Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Ottawa to Chicago from C$ 303

YOW — CHI
22 Oct — 29 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

Sat 17/1010:40 a.m. -
1 stop4h 55m
Wed 21/1011:45 a.m. -
1 stop5h 07m
Deal found 18/9C$ 465
Mon 19/107:20 a.m. -
1 stop10h 20m
Mon 26/1012:20 p.m. -
1 stop6h 49m
Deal found 21/9C$ 479
Thu 22/107:20 a.m. -
1 stop10h 20m
Sun 25/106:20 p.m. -
1 stop22h 38m
Deal found 20/9C$ 493
Fri 20/117:00 a.m. -
1 stop11h 40m
Mon 23/116:20 p.m. -
1 stop22h 54m
Deal found 19/9C$ 542
Tue 27/107:05 a.m. -
2 stops15h 05m
Sun 1/116:20 p.m. -
1 stop16h 14m
Deal found 17/9C$ 548
Tue 3/117:00 a.m. -
1 stop7h 01m
Fri 6/1111:45 a.m. -
1 stop5h 13m
Deal found 18/9C$ 556
Tue 3/117:05 a.m. -
2 stops15h 05m
Fri 6/116:20 p.m. -
1 stop20h 49m
Deal found 20/9C$ 569
Sat 17/1010:40 a.m. -
1 stop4h 55m
Sat 24/1011:45 a.m. -
1 stop6h 22m
Deal found 19/9C$ 589
Fri 16/108:00 a.m. -
1 stop4h 00m
Wed 21/103:20 p.m. -
1 stop3h 42m
Deal found 17/9C$ 594
Mon 19/108:00 a.m. -
1 stop4h 00m
Wed 21/103:20 p.m. -
1 stop3h 42m
Deal found 18/9C$ 600
Fri 16/1010:40 a.m. -
1 stop4h 55m
Mon 19/103:20 p.m. -
1 stop5h 22m
Deal found 20/9C$ 632
Thu 15/108:00 a.m. -
1 stop4h 00m
Sun 18/1011:45 a.m. -
1 stop5h 07m
Deal found 17/9C$ 639

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 465

One-way from

C$ 303

Popular in

January

Cheapest in

February

Average price

C$ 870

Good round-trip deal

C$ 740 or less

Good one-way deal

C$ 376 or less
Porter Airlines
  • Porter Airlines
  • 17/10-21/10
  • 2 total stops
  • 10h 02m total
  • Ottawa to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 28/10-31/12
  • 1 total stop
  • 11h 40m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 5% potential price rise
Search Deals
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 September 2026
Search Deals
Price to beat on a round-trip flight from Ottawa to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Ottawa to Chicago (CHI).
Search Deals

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

Wed 28/10

7:05 a.m.-11:47 p.m.

2 stops17h 42m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 308

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Tue 3/11

7:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 313

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 26/10

5:35 a.m.-5:27 p.m.

3 stops36h 52m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 317

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Fri 26/2

1:45 p.m.-5:43 p.m.

1 stop4h 58m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 329

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 5/11

10:20 a.m.-2:37 p.m.

1 stop5h 17m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 336

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 25/10

5:30 a.m.-11:43 p.m.

3 stops43h 13m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 345

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 3/10

6:25 p.m.-5:51 p.m.

3 stops48h 26m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 362

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$ 373

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$ 373

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 17/10

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$ 388

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/9

Showing 1-10 of 40 resultsSorted by cheapest first
1
2
3
4

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$ 1,130). 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 (13 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 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$ 579 and C$ 1,206 in October.
The cheapest round-trip price found within the last 5 days was C$ 465 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$ 430.

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, 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
462 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

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
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

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
7.4
Good
10,224 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

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
11,661 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

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
12,082 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

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. 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 11 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 2h 43m. 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 are the cheapest airlines flying from Ottawa to Chicago round-trip?

    Currently priced at C$ 420, 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$ 477. You may be able to fly from Ottawa to Chicago for 46% 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$ 314. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 542 on average, our data indicates C$ 1,700 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$ 1,130). 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$ 420AverageC$ 953FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 477AverageC$ 793FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.