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Cheap flights from Ottawa to Chicago from C$ 294

YOW — CHI
8 Dec — 15 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 4/1212:15 p.m. -
1 stop6h 25m
Sun 6/1212:15 p.m. -
1 stop4h 58m
Deal found 4/11C$ 533
Fri 11/1212:15 p.m. -
1 stop6h 25m
Mon 14/1212:15 p.m. -
1 stop4h 58m
Deal found 7/11C$ 537
Sat 5/1212:40 p.m. -
1 stop6h 00m
Sun 6/1212:15 p.m. -
1 stop4h 58m
Deal found 4/11C$ 540
Thu 26/1112:15 p.m. -
1 stop6h 25m
Fri 27/1112:15 p.m. -
1 stop4h 57m
Deal found 5/11C$ 542
Thu 3/1212:15 p.m. -
1 stop6h 25m
Mon 7/1212:15 p.m. -
1 stop4h 58m
Deal found 7/11C$ 545
Thu 3/1212:15 p.m. -
1 stop6h 25m
Sun 6/1212:15 p.m. -
1 stop4h 58m
Deal found 3/11C$ 548
Sat 5/1212:40 p.m. -
1 stop6h 00m
Mon 7/1212:15 p.m. -
1 stop4h 58m
Deal found 7/11C$ 550
Thu 3/1212:15 p.m. -
1 stop6h 25m
Thu 10/1212:15 p.m. -
1 stop4h 58m
Deal found 6/11C$ 568
Thu 10/1212:15 p.m. -
1 stop6h 25m
Sun 13/1212:15 p.m. -
1 stop4h 58m
Deal found 6/11C$ 572
Fri 27/1112:15 p.m. -
1 stop6h 25m
Sat 28/1112:15 p.m. -
1 stop6h 52m
Deal found 4/11C$ 575
Tue 8/1212:15 p.m. -
1 stop6h 25m
Wed 9/1212:15 p.m. -
1 stop4h 58m
Deal found 7/11C$ 593
Thu 3/127:00 a.m. -
2 stops27h 46m
Thu 10/125:02 p.m. -
3 stops23h 54m
Deal found 6/11C$ 792

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 533

One-way from

C$ 294

Popular in

January

Cheapest in

February

Average price

C$ 1,088

Good round-trip deal

C$ 852 or less

Good one-way deal

C$ 525 or less
Porter Airlines
  • Porter Airlines
  • 4/12-6/12
  • 2 total stops
  • 11h 23m 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, 7% potential price rise
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Cheapest flight prices on average. 4% potential price decrease (C$ 49 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 - 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$ 350

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 9/1

7:00 a.m.-4:46 p.m.

3 stops34h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 353

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 11/1

1:45 p.m.-4:39 p.m.

3 stops27h 54m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 377

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 9/1

4:35 p.m.-9:43 a.m.

2 stops18h 08m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 383

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 24/11

7:05 a.m.-8:12 a.m.

2 stops26h 07m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 476

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 10/12

12:50 p.m.-10:05 a.m.

3 stops22h 15m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 479

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Mon 11/1

12:00 p.m.-5:30 p.m.

1 stop6h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 480

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 23/12

8:50 p.m.-11:34 a.m.

1 stop15h 44m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 483

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 22/11

7:05 a.m.-7:23 a.m.

2 stops25h 18m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 492

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 30/12

6:15 a.m.-8:00 a.m.

Nonstop2h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 517

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 30 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$ 357). Flying from Ottawa to Chicago in October is currently the most expensive (average of C$ 1,067). 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 Wednesday, which is when the least amount of flights are scheduled (6 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$ 647 and C$ 1,105 in December.
The cheapest round-trip price found within the last 5 days was C$ 533 on Porter Airlines (4 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$ 463.

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
468 reviews
Check prices

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

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
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

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
10,474 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

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
11,875 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

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
12,233 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Comfort

8.0

Overall

8.0

Boarding

8.2

Entertainment

6.9

Food

7.6

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 7 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$ 834, 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$ 397. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 541 on average, our data indicates C$ 906 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$ 357). Flying from Ottawa to Chicago in October is currently the most expensive (average of C$ 1,067). 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$ 834AverageC$ 1,033FlexibilityNo 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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