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Cheap flights from Ottawa to Chicago from C$ 261

YOW — CHI
13 Oct — 20 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 11/107:20 a.m. -
1 stop10h 20m
Thu 15/105:30 p.m. -
1 stop11h 05m
Deal found 8/9C$ 454
Sat 17/109:15 a.m. -
1 stop6h 20m
Wed 21/1011:45 a.m. -
1 stop5h 07m
Deal found 9/9C$ 459
Sat 10/106:01 p.m. -
1 stop6h 20m
Sun 11/1010:40 a.m. -
Nonstop2h 19m
Deal found 10/9C$ 497
Sat 10/106:55 a.m. -
1 stop8h 40m
Sun 11/103:20 p.m. -
1 stop8h 00m
Deal found 10/9C$ 502
Thu 15/106:50 a.m. -
1 stop8h 45m
Sun 18/103:20 p.m. -
1 stop8h 00m
Deal found 11/9C$ 522
Sat 24/106:55 a.m. -
1 stop13h 53m
Sun 25/1010:15 a.m. -
1 stop13h 29m
Deal found 10/9C$ 523
Tue 27/105:35 a.m. -
1 stop13h 08m
Tue 3/1112:50 p.m. -
1 stop10h 54m
Deal found 12/9C$ 527
Sun 1/1112:15 p.m. -
1 stop6h 25m
Sun 29/1112:20 p.m. -
1 stop4h 54m
Deal found 13/9C$ 542
Tue 27/108:25 a.m. -
1 stop4h 15m
Fri 30/1012:20 p.m. -
1 stop4h 54m
Deal found 13/9C$ 545
Sun 25/1012:15 p.m. -
1 stop6h 25m
Sun 1/1112:20 p.m. -
1 stop4h 54m
Deal found 10/9C$ 546
Fri 30/1012:15 p.m. -
1 stop6h 25m
Sun 1/1112:20 p.m. -
1 stop4h 54m
Deal found 9/9C$ 548
Sat 10/106:55 a.m. -
2 stops14h 17m
Sun 11/109:55 a.m. -
1 stop6h 40m
Deal found 10/9C$ 549

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 454

One-way from

C$ 261

Popular in

January

Cheapest in

February

Average price

C$ 746

Good round-trip deal

C$ 770 or less

Good one-way deal

C$ 387 or less
WestJet
  • WestJet
  • 11/10-15/10
  • 2 total stops
  • 21h 25m total
  • Ottawa to Chicago
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WestJet
  • WestJet
  • 23/10-31/12
  • 1 total stop
  • 10h 20m 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$ 277

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$ 280

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 19/10

12:25 p.m.-11:00 a.m.

2 stops23h 35m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 329

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 3/11

7:05 a.m.-5:47 p.m.

2 stops35h 42m

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

Fri 23/10

8:15 p.m.-6:31 p.m.

2 stops23h 16m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 352

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 10/10

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$ 359

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 24/10

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$ 365
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$ 368

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 25/10

7:05 a.m.-11:43 p.m.

2 stops41h 38m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 369

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$ 370

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/9

Showing 1-10 of 42 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$ 563). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,118). 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 Saturday (13 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$ 555 and C$ 950 in October.
The cheapest round-trip price found within the last 5 days was C$ 459 on Porter Airlines (17 Oct-21 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$ 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, 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
460 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Crew

8.6

Overall

8.0

Food

7.6

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
460 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Crew

8.6

Overall

8.0

Food

7.6

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
7.4
Good
10,211 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Crew

8.6

Overall

8.0

Food

7.6

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
7.1
Good
12,049 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Crew

8.6

Overall

8.0

Food

7.6

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
11,619 reviews
Porter Airlines
8.0
Very good
460 reviews
Check prices

Boarding

8.2

Comfort

8.0

Entertainment

6.9

Crew

8.6

Overall

8.0

Food

7.6

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. 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 9 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 6h 20m. There are 1048 km between Ottawa and Chicago.

  • 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$ 472. 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 Avianca (82%), ANA (80%) 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$ 546 on average, our data indicates C$ 1,595 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$ 563). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,118). 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$ 983FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 472AverageC$ 769FlexibilityNo 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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