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Cheap flights from Chicago Midway Airport to Kelowna from C$ 348

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Kelowna departing on 1/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to Kelowna

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
11:45 a.m. - 9:52 p.m.MDW  Chicago Midway-YLW Kelowna
12h 07m1 stop Toronto Island
Multiple Airlines Logo
7:50 p.m. - 11:00 a.m.YLW  Kelowna-MDW Chicago Midway
13h 10m2 stops Edmonton Toronto Pearson Intl
C$ 666Multiple Airlines
Thu, 24 Sep - Mon, 28 Sep
Porter Airlines Logo
11:45 a.m. - 9:52 p.m.MDW  Chicago Midway-YLW Kelowna
12h 07m1 stop Toronto Island
Porter Airlines Logo
10:50 p.m. - 2:35 p.m.YLW  Kelowna-MDW Chicago Midway
13h 45m1 stop Toronto Pearson Intl
C$ 694Porter Airlines
Thu, 24 Sep - Mon, 28 Sep
Multiple Airlines Logo
11:45 a.m. - 11:50 p.m.MDW  Chicago Midway-YLW Kelowna
14h 05m2 stops Toronto Island Calgary
Multiple Airlines Logo
7:50 p.m. - 11:00 a.m.YLW  Kelowna-MDW Chicago Midway
13h 10m2 stops Edmonton Toronto Pearson Intl
C$ 718Multiple Airlines
Thu, 24 Sep - Mon, 28 Sep
Multiple Airlines Logo
10:20 a.m. - 9:52 p.m.MDW  Chicago Midway-YLW Kelowna
13h 32m1 stop Toronto Island
Multiple Airlines Logo
6:35 p.m. - 2:35 p.m.YLW  Kelowna-MDW Chicago Midway
18h 00m2 stops Edmonton Toronto Pearson Intl
C$ 833Multiple Airlines
Sun, 30 Aug - Sat, 5 Sep
Multiple Airlines Logo
10:25 a.m. - 10:05 p.m.MDW  Chicago Midway-YLW Kelowna
13h 40m2 stops Toronto Island Calgary
Multiple Airlines Logo
2:30 p.m. - 11:00 a.m.YLW  Kelowna-MDW Chicago Midway
18h 30m2 stops Edmonton Toronto Pearson Intl
C$ 847Multiple Airlines
Mon, 31 Aug - Sat, 5 Sep
Multiple Airlines Logo
10:25 a.m. - 10:05 p.m.MDW  Chicago Midway-YLW Kelowna
13h 40m2 stops Toronto Island Calgary
Multiple Airlines Logo
7:05 p.m. - 2:35 p.m.YLW  Kelowna-MDW Chicago Midway
17h 30m3 stops Calgary Ottawa Toronto Pearson Intl
C$ 857Multiple Airlines
Mon, 31 Aug - Sat, 5 Sep
Multiple Airlines Logo
10:25 a.m. - 9:52 p.m.MDW  Chicago Midway-YLW Kelowna
13h 27m1 stop Toronto Island
Multiple Airlines Logo
3:15 p.m. - 11:00 a.m.YLW  Kelowna-MDW Chicago Midway
17h 45m2 stops Calgary Toronto Pearson Intl
C$ 904Multiple Airlines
Mon, 31 Aug - Sat, 5 Sep
Multiple Airlines Logo
10:25 a.m. - 9:52 p.m.MDW  Chicago Midway-YLW Kelowna
13h 27m1 stop Toronto Island
Multiple Airlines Logo
6:35 p.m. - 2:35 p.m.YLW  Kelowna-MDW Chicago Midway
18h 00m2 stops Edmonton Toronto Pearson Intl
C$ 964Multiple Airlines
Fri, 28 Aug - Sat, 5 Sep
Multiple Airlines Logo
11:45 a.m. - 7:00 a.m.MDW  Chicago Midway-YLW Kelowna
21h 15m3 stops Toronto Island Montreal Pierre Elliott Trudeau Intl Edmonton
Multiple Airlines Logo
12:50 p.m. - 11:00 a.m.YLW  Kelowna-MDW Chicago Midway
20h 10m2 stops Ottawa Toronto Island
C$ 988Multiple Airlines
Sun, 13 Sep - Sun, 20 Sep
Multiple Airlines Logo
11:45 a.m. - 7:00 a.m.MDW  Chicago Midway-YLW Kelowna
21h 15m3 stops Toronto Island Montreal Pierre Elliott Trudeau Intl Edmonton
Multiple Airlines Logo
3:10 p.m. - 2:35 p.m.YLW  Kelowna-MDW Chicago Midway
21h 25m3 stops Vancouver Intl Ottawa Toronto Island
C$ 989Multiple Airlines
Sun, 13 Sep - Sun, 20 Sep

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Porter Airlines flights from Chicago Midway Airport to Kelowna

Our best Porter Airlines deals on Chicago Midway Airport to Kelowna flight tickets
Porter Airlines
24 Sep
MDW11:45 a.m.Chicago Midway
12h 07m
1 stop
YLW9:52 p.m.Kelowna
28 Sep
YLW10:50 p.m.Kelowna
13h 45m
1 stop
MDW2:35 p.m.Chicago Midway
C$ 694
Porter Airlines
19 Sep
MDW11:45 a.m.Chicago Midway
26h 10m
2 stops
YLW11:55 a.m.Kelowna
23 Sep
YLW12:50 p.m.Kelowna
20h 10m
2 stops
MDW11:00 a.m.Chicago Midway
C$ 1,330
Porter Airlines
19 Sep
MDW11:45 a.m.Chicago Midway
26h 10m
2 stops
YLW11:55 a.m.Kelowna
23 Sep
YLW12:50 p.m.Kelowna
20h 10m
2 stops
MDW11:00 a.m.Chicago Midway
C$ 1,331

