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Cheap flights from Ottawa to Chicago from C$ 187

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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
3 Apr — 10 Apr1
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 4 March 2026.

Thu 16/46:50 a.m.
YOW
-
MDW
1 stop4h 25m
Porter Airlines
Thu 30/411:00 a.m.
MDW
-
YOW
1 stop6h 24m
Porter Airlines
Deal found 28/2C$ 313
Thu 23/46:50 a.m.
YOW
-
MDW
1 stop4h 25m
Porter Airlines
Thu 30/411:00 a.m.
MDW
-
YOW
1 stop6h 24m
Porter Airlines
Deal found 1/3C$ 314
Sat 18/48:40 a.m.
YOW
-
MDW
1 stop4h 30m
Porter Airlines
Wed 22/411:00 a.m.
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 1/3C$ 316
Thu 16/46:50 a.m.
YOW
-
MDW
1 stop4h 25m
Porter Airlines
Thu 23/411:00 a.m.
MDW
-
YOW
1 stop5h 04m
Porter Airlines
Deal found 2/3C$ 317
Fri 10/48:40 a.m.
YOW
-
MDW
1 stop7h 40m
Porter Airlines
Tue 14/411:00 a.m.
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 4/3C$ 350
Wed 22/47:00 a.m.
YOW
-
ORD
1 stop15h 17m
Multiple Airlines
Sat 25/41:27 p.m.
ORD
-
YOW
1 stop9h 58m
Multiple Airlines
Deal found 2/3C$ 359
Wed 25/36:45 a.m.
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Sun 29/34:15 p.m.
MDW
-
YOW
1 stop5h 14m
Porter Airlines
Deal found 28/2C$ 366
Tue 24/34:15 p.m.
YOW
-
ORD
1 stop19h 21m
Multiple Airlines
Thu 26/36:01 p.m.
ORD
-
YOW
1 stop17h 34m
Multiple Airlines
Deal found 28/2C$ 370
Mon 13/46:45 a.m.
YOW
-
MDW
1 stop4h 30m
Multiple Airlines
Sat 18/412:55 p.m.
MDW
-
YOW
1 stop10h 44m
Multiple Airlines
Deal found 2/3C$ 372
Thu 26/36:45 a.m.
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Sun 29/34:15 p.m.
MDW
-
YOW
1 stop5h 14m
Porter Airlines
Deal found 2/3C$ 373
Sat 4/48:40 a.m.
YOW
-
MDW
1 stop4h 30m
Porter Airlines
Sun 5/411:00 a.m.
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 2/3C$ 380
Sat 28/38:40 a.m.
YOW
-
MDW
1 stop4h 10m
Multiple Airlines
Sat 4/412:55 p.m.
MDW
-
YOW
1 stop10h 44m
Multiple Airlines
Deal found 28/2C$ 383

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 4 March 2026.

Round-trip from

C$ 313

One-way from

C$ 187

Popular in

January

Cheapest in

May

Average price

C$ 574

Good round-trip deal

C$ 603 or less

Good one-way deal

C$ 374 or less
Porter Airlines
  • Porter Airlines
  • 16/4-30/4
  • 2 total stops
  • 10h 49m total
  • Ottawa to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 8/4
  • 1 total stop
  • 4h 30m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 20% potential increase in price (C$ 218 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 61 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
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 4 March 2026.
Use the filters below to find and compare flights from Ottawa to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 4/4

8:40 a.m.-12:10 p.m.

1 stop4h 30m

Chicago Midway

Tue 7/4

11:00 a.m.-8:24 a.m.

1 stop20h 24m

C$ 469

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 4/4

8:40 a.m.-12:10 p.m.

1 stop4h 30m

Chicago Midway

Tue 7/4

11:00 a.m.-7:54 p.m.

1 stop7h 54m

C$ 497

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/4

6:55 p.m.-12:10 p.m.

1 stop18h 15m

Chicago Midway

Sun 5/4

11:00 a.m.-12:39 a.m.

1 stop12h 39m

C$ 551

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/4

7:00 a.m.-10:15 a.m.

1 stop4h 15m

Chicago Midway

Sun 5/4

4:05 p.m.-10:29 p.m.

1 stop5h 24m

C$ 555

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 27/3

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Fri 3/4

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

1 stop23h 29m

C$ 563

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 1/5

6:55 a.m.-12:43 p.m.

2 stops6h 48m

Chicago Midway

Sun 3/5

9:27 a.m.-12:20 a.m.

2 stops13h 53m

C$ 619

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 8/4

6:45 a.m.-10:15 a.m.

1 stop4h 30m

Chicago Midway

Sat 11/4

12:55 p.m.-9:19 a.m.

1 stop19h 24m

C$ 645

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/7

11:00 a.m.-2:35 p.m.

1 stop4h 35m

Chicago Midway

Sat 11/7

10:25 a.m.-7:09 p.m.

1 stop7h 44m

C$ 653

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Wed 8/4

10:00 a.m.-2:20 p.m.

1 stop5h 20m

Chicago O'Hare Intl

Sat 11/4

9:50 a.m.-4:51 p.m.

1 stop6h 01m

C$ 663

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 16/4

10:44 a.m.-12:17 p.m.

Nonstop2h 33m

Chicago O'Hare Intl

Thu 30/4

12:55 p.m.-11:54 p.m.

1 stop9h 59m

C$ 780

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 34 resultsSorted by cheapest first
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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 27 February 2026.

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$ 179). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 335). 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 March 2026.

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.

How much does it cost to fly round-trip from Ottawa to Chicago?

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 89% 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.

Toronto (YTZ) is the most affordable 1-stop option, with an average round-trip price of C$ 522.

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 March 2026.
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
421 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
421 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
United Airlines
7.4
Good
9,388 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Air Canada
7.1
Good
10,776 reviews
Porter Airlines
8.0
Very good
421 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Entertainment

7.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 2h 27m. There are 1051 km between Ottawa and Chicago. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

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

    Currently priced at C$ 317, 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$ 458 and C$ 486, respectively. You may be able to fly from Ottawa to Chicago for 47% 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 (76%), Republic Airways (76%) and Air Canada (73%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 256. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 384 on average, our data indicates C$ 1,509 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$ 179). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 335). 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

Browse thousands of different options on Cheapflights for your next trip

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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 4 March 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 317AverageC$ 473FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
United AirlinesCheapestC$ 458AverageC$ 611FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 486AverageC$ 629FlexibilityNo 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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