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Cheap flights from Ottawa to Chicago Midway Airport from C$ 272

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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
22 Nov — 29 Nov1
1 adult
1 adult, Economy, 0 bags

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 23 October 2025.

Round-trip from

C$ 426

One-way from

C$ 272

Popular in

March

Cheapest in

December

Average price

C$ 617
11/12-9/1
  • 11/12-9/1
  • 3 total stops
  • 19h 51m total
  • Ottawa to Chicago
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12/11
  • 12/11
  • 2 total stops
  • 32h 40m total
  • Ottawa to Chicago
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Highest demand for flights based on searches. 11% potential increase in price (C$ 106 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 64 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Ottawa to Midway

Enter your travel dates to find the best prices.

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 23 October 2025.

Thu 11/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Fri 9/110:18 a.m.MDW - YOW
1 stop12h 40mMultiple Airlines
Deal found 23/10C$ 426
Thu 18/129:30 a.m.YOW - MDW
1 stop13h 28mMultiple Airlines
Sun 11/110:18 a.m.MDW - YOW
1 stop12h 40mMultiple Airlines
Deal found 21/10C$ 465
Tue 18/113:35 p.m.YOW - MDW
2 stops9h 20mMultiple Airlines
Thu 20/116:20 a.m.MDW - YOW
1 stop10h 05mMultiple Airlines
Deal found 21/10C$ 493
Tue 18/113:55 p.m.YOW - MDW
1 stop9h 00mMultiple Airlines
Tue 25/116:20 a.m.MDW - YOW
1 stop5h 15mMultiple Airlines
Deal found 21/10C$ 498
Fri 21/115:40 a.m.YOW - MDW
1 stop10h 40mMultiple Airlines
Mon 24/116:05 a.m.MDW - YOW
2 stops34h 20mMultiple Airlines
Deal found 23/10C$ 501
Tue 16/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Fri 9/110:18 a.m.MDW - YOW
1 stop12h 40mMultiple Airlines
Deal found 21/10C$ 503
Fri 19/129:30 a.m.YOW - MDW
1 stop13h 28mMultiple Airlines
Fri 9/110:18 a.m.MDW - YOW
1 stop12h 40mMultiple Airlines
Deal found 21/10C$ 510
Tue 11/113:55 p.m.YOW - MDW
1 stop9h 00mMultiple Airlines
Thu 13/116:26 p.m.MDW - YOW
2 stops16h 03mMultiple Airlines
Deal found 21/10C$ 515
Thu 4/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Mon 8/123:10 p.m.MDW - YOW
1 stop25h 03mMultiple Airlines
Deal found 21/10C$ 528

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 23 October 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

Thu 4/12

6:50 a.m.-1:01 p.m.

2 stops7h 11m

Chicago Midway

Mon 8/12

3:10 p.m.-5:13 p.m.

1 stop25h 03m

C$ 528

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 12/12

12:10 p.m.-3:20 p.m.

1 stop4h 10m

Chicago Midway

Fri 9/1

10:18 a.m.-11:58 p.m.

1 stop12h 40m

C$ 532

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 16/11

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

1 stop10h 40m

Chicago Midway

Thu 20/11

6:20 a.m.-12:35 p.m.

1 stop5h 15m

C$ 552

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 13/4

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

1 stop10h 40m

Chicago Midway

Wed 22/4

11:00 a.m.-12:39 a.m.

1 stop12h 39m

C$ 567

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 21/11

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

1 stop10h 40m

Chicago Midway

Mon 24/11

11:00 a.m.-12:42 a.m.

1 stop12h 42m

C$ 570

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 16/4

6:50 a.m.-3:20 p.m.

1 stop9h 30m

Chicago Midway

Thu 23/4

11:00 a.m.-12:39 a.m.

1 stop12h 39m

C$ 571

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 27/11

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

1 stop10h 40m

Chicago Midway

Tue 2/12

7:44 a.m.-5:25 p.m.

1 stop8h 41m

C$ 574

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 12/11

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Tue 25/11

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 585

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 7/12

4:20 p.m.-11:20 a.m.

2 stops20h 00m

Chicago Midway

Sun 14/12

11:00 a.m.-5:29 p.m.

1 stop5h 29m

C$ 588

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 19/4

12:10 p.m.-3:20 p.m.

1 stop4h 10m

Chicago Midway

Wed 22/4

11:00 a.m.-12:39 a.m.

1 stop12h 39m

C$ 588

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/10

Showing 1-10 of 22 results
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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$ 183). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). 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 23 October 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 in the evening could potentially save you up to 23% 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 23 October 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
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Crew

8.6

Boarding

8.2

Food

7.6

Overall

8.0

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
8.0
Very good
382 reviews
Porter Airlines
8.0
Very good
382 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Crew

8.6

Boarding

8.2

Food

7.6

Overall

8.0

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.

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

    Currently priced at C$ 376, 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$ 183). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). 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 23 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 376AverageC$ 498FlexibilityNo 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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