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Cheap flights from Ottawa to Chicago from C$ 223

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 3/11. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
15 Nov — 22 Nov1
1 adult
1 adult, Economy

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 16 October 2025.

Round-trip from

C$ 400

One-way from

C$ 223

Popular in

November

Cheapest in

May

Average price

C$ 586

Good round-trip deal

C$ 548 or less

Good one-way deal

C$ 404 or less
28/10-31/10
  • 28/10-31/10
  • 2 total stops
  • 20h 36m total
  • Ottawa to Chicago
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3/11
  • 3/11
  • 1 total stop
  • 18h 32m total
  • Ottawa to Chicago
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Highest demand for flights based on searches. 10% potential increase in price (C$ 88 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 15 potential savings vs. average RT price).
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Average for round-trip flights in October 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 16 October 2025.

Tue 28/104:15 p.m.YOW - ORD
1 stop9h 48mMultiple Airlines
Fri 31/105:25 a.m.ORD - YOW
1 stop10h 48mMultiple Airlines
Deal found 14/10C$ 400
Wed 29/109:30 a.m.YOW - ORD
1 stop27h 56mMultiple Airlines
Sat 1/118:00 a.m.ORD - YOW
1 stop8h 13mMultiple Airlines
Deal found 16/10C$ 424
Thu 30/109:30 a.m.YOW - ORD
1 stop9h 19mMultiple Airlines
Mon 3/115:15 a.m.ORD - YOW
1 stop10h 58mMultiple Airlines
Deal found 14/10C$ 428
Tue 28/104:15 p.m.YOW - ORD
1 stop9h 48mMultiple Airlines
Thu 30/105:05 a.m.ORD - YOW
1 stop11h 20mMultiple Airlines
Deal found 14/10C$ 432
Tue 11/114:35 p.m.YOW - ORD
2 stops22h 56mMultiple Airlines
Tue 18/113:26 p.m.ORD - YOW
1 stop24h 59mMultiple Airlines
Deal found 14/10C$ 434
Wed 29/104:15 p.m.YOW - ORD
1 stop9h 48mMultiple Airlines
Mon 3/115:10 a.m.ORD - YOW
1 stop11h 15mMultiple Airlines
Deal found 15/10C$ 444
Wed 29/109:30 a.m.YOW - MDW
1 stop24h 42mMultiple Airlines
Sun 2/116:06 p.m.MDW - YOW
2 stops22h 19mMultiple Airlines
Deal found 16/10C$ 452
Tue 11/114:35 p.m.YOW - MDW
2 stops8h 20mMultiple Airlines
Tue 18/116:26 p.m.MDW - YOW
1 stop17h 09mMultiple Airlines
Deal found 14/10C$ 459
Tue 28/104:15 p.m.YOW - ORD
1 stop27h 23mMultiple Airlines
Sun 2/1110:52 a.m.ORD - YOW
1 stop29h 33mMultiple Airlines
Deal found 15/10C$ 469
Tue 4/113:55 p.m.YOW - MDW
1 stop9h 00mMultiple Airlines
Tue 11/116:26 p.m.MDW - YOW
1 stop17h 09mMultiple Airlines
Deal found 14/10C$ 475
Wed 29/109:30 a.m.YOW - MDW
1 stop24h 42mMultiple Airlines
Mon 3/116:06 p.m.MDW - YOW
2 stops22h 19mMultiple Airlines
Deal found 15/10C$ 500
Tue 28/102:50 p.m.YOW - MDW
2 stops9h 35mMultiple Airlines
Fri 31/109:32 a.m.MDW - YOW
1 stop30h 41mMultiple Airlines
Deal found 14/10C$ 505

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 16 October 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

Wed 29/10

9:30 a.m.-12:26 p.m.

1 stop27h 56m

Chicago O'Hare Intl

Sat 1/11

8:00 a.m.-5:13 p.m.

1 stop8h 13m

C$ 424

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 30/10

9:30 a.m.-5:49 p.m.

1 stop9h 19m

Chicago O'Hare Intl

Mon 3/11

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

1 stop10h 58m

C$ 428

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 29/10

9:30 a.m.-9:12 a.m.

1 stop24h 42m

Chicago Midway

Sun 2/11

6:06 p.m.-5:25 p.m.

2 stops22h 19m

C$ 452

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 4/11

3:55 p.m.-11:55 p.m.

1 stop9h 00m

Chicago Midway

Tue 11/11

6:26 p.m.-12:35 p.m.

1 stop17h 09m

C$ 475

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 28/10

2:50 p.m.-11:25 p.m.

2 stops9h 35m

Chicago Midway

Fri 31/10

9:32 a.m.-5:13 p.m.

1 stop30h 41m

C$ 505

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 30/10

4:15 p.m.-1:03 a.m.

1 stop9h 48m

Chicago O'Hare Intl

Sun 2/11

5:25 a.m.-9:54 p.m.

2 stops15h 29m

C$ 508

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 16/11

9:30 a.m.-8:32 a.m.

1 stop24h 02m

Chicago Midway

Sun 23/11

6:20 a.m.-12:35 p.m.

1 stop5h 15m

C$ 525

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 7/11

3:55 p.m.-11:30 a.m.

2 stops20h 35m

Chicago O'Hare Intl

Sat 15/11

2:31 p.m.-12:35 p.m.

1 stop21h 04m

C$ 534

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 30/10

9:30 a.m.-8:32 a.m.

1 stop24h 02m

Chicago Midway

Mon 3/11

9:32 a.m.-7:59 a.m.

2 stops21h 27m

C$ 543

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Tue 28/10

9:30 a.m.-1:03 a.m.

2 stops16h 33m

Chicago O'Hare Intl

Fri 31/10

7:43 p.m.-5:13 p.m.

2 stops20h 30m

C$ 552

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/10

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 10 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 January is currently the most expensive (average of C$ 400). 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 16 October 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 53% 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 16 October 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 (YTZ) have the shortest average one-way travel time for 1-stop routes: 4h 55m.

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 2h 02m.

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 16 October 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
381 reviews
Check prices

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
381 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,982 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,306 reviews
Porter Airlines
8.0
Very good
381 reviews
Check prices

Crew

8.6

Comfort

8.0

Boarding

8.2

Overall

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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$ 512, 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 GoJet (92%), ANA (91%) and Avianca (90%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 251. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 400 on average, our data indicates C$ 1,241 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 January is currently the most expensive (average of C$ 400). 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.
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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 629,999 searches. Data last updated 16 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 377AverageC$ 506FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 472AverageC$ 689FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 512AverageC$ 661FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

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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?

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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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