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$196+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/249:30 am
YOW
-
MDW
1 stop9h 43m
Multiple Airlines
Thu 3/267:30 am
MDW
-
YOW
2 stops9h 54m
Multiple Airlines
Deal found 2/4$354
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 3/69:30 am
YOW
-
MDW
1 stop12h 23m
Multiple Airlines
Fri 3/136:05 am
MDW
-
YOW
2 stops17h 20m
Multiple Airlines
Deal found 2/4$367
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/187:00 am
YOW
-
MDW
2 stops13h 07m
Multiple Airlines
Mon 2/239:22 pm
MDW
-
YOW
1 stop25h 36m
Multiple Airlines
Deal found 2/2$381
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Mon 3/163:35 pm
YOW
-
MDW
2 stops22h 27m
Multiple Airlines
Sun 3/224:15 pm
MDW
-
YOW
1 stop24h 14m
Multiple Airlines
Deal found 2/3$395
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 4/216:50 am
YOW
-
MDW
1 stop4h 15m
Porter Airlines
Sat 4/2512:45 pm
MDW
-
YOW
1 stop3h 44m
Porter Airlines
Deal found 2/4$404
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Sat 4/46:55 pm
YOW
-
MDW
1 stop16h 10m
Porter Airlines
Tue 4/711:00 am
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 2/3$419
This Trip.com deal was found by Cheapflights users on 2/2. 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.
Sun 3/2211:00 am
YOW
-
MDW
1 stop5h 20m
Porter Airlines
Sun 3/294:15 pm
MDW
-
YOW
1 stop5h 14m
Porter Airlines
Deal found 2/2$424
This Trip.com deal was found by Cheapflights users on 2/3. 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.
Sun 3/812:10 pm
YOW
-
MDW
1 stop4h 10m
Porter Airlines
Sun 3/154:15 pm
MDW
-
YOW
1 stop5h 14m
Porter Airlines
Deal found 2/3$430

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(Kiwi.com)

One-way from

$196
(Kiwi.com)

Popular in

January

Cheapest in

February

Average price

$261
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. 17% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 12% potential price decrease ($46 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 5, 2026.
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 3/24

9:30 am-6:13 pm

1 stop9h 43m

Chicago Midway

Thu 3/26

7:30 am-6:24 pm

2 stops9h 54m

$354

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Fri 3/6

9:30 am-8:53 pm

1 stop12h 23m

Chicago Midway

Fri 3/13

6:05 am-12:25 am

2 stops17h 20m

$367

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/16

3:35 pm-1:02 pm

2 stops22h 27m

Chicago Midway

Sun 3/22

4:15 pm-5:29 pm

1 stop24h 14m

$395

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 3/8

12:10 pm-3:20 pm

1 stop4h 10m

Chicago Midway

Sun 3/15

4:15 pm-10:29 pm

1 stop5h 14m

$430

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/12

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 3/15

4:15 pm-10:29 pm

1 stop5h 14m

$432

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Mon 3/2

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 3/9

11:00 am-5:29 pm

1 stop5h 29m

$445

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 3/15

11:00 am-3:20 pm

1 stop5h 20m

Chicago Midway

Sat 3/21

12:45 pm-5:29 pm

1 stop3h 44m

$463

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 5/14

11:00 am-1:00 pm

2 stops27h 00m

$196

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 3/19

9:30 am-5:44 pm

1 stop9h 14m

$211

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sun 4/12

2:50 pm-10:05 am

1 stop20h 15m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Showing 1-10 of 13 results
1
2
  • Most accurate provider: When it comes to deals on Ottawa-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Ottawa-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $490). 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.

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, 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 $490). 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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