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Cheap flights from Ottawa to Chicago from C$ 264

YOW — CHI
18 Sep — 25 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Ottawa to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Ottawa to Chicago

Thu 17/98:00 a.m. -
1 stop4h 00m
Sun 20/93:20 p.m. -
1 stop3h 42m
Deal found 14/8C$ 461
Sun 20/96:55 a.m. -
1 stop8h 40m
Fri 25/93:20 p.m. -
1 stop8h 00m
Deal found 17/8C$ 472
Thu 17/96:55 a.m. -
1 stop8h 40m
Sun 20/93:20 p.m. -
1 stop8h 00m
Deal found 15/8C$ 480
Wed 23/98:00 a.m. -
1 stop4h 00m
Tue 29/93:20 p.m. -
1 stop3h 42m
Deal found 15/8C$ 489
Mon 14/96:55 a.m. -
1 stop8h 40m
Sun 20/93:20 p.m. -
1 stop3h 42m
Deal found 15/8C$ 491
Sat 5/910:30 a.m. -
1 stop5h 05m
Wed 9/93:20 p.m. -
1 stop3h 42m
Deal found 14/8C$ 497
Fri 2/107:20 a.m. -
1 stop10h 20m
Fri 9/105:30 p.m. -
1 stop11h 05m
Deal found 17/8C$ 500
Thu 17/96:55 a.m. -
1 stop7h 26m
Sun 20/92:15 p.m. -
1 stop9h 05m
Deal found 17/8C$ 509
Fri 25/97:20 a.m. -
1 stop10h 20m
Sun 27/95:30 p.m. -
2 stops17h 05m
Deal found 15/8C$ 514
Sun 6/97:20 a.m. -
1 stop10h 20m
Fri 11/95:30 p.m. -
1 stop11h 05m
Deal found 15/8C$ 516
Sun 20/97:20 a.m. -
1 stop10h 20m
Fri 25/95:30 p.m. -
1 stop11h 05m
Deal found 17/8C$ 518
Fri 2/107:20 a.m. -
1 stop10h 20m
Sun 4/105:30 p.m. -
1 stop11h 05m
Deal found 18/8C$ 532

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 464

One-way from

C$ 264

Popular in

January

Cheapest in

February

Average price

C$ 773

Good round-trip deal

C$ 744 or less

Good one-way deal

C$ 364 or less
Porter Airlines
  • Porter Airlines
  • 17/9-20/9
  • 2 total stops
  • 8h 37m total
  • Ottawa to Chicago
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Porter Airlines
  • Porter Airlines
  • 14/9
  • 1 total stop
  • 4h 55m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 26 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 57 potential savings vs. average RT price).
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Average for round-trip flights in August 2026
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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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Cheapflights Fare Finder

 
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 Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 17/9

6:55 a.m.-2:35 p.m.

1 stop8h 40m

Chicago Midway

Sun 20/9

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 508

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 17/9

1:20 p.m.-5:38 a.m.

2 stops17h 18m

Chicago O'Hare Intl

Sun 20/9

5:30 p.m.-5:35 a.m.

1 stop11h 05m

C$ 591

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 15/10

6:50 a.m.-2:35 p.m.

1 stop8h 45m

Chicago Midway

Mon 19/10

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 720

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 2/9

8:00 a.m.-2:35 p.m.

1 stop7h 35m

Chicago Midway

Wed 9/9

3:20 p.m.-8:02 p.m.

1 stop3h 42m

C$ 765

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 31/8

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Thu 3/9

3:20 p.m.-9:42 p.m.

1 stop5h 22m

C$ 779

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 21/9

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

1 stop4h 00m

Chicago Midway

Tue 22/9

11:45 a.m.-5:52 p.m.

1 stop5h 07m

C$ 861

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 19/9

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Tue 22/9

3:20 p.m.-9:42 p.m.

1 stop5h 22m

C$ 870

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Mon 21/9

10:40 a.m.-7:35 p.m.

1 stop9h 55m

Chicago O'Hare Intl

Tue 22/9

9:39 p.m.-9:56 a.m.

1 stop11h 17m

C$ 888

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 19/9

9:15 a.m.-2:35 p.m.

1 stop6h 20m

Chicago Midway

Sat 26/9

11:45 a.m.-5:35 p.m.

2 stops28h 50m

C$ 912

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 3/9

7:30 a.m.-11:00 a.m.

1 stop4h 30m

Chicago Midway

Thu 10/9

11:45 a.m.-5:52 p.m.

1 stop5h 07m

C$ 924

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/8

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

Cheapflights Insights

Everything you need to know about your flight from Ottawa to Chicago

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$ 537). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,119). 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?

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

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?

Airfare is below average for this route at the moment.
Ottawa to Chicago flights typically cost between C$ 561 and C$ 938 in September.
The cheapest round-trip price found within the last 5 days was C$ 464 on Porter Airlines (17 Sep-20 Sep).

What’s the top layover airport for flights from Ottawa to Chicago?

Toronto (YTZ) – chosen by Cheapflights users on 80% of one-stop itineraries from Ottawa to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Ottawa to Chicago?

Toronto (YTZ) is the most affordable 1-stop option, with an average round-trip price of C$ 426.

What’s the fastest layover option from Ottawa to Chicago?

Flights via Toronto (YTZ) have the shortest average one-way travel time for 1-stop routes: 4h 00m.

Which airport typically offers the quickest layover for flights from Ottawa to Chicago?

Flights via Toronto (YTZ) offer the fastest connection on this route, with an average layover time of 1h 11m.

Reviews of airlines servicing Chicago

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
457 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
457 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,104 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,505 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Crew

8.6

Overall

8.0

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Related info for your journey

  • 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. 2 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 7h 35m. There are 1048 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$ 416, Air Canada will fly you from Ottawa to Chicago and back. In addition to Air Canada, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as C$ 474. You may be able to fly from Ottawa to Chicago for 42% 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 (84%), ANA (82%) and Air Canada (72%).

  • 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$ 540 on average, our data indicates C$ 1,450 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$ 537). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,119). 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

Top 2 airlines flying from Ottawa to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 416AverageC$ 1,122FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 474AverageC$ 766FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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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