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Cheap flights from Ottawa to Chicago Midway Airport from C$ 236

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 14/1. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
25 Dec — 1 Jan1
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 25 November 2025.

Round-trip from

C$ 449

One-way from

C$ 236

Popular in

March

Cheapest in

December

Average price

C$ 714
Porter Airlines
  • Porter Airlines
  • 31/12-1/1
  • 2 total stops
  • 7h 54m total
  • Ottawa to Chicago
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14/1
  • 14/1
  • 1 total stop
  • 26h 02m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 124 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease (C$ 65 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 25 November 2025.

Wed 31/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Thu 1/14:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 24/11C$ 449
Thu 25/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Sun 28/1211:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 24/11C$ 467
Sat 20/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Fri 26/124:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 24/11C$ 470
Thu 25/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Mon 29/1211:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 24/11C$ 522
Wed 24/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Mon 29/1211:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 24/11C$ 545
Fri 26/128:40 a.m.YOW - MDW
1 stop7h 40mPorter Airlines
Mon 29/124:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 24/11C$ 553
Thu 11/128:40 a.m.YOW - MDW
1 stop7h 40mPorter Airlines
Sun 14/124:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 24/11C$ 573
Thu 11/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Sun 14/127:44 a.m.MDW - YOW
1 stop8h 41mMultiple Airlines
Deal found 24/11C$ 612
Wed 24/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Sun 28/1211:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 24/11C$ 625
Fri 26/128:40 a.m.YOW - MDW
1 stop7h 40mPorter Airlines
Sun 28/124:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 24/11C$ 649

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 25 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

Wed 31/12

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

1 stop4h 15m

Chicago Midway

Thu 1/1

4:15 p.m.-8:54 p.m.

1 stop3h 39m

C$ 449

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 2/1

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

1 stop4h 20m

Chicago Midway

Sun 4/1

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

1 stop5h 14m

C$ 466

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 25/12

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

1 stop4h 10m

Chicago Midway

Sun 28/12

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

1 stop5h 29m

C$ 467

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 20/12

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

1 stop4h 10m

Chicago Midway

Fri 26/12

4:15 p.m.-8:54 p.m.

1 stop3h 39m

C$ 470

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/1

7:00 a.m.-10:10 a.m.

1 stop4h 10m

Chicago Midway

Fri 16/1

11:05 a.m.-7:59 a.m.

1 stop19h 54m

C$ 471

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 21/1

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

1 stop14h 15m

Chicago Midway

Tue 27/1

11:05 a.m.-5:29 p.m.

1 stop5h 24m

C$ 480

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 9/4

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

1 stop4h 10m

Chicago Midway

Tue 14/4

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

1 stop5h 29m

C$ 504

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 20/3

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

1 stop4h 15m

Chicago Midway

Mon 23/3

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

1 stop5h 29m

C$ 518

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 25/12

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

1 stop4h 10m

Chicago Midway

Mon 29/12

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

1 stop5h 29m

C$ 522

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 14/1

9:30 a.m.-10:32 a.m.

1 stop26h 02m

C$ 236

Flights are sorted by cheapest round-trip flights first.

Deals found on 23/11

Showing 1-10 of 17 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$ 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.

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 25 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
394 reviews
Check prices

Entertainment

7.0

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
394 reviews
Porter Airlines
8.0
Very good
394 reviews
Check prices

Entertainment

7.0

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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 15m. 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$ 392, 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 29% 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 25 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 392AverageC$ 619FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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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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