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Cheap flights from Ottawa to Chicago from C$ 278

YOW — CHI
17 Oct — 24 Oct1
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

Sun 25/105:30 a.m. -
1 stop13h 10m
Thu 29/108:00 a.m. -
1 stop8h 20m
Deal found 13/9C$ 478
Sat 24/106:25 p.m. -
1 stop18h 15m
Thu 29/108:00 a.m. -
1 stop8h 20m
Deal found 13/9C$ 491
Sun 25/105:30 a.m. -
1 stop13h 10m
Fri 30/1012:20 p.m. -
1 stop11h 24m
Deal found 13/9C$ 499
Thu 15/107:20 a.m. -
1 stop10h 20m
Mon 19/105:30 p.m. -
1 stop11h 05m
Deal found 16/9C$ 501
Sat 24/106:25 p.m. -
1 stop18h 15m
Sat 31/1012:20 p.m. -
1 stop11h 24m
Deal found 13/9C$ 512
Thu 29/105:30 a.m. -
1 stop8h 43m
Thu 5/114:30 p.m. -
1 stop7h 14m
Deal found 13/9C$ 517
Sat 24/106:25 p.m. -
1 stop18h 15m
Fri 30/108:00 a.m. -
1 stop8h 20m
Deal found 13/9C$ 519
Wed 28/105:30 a.m. -
1 stop8h 43m
Wed 4/1110:15 a.m. -
1 stop13h 29m
Deal found 13/9C$ 524
Tue 27/105:35 a.m. -
1 stop13h 08m
Tue 3/1112:50 p.m. -
1 stop10h 54m
Deal found 12/9C$ 530
Sat 24/106:55 a.m. -
1 stop7h 28m
Wed 28/1012:50 p.m. -
1 stop10h 54m
Deal found 13/9C$ 537
Fri 16/106:50 a.m. -
1 stop9h 05m
Sun 18/109:55 a.m. -
1 stop13h 25m
Deal found 16/9C$ 540
Thu 15/1010:40 a.m. -
1 stop4h 55m
Mon 19/103:20 p.m. -
1 stop3h 42m
Deal found 16/9C$ 590

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 478

One-way from

C$ 278

Popular in

January

Cheapest in

February

Average price

C$ 750

Good round-trip deal

C$ 774 or less

Good one-way deal

C$ 389 or less
25/10-29/10
  • 25/10-29/10
  • 2 total stops
  • 21h 30m total
  • Ottawa to Chicago
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3/11-31/12
  • 3/11-31/12
  • 1 total stop
  • 13h 10m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 5% potential price decrease (C$ 53 potential savings vs. average RT price).
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Average for round-trip flights in September 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

Sun 25/10

5:30 a.m.-5:40 p.m.

1 stop13h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 279

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 21/10

6:50 a.m.-1:23 p.m.

1 stop7h 33m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 282

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 14/10

8:15 p.m.-4:40 p.m.

1 stop21h 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

Tue 3/11

7:00 a.m.-11:47 p.m.

3 stops17h 47m

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

Wed 14/10

2:10 p.m.-9:21 a.m.

2 stops20h 11m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 368
Quickest round-trip

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 21/10

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

1 stop4h 00m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 370

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 8/10

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

1 stop4h 55m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 372

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 3/10

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

1 stop6h 20m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 393

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Fri 16/10

6:15 p.m.-4:40 p.m.

2 stops47h 25m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 400

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 8/10

10:00 a.m.-2:20 p.m.

1 stop5h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 411

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 41 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$ 566). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,124). 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 Wednesday (13 on average). You will have fewer flight options on Friday, 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$ 558 and C$ 955 in October.
The cheapest round-trip price found within the last 5 days was C$ 478 on Multiple Airlines (25 Oct-29 Oct).

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

Toronto (YTZ) – chosen by Cheapflights users on 76% 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$ 428.

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, andAmerican Airlines 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
462 reviews
Check prices

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

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
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

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
7.4
Good
10,214 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

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
7.1
Good
12,076 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

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
11,640 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Food

7.6

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

6.9

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. 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 10 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 4h 15m. There are 1051 km between Ottawa and Chicago.

  • What are the cheapest airlines flying from Ottawa to Chicago round-trip?

    Currently priced at C$ 418, 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$ 475. You may be able to fly from Ottawa to Chicago for 45% 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 ANA (82%), Avianca (82%) and United Airlines (80%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 321. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 499 on average, our data indicates C$ 1,651 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$ 566). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,124). 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$ 418AverageC$ 989FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 475AverageC$ 773FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

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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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