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Cheap flights from Ottawa to Chicago from C$ 239

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 29/5. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
18 May — 25 May1
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 Friday 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 18 April 2026.

Sat 30/57:00 a.m.
YOW
-
ORD
1 stop17h 13m
Multiple Airlines
Sat 6/68:05 a.m.
ORD
-
YOW
2 stops15h 15m
Multiple Airlines
Deal found 15/4C$ 458
Tue 21/47:00 a.m.
YOW
-
ORD
1 stop15h 17m
Multiple Airlines
Tue 28/47:15 p.m.
ORD
-
YOW
1 stop21h 10m
Multiple Airlines
Deal found 14/4C$ 469
Wed 6/56:55 a.m.
YOW
-
MDW
1 stop8h 40m
Multiple Airlines
Mon 11/54:52 p.m.
MDW
-
YOW
2 stops30h 28m
Multiple Airlines
Deal found 13/4C$ 484
Thu 30/44:15 p.m.
YOW
-
ORD
1 stop9h 09m
Multiple Airlines
Mon 4/51:49 p.m.
ORD
-
YOW
1 stop21h 26m
Multiple Airlines
Deal found 13/4C$ 494
Wed 6/58:00 a.m.
YOW
-
ORD
2 stops13h 11m
Multiple Airlines
Thu 14/55:30 p.m.
ORD
-
YOW
1 stop20h 03m
Multiple Airlines
Deal found 14/4C$ 501
Sat 2/57:00 a.m.
YOW
-
ORD
2 stops15h 17m
Multiple Airlines
Mon 4/512:59 p.m.
ORD
-
YOW
1 stop22h 16m
Multiple Airlines
Deal found 14/4C$ 508
Tue 5/58:00 a.m.
YOW
-
ORD
2 stops13h 11m
Multiple Airlines
Thu 7/51:49 p.m.
ORD
-
YOW
1 stop21h 26m
Multiple Airlines
Deal found 14/4C$ 513
Tue 5/58:00 a.m.
YOW
-
ORD
2 stops13h 11m
Multiple Airlines
Fri 8/51:49 p.m.
ORD
-
YOW
1 stop26h 46m
Multiple Airlines
Deal found 14/4C$ 516
Thu 2/79:05 a.m.
YOW
-
ORD
1 stop8h 06m
Multiple Airlines
Mon 31/87:55 a.m.
ORD
-
YOW
2 stops15h 25m
Multiple Airlines
Deal found 15/4C$ 523
Tue 5/52:20 p.m.
YOW
-
MDW
2 stops21h 49m
Multiple Airlines
Fri 29/53:20 p.m.
MDW
-
YOW
1 stop3h 44m
Multiple Airlines
Deal found 14/4C$ 528
Thu 4/66:55 a.m.
YOW
-
MDW
1 stop8h 40m
Multiple Airlines
Sun 7/610:25 a.m.
MDW
-
YOW
1 stop12h 55m
Multiple Airlines
Deal found 13/4C$ 532
Thu 30/47:00 a.m.
YOW
-
MDW
2 stops13h 31m
Multiple Airlines
Mon 4/53:20 p.m.
MDW
-
YOW
1 stop25h 34m
Multiple Airlines
Deal found 13/4C$ 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 18 April 2026.

Round-trip from

C$ 458

One-way from

C$ 239

Popular in

January

Cheapest in

February

Average price

C$ 581

Good round-trip deal

C$ 551 or less

Good one-way deal

C$ 289 or less
30/5-6/6
  • 30/5-6/6
  • 3 total stops
  • 32h 28m total
  • Ottawa to Chicago
Search Deals
29/5
  • 29/5
  • 1 total stop
  • 17h 13m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 15% potential increase in price (C$ 155 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 62 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 18 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 26/6

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

1 stop4h 35m

Chicago Midway

Thu 2/7

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

1 stop3h 44m

C$ 599

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.-8:04 p.m.

1 stop3h 44m

C$ 602

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 30/4

6:50 a.m.-10:15 a.m.

1 stop4h 25m

Chicago Midway

Mon 4/5

3:20 p.m.-5:54 p.m.

1 stop25h 34m

C$ 612

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 28/5

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

1 stop4h 35m

Chicago Midway

Mon 8/6

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

1 stop5h 24m

C$ 621

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 29/7

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

1 stop4h 35m

Chicago Midway

Sun 2/8

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

1 stop3h 44m

C$ 633

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 26/6

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

1 stop4h 35m

Chicago Midway

Sun 28/6

10:25 a.m.-5:54 p.m.

1 stop6h 29m

C$ 635

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 29/6

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

1 stop4h 35m

Chicago Midway

Mon 6/7

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

1 stop3h 44m

C$ 642

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 23/7

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

1 stop4h 35m

Chicago Midway

Wed 29/7

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

1 stop3h 44m

C$ 642

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 24/6

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

1 stop4h 35m

Chicago Midway

Tue 30/6

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

1 stop3h 44m

C$ 648

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 17/6

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

1 stop4h 35m

Chicago Midway

Wed 24/6

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

1 stop3h 44m

C$ 654

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/4

Showing 1-10 of 44 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 10 April 2026.

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$ 737). 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 18 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 18 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 (12 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 85% 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$ 506.

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 09m.

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 18 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

Food

7.6

Crew

8.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

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

Food

7.6

Crew

8.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

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
9,604 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Crew

8.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

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
10,934 reviews
Porter Airlines
8.0
Very good
435 reviews
Check prices

Food

7.6

Crew

8.6

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.0

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 12 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 2h 08m. 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 Air Canada and United Airlines - these airlines can fly you to your destination from C$ 419 and C$ 458, respectively. You may be able to fly from Ottawa to Chicago for 46% 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$ 247. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 538 on average, our data indicates C$ 574 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$ 737). 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 18 April 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 317AverageC$ 436FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 419AverageC$ 548FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 458AverageC$ 566FlexibilityNo 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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