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Cheap flights from Ottawa to Chicago from C$ 273

YOW — CHI
23 Nov — 30 Nov1
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 3/128:25 a.m. -
1 stop4h 10m
Sun 6/1212:15 p.m. -
1 stop4h 58m
Deal found 21/10C$ 504
Tue 8/1212:15 p.m. -
1 stop6h 25m
Sat 12/1212:15 p.m. -
1 stop6h 53m
Deal found 22/10C$ 518
Tue 8/127:00 a.m. -
2 stops16h 00m
Sat 12/126:20 p.m. -
1 stop16h 13m
Deal found 22/10C$ 529
Tue 24/118:25 a.m. -
1 stop4h 10m
Fri 27/1112:15 p.m. -
1 stop4h 57m
Deal found 22/10C$ 534
Fri 20/118:25 a.m. -
1 stop4h 10m
Wed 2/1212:15 p.m. -
1 stop4h 58m
Deal found 22/10C$ 538
Fri 20/118:25 a.m. -
1 stop4h 10m
Sun 22/1112:15 p.m. -
1 stop4h 57m
Deal found 21/10C$ 541
Thu 26/118:25 a.m. -
1 stop4h 10m
Wed 2/1212:15 p.m. -
1 stop4h 58m
Deal found 20/10C$ 545
Sat 21/1112:40 p.m. -
1 stop6h 00m
Mon 23/1112:15 p.m. -
1 stop4h 57m
Deal found 23/10C$ 550
Sat 5/124:40 p.m. -
1 stop30h 34m
Sat 12/126:20 p.m. -
1 stop16h 13m
Deal found 21/10C$ 552
Sat 21/1110:15 a.m. -
2 stops15h 28m
Mon 23/116:20 p.m. -
1 stop12h 37m
Deal found 23/10C$ 557
Wed 18/118:00 a.m. -
2 stops10h 47m
Wed 25/118:42 p.m. -
1 stop19h 03m
Deal found 21/10C$ 627
Fri 20/113:10 p.m. -
2 stops17h 23m
Sun 22/111:16 p.m. -
2 stops22h 55m
Deal found 21/10C$ 749

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 504

One-way from

C$ 273

Popular in

January

Cheapest in

February

Average price

C$ 1,134

Good round-trip deal

C$ 874 or less

Good one-way deal

C$ 493 or less
Porter Airlines
  • Porter Airlines
  • 3/12-6/12
  • 2 total stops
  • 9h 08m total
  • Ottawa to Chicago
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5/12-31/12
  • 5/12-31/12
  • 2 total stops
  • 30h 02m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 8% potential price rise
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Cheapest flight prices on average. 4% potential price decrease (C$ 51 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 5/12

4:40 p.m.-9:42 p.m.

2 stops30h 02m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 273

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 30/1

10:35 a.m.-11:50 a.m.

2 stops26h 15m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 298

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Mon 11/1

10:35 a.m.-12:55 a.m.

2 stops39h 20m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 309

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 5/12

10:25 a.m.-4:06 p.m.

2 stops30h 41m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 321

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 6/12

8:00 a.m.-11:33 a.m.

2 stops52h 33m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 328

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 4/1

3:10 p.m.-4:26 p.m.

2 stops26h 16m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 339

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 13/12

12:50 p.m.-9:42 p.m.

3 stops33h 52m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 339

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 29/1

5:40 p.m.-11:46 p.m.

3 stops31h 06m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 340
Quickest round-trip

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 6/12

12:15 p.m.-5:40 p.m.

1 stop6h 25m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 344

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 14/12

8:00 a.m.-11:33 a.m.

2 stops28h 33m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 353

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/10

Showing 1-10 of 35 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, March is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 569). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,129). 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.

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$ 700 and C$ 1,077 in December.
The cheapest round-trip price found within the last 5 days was C$ 504 on Porter Airlines (3 Dec-6 Dec).

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

Toronto (YTZ) – chosen by Cheapflights users on 77% 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$ 459.

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 18m.

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
467 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
United Airlines
7.3
Good
10,435 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,808 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
American Airlines
7.0
Good
12,192 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Entertainment

6.9

Overall

8.0

Comfort

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

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. 1 airline 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 3 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 6h. 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 is the cheapest airline to fly from Ottawa to Chicago round-trip?

    Currently priced at C$ 826, 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.

  • What are the most reliable airlines from Ottawa to Chicago?

    The top 3 most reliable airlines when flying from Ottawa to Chicago are ANA (85%), United Airlines (84%) and Air Canada (82%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 342. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 518 on average, our data indicates C$ 2,067 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, March is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 569). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,129). 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 airline flying from Ottawa to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 826AverageC$ 1,024FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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.

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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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