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Cheap flights from Ottawa to Chicago from C$ 253

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/7. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — CHI
5 Jul — 12 Jul1
1 adult

Cheapflights Tip: The best prices from Ottawa to Chicago are usually found in May or April, booked 65 days in advance, depart on a Tuesday or Friday and return on a Tuesday

Cheap flight deals from Ottawa to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Ottawa (YOW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 30 June 2025.

Round-trip from

C$ 410

One-way from

C$ 253

Popular in

November

Cheapest in

May

Average price

C$ 622

Good round-trip deal

C$ 652 or less

Good one-way deal

C$ 363 or less
Porter Airlines
  • Porter Airlines
  • 19/9-22/9
  • 2 total stops
  • 10h 18m total
  • Ottawa to Chicago
Porter Airlines
  • Porter Airlines
  • 28/7
  • 1 total stop
  • 4h 49m total
  • Ottawa to Chicago
Highest demand for flights based on searches. 5% potential increase in price (C$ 44 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease (C$ 9 potential savings vs. average RT price).
Average for round-trip flights in June 2025
Price to beat on a round-trip flight from Ottawa to Chicago (CHI).
Price to beat on a one-way flight from Ottawa to Chicago (CHI).

Find flight deals from Ottawa to Chicago

Cheapest flights from Ottawa to Chicago
Explore the most affordable flight options available from Ottawa to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 June 2025.

Fri 19/91:25 p.m.YOW - MDW
1 stop3h 59mPorter Airlines
Mon 22/99:15 a.m.MDW - YOW
1 stop6h 19mPorter Airlines
Deal found 29/6C$ 410
Thu 25/910:37 a.m.YOW - ORD
Nonstop2h 24mUnited Airlines
Wed 8/1010:50 a.m.ORD - YOW
Nonstop2h 14mUnited Airlines
Deal found 28/6C$ 435
Thu 18/99:05 a.m.YOW - ORD
1 stop6h 50mAir Canada
Sun 28/96:20 p.m.ORD - YOW
1 stop4h 59mAir Canada
Deal found 28/6C$ 471
Fri 11/73:50 p.m.YOW - ORD
1 stop9h 03mMultiple Airlines
Sun 13/75:05 a.m.ORD - YOW
1 stop11h 10mMultiple Airlines
Deal found 27/6C$ 520
Mon 8/96:00 a.m.YOW - ORD
1 stop11h 43mWestJet
Wed 10/95:30 p.m.ORD - YOW
2 stops21h 49mWestJet
Deal found 28/6C$ 546
Wed 30/711:00 a.m.YOW - MDW
1 stop6h 24mMultiple Airlines
Wed 6/811:39 a.m.MDW - YOW
2 stops18h 06mMultiple Airlines
Deal found 30/6C$ 647
Fri 19/95:55 a.m.YOW - MDW
2 stops16h 49mWestJet
Tue 23/91:05 p.m.MDW - YOW
2 stops10h 17mWestJet
Deal found 28/6C$ 706
Tue 12/85:55 a.m.YOW - MDW
2 stops12h 52mDelta
Tue 19/812:43 p.m.MDW - YOW
2 stops10h 39mDelta
Deal found 28/6C$ 795

Cheapflights Fare Finder

Customize your flight search to find flights from Ottawa to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 30 June 2025.
Use the filters below to find and compare flights from Ottawa to Chicago that are best for you.

Fly from

Ottawa

Fly to

Chicago

Route

Depart

Return

Price

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 19/9

1:25 p.m.-4:24 p.m.

1 stop3h 59m

Chicago Midway

Mon 22/9

9:15 a.m.-4:34 p.m.

1 stop6h 19m

C$ 410

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 25/9

10:37 a.m.-12:01 p.m.

Nonstop2h 24m

Chicago O'Hare Intl

Wed 8/10

10:50 a.m.-2:04 p.m.

Nonstop2h 14m

C$ 435

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Thu 18/9

9:05 a.m.-2:55 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Sun 28/9

6:20 p.m.-12:19 a.m.

1 stop4h 59m

C$ 471

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Fri 11/7

3:50 p.m.-11:53 p.m.

