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Cheap flights from Ottawa to Chicago from C$ 230

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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
4 Dec — 11 Dec1
1 adult
1 adult, Economy, 0 bags

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 Wednesday

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 4 November 2025.

Round-trip from

C$ 399

One-way from

C$ 230

Popular in

November

Cheapest in

May

Average price

C$ 710

Good round-trip deal

C$ 564 or less

Good one-way deal

C$ 334 or less
8/12-11/12
  • 8/12-11/12
  • 2 total stops
  • 37h 03m total
  • Ottawa to Chicago
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2/12
  • 2/12
  • 1 total stop
  • 18h 02m total
  • Ottawa to Chicago
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Highest demand for flights based on searches. 10% potential increase in price (C$ 91 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 19 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Ottawa to Chicago (CHI).
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Price to beat on a one-way flight from Ottawa to Chicago (CHI).
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Find 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 4 November 2025.

Mon 8/124:15 p.m.YOW - ORD
1 stop19h 53mMultiple Airlines
Thu 11/126:15 a.m.ORD - YOW
1 stop17h 10mMultiple Airlines
Deal found 3/11C$ 399
Tue 2/124:15 p.m.YOW - ORD
1 stop18h 02mMultiple Airlines
Tue 9/124:22 p.m.ORD - YOW
2 stops47h 51mMultiple Airlines
Deal found 2/11C$ 428
Mon 8/124:15 p.m.YOW - ORD
1 stop19h 53mMultiple Airlines
Wed 17/127:10 a.m.ORD - YOW
1 stop9h 15mMultiple Airlines
Deal found 4/11C$ 435
Thu 4/129:30 a.m.YOW - ORD
3 stops26h 38mMultiple Airlines
Sun 7/127:20 a.m.ORD - YOW
2 stops13h 34mMultiple Airlines
Deal found 2/11C$ 444
Fri 5/127:15 p.m.YOW - ORD
2 stops17h 39mMultiple Airlines
Mon 8/127:10 a.m.ORD - YOW
1 stop16h 15mMultiple Airlines
Deal found 2/11C$ 476
Tue 11/114:15 p.m.YOW - ORD
1 stop9h 12mMultiple Airlines
Mon 17/115:10 a.m.ORD - YOW
1 stop11h 15mMultiple Airlines
Deal found 2/11C$ 487
Tue 2/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Tue 9/127:44 a.m.MDW - YOW
1 stop8h 41mMultiple Airlines
Deal found 2/11C$ 491
Tue 11/114:15 p.m.YOW - ORD
1 stop9h 12mMultiple Airlines
Sat 15/118:00 a.m.ORD - YOW
1 stop14h 58mMultiple Airlines
Deal found 2/11C$ 491
Thu 4/125:40 a.m.YOW - MDW
1 stop10h 40mMultiple Airlines
Sun 7/127:44 a.m.MDW - YOW
1 stop27h 51mMultiple Airlines
Deal found 3/11C$ 497
Wed 12/116:45 a.m.YOW - MDW
2 stops27h 27mMultiple Airlines
Sat 15/1111:36 a.m.MDW - YOW
1 stop11h 22mMultiple Airlines
Deal found 2/11C$ 503
Fri 5/125:40 a.m.YOW - MDW
1 stop10h 40mMultiple Airlines
Sun 7/126:37 p.m.MDW - YOW
2 stops21h 14mMultiple Airlines
Deal found 2/11C$ 510
Fri 12/1212:10 p.m.YOW - MDW
1 stop4h 10mMultiple Airlines
Mon 15/123:52 p.m.MDW - YOW
2 stops24h 21mMultiple Airlines
Deal found 3/11C$ 519

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 4 November 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 4/12

4:15 p.m.-11:08 a.m.

1 stop19h 53m

Chicago O'Hare Intl

Sun 7/12

7:10 a.m.-12:25 a.m.

1 stop16h 15m

C$ 446

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 2/12

6:50 a.m.-1:01 p.m.

2 stops7h 11m

Chicago Midway

Tue 9/12

7:44 a.m.-5:25 p.m.

1 stop8h 41m

C$ 491

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/12

6:50 a.m.-1:01 p.m.

2 stops7h 11m

Chicago Midway

Sun 7/12

6:37 p.m.-5:13 p.m.

1 stop21h 36m

C$ 501

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sun 23/11

9:30 a.m.-5:11 p.m.

1 stop8h 41m

Chicago O'Hare Intl

Wed 26/11

6:15 p.m.-5:13 p.m.

1 stop21h 58m

C$ 505

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 5/12

5:40 a.m.-3:20 p.m.

1 stop10h 40m

Chicago Midway

Sun 7/12

6:37 p.m.-4:51 p.m.

2 stops21h 14m

C$ 510

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 19/2

4:15 p.m.-12:18 a.m.

1 stop9h 03m

Chicago O'Hare Intl

Sun 22/2

11:42 a.m.-12:25 a.m.

1 stop11h 43m

C$ 515

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 12/12

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

1 stop4h 10m

Chicago Midway

Mon 15/12

3:52 p.m.-5:13 p.m.

2 stops24h 21m

C$ 519

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 8/12

4:15 p.m.-1:58 p.m.

2 stops22h 43m

Chicago O'Hare Intl

Wed 17/12

7:10 a.m.-11:58 p.m.

2 stops15h 48m

C$ 525

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 8/12

4:35 p.m.-1:01 p.m.

2 stops21h 26m

Chicago Midway

Thu 11/12

7:44 a.m.-5:25 p.m.

1 stop8h 41m

C$ 529

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 27/11

5:40 a.m.-3:20 p.m.

1 stop10h 40m

Chicago Midway

Sun 30/11

4:15 p.m.-10:29 p.m.

1 stop5h 14m

C$ 535

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/11

Showing 1-10 of 34 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 31 October 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 C$ 184). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 359). 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 4 November 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 52% on flights from Ottawa to Chicago by exploring options for tickets at noon.

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 4 November 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).

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 91% 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$ 452.

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 4 November 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
387 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

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
Check prices

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

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
8,998 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

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.
Air Canada
7.1
Good
10,400 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.0

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?

    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 12 outbound flights to Chicago per day.

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

    Currently priced at C$ 377, 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$ 472 and C$ 499, respectively. You may be able to fly from Ottawa to Chicago for 34% 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 ANA (90%), GoJet (89%) and United Airlines (88%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 249. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 428 on average, our data indicates C$ 1,227 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$ 184). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 359). 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
Pierre Elliott Trudeau Intl to O'Hare Intl flights
Toronto Island to Midway flights
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
Pearson Intl to Peoria flights
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Region of Waterloo Intl to O'Hare Intl flights
Pearson Intl to Bloomington flights
Pearson Intl to Quincy flights
Kingston to O'Hare Intl 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 4 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 377AverageC$ 497FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 472AverageC$ 679FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 499AverageC$ 647FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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