiple Airlines
Sun 28/124:44 p.m.ORD - YOW
1 stop23h 41mMultiple Airlines
Deal found 22/12C$ 947
Mon 29/125:40 a.m.YOW - MDW
2 stops28h 09mWestJet
Sun 4/16:08 p.m.MDW - YOW
2 stops29h 34mWestJet
Deal found 20/12C$ 1,001
Mon 29/125:40 a.m.YOW - ORD
2 stops28h 21mWestJet
Sun 4/16:02 p.m.ORD - YOW
2 stops29h 40mWestJet
Deal found 20/12C$ 1,001
Wed 24/124:15 p.m.YOW - ORD
1 stop9h 15mMultiple Airlines
Thu 25/126:00 a.m.ORD - YOW
2 stops17h 25mMultiple Airlines
Deal found 22/12C$ 1,103
Fri 26/125:40 a.m.YOW - ORD
2 stops16h 54mMultiple Airlines
Thu 1/17:20 a.m.ORD - YOW
1 stop15h 38mMultiple Airlines
Deal found 23/12C$ 1,163
Sat 27/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Sat 3/14:15 p.m.MDW - YOW
1 stop5h 14mPorter Airlines
Deal found 22/12C$ 1,170

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 23 December 2025.

Round-trip from

C$ 326

One-way from

C$ 184

Popular in

November

Cheapest in

May

Average price

C$ 708

Good round-trip deal

C$ 542 or less

Good one-way deal

C$ 288 or less
22/1-26/1
  • 22/1-26/1
  • 2 total stops
  • 35h 13m total
  • Ottawa to Chicago
Search Deals
7/2
  • 7/2
  • 1 total stop
  • 15h 03m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 145 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 629,999 searches. Data last updated 23 December 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

Thu 22/1

7:00 a.m.-10:36 p.m.

1 stop16h 36m

Chicago O'Hare Intl

Sun 25/1

5:15 a.m.-5:25 p.m.

1 stop11h 10m

C$ 333

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 14/1

7:00 a.m.-5:52 p.m.

2 stops11h 52m

Chicago O'Hare Intl

Wed 28/1

7:20 a.m.-12:42 a.m.

2 stops16h 22m

C$ 398

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sun 11/1

12:10 p.m.-10:42 p.m.

2 stops11h 32m

Chicago O'Hare Intl

Mon 12/1

7:21 p.m.-2:58 p.m.

1 stop18h 37m

C$ 428

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 16/1

7:00 a.m.-7:38 p.m.

1 stop13h 38m

Chicago O'Hare Intl

Mon 19/1

8:43 p.m.-5:13 p.m.

2 stops19h 30m

C$ 441

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 5/2

7:00 a.m.-5:52 p.m.

2 stops11h 52m

Chicago O'Hare Intl

Sat 7/2

5:15 a.m.-12:39 a.m.

2 stops18h 24m

C$ 453

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 23/1

9:30 a.m.-5:52 p.m.

1 stop9h 22m

Chicago O'Hare Intl

Sat 24/1

12:00 p.m.-12:42 a.m.

2 stops11h 42m

C$ 458

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 23/1

3:55 p.m.-10:42 p.m.

1 stop7h 47m

Chicago O'Hare Intl

Sun 25/1

12:44 p.m.-11:58 p.m.

1 stop10h 14m

C$ 496

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 23/1

1:20 p.m.-10:42 p.m.

2 stops10h 22m

Chicago O'Hare Intl

Mon 26/1

7:20 a.m.-5:25 p.m.

1 stop9h 05m

C$ 498

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 4/2

10:00 a.m.-11:47 p.m.

3 stops14h 47m

Chicago O'Hare Intl

Wed 11/2

7:20 a.m.-12:39 a.m.

2 stops16h 19m

C$ 500

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 22/2

12:10 p.m.-3:20 p.m.

1 stop4h 10m

Chicago Midway

Thu 26/2

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 522

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/12

Showing 1-10 of 33 results
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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 19 December 2025.

Booking 51 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 C$ 180). Flying from Ottawa to Chicago in December is currently the most expensive (average of C$ 374). 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 23 December 2025.

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 23 December 2025.

The most flights from YOW to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

What’s the top layover airport for flights from Ottawa to Chicago?

Share of one-stop round-trip flights from Ottawa to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YTZ) – chosen by Cheapflights users on 90% of one-stop itineraries from Ottawa to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Ottawa to Chicago?

Average round-trip fare for 1-stop flights from Ottawa to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Calgary (YYC) is the most affordable 1-stop option, with an average round-trip price of C$ 443.

What’s the fastest layover option from Ottawa to Chicago?

Shortest average travel time for 1-stop one-way flights from Ottawa to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YYZ) have the shortest average one-way travel time for 1-stop routes: 4h 20m.

Which airport typically offers the quickest layover for flights from Ottawa to Chicago?

Average layover duration for 1-stop one-way flights from Ottawa to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Toronto (YYZ) offer the fastest connection on this route, with an average layover time of 1h 19m.

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 23 December 2025.
Get a feel of what it's like to fly with Porter Airlines,United Airlines, andAir Canada 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
399 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
399 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,106 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,551 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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?

    Ottawa (YOW), located 10.6 km from the city centre, is the airport you fly out of when you book flights from Ottawa to Chicago. 3 airlines have flights from Ottawa to Chicago on a regular basis. Booking flights from Ottawa to Chicago should not be difficult; the airport handles an average of 8 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 4h 10m. There are 1048 km between Ottawa and Chicago.

  • What are the cheapest airlines flying from Ottawa to Chicago round-trip?

    Currently priced at C$ 330, Porter Airlines will fly you from Ottawa to Chicago and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Air Canada - these airlines can fly you to your destination from C$ 462 and C$ 490, respectively. You may be able to fly from Ottawa to Chicago for 42% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Ottawa to Chicago?

    The top 3 most reliable airlines when flying from Ottawa to Chicago are SkyWest Airlines (100%), ANA (83%) and United Airlines (80%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 225. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 326 on average, our data indicates C$ 1,384 when flying from Ottawa to Chicago.

  • 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 C$ 180). Flying from Ottawa to Chicago in December is currently the most expensive (average of C$ 374). 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

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Alternative routes for Ottawa to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Pearson Intl to O'Hare Intl flights
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Pierre Elliott Trudeau Intl to Midway flights
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Toronto Island to O'Hare Intl flights
Ottawa to Midway flights
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Ottawa to St. Louis flights
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Region of Waterloo Intl to O'Hare Intl flights
Pearson Intl to Bloomington flights
Kingston to O'Hare Intl flights
Pearson Intl to Quincy flights
Pearson Intl to Champaign flights
Ottawa to Champaign flights

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 629,999 searches. Data last updated 23 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 330AverageC$ 480FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 463AverageC$ 670FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 502AverageC$ 649FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Ottawa to Chicago?

When you search for this flight from Ottawa to Chicago, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Ottawa to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Ottawa by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Ottawa to Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Ottawa to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Ottawa to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Ottawa to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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