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Cheap flights from Ottawa to Chicago from C$ 258

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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
29 May — 5 Jun1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in February or May, booked 29 days in advance, depart on a Saturday or Thursday and return on a Monday

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 29 April 2026.

Tue 19/57:00 a.m.
YOW
-
ORD
2 stops17h 13m
Multiple Airlines
Tue 26/55:30 p.m.
ORD
-
YOW
1 stop23h 30m
Multiple Airlines
Deal found 26/4C$ 482
Mon 25/510:10 a.m.
YOW
-
MDW
2 stops49h 59m
Multiple Airlines
Mon 1/610:15 a.m.
MDW
-
YOW
1 stop4h 44m
Multiple Airlines
Deal found 26/4C$ 515
Wed 20/57:20 a.m.
YOW
-
ORD
1 stop10h 20m
WestJet
Mon 25/55:30 p.m.
ORD
-
YOW
1 stop11h 05m
WestJet
Deal found 29/4C$ 534
Fri 12/68:00 a.m.
YOW
-
MDW
1 stop7h 35m
Porter Airlines
Fri 19/63:20 p.m.
MDW
-
YOW
1 stop3h 44m
Porter Airlines
Deal found 28/4C$ 546
Mon 1/67:00 a.m.
YOW
-
ORD
1 stop30h 37m
Multiple Airlines
Thu 4/612:59 p.m.
ORD
-
YOW
1 stop22h 18m
Multiple Airlines
Deal found 25/4C$ 546
Thu 21/58:40 a.m.
YOW
-
ORD
1 stop6h 37m
American Airlines
Mon 25/58:08 a.m.
ORD
-
YOW
1 stop5h 22m
American Airlines
Deal found 29/4C$ 548
Thu 4/66:55 a.m.
YOW
-
MDW
1 stop8h 40m
Multiple Airlines
Mon 8/63:20 p.m.
MDW
-
YOW
1 stop22h 34m
Multiple Airlines
Deal found 28/4C$ 549
Mon 25/57:20 a.m.
YOW
-
ORD
1 stop10h 20m
Multiple Airlines
Mon 1/67:33 p.m.
ORD
-
YOW
2 stops21h 04m
Multiple Airlines
Deal found 27/4C$ 553
Tue 26/59:05 a.m.
YOW
-
ORD
1 stop12h 06m
Multiple Airlines
Tue 2/61:49 p.m.
ORD
-
YOW
1 stop26h 48m
Multiple Airlines
Deal found 26/4C$ 560
Fri 29/57:00 a.m.
YOW
-
ORD
1 stop17h 13m
Multiple Airlines
Tue 2/65:05 a.m.
ORD
-
YOW
2 stops14h 00m
Multiple Airlines
Deal found 25/4C$ 564
Fri 29/57:00 a.m.
YOW
-
ORD
1 stop17h 13m
Multiple Airlines
Mon 1/61:50 p.m.
ORD
-
YOW
2 stops26h 03m
Multiple Airlines
Deal found 26/4C$ 567
Sat 30/59:35 a.m.
YOW
-
MDW
1 stop25h 10m
Porter Airlines
Mon 1/610:15 a.m.
MDW
-
YOW
1 stop3h 39m
Porter Airlines
Deal found 26/4C$ 568

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 29 April 2026.

Round-trip from

C$ 482

One-way from

C$ 258

Popular in

January

Cheapest in

February

Average price

C$ 650

Good round-trip deal

C$ 586 or less

Good one-way deal

C$ 313 or less
19/5-26/5
  • 19/5-26/5
  • 3 total stops
  • 40h 43m total
  • Ottawa to Chicago
Search Deals
8/5
  • 8/5
  • 1 total stop
  • 9h 57m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 60 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 29 April 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

Cheapest round-trip

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 24/7

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

1 stop4h 35m

Chicago Midway

Sun 26/7

3:20 p.m.-9:44 p.m.

1 stop5h 24m

C$ 613

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/6

7:00 a.m.-10:02 p.m.

2 stops16h 02m

Chicago Midway

Sun 7/6

10:15 a.m.-2:54 p.m.

1 stop3h 39m

C$ 613

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 5/6

2:20 p.m.-11:04 a.m.

2 stops21h 44m

Chicago Midway

Sun 7/6

10:15 a.m.-5:54 p.m.

1 stop6h 39m

C$ 668

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 10/5

5:55 p.m.-9:45 a.m.

1 stop16h 50m

Chicago Midway

Wed 13/5

10:30 a.m.-9:44 p.m.

1 stop10h 14m

C$ 690

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 15/6

8:50 p.m.-9:40 a.m.

1 stop13h 50m

Chicago Midway

Sat 27/6

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

1 stop7h 44m

C$ 713

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/6

9:35 a.m.-9:35 a.m.

1 stop25h 00m

Chicago Midway

Sun 7/6

3:20 p.m.-8:04 p.m.

1 stop3h 44m

C$ 713

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 19/6

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

1 stop4h 35m

Chicago Midway

Sat 27/6

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

1 stop7h 44m

C$ 747

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 12/5

2:20 p.m.-11:09 a.m.

2 stops21h 49m

Chicago Midway

Fri 15/5

3:20 p.m.-8:04 p.m.

1 stop3h 44m

C$ 762

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 9/6

8:00 a.m.-9:35 a.m.

1 stop26h 35m

Chicago Midway

Sat 13/6

10:15 a.m.-6:54 p.m.

1 stop7h 39m

C$ 813

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 15/6

8:50 p.m.-9:40 a.m.

1 stop13h 50m

Chicago Midway

Sat 27/6

6:35 p.m.-8:05 a.m.

2 stops12h 30m

C$ 824

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/4

Showing 1-10 of 38 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?

Booking 29 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, August 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 January is currently the most expensive (average of C$ 736). 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 29 April 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.

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 29 April 2026.

The most flights from YOW to CHI are scheduled on a Monday (13 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (11 on average).

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 83% 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$ 505.

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: 5h 08m.

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 29 April 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
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
435 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,677 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,982 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 11 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 4h 35m. There are 1048 km between Ottawa and Chicago.

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

    Currently priced at C$ 316, 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 Air Canada and United Airlines - these airlines can fly you to your destination from C$ 418 and C$ 458, respectively. You may be able to fly from Ottawa to Chicago for 48% 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 Republic Airways (72%), ANA (70%) and Air Canada (66%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 261. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 574 on average, our data indicates C$ 677 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, August 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 January is currently the most expensive (average of C$ 736). 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 29 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 316AverageC$ 435FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 418AverageC$ 547FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 458AverageC$ 562FlexibilityNo cancel feeOn-time69%
Search United Airlines 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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