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$150+ 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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap 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 December 26, 2025.

This Trip.com deal was found by Cheapflights users on 12/24. 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 2/84:15 pmMDW - YOW
1 stop5h 14mPorter Airlines
Deal found 12/24$745
This FlightHub deal was found by Cheapflights users on 12/23. 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.
Thu 12/255:40 amYOW - MDW
2 stops30h 26mWestJet
Tue 1/69:32 amMDW - YOW
2 stops14h 10mWestJet
Deal found 12/23$886
This Flightnetwork deal was found by Cheapflights users on 12/23. 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 Flightnetwork 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
Tue 1/611:00 amMDW - YOW
1 stop5h 29mPorter Airlines
Deal found 12/23$888
This Expedia deal was found by Cheapflights users on 12/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:40 amYOW - MDW
2 stops12h 46mMultiple Airlines
Tue 1/611:05 amMDW - YOW
1 stop5h 24mMultiple Airlines
Deal found 12/23$952
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 12/255:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Mon 12/296:12 amMDW - YOW
2 stops16h 46mMultiple Airlines
Deal found 12/24$998
This FlightHub deal was found by Cheapflights users on 12/24. 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.
Thu 12/255:40 amYOW - MDW
2 stops12h 46mWestJet
Sat 12/276:08 pmMDW - YOW
2 stops29h 34mWestJet
Deal found 12/24$1,002
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 12/255:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Sun 12/282:16 pmMDW - YOW
1 stop8h 42mMultiple Airlines
Deal found 12/24$1,014
This Justfly.com deal was found by Cheapflights users on 12/24. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:40 amYOW - MDW
2 stops30h 26mWestJet
Mon 12/299:29 amMDW - YOW
2 stops14h 13mWestJet
Deal found 12/24$1,015
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 12/265:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Mon 12/293:10 pmMDW - YOW
1 stop7h 48mMultiple Airlines
Deal found 12/24$1,026
This Kiwi.com deal was found by Cheapflights users on 12/24. 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 12/265:40 amYOW - MDW
1 stop10h 40mMultiple Airlines
Sun 12/282:16 pmMDW - YOW
1 stop8h 42mMultiple Airlines
Deal found 12/24$1,032

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 December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$314
(Kiwi.com)

One-way from

$150
(Kiwi.com)

Popular in

January

Cheapest in

October

Average price

$483
Provider with most accurate pricing for Ottawa-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Ottawa-Chicago Midway flights.
Search Deals
From Ottawa to Chicago Midway
Search Deals
One-way flight from Ottawa to Chicago Midway
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($114 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($44 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 2,558,603 searches. Data last updated December 26, 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

Thu 2/5

7:00 am-10:10 am

1 stop4h 10m

Chicago Midway

Mon 2/9

1:00 pm-11:58 pm

1 stop9h 58m

$314

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 2/6

7:00 am-10:10 am

1 stop4h 10m

Chicago Midway

Mon 2/9

1:00 pm-11:58 pm

1 stop9h 58m

$321

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 2/8

9:30 am-7:52 pm

1 stop11h 22m

Chicago Midway

Sun 2/15

4:15 pm-7:59 am

1 stop14h 44m

$340

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 2/22

8:40 am-3:20 pm

1 stop7h 40m

Chicago Midway

Thu 2/26

11:00 am-5:29 pm

1 stop5h 29m

$357

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/9

4:35 pm-1:02 pm

2 stops21h 27m

Chicago Midway

Sun 3/15

11:00 am-5:29 pm

1 stop5h 29m

$378

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 3/8

8:55 pm-10:05 am

1 stop14h 10m

Chicago Midway

Sat 3/14

12:45 pm-12:39 am

1 stop10h 54m

$397

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/26

6:50 am-10:05 am

1 stop4h 15m

Chicago Midway

Sun 3/29

4:15 pm-10:29 pm

1 stop5h 14m

$412

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 2/7

4:40 pm-11:45 am

2 stops20h 05m

Chicago Midway

Sat 2/14

12:50 pm-5:39 pm

1 stop3h 49m

$414

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 2/4

4:20 pm-7:52 pm

1 stop28h 32m

$150

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 12/31

9:30 am-9:58 pm

1 stop13h 28m

$221

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Showing 1-10 of 14 results
1
2

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 December.
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 $306). 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 December 26, 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 7h 40m. 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 $306). 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
Merrillville
Hammond
Porter
Benton Harbor

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