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Cheap flights from Ottawa to Chicago Midway Airport from C$ 256

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 31/1. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
17 Jan — 24 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 18 December 2025.

Wed 31/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Tue 6/111:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 16/12C$ 580
Wed 31/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Sat 3/14:15 p.m.MDW - YOW
1 stop5h 14mPorter Airlines
Deal found 16/12C$ 586
Wed 31/126:50 a.m.YOW - MDW
1 stop4h 15mPorter Airlines
Mon 5/14:15 p.m.MDW - YOW
1 stop3h 39mPorter Airlines
Deal found 16/12C$ 612
Wed 31/129:30 a.m.YOW - MDW
1 stop13h 28mMultiple Airlines
Fri 2/18:15 a.m.MDW - YOW
2 stops14h 43mMultiple Airlines
Deal found 16/12C$ 635
Tue 30/126:50 a.m.YOW - MDW
1 stop4h 15mMultiple Airlines
Fri 2/18:15 a.m.MDW - YOW
2 stops14h 43mMultiple Airlines
Deal found 16/12C$ 650
Wed 31/129:30 a.m.YOW - MDW
1 stop13h 28mMultiple Airlines
Sun 4/14:15 p.m.MDW - YOW
1 stop3h 39mMultiple Airlines
Deal found 16/12C$ 686
Tue 30/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Sat 3/14:15 p.m.MDW - YOW
1 stop5h 14mMultiple Airlines
Deal found 16/12C$ 730
Wed 31/129:30 a.m.YOW - MDW
1 stop13h 28mMultiple Airlines
Mon 5/16:14 p.m.MDW - YOW
2 stops12h 45mMultiple Airlines
Deal found 16/12C$ 732
Tue 30/1212:10 p.m.YOW - MDW
1 stop4h 10mPorter Airlines
Fri 2/111:00 a.m.MDW - YOW
1 stop5h 29mPorter Airlines
Deal found 16/12C$ 756
Tue 30/126:50 a.m.YOW - MDW
2 stops7h 11mMultiple Airlines
Sun 4/14:15 p.m.MDW - YOW
1 stop3h 39mMultiple Airlines
Deal found 16/12C$ 766

Find 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 18 December 2025.

Round-trip from

C$ 475

One-way from

C$ 256

Popular in

January

Cheapest in

October

Average price

C$ 665
12/1-19/1
  • 12/1-19/1
  • 3 total stops
  • 38h 14m total
  • Ottawa to Chicago
Search Deals
31/1
  • 31/1
  • 1 total stop
  • 28h 32m total
  • Ottawa to Chicago
Search Deals
Highest demand for flights based on searches. 21% potential increase in price (C$ 217 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease (C$ 85 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 18 December 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

Tue 13/1

3:55 p.m.-12:02 a.m.

1 stop9h 07m

Chicago Midway

Wed 21/1

1:20 p.m.-5:13 p.m.

2 stops26h 53m

C$ 489

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 12/1

9:30 a.m.-11:09 p.m.

1 stop14h 39m

Chicago Midway

Mon 19/1

10:07 a.m.-11:58 p.m.

1 stop12h 51m

C$ 504

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 12/3

6:50 a.m.-1:02 p.m.

2 stops7h 12m

Chicago Midway

Tue 17/3

7:30 a.m.-5:25 p.m.

1 stop8h 55m

C$ 536

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 9/1

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Tue 13/1

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

1 stop5h 29m

C$ 554

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 8/1

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Mon 12/1

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

1 stop5h 29m

C$ 554

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 17/2

4:20 p.m.-7:07 p.m.

2 stops27h 47m

Chicago Midway

Sun 22/2

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

1 stop5h 14m

C$ 554

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 22/1

5:40 a.m.-5:55 p.m.

2 stops13h 15m

Chicago Midway

Mon 26/1

9:33 a.m.-12:42 a.m.

2 stops14h 09m

C$ 573

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 22/1

5:40 a.m.-12:46 p.m.

2 stops8h 06m

Chicago Midway

Sun 25/1

9:32 a.m.-12:42 a.m.

2 stops14h 10m

C$ 573

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 6/2

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Sun 8/2

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

1 stop3h 39m

C$ 577

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 23/1

7:00 a.m.-10:05 a.m.

1 stop4h 05m

Chicago Midway

Sun 25/1

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

1 stop5h 14m

C$ 577

Flights are sorted by cheapest round-trip flights first.

Deals found on 17/12

Showing 1-10 of 19 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$ 180). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of C$ 422). 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 18 December 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
399 reviews
Check prices

Food

7.6

Entertainment

7.0

Comfort

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

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
399 reviews
Porter Airlines
8.0
Very good
399 reviews
Check prices

Food

7.6

Entertainment

7.0

Comfort

7.9

Crew

8.6

Overall

8.0

Boarding

8.2

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 05m. 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$ 330, 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 44% 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$ 180). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of C$ 422). 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 18 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 330AverageC$ 481FlexibilityNo 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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