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Cheap flights from Ottawa to Chicago from C$ 245

YOW — CHI
25 Sep — 2 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 4/107:20 a.m. -
1 stop10h 20m
Sun 11/105:30 p.m. -
1 stop11h 05m
Deal found 22/8C$ 417
Fri 16/107:20 a.m. -
1 stop10h 20m
Mon 19/105:30 p.m. -
1 stop11h 05m
Deal found 23/8C$ 424
Sun 4/107:20 a.m. -
1 stop10h 20m
Thu 8/105:30 p.m. -
1 stop11h 05m
Deal found 22/8C$ 433
Sat 3/104:15 p.m. -
1 stop25h 25m
Mon 5/105:30 p.m. -
1 stop11h 05m
Deal found 22/8C$ 464
Thu 22/107:20 a.m. -
1 stop10h 20m
Mon 26/108:04 a.m. -
1 stop8h 16m
Deal found 21/8C$ 465
Thu 17/96:55 a.m. -
1 stop8h 40m
Tue 22/911:45 a.m. -
1 stop11h 35m
Deal found 25/8C$ 467
Fri 2/107:20 a.m. -
1 stop10h 20m
Sun 4/105:30 p.m. -
1 stop24h 50m
Deal found 24/8C$ 467
Thu 15/106:50 a.m. -
1 stop8h 45m
Wed 21/1011:45 a.m. -
1 stop11h 35m
Deal found 25/8C$ 480
Thu 24/96:55 a.m. -
1 stop8h 40m
Sun 27/93:20 p.m. -
1 stop8h 00m
Deal found 25/8C$ 483
Tue 22/98:00 a.m. -
1 stop4h 00m
Tue 29/911:45 a.m. -
1 stop8h 57m
Deal found 25/8C$ 487
Fri 18/96:25 p.m. -
1 stop17h 35m
Mon 21/93:20 p.m. -
1 stop8h 00m
Deal found 21/8C$ 497
Fri 2/107:20 a.m. -
1 stop10h 20m
Mon 5/105:30 p.m. -
1 stop11h 05m
Deal found 25/8C$ 497

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 417

One-way from

C$ 245

Popular in

January

Cheapest in

February

Average price

C$ 930

Good round-trip deal

C$ 768 or less

Good one-way deal

C$ 385 or less
WestJet
  • WestJet
  • 4/10-11/10
  • 2 total stops
  • 21h 25m total
  • Ottawa to Chicago
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WestJet
  • WestJet
  • 4/10
  • 1 total stop
  • 10h 20m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 0% potential increase in price (C$ 5 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease (C$ 56 potential savings vs. average RT price).
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Average for round-trip flights in August 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

Thu 17/9

6:55 a.m.-2:35 p.m.

1 stop8h 40m

Chicago Midway

Tue 22/9

3:20 p.m.-12:20 a.m.

1 stop8h 00m

C$ 500

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 2/10

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Mon 5/10

11:45 a.m.-5:52 p.m.

1 stop5h 07m

C$ 568

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 10/10

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Sat 17/10

11:45 a.m.-7:07 p.m.

1 stop6h 22m

C$ 601

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 19/9

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Tue 22/9

3:20 p.m.-9:42 p.m.

1 stop5h 22m

C$ 651

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Sat 12/9

7:00 a.m.-5:51 p.m.

2 stops11h 51m

Chicago Midway

Thu 17/9

3:20 p.m.-8:02 p.m.

1 stop3h 42m

C$ 677

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 17/9

8:00 a.m.-2:35 p.m.

1 stop7h 35m

Chicago Midway

Mon 21/9

3:20 p.m.-9:42 p.m.

1 stop5h 22m

C$ 703

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sun 13/9

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

1 stop6h 45m

Chicago O'Hare Intl

Tue 15/9

5:30 p.m.-5:35 a.m.

1 stop11h 05m

C$ 738

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 2/10

8:55 p.m.-9:07 a.m.

2 stops13h 12m

Chicago Midway

Sun 4/10

3:20 p.m.-9:42 p.m.

1 stop5h 22m

C$ 843

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Fri 18/9

10:40 a.m.-2:35 p.m.

1 stop4h 55m

Chicago Midway

Mon 21/9

11:45 a.m.-5:35 p.m.

2 stops28h 50m

C$ 856

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 17/9

7:00 a.m.-11:21 a.m.

1 stop5h 21m

Chicago O'Hare Intl

Sun 20/9

1:55 p.m.-5:16 p.m.

Nonstop2h 21m

C$ 857

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/8

Showing 1-10 of 46 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, September is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 555). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,116). 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 (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$ 626 and C$ 948 in October.
The cheapest round-trip price found within the last 5 days was C$ 417 on WestJet (4 Oct-11 Oct).

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

Toronto (YTZ) – chosen by Cheapflights users on 83% 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, 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
458 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

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

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

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
10,122 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

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
11,537 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Boarding

8.2

Overall

8.0

Comfort

8.0

Entertainment

6.9

Food

7.6

Crew

8.6

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 4h 55m. There are 1048 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$ 472. 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 (84%), ANA (82%) 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$ 518 on average, our data indicates C$ 1,385 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, September is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 555). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,116). 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$ 982FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 472AverageC$ 762FlexibilityNo 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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