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$154+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
YOW — MDW
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
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 21, 2026.

This Trip.com deal was found by Cheapflights users on 2/17. 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 4/166:50 am
YOW
-
MDW
1 stop4h 25m
Porter Airlines
Mon 4/2011:00 am
MDW
-
YOW
1 stop6h 24m
Porter Airlines
Deal found 2/17$224
This Trip.com deal was found by Cheapflights users on 2/19. 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 4/96:50 am
YOW
-
MDW
1 stop4h 25m
Porter Airlines
Mon 4/1311:00 am
MDW
-
YOW
1 stop4h 44m
Porter Airlines
Deal found 2/19$240
This Trip.com deal was found by Cheapflights users on 2/17. 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 4/48:40 am
YOW
-
MDW
1 stop4h 10m
Porter Airlines
Sat 4/1112:35 pm
MDW
-
YOW
1 stop3h 54m
Porter Airlines
Deal found 2/17$242
This Trip.com deal was found by Cheapflights users on 2/17. 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.
Wed 4/156:45 am
YOW
-
MDW
1 stop4h 30m
Porter Airlines
Sat 4/1812:35 pm
MDW
-
YOW
1 stop3h 54m
Porter Airlines
Deal found 2/17$263
This Trip.com deal was found by Cheapflights users on 2/18. 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.
Wed 3/116:45 am
YOW
-
MDW
1 stop4h 20m
Porter Airlines
Wed 3/1811:00 am
MDW
-
YOW
1 stop5h 29m
Porter Airlines
Deal found 2/18$267
This Porter Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 4/86:45 am
YOW
-
MDW
1 stop4h 30m
Porter Airlines
Sat 4/1112:35 pm
MDW
-
YOW
1 stop3h 54m
Porter Airlines
Deal found 2/19$293
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/65:55 am
YOW
-
MDW
1 stop11h 55m
Multiple Airlines
Sun 5/1010:25 am
MDW
-
YOW
1 stop12h 55m
Multiple Airlines
Deal found 2/17$300
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/125:55 am
YOW
-
MDW
1 stop11h 55m
Multiple Airlines
Wed 5/205:35 pm
MDW
-
YOW
1 stop23h 00m
Multiple Airlines
Deal found 2/17$301
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/135:55 am
YOW
-
MDW
1 stop11h 55m
Multiple Airlines
Wed 5/2010:25 am
MDW
-
YOW
1 stop12h 55m
Multiple Airlines
Deal found 2/17$309
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 4/166:50 am
YOW
-
MDW
2 stops7h 10m
Multiple Airlines
Mon 4/207:30 am
MDW
-
YOW
1 stop8h 55m
Multiple Airlines
Deal found 2/17$320
This Trip.com deal was found by Cheapflights users on 2/17. 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.
Fri 4/178:40 am
YOW
-
MDW
1 stop7h 40m
Porter Airlines
Sun 4/194:05 pm
MDW
-
YOW
1 stop5h 24m
Porter Airlines
Deal found 2/17$323

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 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$240
(Trip.com)

One-way from

$154
(Kiwi.com)

Popular in

January

Cheapest in

May

Average price

$383
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. 20% potential increase in price ($117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($32 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 21, 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

Thu 4/16

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Mon 4/20

11:00 am-6:24 pm

1 stop6h 24m

$224

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/9

6:50 am-10:15 am

1 stop4h 25m

Chicago Midway

Mon 4/13

11:00 am-4:44 pm

1 stop4h 44m

$240

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Sat 4/4

8:40 am-11:50 am

1 stop4h 10m

Chicago Midway

Sat 4/11

12:35 pm-5:29 pm

1 stop3h 54m

$242

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 4/15

6:45 am-10:15 am

1 stop4h 30m

Chicago Midway

Sat 4/18

12:35 pm-5:29 pm

1 stop3h 54m

$263

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 3/11

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Wed 3/18

11:00 am-5:29 pm

1 stop5h 29m

$267

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 4/8

6:45 am-10:15 am

1 stop4h 30m

Chicago Midway

Sat 4/11

12:35 pm-5:29 pm

1 stop3h 54m

$293

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 5/6

5:55 am-4:50 pm

1 stop11h 55m

Chicago Midway

Sun 5/10

10:25 am-12:20 am

1 stop12h 55m

$300

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Tue 5/12

5:55 am-4:50 pm

1 stop11h 55m

Chicago Midway

Wed 5/20

5:35 pm-5:35 pm

1 stop23h 00m

$301

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Wed 5/13

5:55 am-4:50 pm

1 stop11h 55m

Chicago Midway

Wed 5/20

10:25 am-12:20 am

1 stop12h 55m

$309

OttawaChicago

YOW - MDW

YOWMDW

Ottawa

Thu 4/16

6:50 am-1:00 pm

2 stops7h 10m

Chicago Midway

Mon 4/20

7:30 am-5:25 pm

1 stop8h 55m

$320

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 16 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.

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 25m. 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.

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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