1 stop9h 03m

Chicago O'Hare Intl

Sun 13/7

5:05 a.m.-5:15 p.m.

1 stop11h 10m

C$ 520

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 8/9

6:00 a.m.-4:43 p.m.

1 stop11h 43m

Chicago O'Hare Intl

Wed 10/9

5:30 p.m.-4:19 p.m.

2 stops21h 49m

C$ 546

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 30/7

11:00 a.m.-4:24 p.m.

1 stop6h 24m

Chicago Midway

Wed 6/8

11:39 a.m.-6:45 a.m.

2 stops18h 06m

C$ 647

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 19/9

5:55 a.m.-9:44 p.m.

2 stops16h 49m

Chicago Midway

Tue 23/9

1:05 p.m.-12:22 a.m.

2 stops10h 17m

C$ 706

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 12/8

5:55 a.m.-5:47 p.m.

2 stops12h 52m

Chicago Midway

Tue 19/8

12:43 p.m.-12:22 a.m.

2 stops10h 39m

C$ 795

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 28/7

12:35 p.m.-4:24 p.m.

1 stop4h 49m

C$ 253

OttawaChicago

YOW - ORD

YOWORD

Ottawa

Mon 28/7

4:25 p.m.-10:14 a.m.

1 stop18h 49m

C$ 287

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/6

Showing 1-10 of 15 results
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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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Ottawa to Chicago

How far ahead should I book a flight from Ottawa to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Ottawa to Chicago. Price data was last updated on 27 June 2025.

Booking 65 days in advance of your planned departure date is, on average, the best time to get cheap flights from Ottawa to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Ottawa to Chicago?

Currently, January is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 261). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 351). 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?

Find hourly flight availability from Ottawa to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 30 June 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 45% on flights from Ottawa to Chicago by exploring options for tickets at noon.

Weekly flight availability from Ottawa to Chicago

Explore weekly flight availability from Ottawa to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 30 June 2025.

The most flights from YOW to CHI are scheduled on a Monday (12 on average). You will have fewer flight options on Monday, 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?

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 30 June 2025.
Get a feel of what it's like to fly with Porter Airlines,Delta, andUnited 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.

Overall

8.0

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Overall

8.0

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
8.0
Very good

Overall

8.0

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Overall

8.0

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Overall

8.0

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Overall

8.0

Food

7.6

Comfort

8.1

Entertainment

7.0

Boarding

8.2

Crew

8.7

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

Related info for your journey

Find useful and relevant information for your journey from Ottawa to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • 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. 3 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.

  • What are the cheapest airlines flying from Ottawa to Chicago round-trip?

    Currently priced at C$ 410, Porter Airlines will fly you from Ottawa to Chicago and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from United Airlines and Air Canada - these airlines can fly you to your destination from C$ 435 and C$ 471, respectively. You may be able to fly from Ottawa to Chicago for 27% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Ottawa to Chicago one-way?

    The cheapest airlines for a one-way flight from Ottawa to Chicago are Porter Airlines (C$ 253), Air Canada (C$ 298), and United Airlines (C$ 302).

  • What are the most reliable airlines from Ottawa to Chicago?

    The top 3 most reliable airlines when flying from Ottawa to Chicago are Avianca (92%), ANA (90%) and GoJet (89%).

  • What are the cheapest flights from Ottawa to Chicago?

    Looking at all options, your cheapest flight can be booked for C$ 233. While the most popular route (Ottawa - Chicago O'Hare Intl) can be booked for C$ 435 on average our data indicates C$ 1,655 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, January is the cheapest month in which you can book a flight from Ottawa to Chicago (average of C$ 261). Flying from Ottawa to Chicago in March is currently the most expensive (average of C$ 351). 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

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Top 3 airlines flying from Ottawa to Chicago

Discover the top 3 airlines that operate flights from Ottawa to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 30 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 367AverageC$ 497FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights
Air CanadaCheapestC$ 498AverageC$ 658FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
United AirlinesCheapestC$ 532AverageC$ 687FlexibilityNo cancel feeOn-time69%
Search United Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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