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Cheap flights from Ottawa to Chicago from C$ 261

YOW — CHI
7 Oct — 14 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 3/106:55 a.m. -
1 stop8h 40m
Sun 4/1011:45 a.m. -
1 stop11h 35m
Deal found 6/9C$ 447
Sat 17/106:55 a.m. -
1 stop8h 40m
Sun 18/103:20 p.m. -
1 stop8h 00m
Deal found 4/9C$ 462
Sat 3/106:01 p.m. -
1 stop6h 20m
Sun 4/1010:40 a.m. -
Nonstop2h 19m
Deal found 3/9C$ 479
Fri 23/107:20 a.m. -
1 stop10h 20m
Wed 28/106:20 p.m. -
1 stop17h 54m
Deal found 6/9C$ 484
Wed 25/115:30 a.m. -
1 stop13h 10m
Fri 27/1112:20 p.m. -
1 stop11h 24m
Deal found 6/9C$ 488
Thu 12/115:30 a.m. -
1 stop13h 10m
Mon 16/1112:20 p.m. -
1 stop11h 24m
Deal found 5/9C$ 495
Sat 3/106:55 a.m. -
1 stop7h 28m
Sun 4/109:55 a.m. -
1 stop13h 25m
Deal found 3/9C$ 501
Thu 12/115:30 a.m. -
1 stop13h 10m
Sun 15/116:20 p.m. -
1 stop12h 39m
Deal found 5/9C$ 516
Sat 17/106:01 p.m. -
1 stop6h 20m
Sun 18/1010:40 a.m. -
Nonstop2h 19m
Deal found 4/9C$ 533
Fri 2/106:55 a.m. -
1 stop7h 28m
Sun 4/103:45 p.m. -
1 stop7h 35m
Deal found 2/9C$ 541
Fri 16/108:00 a.m. -
1 stop4h 00m
Tue 20/103:20 p.m. -
1 stop20h 32m
Deal found 4/9C$ 553
Fri 2/108:50 p.m. -
1 stop15h 10m
Sun 4/1011:45 a.m. -
1 stop7h 17m
Deal found 3/9C$ 577

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 447

One-way from

C$ 261

Popular in

January

Cheapest in

February

Average price

C$ 606

Good round-trip deal

C$ 751 or less

Good one-way deal

C$ 385 or less
3/10-4/10
  • 3/10-4/10
  • 2 total stops
  • 20h 15m total
  • Ottawa to Chicago
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WestJet
  • WestJet
  • 15/10-31/12
  • 1 total stop
  • 10h 20m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 0% potential increase in price (C$ 0 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 55 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).
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 - MDW Chicago Midway

YOWMDW

Ottawa

Thu 1/10

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$ 349

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Mon 21/9

7:00 a.m.-11:51 a.m.

2 stops29h 51m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 364

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 21/9

7:00 a.m.-11:44 p.m.

2 stops17h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 376

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 28/11

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

1 stop6h 00m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 386

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 17/10

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$ 408

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Fri 25/9

7:00 a.m.-12:45 p.m.

1 stop6h 45m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 411

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sun 20/9

6:25 p.m.-5:46 p.m.

3 stops48h 21m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 426

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Mon 21/9

3:30 p.m.-11:00 a.m.

1 stop20h 30m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 455

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 1/10

7:00 a.m.-11:44 p.m.

3 stops17h 44m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 462

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 12/9

1:20 p.m.-5:38 a.m.

2 stops17h 18m

Chicago O'Hare Intl

Wed 31/12

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

Nonstop0h 00m

C$ 466

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

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$ 562). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,115). 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 Friday (17 on average). You will have fewer flight options on Tuesday, 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$ 501 and C$ 908 in October.
The cheapest round-trip price found within the last 5 days was C$ 447 on Multiple Airlines (3 Oct-4 Oct).

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

Toronto (YTZ) – chosen by Cheapflights users on 73% 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$ 425.

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
458 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,173 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
American Airlines
7.1
Good
12,042 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,593 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Boarding

8.2

Crew

8.6

Entertainment

6.9

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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. 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$ 415, 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$ 471. You may be able to fly from Ottawa to Chicago for 43% 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$ 484 on average, our data indicates C$ 1,591 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$ 562). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,115). 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$ 415AverageC$ 981FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 471AverageC$ 767FlexibilityNo 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.

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