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Cheap flights from Ottawa to Chicago Midway Airport 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 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
6 Dec — 13 Dec1
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 6 November 2025.

Round-trip from

C$ 453

One-way from

C$ 253

Popular in

March

Cheapest in

December

Average price

C$ 602
5/12-8/12
  • 5/12-8/12
  • 2 total stops
  • 35h 43m total
  • Ottawa to Chicago
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4/12
  • 4/12
  • 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$ 107 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease (C$ 63 potential savings vs. average RT price).
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Average for round-trip flights in November 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 6 November 2025.

Fri 5/125:40 a.m.YOW - MDW
1 stop10h 40mMultiple Airlines
Mon 8/123:10 p.m.MDW - YOW
1 stop25h 03mMultiple Airlines
Deal found 6/11C$ 453
Thu 4/125:40 a.m.YOW - MDW
1 stop10h 40mMultiple Airlines
Sun 7/127:44 a.m.MDW - YOW
1 stop27h 51mMultiple Airlines
Deal found 5/11C$ 480
Fri 19/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Fri 26/124:15 p.m.MDW - YOW
1 stop5h 14mPorter Airlines
Deal found 6/11C$ 546
Sat 6/128:40 a.m.YOW - MDW
1 stop4h 10mMultiple Airlines
Mon 8/128:42 p.m.MDW - YOW
2 stops19h 43mMultiple Airlines
Deal found 4/11C$ 560
Fri 26/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Sun 4/14:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 6/11C$ 571
Sun 14/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Wed 17/1211:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 6/11C$ 577
Sat 6/128:40 a.m.YOW - MDW
1 stop4h 10mPorter Airlines
Mon 8/1211:00 a.m.MDW - YOW
1 stop7h 54mPorter Airlines
Deal found 4/11C$ 601

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 6 November 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

Fri 5/12

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

1 stop10h 40m

Chicago Midway

Mon 8/12

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

1 stop25h 03m

C$ 453

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/12

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

1 stop10h 40m

Chicago Midway

Sun 7/12

6:37 p.m.-5:13 p.m.

1 stop21h 36m

C$ 512

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 19/12

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

1 stop4h 10m

Chicago Midway

Fri 26/12

4:15 p.m.-10:29 p.m.

1 stop5h 14m

C$ 546

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 13/3

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

1 stop4h 15m

Chicago Midway

Mon 16/3

4:15 p.m.-10:29 p.m.

1 stop5h 14m

C$ 553

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/12

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

1 stop4h 10m

Chicago Midway

Mon 8/12

8:42 p.m.-5:25 p.m.

2 stops19h 43m

C$ 560

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 1/1

8:55 p.m.-10:05 a.m.

1 stop14h 10m

Chicago Midway

Thu 8/1

9:07 p.m.-11:58 p.m.

2 stops25h 51m

C$ 566

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/12

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

1 stop4h 10m

Chicago Midway

Mon 8/12

11:00 a.m.-7:54 p.m.

1 stop7h 54m

C$ 601

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 8/12

4:35 p.m.-1:01 p.m.

2 stops21h 26m

Chicago Midway

Wed 17/12

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

1 stop5h 29m

C$ 608

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 8/12

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

1 stop4h 15m

Chicago Midway

Thu 11/12

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

1 stop12h 42m

C$ 631

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 6/12

5:40 a.m.-1:10 p.m.

2 stops32h 30m

Chicago Midway

Mon 8/12

10:49 a.m.-12:42 a.m.

2 stops12h 53m

C$ 640

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 16 results
1
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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$ 185). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of C$ 423). 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 6 November 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 6 November 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
387 reviews
Check prices

Food

7.6

Comfort

8.0

Crew

8.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
387 reviews
Porter Airlines
8.0
Very good
387 reviews
Check prices

Food

7.6

Comfort

8.0

Crew

8.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 10m. 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$ 379, 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$ 185). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of C$ 423). 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 6 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 379AverageC$ 499FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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How does Cheapflights help users find flights from Ottawa to Midway?

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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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