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Cheap flights from Ottawa to Chicago from C$ 236

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 15/9. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
21 Aug — 28 Aug1
1 adult

Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in May or June, booked 22 days in advance, depart on a Friday or Tuesday 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 August 2025.

Round-trip from

C$ 453

One-way from

C$ 236

Popular in

November

Cheapest in

May

Average price

C$ 572

Good round-trip deal

C$ 527 or less

Good one-way deal

C$ 393 or less
Porter Airlines
  • Porter Airlines
  • 27/8-3/9
  • 2 total stops
  • 12h 53m total
  • Ottawa to Chicago
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Porter Airlines
  • Porter Airlines
  • 15/9
  • 1 total stop
  • 3h 59m total
  • Ottawa to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease (C$ 11 potential savings vs. average RT price).
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Average for round-trip flights in August 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

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 August 2025.

Wed 27/811:00 a.m.YOW - MDW
1 stop6h 24mPorter Airlines
Wed 3/99:35 a.m.MDW - YOW
1 stop6h 29mPorter Airlines
Deal found 14/8C$ 453
Sat 18/106:33 a.m.YOW - ORD
Nonstop2h 27mMultiple Airlines
Sun 19/108:40 a.m.ORD - YOW
1 stop4h 11mMultiple Airlines
Deal found 13/8C$ 453
Tue 26/811:00 a.m.YOW - MDW
1 stop6h 24mPorter Airlines
Wed 3/99:35 a.m.MDW - YOW
1 stop6h 29mPorter Airlines
Deal found 13/8C$ 454
Fri 19/97:00 a.m.YOW - ORD
2 stops13h 44mMultiple Airlines
Mon 22/98:49 p.m.ORD - YOW
1 stop19h 08mMultiple Airlines
Deal found 15/8C$ 456
Fri 19/95:25 p.m.YOW - ORD
Nonstop2h 29mUnited Airlines
Mon 22/912:50 p.m.ORD - YOW
1 stop5h 02mUnited Airlines
Deal found 15/8C$ 460
Fri 17/105:15 p.m.YOW - ORD
2 stops24h 28mWestJet
Mon 20/105:30 p.m.ORD - YOW
1 stop30h 10mWestJet
Deal found 15/8C$ 462
Sat 27/95:25 p.m.YOW - ORD
Nonstop2h 29mUnited Airlines
Sat 4/102:35 p.m.ORD - YOW
1 stop6h 30mUnited Airlines
Deal found 13/8C$ 464
Sat 6/97:00 a.m.YOW - ORD
2 stops10h 50mMultiple Airlines
Sun 7/96:30 a.m.ORD - YOW
1 stop9h 27mMultiple Airlines
Deal found 12/8C$ 465
Fri 19/95:15 p.m.YOW - ORD
1 stop20h 24mWestJet
Mon 22/95:30 p.m.ORD - YOW
1 stop23h 50mWestJet
Deal found 13/8C$ 468
Sat 6/911:50 a.m.YOW - ORD
1 stop11h 21mMultiple Airlines
Wed 17/96:30 a.m.ORD - YOW
2 stops13h 05mMultiple Airlines
Deal found 12/8C$ 476
Sat 30/87:00 a.m.YOW - MDW
1 stop3h 50mPorter Airlines
Wed 3/99:35 a.m.MDW - YOW
1 stop6h 29mPorter Airlines
Deal found 14/8C$ 501
Fri 29/87:00 a.m.YOW - MDW
1 stop3h 50mPorter Airlines
Wed 3/99:35 a.m.MDW - YOW
1 stop7h 34mPorter Airlines
Deal found 14/8C$ 507

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 August 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

Sun 31/8

7:00 a.m.-9:45 a.m.

1 stop3h 45m

Chicago Midway

Wed 3/9

9:35 a.m.-5:04 p.m.

1 stop6h 29m

C$ 453

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 18/10

6:33 a.m.-8:00 a.m.

Nonstop2h 27m

Chicago O'Hare Intl

Sun 19/10

8:40 a.m.-1:51 p.m.

1 stop4h 11m

C$ 453

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 27/8

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Wed 3/9

9:35 a.m.-5:04 p.m.

1 stop6h 29m

C$ 453

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 28/8

12:35 p.m.-4:24 p.m.

1 stop4h 49m

Chicago Midway

Wed 3/9

9:35 a.m.-5:04 p.m.

1 stop6h 29m

C$ 454

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 26/8

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Wed 3/9

9:35 a.m.-5:04 p.m.

1 stop6h 29m

C$ 454

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 19/9

7:00 a.m.-7:44 p.m.

2 stops13h 44m

Chicago O'Hare Intl

Mon 22/9

8:49 p.m.-4:57 p.m.

1 stop19h 08m

C$ 456

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Sat 18/10

6:00 a.m.-9:51 a.m.

1 stop4h 51m

Chicago O'Hare Intl

Sun 19/10

8:40 a.m.-1:51 p.m.

1 stop4h 11m

C$ 460

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 29/9

5:25 p.m.-6:54 p.m.

Nonstop2h 29m

Chicago O'Hare Intl

Mon 6/10

8:50 a.m.-2:13 p.m.

1 stop4h 23m

C$ 460

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 19/9

5:25 p.m.-6:54 p.m.

Nonstop2h 29m

Chicago O'Hare Intl

Mon 22/9

8:50 a.m.-2:13 p.m.

1 stop4h 23m

C$ 460

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 17/10

5:15 p.m.-4:43 p.m.

2 stops24h 28m

Chicago O'Hare Intl

Mon 20/10

5:30 p.m.-12:40 a.m.

1 stop30h 10m

C$ 462

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

Showing 1-10 of 37 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 8 August 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, January is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 261). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 352). 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 August 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 46% on flights from Ottawa to Chicago by exploring options for tickets at noon.

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 94% 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$ 444.

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 46m.

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 31m.

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 August 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
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,916 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Air Canada
7.1
Good
9,966 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Food

7.6

Overall

8.0

Crew

8.7

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 10 outbound flights to Chicago per day.

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

    Currently priced at C$ 371, 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$ 464 and C$ 503, 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 Avianca (90%), ANA (86%) and GoJet (82%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 235. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 442 on average our data indicates C$ 1,529 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, January is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 261). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 352). 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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Pearson Intl 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 16 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 371AverageC$ 502FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 464AverageC$ 689FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 503AverageC$ 642FlexibilityNo 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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