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Cheap flights from Ottawa to Chicago Midway Airport from C$ 304

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 30/10. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy

Cheap flight deals from Ottawa to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Ottawa (YOW) to Midway (MDW). 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 17 September 2025.

Round-trip from

C$ 413

One-way from

C$ 304

Popular in

March

Cheapest in

December

Average price

C$ 597
Porter Airlines
  • Porter Airlines
  • 12/10-19/10
  • 2 total stops
  • 10h 08m total
  • Ottawa to Chicago
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30/10
  • 30/10
  • 1 total stop
  • 10h 40m total
  • Ottawa to Chicago
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Highest demand for flights based on searches. 11% potential increase in price (C$ 102 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 55 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Ottawa to Midway

Cheapest flights from Ottawa to Midway
Explore the most affordable flight options available from Ottawa to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 September 2025.

Sun 12/101:15 p.m.YOW - MDW
1 stop4h 09mPorter Airlines
Sun 19/109:35 a.m.MDW - YOW
1 stop5h 59mPorter Airlines
Deal found 16/9C$ 413
Tue 14/1011:00 a.m.YOW - MDW
1 stop6h 24mMultiple Airlines
Tue 21/109:35 a.m.MDW - YOW
1 stop13h 47mMultiple Airlines
Deal found 16/9C$ 432
Tue 14/101:25 p.m.YOW - MDW
1 stop3h 59mPorter Airlines
Tue 21/109:35 a.m.MDW - YOW
1 stop7h 34mPorter Airlines
Deal found 16/9C$ 444
Thu 16/101:25 p.m.YOW - MDW
1 stop3h 59mPorter Airlines
Fri 24/109:35 a.m.MDW - YOW
1 stop7h 34mPorter Airlines
Deal found 17/9C$ 477
Thu 6/115:40 a.m.YOW - MDW
1 stop10h 40mMultiple Airlines
Mon 10/118:00 a.m.MDW - YOW
2 stops15h 42mMultiple Airlines
Deal found 16/9C$ 498
Thu 9/1011:00 a.m.YOW - MDW
1 stop6h 24mPorter Airlines
Sun 12/109:35 a.m.MDW - YOW
1 stop5h 59mPorter Airlines
Deal found 17/9C$ 521
Fri 3/104:25 p.m.YOW - MDW
1 stop18h 56mMultiple Airlines
Mon 6/1012:48 p.m.MDW - YOW
2 stops10h 34mMultiple Airlines
Deal found 15/9C$ 538
Sun 12/105:15 p.m.YOW - MDW
2 stops7h 10mMultiple Airlines
Sun 19/109:35 a.m.MDW - YOW
1 stop8h 59mMultiple Airlines
Deal found 16/9C$ 585
Thu 16/101:25 p.m.YOW - MDW
1 stop3h 59mMultiple Airlines
Fri 24/109:45 a.m.MDW - YOW
2 stops13h 37mMultiple Airlines
Deal found 17/9C$ 590
Tue 14/105:55 a.m.YOW - MDW
2 stops28h 45mWestJet
Tue 21/1012:48 p.m.MDW - YOW
2 stops10h 34mWestJet
Deal found 16/9C$ 608

Cheapflights Fare Finder

 
Customize your flight search to find flights from Ottawa to Midway 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 17 September 2025.
Use the filters below to find and compare flights from Ottawa to Chicago Midway Airport that are best for you.

Fly from

Ottawa

Fly to

Midway

Route

Depart

Return

Price

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 12/10

1:15 p.m.-4:24 p.m.

1 stop4h 09m

Chicago Midway

Sun 19/10

9:35 a.m.-4:34 p.m.

1 stop5h 59m

C$ 413

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 15/10

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

1 stop6h 24m

Chicago Midway

Wed 22/10

9:35 a.m.-4:34 p.m.

1 stop5h 59m

C$ 413

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 14/10

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

1 stop6h 24m

Chicago Midway

Tue 21/10

9:35 a.m.-12:22 a.m.

