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Cheap flights from Ottawa to Chicago from C$ 300

YOW — CHI
1 Oct — 8 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 26/96:01 p.m. -
1 stop6h 20m
Sun 27/910:40 a.m. -
Nonstop2h 19m
Deal found 27/8C$ 414
Sat 17/106:01 p.m. -
1 stop6h 20m
Sun 18/1010:40 a.m. -
Nonstop2h 19m
Deal found 29/8C$ 416
Thu 15/107:20 a.m. -
1 stop10h 20m
Sun 18/105:30 p.m. -
1 stop11h 05m
Deal found 28/8C$ 483
Sun 11/107:20 a.m. -
1 stop10h 20m
Sun 18/105:30 p.m. -
1 stop11h 05m
Deal found 27/8C$ 484
Thu 1/106:55 a.m. -
1 stop7h 30m
Sun 4/107:25 a.m. -
1 stop9h 10m
Deal found 31/8C$ 497
Wed 11/1112:15 p.m. -
1 stop6h 15m
Sun 15/1111:45 a.m. -
1 stop5h 29m
Deal found 27/8C$ 504
Thu 1/108:15 p.m. -
1 stop21h 25m
Sun 4/105:30 p.m. -
1 stop11h 05m
Deal found 27/8C$ 518
Thu 1/107:00 a.m. -
2 stops32h 45m
Fri 16/105:30 p.m. -
1 stop11h 05m
Deal found 27/8C$ 520
Mon 21/98:15 p.m. -
1 stop21h 25m
Tue 29/95:30 p.m. -
1 stop11h 05m
Deal found 31/8C$ 530
Sat 26/96:55 a.m. -
1 stop8h 40m
Sun 27/911:45 a.m. -
1 stop11h 35m
Deal found 27/8C$ 533
Thu 1/108:15 p.m. -
1 stop21h 25m
Fri 16/105:30 p.m. -
1 stop11h 05m
Deal found 27/8C$ 541
Mon 21/98:00 a.m. -
1 stop7h 35m
Tue 29/911:45 a.m. -
1 stop5h 07m
Deal found 31/8C$ 562

Find flight deals from Ottawa to Chicago

Round-trip from

C$ 414

One-way from

C$ 300

Popular in

January

Cheapest in

February

Average price

C$ 576

Good round-trip deal

C$ 761 or less

Good one-way deal

C$ 387 or less
Lufthansa
  • Lufthansa
  • 26/9-27/9
  • 1 total stop
  • 8h 39m total
  • Ottawa to Chicago
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28/9
  • 28/9
  • 1 total stop
  • 8h 40m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 0% potential increase in price (C$ 4 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).
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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 - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 1/10

6:55 a.m.-1:25 p.m.

1 stop7h 30m

Chicago O'Hare Intl

Sun 4/10

7:25 a.m.-5:35 p.m.

1 stop9h 10m

C$ 497

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 24/9

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

1 stop7h 35m

Chicago Midway

Fri 25/9

11:45 a.m.-8:02 p.m.

1 stop7h 17m

C$ 563

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Thu 1/10

8:00 a.m.-11:00 a.m.

1 stop4h 00m

Chicago Midway

Fri 16/10

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

1 stop5h 22m

C$ 609

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 - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Sat 19/9

10:00 a.m.-2:20 p.m.

1 stop5h 20m

Chicago O'Hare Intl

Tue 22/9

8:03 a.m.-2:55 p.m.

1 stop5h 52m

C$ 765

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Wed 14/10

10:00 a.m.-2:20 p.m.

1 stop5h 20m

Chicago O'Hare Intl

Wed 21/10

8:06 a.m.-2:55 p.m.

1 stop5h 49m

C$ 819

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 1/10

12:25 p.m.-4:40 p.m.

2 stops29h 15m

Chicago O'Hare Intl

Fri 16/10

5:30 p.m.-11:35 a.m.

2 stops17h 05m

C$ 826

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Tue 15/9

8:00 a.m.-11:00 a.m.

1 stop4h 00m

Chicago Midway

Sat 19/9

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

2 stops28h 50m

C$ 944

OttawaChicago

YOW Ottawa - MDW Chicago Midway

YOWMDW

Ottawa

Wed 16/9

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

1 stop4h 55m

Chicago Midway

Sat 19/9

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

2 stops28h 50m

C$ 944

OttawaChicago

YOW Ottawa - ORD Chicago O'Hare Intl

YOWORD

Ottawa

Thu 1/10

10:37 a.m.-12:00 p.m.

Nonstop2h 23m

Chicago O'Hare Intl

Fri 16/10

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

Nonstop2h 21m

C$ 948

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/8

Showing 1-10 of 36 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$ 563). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,119). 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 (9 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$ 502 and C$ 862 in September.
The cheapest round-trip price found within the last 5 days was C$ 414 on Lufthansa (26 Sep-27 Sep).

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

Toronto (YTZ) – chosen by Cheapflights users on 79% 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$ 426.

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

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

Comfort

8.0

Overall

8.0

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

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

Comfort

8.0

Overall

8.0

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
10,151 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

Comfort

8.0

Overall

8.0

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
11,566 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Crew

8.6

Boarding

8.2

Food

7.6

Entertainment

6.9

Comfort

8.0

Overall

8.0

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 11 outbound flights to Chicago per day.

  • How long is the flight from Ottawa to Chicago?

    Departing from Ottawa to Chicago will take you 6h 20m. 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$ 416, 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$ 497 on average, our data indicates C$ 1,625 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$ 563). Flying from Ottawa to Chicago in January is currently the most expensive (average of C$ 1,119). 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$ 416AverageC$ 984FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 474AverageC$ 763FlexibilityNo 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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