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$175+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Dec 16 — Dec 231
Tue 12/16
Tue 12/23
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 November 16, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$382
(Trip.com)

One-way from

$175
(Kiwi.com)

Popular in

March

Cheapest in

December

Average price

$506
Provider with most accurate pricing for Ottawa-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Ottawa-Chicago Midway flights.
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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. 13% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($33 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

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 November 16, 2025.

This Trip.com deal was found by Cheapflights users on 11/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/186:50 amYOW - MDW
1 stop4h 15mPorter Airlines
Thu 1/14:15 pmMDW - YOW
1 stop3h 39mPorter Airlines
Deal found 11/15$382
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Wed 12/246:50 amYOW - MDW
1 stop4h 15mPorter Airlines
Mon 12/294:15 pmMDW - YOW
1 stop3h 39mPorter Airlines
Deal found 11/13$391
This Trip.com deal was found by Cheapflights users on 11/13. 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.
Thu 12/2512:10 pmYOW - MDW
1 stop4h 10mPorter Airlines
Sun 12/284:15 pmMDW - YOW
1 stop3h 39mPorter Airlines
Deal found 11/13$396
This Trip.com deal was found by Cheapflights users on 11/13. 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.
Sat 12/138:40 amYOW - MDW
1 stop4h 10mPorter Airlines
Sat 12/2011:00 amMDW - YOW
1 stop5h 29mPorter Airlines
Deal found 11/13$398
This FlightHub deal was found by Cheapflights users on 11/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:50 amYOW - MDW
1 stop4h 15mPorter Airlines
Mon 12/224:15 pmMDW - YOW
1 stop5h 14mPorter Airlines
Deal found 11/15$405
This Trip.com deal was found by Cheapflights users on 11/14. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2912:10 pmYOW - MDW
1 stop4h 10mPorter Airlines
Mon 1/54:15 pmMDW - YOW
1 stop5h 14mPorter Airlines
Deal found 11/14$406
This Kiwi.com deal was found by Cheapflights users on 11/15. 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 12/186:50 amYOW - MDW
2 stops7h 11mMultiple Airlines
Thu 1/17:44 amMDW - YOW
1 stop8h 41mMultiple Airlines
Deal found 11/15$408
This Porter Airlines deal was found by Cheapflights users on 11/15. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/138:40 amYOW - MDW
1 stop4h 10mPorter Airlines
Tue 12/1611:00 amMDW - YOW
1 stop5h 29mPorter Airlines
Deal found 11/15$414
This Porter Airlines deal was found by Cheapflights users on 11/15. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:10 pmYOW - MDW
1 stop4h 10mPorter Airlines
Mon 12/294:15 pmMDW - YOW
1 stop3h 39mPorter Airlines
Deal found 11/15$422
This Kiwi.com deal was found by Cheapflights users on 11/16. 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 12/306:50 amYOW - MDW
1 stop4h 15mMultiple Airlines
Thu 1/17:44 amMDW - YOW
2 stops26h 45mMultiple Airlines
Deal found 11/16$428
This Porter Airlines deal was found by Cheapflights users on 11/15. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:10 pmYOW - MDW
1 stop4h 10mPorter Airlines
Tue 12/304:15 pmMDW - YOW
1 stop3h 39mPorter Airlines
Deal found 11/15$429
This Kiwi.com deal was found by Cheapflights users on 11/15. 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.
Sun 12/2812:10 pmYOW - MDW
1 stop4h 10mPorter Airlines
Sun 1/44:15 pmMDW - YOW
1 stop5h 14mPorter Airlines
Deal found 11/15$430

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 November 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 12/30

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Thu 1/1

4:15 pm-10:29 pm

1 stop5h 14m

$391

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 12/24

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Mon 12/29

4:15 pm-8:54 pm

1 stop3h 39m

$391

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 12/25

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Sun 12/28

4:15 pm-8:54 pm

1 stop3h 39m

$396

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 12/13

8:40 am-11:50 am

1 stop4h 10m

Chicago Midway

Sat 12/20

11:00 am-5:29 pm

1 stop5h 29m

$398

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 12/29

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Mon 1/5

4:15 pm-10:29 pm

1 stop5h 14m

$406

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 12/18

6:50 am-1:01 pm

2 stops7h 11m

Chicago Midway

Thu 1/1

7:44 am-5:25 pm

1 stop8h 41m

$408

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 12/14

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Thu 12/18

4:15 pm-8:54 pm

1 stop3h 39m

$414

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 1/2

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Tue 1/6

11:00 am-5:29 pm

1 stop5h 29m

$422

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 12/25

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Mon 12/29

4:15 pm-8:54 pm

1 stop3h 39m

$422

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 12/30

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Thu 1/1

7:44 am-11:29 am

2 stops26h 45m

$428

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/16

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from Ottawa to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Ottawa to Midway in November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Ottawa-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Ottawa-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Ottawa-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Ottawa-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Ottawa-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 $131). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of $300). 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 November 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 in the afternoon tend to be the most expensive. A flight in the morning could potentially save you up to 36% 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.

  • How long is the flight from Ottawa to Chicago Midway Airport?

    Airlines like Porter Airlines fly from Ottawa to Chicago Midway Airport in about 4h 15m. The time it takes to get you to your destination can typically vary by up to . The distance from Ottawa to Chicago Midway Airport is about 651 mi.

  • 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 $131). Flying from Ottawa to Chicago Midway Airport in January is currently the most expensive (average of $300). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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