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Cheap flights from Ottawa to Chicago from C$ 289

YOW — CHI
3 Dec — 10 Dec1
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

Fri 20/1112:15 p.m. -
1 stop6h 25m
Mon 23/1112:15 p.m. -
1 stop4h 57m
Deal found 29/10C$ 533
Mon 23/117:05 a.m. -
1 stop17h 29m
Wed 2/128:15 a.m. -
2 stops14h 05m
Deal found 29/10C$ 534
Mon 23/1112:15 p.m. -
1 stop6h 25m
Wed 2/1212:15 p.m. -
1 stop4h 58m
Deal found 29/10C$ 535
Sat 5/1212:40 p.m. -
1 stop6h 00m
Mon 7/1212:15 p.m. -
1 stop4h 58m
Deal found 1/11C$ 552
Thu 3/1212:15 p.m. -
1 stop6h 25m
Sun 6/1212:15 p.m. -
1 stop4h 58m
Deal found 31/10C$ 556
Tue 24/1112:15 p.m. -
1 stop6h 25m
Sat 28/1112:15 p.m. -
1 stop6h 52m
Deal found 29/10C$ 567
Sat 5/1212:40 p.m. -
1 stop6h 00m
Sat 12/1212:15 p.m. -
1 stop6h 53m
Deal found 1/11C$ 587
Sat 5/1212:40 p.m. -
1 stop6h 00m
Tue 8/1212:15 p.m. -
1 stop4h 58m
Deal found 29/10C$ 593
Mon 30/1112:15 p.m. -
1 stop6h 25m
Mon 7/1212:15 p.m. -
1 stop4h 58m
Deal found 2/11C$ 598
Tue 15/123:15 p.m. -
2 stops21h 18m
Tue 22/128:35 p.m. -
1 stop26h 32m
Deal found 31/10C$ 755
Wed 16/123:15 p.m. -
2 stops33h 02m
Wed 23/128:35 p.m. -
1 stop26h 32m
Deal found 1/11C$ 815
Thu 3/1212:10 p.m. -
3 stops28h 57m
Sun 6/125:02 p.m. -
3 stops21h 55m
Deal found 30/10C$ 822

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 533

One-way from

C$ 289

Popular in

January

Cheapest in

February

Average price

C$ 1,076

Good round-trip deal

C$ 872 or less

Good one-way deal

C$ 565 or less
Porter Airlines
  • Porter Airlines
  • 20/11-23/11
  • 2 total stops
  • 11h 22m total
  • Ottawa to Chicago
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10/1-31/12
  • 10/1-31/12
  • 1 total stop
  • 24h 38m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 12% potential price rise
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Cheapest flight prices on average. 4% potential price decrease (C$ 50 potential savings vs. average RT price).
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Average for round-trip flights in November 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

Mon 11/1

5:30 a.m.-11:50 a.m.

3 stops31h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 328

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 15/12

7:00 a.m.-11:33 a.m.

2 stops29h 33m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 334

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 11/1

5:30 a.m.-11:46 p.m.

3 stops43h 16m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 337

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 10/1

1:45 p.m.-7:44 p.m.

1 stop6h 59m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 338

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 10/1

1:45 p.m.-11:50 a.m.

3 stops47h 05m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 340

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 10/1

5:30 a.m.-4:26 p.m.

3 stops35h 56m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 347

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 8/1

5:30 a.m.-4:26 p.m.

3 stops35h 56m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 351

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Fri 8/1

1:45 p.m.-9:45 p.m.

3 stops33h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 366

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 13/12

10:15 a.m.-4:42 p.m.

1 stop7h 27m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 368

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 16/11

5:30 a.m.-5:47 p.m.

3 stops37h 17m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 372

Flights are sorted by cheapest round-trip flights first.

Deals found on 30/10

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, February is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 376). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,127). 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 (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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$ 640 and C$ 1,093 in November.
The cheapest round-trip price found within the last 5 days was C$ 533 on Porter Airlines (20 Nov-23 Nov).

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$ 458.

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

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

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

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

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
10,461 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

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
11,847 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

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
12,223 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

Food

7.6

Boarding

8.2

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 8 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 2h 44m. 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$ 825, 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 United Airlines (91%), ANA (91%) and Republic Airways (90%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 393. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 552 on average, our data indicates C$ 896 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, February is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 376). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,127). 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$ 825AverageC$ 1,022FlexibilityNo 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.

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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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