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Cheap flights from Ottawa to Chicago from C$ 312

YOW — CHI
13 Nov — 20 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 21/1112:10 p.m. -
1 stop4h 28m
Sun 22/111:55 p.m. -
1 stop4h 57m
Deal found 10/10C$ 357
Fri 27/118:25 a.m. -
1 stop4h 10m
Tue 1/1212:15 p.m. -
1 stop4h 58m
Deal found 12/10C$ 543
Thu 12/1112:15 p.m. -
1 stop6h 25m
Sun 15/1112:15 p.m. -
1 stop4h 57m
Deal found 9/10C$ 544
Fri 27/118:25 a.m. -
1 stop4h 10m
Fri 4/1212:15 p.m. -
1 stop4h 58m
Deal found 12/10C$ 545
Sat 21/1112:40 p.m. -
1 stop6h 00m
Sun 22/1112:15 p.m. -
1 stop4h 57m
Deal found 10/10C$ 548
Tue 10/118:25 a.m. -
1 stop4h 10m
Tue 17/1112:15 p.m. -
1 stop4h 57m
Deal found 11/10C$ 551
Fri 20/118:25 a.m. -
1 stop4h 10m
Mon 23/1112:15 p.m. -
1 stop4h 57m
Deal found 12/10C$ 553
Wed 11/118:25 a.m. -
1 stop4h 10m
Sun 15/1112:15 p.m. -
1 stop4h 57m
Deal found 12/10C$ 554
Fri 6/1112:15 p.m. -
1 stop6h 25m
Sun 8/1112:15 p.m. -
1 stop4h 57m
Deal found 9/10C$ 555
Thu 31/128:00 a.m. -
1 stop12h 02m
Wed 6/16:01 a.m. -
2 stops31h 29m
Deal found 14/10C$ 850
Fri 27/1110:20 a.m. -
3 stops22h 17m
Thu 3/123:50 p.m. -
3 stops31h 51m
Deal found 13/10C$ 914
Wed 23/126:35 a.m. -
2 stops25h 26m
Sun 27/128:07 p.m. -
1 stop17h 23m
Deal found 11/10C$ 1,027

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 357

One-way from

C$ 312

Popular in

January

Cheapest in

February

Average price

C$ 1,065

Good round-trip deal

C$ 757 or less

Good one-way deal

C$ 384 or less
Air Canada
  • Air Canada
  • 21/11-22/11
  • 2 total stops
  • 9h 25m total
  • Ottawa to Chicago
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Porter Airlines
  • Porter Airlines
  • 10/11-31/12
  • 1 total stop
  • 4h 10m 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 October 2026
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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).
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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

Fri 27/11

8:25 a.m.-11:35 a.m.

1 stop4h 10m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 316

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 27/12

7:00 a.m.-1:15 p.m.

1 stop7h 15m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 348

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 10/11

10:30 a.m.-5:47 p.m.

2 stops32h 17m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 350

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Tue 10/11

10:30 a.m.-6:30 p.m.

2 stops33h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 352

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 18/2

7:05 a.m.-4:14 p.m.

1 stop10h 09m

Chicago O'Hare Intl

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

Mon 23/11

5:30 a.m.-11:34 p.m.

2 stops19h 04m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 377

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 26/10

7:05 a.m.-5:27 p.m.

2 stops35h 22m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 383

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 14/11

12:40 p.m.-9:00 a.m.

3 stops21h 20m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 390

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 17/2

4:25 p.m.-12:55 a.m.

1 stop9h 30m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 409

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 6/12

3:15 p.m.-8:42 p.m.

2 stops30h 27m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 424

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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$ 578). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,148). 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 Saturday, which is when the least amount of flights are scheduled (12 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$ 772 and C$ 1,172 in November.
The cheapest round-trip price found within the last 5 days was C$ 357 on Air Canada (21 Nov-22 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$ 437.

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
468 reviews
Check prices

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

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
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

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
10,364 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

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
11,774 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

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
12,170 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Boarding

8.2

Food

7.6

Overall

8.0

Comfort

8.0

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 6h 25m. 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$ 751, United Airlines will fly you from Ottawa to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on Air Canada for as low as C$ 840. You may be able to fly from Ottawa to Chicago for 6% 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 United Airlines (81%), ANA (81%) and Avianca (79%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 328. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 543 on average, our data indicates C$ 2,014 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$ 578). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,148). 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
United AirlinesCheapestC$ 751AverageC$ 906FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 840AverageC$ 1,065FlexibilityNo 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.

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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