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Cheap flights from Ottawa to Chicago from C$ 328

YOW — CHI
27 Oct — 3 Nov1
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 31/107:00 a.m. -
1 stop11h 40m
Sun 1/116:20 p.m. -
1 stop22h 54m
Deal found 23/9C$ 515
Mon 16/117:05 a.m. -
2 stops30h 46m
Thu 19/1112:20 p.m. -
1 stop4h 54m
Deal found 22/9C$ 547
Thu 15/1012:25 p.m. -
2 stops23h 35m
Sun 18/103:20 p.m. -
1 stop22h 35m
Deal found 22/9C$ 554
Tue 3/117:00 a.m. -
1 stop11h 40m
Fri 6/116:20 p.m. -
1 stop20h 49m
Deal found 22/9C$ 563
Mon 2/115:40 p.m. -
1 stop19h 00m
Thu 5/116:20 p.m. -
1 stop20h 49m
Deal found 22/9C$ 566
Thu 22/107:20 a.m. -
1 stop10h 20m
Thu 29/108:00 a.m. -
1 stop8h 20m
Deal found 23/9C$ 587
Tue 20/107:20 a.m. -
2 stops23h 20m
Tue 27/1012:20 p.m. -
1 stop4h 54m
Deal found 22/9C$ 594
Tue 3/117:00 a.m. -
1 stop7h 01m
Fri 6/1111:45 a.m. -
1 stop5h 13m
Deal found 22/9C$ 604
Fri 16/108:00 a.m. -
1 stop4h 00m
Mon 19/103:20 p.m. -
1 stop3h 42m
Deal found 22/9C$ 612
Wed 21/108:15 p.m. -
1 stop21h 25m
Fri 30/108:00 a.m. -
1 stop8h 20m
Deal found 23/9C$ 612
Mon 2/117:05 a.m. -
2 stops30h 46m
Thu 5/1112:20 p.m. -
1 stop4h 54m
Deal found 22/9C$ 619
Tue 3/117:05 a.m. -
2 stops30h 46m
Fri 6/1112:20 p.m. -
1 stop4h 54m
Deal found 22/9C$ 624

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 515

One-way from

C$ 328

Popular in

January

Cheapest in

February

Average price

C$ 878

Good round-trip deal

C$ 746 or less

Good one-way deal

C$ 380 or less
Porter Airlines
  • Porter Airlines
  • 31/10-1/11
  • 2 total stops
  • 34h 34m total
  • Ottawa to Chicago
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17/11-31/12
  • 17/11-31/12
  • 2 total stops
  • 35h 42m total
  • Ottawa to Chicago
Search Deals
High demand for flights, 5% potential price rise
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Cheapest flight prices on average. 4% potential price decrease (C$ 53 potential savings vs. average RT price).
Search Deals
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 - MDW Chicago Midway

YOWMDW

Ottawa

Tue 17/11

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$ 328

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 11/11

7:05 a.m.-8:56 a.m.

2 stops26h 51m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 335

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Tue 17/11

5:30 a.m.-12:51 p.m.

3 stops32h 21m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 349

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 11/11

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$ 353

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 1/11

12:15 p.m.-5:40 p.m.

1 stop6h 25m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 365

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 11/11

12:15 p.m.-5:40 p.m.

1 stop6h 25m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 370

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 10/11

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$ 383

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 9/11

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$ 390

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 26/1

4:35 p.m.-11:46 p.m.

2 stops32h 11m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 390

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 10/10

6:25 p.m.-11:00 a.m.

1 stop17h 35m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 416

Flights are sorted by cheapest round-trip flights first.

Deals found on 22/9

Showing 1-10 of 37 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$ 574). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,140). 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 Tuesday, which is when the least amount of flights are scheduled (11 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$ 597 and C$ 1,314 in October.
The cheapest round-trip price found within the last 5 days was C$ 515 on Porter Airlines (31 Oct-1 Nov).

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$ 434.

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
463 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

6.9

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
463 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

6.9

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
10,244 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

6.9

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
11,695 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

6.9

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
12,099 reviews
Porter Airlines
8.0
Very good
463 reviews
Check prices

Comfort

8.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Entertainment

6.9

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 12 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 2h 48m. 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$ 424, 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$ 481. 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$ 325. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 604 on average, our data indicates C$ 1,759 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$ 574). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,140). 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$ 424AverageC$ 961FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 481AverageC$ 800FlexibilityNo 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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