WestJet flights from Chicago Midway Airport to Kelowna

Our best WestJet deals on Chicago Midway Airport to Kelowna flight tickets
WestJet
3 Jan
MDW11:20 a.m.Chicago Midway
28h 25m
2 stops
YLW2:45 p.m.Kelowna
9 Jan
YLW7:55 p.m.Kelowna
11h 57m
2 stops
MDW8:52 a.m.Chicago Midway
C$ 1,625
WestJet
30 Jan
MDW10:35 a.m.Chicago Midway
15h 18m
2 stops
YLW12:53 a.m.Kelowna
7 Feb
YLW6:05 a.m.Kelowna
27h 46m
2 stops
MDW10:51 a.m.Chicago Midway
C$ 1,628
WestJet
24 Sep
MDW1:19 p.m.Chicago Midway
12h 31m
2 stops
YLW11:50 p.m.Kelowna
28 Sep
YLW6:05 a.m.Kelowna
10h 14m
2 stops
MDW6:19 p.m.Chicago Midway
C$ 1,632

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 96,600 searches. Data last updated 10 August 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
Quickest round-trip

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Thu 24/9

11:45 a.m.-9:52 p.m.

1 stop12h 07m

Kelowna

Mon 28/9

7:50 p.m.-11:00 a.m.

2 stops13h 10m

C$ 666

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Thu 24/9

11:45 a.m.-9:52 p.m.

1 stop12h 07m

Kelowna

Mon 28/9

10:50 p.m.-2:35 p.m.

1 stop13h 45m

C$ 694

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Thu 24/9

11:45 a.m.-11:50 p.m.

2 stops14h 05m

Kelowna

Mon 28/9

7:50 p.m.-11:00 a.m.

2 stops13h 10m

C$ 718

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Sun 30/8

10:20 a.m.-9:52 p.m.

1 stop13h 32m

Kelowna

Sat 5/9

6:35 p.m.-2:35 p.m.

2 stops18h 00m

C$ 833

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Mon 31/8

10:25 a.m.-10:05 p.m.

2 stops13h 40m

Kelowna

Sat 5/9

2:30 p.m.-11:00 a.m.

2 stops18h 30m

C$ 847

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Mon 31/8

10:25 a.m.-10:05 p.m.

2 stops13h 40m

Kelowna

Sat 5/9

7:05 p.m.-2:35 p.m.

3 stops17h 30m

C$ 857

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Mon 31/8

10:25 a.m.-9:52 p.m.

1 stop13h 27m

Kelowna

Sat 5/9

3:15 p.m.-11:00 a.m.

2 stops17h 45m

C$ 904

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Fri 28/8

10:25 a.m.-9:52 p.m.

1 stop13h 27m

Kelowna

Sat 5/9

6:35 p.m.-2:35 p.m.

2 stops18h 00m

C$ 964

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Sun 13/9

11:45 a.m.-7:00 a.m.

3 stops21h 15m

Kelowna

Sun 20/9

12:50 p.m.-11:00 a.m.

2 stops20h 10m

C$ 988

ChicagoKelowna

MDW Chicago Midway - YLW Kelowna

MDWYLW

Chicago Midway

Sun 13/9

11:45 a.m.-7:00 a.m.

3 stops21h 15m

Kelowna

Sun 20/9

3:10 p.m.-2:35 p.m.

3 stops21h 25m

C$ 989

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
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See travel insights to Kelowna from

How to get the cheapest flight ticket from Chicago Midway Airport to Kelowna

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Kelowna?

Delta and WestJet are the most popular carriers operating from Chicago Midway to Kelowna

When to book flights from Chicago Midway Airport to Kelowna

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago Midway Airport to Kelowna according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago Midway Airport to Kelowna (MDW to YLW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Kelowna

Fastest flight time

12h 07m

Direct flights

None
The fastest flight from Chicago Midway Airport to Kelowna takes 12h 07m
There are no direct flights from Chicago Midway Airport to Kelowna. There are no popular flight routes from Chicago Midway Airport to Kelowna.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Kelowna

  • How far is Chicago Midway to Kelowna by plane?

    A flight from Chicago Midway to Kelowna will travel around 2593.3 km. In terms of flight time, this usually takes a little over 12h 07m.

  • When did momondo last update prices for flights from Chicago Midway Airport to Kelowna Airport?

    Prices for flights from Chicago Midway Airport to Kelowna Airport were last updated today.

  • How old do you have to be to fly from Chicago Midway Airport to Kelowna Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Kelowna Airport.

  • What documentation or ID do you need to fly to Kelowna Airport?

    The travel and health documents you'll need for your trip to Kelowna Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Kelowna Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Travelling to a place near Kelowna?

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

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Kelowna?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Kelowna for you.

Can I find flights from Chicago to Kelowna with flexible booking policies on momondo?

Flights from Chicago to Kelowna with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to Kelowna?

momondo provides multiple filters to help you find the best flight to Kelowna from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Chicago to Kelowna right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Kelowna from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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