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Kelowna

$418+ Cheap flights from Midway (MDW) to Kelowna (YLW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YLW
Feb 1 — Feb 81
Sun 2/1
Sun 2/8
1 adult, Economy
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Find cheap flights from Midway to Kelowna with Cheapflights

1. Tell us where you want to go

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3. Compare prices and book

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Cheap flight deals from Midway to Kelowna

Best flights from Midway to Kelowna
Discover carefully curated flight deals from Midway to Kelowna that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 2, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/1. 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 2/14:15 pmMDW - YLW
2 stops27h 46mMultiple Airlines
Thu 2/51:05 pmYLW - MDW
1 stop19h 05mMultiple Airlines
Deal found 1/1$418
This Delta deal was found by Cheapflights users on 1/1. 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.
Wed 2/111:51 pmMDW - YLW
2 stops12h 02mDelta
Sat 2/149:05 amYLW - MDW
2 stops21h 49mDelta
Deal found 1/1$532
This Delta deal was found by Cheapflights users on 1/1. 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 2/101:51 pmMDW - YLW
2 stops12h 02mDelta
Sat 2/149:05 amYLW - MDW
2 stops21h 49mDelta
Deal found 1/1$532
This Delta deal was found by Cheapflights users on 1/1. 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.
Mon 2/91:51 pmMDW - YLW
2 stops12h 02mDelta
Mon 2/169:05 amYLW - MDW
2 stops21h 49mDelta
Deal found 1/1$532
This Delta deal was found by Cheapflights users on 1/1. 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 2/101:51 pmMDW - YLW
2 stops12h 02mDelta
Mon 2/169:05 amYLW - MDW
2 stops21h 49mDelta
Deal found 1/1$532
This Delta deal was found by Cheapflights users on 1/1. 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.
Fri 2/131:29 pmMDW - YLW
2 stops11h 12mDelta
Mon 2/169:05 amYLW - MDW
2 stops21h 49mDelta
Deal found 1/1$541
This Delta deal was found by Cheapflights users on 1/1. 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.
Wed 2/111:51 pmMDW - YLW
2 stops12h 02mDelta
Tue 2/178:55 amYLW - MDW
2 stops22h 11mDelta
Deal found 1/1$578
This Delta deal was found by Cheapflights users on 1/1. 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.
Mon 2/91:51 pmMDW - YLW
2 stops12h 02mDelta
Tue 2/178:55 amYLW - MDW
2 stops31h 45mDelta
Deal found 1/1$578
This Delta deal was found by Cheapflights users on 1/1. 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.
Sun 2/151:29 pmMDW - YLW
2 stops11h 12mDelta
Tue 2/178:55 amYLW - MDW
2 stops22h 11mDelta
Deal found 1/1$586
This Delta deal was found by Cheapflights users on 1/1. 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.
Fri 2/131:29 pmMDW - YLW
2 stops11h 12mDelta
Tue 2/178:55 amYLW - MDW
2 stops22h 11mDelta
Deal found 1/1$586
This Delta deal was found by Cheapflights users on 12/31. 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.
Sat 1/3111:45 amMDW - YLW
2 stops14h 10mDelta
Wed 2/47:35 pmYLW - MDW
2 stops14h 24mDelta
Deal found 12/31$588
This Delta deal was found by Cheapflights users on 1/1. 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 2/101:51 pmMDW - YLW
2 stops12h 02mDelta
Wed 2/187:35 pmYLW - MDW
2 stops14h 24mDelta
Deal found 1/1$620

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 January 2, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$398
(Kiwi.com)

Popular in

October

Cheapest in

March

Average price

$509
Provider with most accurate pricing for Chicago Midway-Kelowna flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Kelowna flights.
Search Deals
From Chicago Midway to Kelowna
Search Deals
Highest demand for flights based on searches. 23% potential increase in price ($172 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($56 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 2, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Kelowna that are best for you.

Fly from

Midway

Fly to

Kelowna

Route

Depart

Return

Price

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 2/1

4:15 pm-6:01 pm

2 stops27h 46m

Kelowna

Thu 2/5

1:05 pm-10:10 am

1 stop19h 05m

$418

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 2/11

1:51 pm-11:53 pm

2 stops12h 02m

Kelowna

Sat 2/14

9:05 am-8:54 am

2 stops21h 49m

$532

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 2/10

1:51 pm-11:53 pm

2 stops12h 02m

Kelowna

Sat 2/14

9:05 am-8:54 am

2 stops21h 49m

$532

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 2/9

1:51 pm-11:53 pm

2 stops12h 02m

Kelowna

Mon 2/16

9:05 am-8:54 am

2 stops21h 49m

$532

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 2/10

1:51 pm-11:53 pm

2 stops12h 02m

Kelowna

Mon 2/16

9:05 am-8:54 am

2 stops21h 49m

$532

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 2/13

1:29 pm-10:41 pm

2 stops11h 12m

Kelowna

Mon 2/16

9:05 am-8:54 am

2 stops21h 49m

$541

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Wed 2/11

1:51 pm-11:53 pm

2 stops12h 02m

Kelowna

Tue 2/17

8:55 am-9:06 am

2 stops22h 11m

$578

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 2/9

1:51 pm-11:53 pm

2 stops12h 02m

Kelowna

Tue 2/17

8:55 am-6:40 pm

2 stops31h 45m

$578

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 2/15

1:29 pm-10:41 pm

2 stops11h 12m

Kelowna

Tue 2/17

8:55 am-9:06 am

2 stops22h 11m

$586

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 2/13

1:29 pm-10:41 pm

2 stops11h 12m

Kelowna

Tue 2/17

8:55 am-9:06 am

2 stops22h 11m

$586

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/1

Showing 1-10 of 12 results
1
2

Compare providers for flights from Midway to Kelowna

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 Midway to Kelowna in January.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Chicago Midway Airport-Kelowna flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Kelowna flight deals on Cheapflights vs. eDreams >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 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 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 Delta fly from Chicago Midway Airport to Kelowna in about 12h 02m. The time it takes to get you to your destination can typically vary by up to . Chicago Midway Airport and Kelowna are separated by a distance of 1607 mi.

  • 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
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