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$176+ Cheap flights from Ottawa (YOW) to Midway (MDW)

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 10/29. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$314
(Kiwi.com)

One-way from

$176
(Kiwi.com)

Popular in

March

Cheapest in

December

Average price

$434
From Ottawa to Chicago Midway
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One-way flight from Ottawa to Chicago Midway
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Highest demand for flights based on searches. 11% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($29 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 September 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1411:00 amYOW - MDW
1 stop6h 24mMultiple Airlines
Tue 10/219:35 amMDW - YOW
1 stop13h 47mMultiple Airlines
Deal found 9/16$314
This Trip.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/141:25 pmYOW - MDW
1 stop3h 59mPorter Airlines
Tue 10/219:35 amMDW - YOW
1 stop7h 34mPorter Airlines
Deal found 9/16$323
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:25 pmYOW - MDW
1 stop18h 56mMultiple Airlines
Wed 10/158:05 amMDW - YOW
2 stops32h 15mMultiple Airlines
Deal found 9/14$340
This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/65:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Mon 11/108:00 amMDW - YOW
2 stops15h 42mMultiple Airlines
Deal found 9/16$362
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/79:30 amYOW - MDW
1 stop13h 50mMultiple Airlines
Mon 11/1011:00 amMDW - YOW
1 stop7h 54mMultiple Airlines
Deal found 9/14$366
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/209:30 amYOW - MDW
1 stop8h 00mMultiple Airlines
Sat 11/229:41 amMDW - YOW
2 stops14h 01mMultiple Airlines
Deal found 9/15$380
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/34:25 pmYOW - MDW
1 stop18h 56mMultiple Airlines
Mon 10/612:48 pmMDW - YOW
2 stops10h 34mMultiple Airlines
Deal found 9/15$391
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/21:25 pmYOW - MDW
1 stop3h 59mMultiple Airlines
Mon 10/612:48 pmMDW - YOW
2 stops10h 34mMultiple Airlines
Deal found 9/14$412
This FlightHub deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:40 amYOW - MDW
2 stops29h 00mWestJet
Mon 11/1010:47 amMDW - YOW
2 stops12h 55mWestJet
Deal found 9/14$422

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 2,558,603 searches. Data last updated September 16, 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 10/14

11:00 am-4:24 pm

1 stop6h 24m

Chicago Midway

Tue 10/21

9:35 am-12:22 am

1 stop13h 47m

$314

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 10/3

4:25 pm-10:21 am

1 stop18h 56m

Chicago Midway

Wed 10/15

8:05 am-5:20 pm

2 stops32h 15m

$340

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 11/6

5:40 am-3:20 pm

1 stop10h 40m

Chicago Midway

Mon 11/10

8:00 am-12:42 am

2 stops15h 42m

$362

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 11/7

9:30 am-10:20 pm

1 stop13h 50m

Chicago Midway

Mon 11/10

11:00 am-7:54 pm

1 stop7h 54m

$366

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 11/20

9:30 am-4:30 pm

1 stop8h 00m

Chicago Midway

Sat 11/22

9:41 am-12:42 am

2 stops14h 01m

$380

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 10/2

1:25 pm-4:24 pm

1 stop3h 59m

Chicago Midway

Mon 10/6

12:48 pm-12:22 am

2 stops10h 34m

$412

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 11/7

5:40 am-9:40 am

2 stops29h 00m

Chicago Midway

Mon 11/10

10:47 am-12:42 am

2 stops12h 55m

$422

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 11/10

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Sun 11/16

4:15 pm-10:29 pm

1 stop5h 14m

$466

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 10/3

5:55 am-1:03 pm

2 stops32h 08m

Chicago Midway

Wed 10/15

12:48 pm-12:22 am

2 stops10h 34m

$471

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 11/1

8:40 am-11:50 am

1 stop4h 10m

Chicago Midway

Sun 11/2

11:00 am-5:29 pm

1 stop5h 29m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 16 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, April is the cheapest month in which you can book a flight from Ottawa to Chicago Midway Airport (average of $160). Flying from Ottawa to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 16, 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 at noon tend to be the most expensive. A flight in the morning could potentially save you up to 37% on airfare.

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 6.6 mi from the city center, Ottawa is the airport most travelers 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 0 different airlines.

  • 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, April is the cheapest month in which you can book a flight from Ottawa to Chicago Midway Airport (average of $160). Flying from Ottawa to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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