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Cheap flights from Chicago Midway Airport to Kelowna from C$ 439

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 25/6. 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

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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
6:00 a.m. - 8:20 p.m.
MDW
-
YLW
40h 20m
2 stops
Multiple Airlines Logo
11:45 a.m. - 9:40 a.m.
YLW
-
MDW
19h 55m
1 stop
C$ 838Multiple Airlines
Tue, 14 Jul - Tue, 21 Jul
Porter Airlines Logo
3:20 p.m. - 10:47 a.m.
MDW
-
YLW
21h 27m
1 stop
Porter Airlines Logo
11:45 a.m. - 9:40 a.m.
YLW
-
MDW
19h 55m
1 stop
C$ 964Porter Airlines
Tue, 14 Jul - Tue, 21 Jul
Multiple Airlines Logo
10:25 a.m. - 11:50 p.m.
MDW
-
YLW
15h 25m
2 stops
Multiple Airlines Logo
5:05 a.m. - 6:25 p.m.
YLW
-
MDW
11h 20m
3 stops
C$ 1,155Multiple Airlines
Tue, 14 Jul - Tue, 21 Jul
Porter Airlines Logo
10:25 a.m. - 11:55 a.m.
MDW
-
YLW
27h 30m
2 stops
Porter Airlines Logo
12:50 p.m. - 9:40 a.m.
YLW
-
MDW
18h 50m
2 stops
C$ 1,233Porter Airlines
Tue, 14 Jul - Tue, 21 Jul
WestJet Logo
1:18 p.m. - 11:15 a.m.
MDW
-
YLW
23h 57m
3 stops
WestJet Logo
5:05 a.m. - 6:25 p.m.
YLW
-
MDW
11h 20m
3 stops
C$ 1,310WestJet
Tue, 14 Jul - Tue, 21 Jul
Multiple Airlines Logo
9:17 a.m. - 8:05 p.m.
MDW
-
YLW
12h 48m
3 stops
Multiple Airlines Logo
12:50 p.m. - 9:40 a.m.
YLW
-
MDW
18h 50m
2 stops
C$ 1,341Multiple Airlines
Sun, 21 Jun - Sun, 28 Jun
WestJet Logo
9:54 a.m. - 7:25 p.m.
MDW
-
YLW
11h 31m
2 stops
WestJet Logo
5:05 a.m. - 6:18 p.m.
YLW
-
MDW
11h 13m
2 stops
C$ 1,481WestJet
Fri, 19 Jun - Mon, 22 Jun
WestJet Logo
1:26 p.m. - 10:05 p.m.
MDW
-
YLW
10h 39m
2 stops
WestJet Logo
6:00 a.m. - 6:18 p.m.
YLW
-
MDW
10h 18m
2 stops
C$ 1,486WestJet
Mon, 29 Jun - Sun, 5 Jul
Delta Logo
1:52 p.m. - 10:05 p.m.
MDW
-
YLW
10h 13m
2 stops
Delta Logo
6:05 a.m. - 6:33 p.m.
YLW
-
MDW
10h 28m
2 stops
C$ 1,488Delta
Tue, 11 Aug - Sun, 16 Aug
WestJet Logo
12:46 p.m. - 11:50 p.m.
MDW
-
YLW
13h 04m
2 stops
WestJet Logo
6:00 a.m. - 6:01 p.m.
YLW
-
MDW
10h 01m
2 stops
C$ 1,519WestJet
Mon, 10 Aug - Tue, 18 Aug

Porter Airlines flights from Chicago Midway Airport to Kelowna

Our best Porter Airlines deals on Chicago Midway Airport to Kelowna flight tickets
Porter Airlines
14 Jul
MDW3:20 p.m.Chicago Midway
21h 27m
1 stop
YLW10:47 a.m.Kelowna
21 Jul
YLW11:45 a.m.Kelowna
19h 55m
1 stop
MDW9:40 a.m.Chicago Midway
C$ 964
Porter Airlines
14 Jul
MDW10:25 a.m.Chicago Midway
27h 30m
2 stops
YLW11:55 a.m.Kelowna
21 Jul
YLW12:50 p.m.Kelowna
18h 50m
2 stops
MDW9:40 a.m.Chicago Midway
C$ 1,233