1 stop13h 47m

C$ 432

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 16/10

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

1 stop3h 59m

Chicago Midway

Fri 24/10

9:35 a.m.-6:09 p.m.

1 stop7h 34m

C$ 477

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 6/11

5:40 a.m.-3:20 p.m.

1 stop10h 40m

Chicago Midway

Mon 10/11

8:00 a.m.-12:42 a.m.

2 stops15h 42m

C$ 498

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 9/10

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

1 stop6h 24m

Chicago Midway

Sun 12/10

9:35 a.m.-4:34 p.m.

1 stop5h 59m

C$ 521

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 7/11

5:40 a.m.-3:20 p.m.

1 stop10h 40m

Chicago Midway

Mon 10/11

8:00 a.m.-12:42 a.m.

2 stops15h 42m

C$ 556

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 16/10

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

1 stop3h 59m

Chicago Midway

Fri 24/10

9:45 a.m.-12:22 a.m.

2 stops13h 37m

C$ 590

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 10/10

5:55 a.m.-8:39 a.m.

1 stop27h 44m

Chicago Midway

Sun 12/10

9:35 a.m.-4:34 p.m.

1 stop5h 59m

C$ 619

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 8/11

8:40 a.m.-11:50 a.m.

1 stop4h 10m

Chicago Midway

Mon 10/11

8:00 a.m.-12:42 a.m.

2 stops15h 42m

C$ 625

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 15 results
1
2

Best time to book a flight from Ottawa to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway 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 Midway Airport

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

Currently, September is the cheapest month in which you can book a flight from Ottawa to Chicago Midway Airport (average of C$ 207). Flying from Ottawa to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 MDW?

Find hourly flight availability from Ottawa to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 17 September 2025.

One of the essential ways to save on airfare from Ottawa to Chicago Midway Airport is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 17% on airfare.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated 17 September 2025.
Get a feel of what it's like to fly with Porter Airlines from Ottawa to Chicago Midway Airport 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
7.9
Good
365 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.6

Crew

8.6

Entertainment

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Comfort

7.9

Boarding

8.2

Food

7.6

Crew

8.6

Entertainment

7.0

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

Related info for your journey

Find useful and relevant information for your journey from Ottawa to Midway. 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 Midway?

    Located just 10.6 km from the city centre, Ottawa is the airport most travellers will use when flying to Chicago Midway from Ottawa. Booking flights from Ottawa (YOW) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 1 airline.

  • How long is the flight from Ottawa to Chicago Midway Airport?

    There are many flights that can get you from Ottawa to Chicago Midway Airport in 4h 09m. Fly via Porter Airlines to get the fastest option. There are 1048 km between Ottawa and Chicago Midway Airport.

  • What is the cheapest airline to fly from Ottawa to Chicago Midway Airport round-trip?

    Currently priced at C$ 369, Porter Airlines will fly you from Ottawa to Chicago Midway Airport and back. In addition to Porter Airlines, many other airlines offer competitively priced options for your trip. Users have found that Porter Airlines is 33% cheaper than the other options available to this destination.

  • Can I find deals for flights from Ottawa to Midway that include hotel bookings?

    Yes. In addition to deals on Ottawa to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Ottawa to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Ottawa to Midway.

  • Can I find deals for business class flights from Ottawa to Midway?

    Yes. Cheapflights offers flight deals from Ottawa to Midway 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 Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Ottawa to Chicago Midway Airport (average of C$ 207). Flying from Ottawa to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 airline flying from Ottawa to Midway

Discover the top airline that operate flights from Ottawa to Midway. 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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 369AverageC$ 499FlexibilityNo cancel feeOn-time52%
Search Porter 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 Midway?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Midway from Ottawa today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Ottawa to Midway?

Cheapflights simply makes it quick and affordable to book flights from Ottawa to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Ottawa to Midway with no change fees?

Certainly. Search results for flights to Midway from Ottawa shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Ottawa to Midway become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Midway from Ottawa today and book when prices fit your budget.

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