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Kelowna

$193+ Cheap flights from Midway (MDW) to Kelowna (YLW)

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.
MDW — YLW
Jun 15 — Jun 221
Mon 6/15
Mon 6/22
1 adult, Economy
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Cheap flight deals from Midway to Kelowna

Cheapest flights from Midway to Kelowna
Explore the most affordable flight options available from Midway to Kelowna. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 16, 2026.

This Mytrip deal was found by Cheapflights users on 5/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:15 am
MDW
-
YLW
3 stops22h 45m
Multiple Airlines
Wed 6/1012:50 pm
YLW
-
MDW
2 stops18h 45m
Multiple Airlines
Deal found 5/11$700
This Mytrip deal was found by Cheapflights users on 5/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/83:20 pm
MDW
-
YLW
3 stops21h 55m
Multiple Airlines
Fri 6/129:10 am
YLW
-
MDW
3 stops25h 59m
Multiple Airlines
Deal found 5/13$831
This Mytrip deal was found by Cheapflights users on 5/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:15 am
MDW
-
YLW
2 stops27h 40m
Porter Airlines
Wed 6/1012:50 pm
YLW
-
MDW
2 stops18h 45m
Porter Airlines
Deal found 5/11$896
This Delta deal was found by Cheapflights users on 5/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:27 pm
MDW
-
YLW
2 stops12h 23m
Delta
Sun 8/166:05 am
YLW
-
MDW
2 stops10h 28m
Delta
Deal found 5/14$1,087
This oojo deal was found by Cheapflights users on 5/14. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/265:59 pm
MDW
-
YLW
2 stops31h 45m
WestJet
Wed 12/307:00 pm
YLW
-
MDW
2 stops19h 50m
WestJet
Deal found 5/14$1,090
This oojo deal was found by Cheapflights users on 5/12. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:27 pm
MDW
-
YLW
2 stops12h 23m
WestJet
Sun 8/166:30 pm
YLW
-
MDW
2 stops13h 29m
WestJet
Deal found 5/12$1,091
This oojo deal was found by Cheapflights users on 5/13. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/81:26 pm
MDW
-
YLW
2 stops12h 24m
WestJet
Fri 6/1210:20 am
YLW
-
MDW
2 stops20h 54m
WestJet
Deal found 5/13$1,096
This oojo deal was found by Cheapflights users on 5/12. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:27 pm
MDW
-
YLW
2 stops10h 38m
WestJet
Mon 8/175:05 am
YLW
-
MDW
2 stops10h 56m
WestJet
Deal found 5/12$1,111
This Mytrip deal was found by Cheapflights users on 5/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2110:30 am
MDW
-
YLW
3 stops22h 30m
Multiple Airlines
Wed 5/275:05 am
YLW
-
MDW
2 stops10h 51m
Multiple Airlines
Deal found 5/12$1,132
This WestJet deal was found by Cheapflights users on 5/12. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:00 pm
MDW
-
YLW
2 stops11h 05m
WestJet
Sat 10/249:10 am
YLW
-
MDW
2 stops22h 42m
WestJet
Deal found 5/12$1,205

Find flight deals from Midway to Kelowna

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Kelowna (YLW). 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 May 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$700
(Mytrip)

One-way from

$193
(Kiwi.com)
Provider with most accurate pricing for Chicago Midway-Kelowna flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kelowna flights.
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From Chicago Midway to Kelowna
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One-way flight from Chicago Midway to Kelowna
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Kelowna 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 May 16, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kelowna that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 6/8

3:20 pm-11:15 am

3 stops21h 55m

Kelowna

Fri 6/12

9:10 am-1:09 pm

3 stops25h 59m

$831

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 6/1

10:15 am-11:55 am

2 stops27h 40m

Kelowna

Wed 6/10

12:50 pm-9:35 am

2 stops18h 45m

$896

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 8/11

1:27 pm-11:50 pm

2 stops12h 23m

Kelowna

Sun 8/16

6:05 am-6:33 pm

2 stops10h 28m

$1,087

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 8/11

1:27 pm-11:50 pm

2 stops12h 23m

Kelowna

Sun 8/16

6:30 pm-9:59 am

2 stops13h 29m

$1,091

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 6/8

1:26 pm-11:50 pm

2 stops12h 24m

Kelowna

Fri 6/12

10:20 am-9:14 am

2 stops20h 54m

$1,096
Quickest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 8/13

1:27 pm-10:05 pm

2 stops10h 38m

Kelowna

Mon 8/17

5:05 am-6:01 pm

2 stops10h 56m

$1,111

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 10/20

1:00 pm-10:05 pm

2 stops11h 05m

Kelowna

Sat 10/24

9:10 am-9:52 am

2 stops22h 42m

$1,218
Cheapest one-way

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 10/29

12:03 pm-3:30 pm

2 stops29h 27m

$193
Quickest one-way

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Thu 6/25

4:10 pm-7:25 pm

3 stops29h 15m

$321

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 6/21

6:00 am-8:20 am

2 stops52h 20m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/13

Showing 1-10 of 11 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Kelowna flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Kelowna flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Kelowna flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Kelowna 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 Chicago Midway Airport-Kelowna 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 Midway to Kelowna

Have a flexible travel schedule? Discover the best time to fly to Kelowna from Midway 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 Midway to Kelowna. 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 into for flights to Kelowna from Chicago Midway?

    Kelowna (YLW) is the airport you will fly into if you book a flight from Chicago Midway to Kelowna. You should not have trouble finding flights to Kelowna from Chicago Midway; the airport handles an average of 0 inbound flights from Chicago Midway per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the Kelowna airport from Chicago Midway. It is only a 7.0 mi journey from Kelowna (YLW) to Kelowna’s city center.

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

    Airlines like Porter Airlines and Delta fly from Chicago Midway Airport to Kelowna in about 12h 23m. The time it takes to get you to your destination can typically vary by up to 15h 17m. Chicago Midway Airport and Kelowna are separated by a distance of 1607 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Midway to Kelowna that include hotel bookings?

    Yes. In addition to deals on Midway to Kelowna flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Kelowna?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Kelowna.

  • Can I find deals for business class flights from Midway to Kelowna?

    Yes. Cheapflights offers flight deals from Midway to Kelowna 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 Kelowna?

Book flights to Kelowna if you plan to visit one of these locations
West Kelowna
Salmon Arm

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