WestJet flights from Chicago Midway Airport to Kelowna

Our best WestJet deals on Chicago Midway Airport to Kelowna flight tickets
WestJet
14 Jul
MDW1:18 p.m.Chicago Midway
23h 57m
3 stops
YLW11:15 a.m.Kelowna
21 Jul
YLW5:05 a.m.Kelowna
11h 20m
3 stops
MDW6:25 p.m.Chicago Midway
C$ 1,310
WestJet
19 Jun
MDW9:54 a.m.Chicago Midway
11h 31m
2 stops
YLW7:25 p.m.Kelowna
22 Jun
YLW5:05 a.m.Kelowna
11h 13m
2 stops
MDW6:18 p.m.Chicago Midway
C$ 1,481
WestJet
29 Jun
MDW1:26 p.m.Chicago Midway
10h 39m
2 stops
YLW10:05 p.m.Kelowna
5 Jul
YLW6:00 a.m.Kelowna
10h 18m
2 stops
MDW6:18 p.m.Chicago Midway
C$ 1,486

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 12 May 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

Tue 14/7

6:00 a.m.-8:20 p.m.

2 stops40h 20m

Kelowna

Tue 21/7

11:45 a.m.-9:40 a.m.

1 stop19h 55m

C$ 838

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 14/7

3:20 p.m.-10:47 a.m.

1 stop21h 27m

Kelowna

Tue 21/7

11:45 a.m.-9:40 a.m.

1 stop19h 55m

C$ 964

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 14/7

10:25 a.m.-11:50 p.m.

2 stops15h 25m

Kelowna

Tue 21/7

5:05 a.m.-6:25 p.m.

3 stops11h 20m

C$ 1,155

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 14/7

10:25 a.m.-11:55 a.m.

2 stops27h 30m

Kelowna

Tue 21/7

12:50 p.m.-9:40 a.m.

2 stops18h 50m

C$ 1,233

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 14/7

1:18 p.m.-11:15 a.m.

3 stops23h 57m

Kelowna

Tue 21/7

5:05 a.m.-6:25 p.m.

3 stops11h 20m

C$ 1,310

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Sun 21/6

9:17 a.m.-8:05 p.m.

3 stops12h 48m

Kelowna

Sun 28/6

12:50 p.m.-9:40 a.m.

2 stops18h 50m

C$ 1,341

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Fri 19/6

9:54 a.m.-7:25 p.m.

2 stops11h 31m

Kelowna

Mon 22/6

5:05 a.m.-6:18 p.m.

2 stops11h 13m

C$ 1,481

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 29/6

1:26 p.m.-10:05 p.m.

2 stops10h 39m

Kelowna

Sun 5/7

6:00 a.m.-6:18 p.m.

2 stops10h 18m

C$ 1,486
Quickest round-trip

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Tue 11/8

1:52 p.m.-10:05 p.m.

2 stops10h 13m

Kelowna

Sun 16/8

6:05 a.m.-6:33 p.m.

2 stops10h 28m

C$ 1,488

ChicagoKelowna

MDW - YLW

MDWYLW

Chicago Midway

Mon 10/8

12:46 p.m.-11:50 p.m.

2 stops13h 04m

Kelowna

Tue 18/8

6:00 a.m.-6:01 p.m.

2 stops10h 01m

C$ 1,519

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
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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

10h 38m

Direct flights

None
The fastest flight from Chicago Midway Airport to Kelowna takes 10h 38m
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 10h 38m.

  • 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.

Frequently asked questions about flying from Chicago Midway Airport to Kelowna

  • How do I get Price Alerts for flights from Chicago Midway Airport to Kelowna?

    Search flight deals from Chicago Midway Airport to Kelowna. While viewing offers you’ll have the option to create a Price Alert.

  • How can I save money on flights from Chicago Midway Airport to Kelowna with momondo?

    Leverage our AI within our “Price Forecast” tool, which predicts if it’s better to book now or wait until prices decrease. You can strategically pick the best days to fly and save money on your trip by using our “Price Calendar” tool. “Explore” shows an overview of how much it costs to fly to anywhere from a selected city or airport. Our “Discover” content is a great option for travel inspiration and money-saving tips, while “Price Alerts” will update you when prices change, so you can book when fares are right.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Travelling to a place near Kelowna?

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

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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