Find flights
When to book
FAQs

Cheap flights from Kelowna to Chicago Midway Airport from C$ 293

YLW — MDW
29 Sep — 6 Oct1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Kelowna to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Kelowna to Midway

Sat 17/106:05 a.m. -
2 stops9h 55m
Wed 21/101:27 p.m. -
2 stops10h 38m
Deal found 29/8C$ 489
Sun 11/108:15 p.m. -
2 stops13h 39m
Sun 18/101:27 p.m. -
2 stops12h 23m
Deal found 28/8C$ 838
Sun 11/107:50 p.m. -
2 stops13h 10m
Sun 18/1011:45 a.m. -
1 stop12h 04m
Deal found 28/8C$ 977
Sun 11/1010:45 p.m. -
1 stop13h 50m
Sun 18/1011:45 a.m. -
1 stop12h 04m
Deal found 28/8C$ 1,009
Sat 5/125:20 a.m. -
2 stops9h 30m
Mon 14/126:00 a.m. -
2 stops18h 20m
Deal found 28/8C$ 1,047
Thu 12/118:25 p.m. -
2 stops13h 34m
Mon 16/1112:30 p.m. -
2 stops13h 45m
Deal found 29/8C$ 1,208
Fri 4/95:05 a.m. -
2 stops26h 12m
Mon 7/99:59 a.m. -
2 stops11h 01m
Deal found 27/8C$ 1,271
Sat 5/98:15 p.m. -
2 stops11h 55m
Sat 12/99:59 a.m. -
2 stops12h 01m
Deal found 25/8C$ 1,287
Fri 30/107:55 p.m. -
2 stops12h 42m
Sun 1/1110:01 a.m. -
2 stops11h 24m
Deal found 28/8C$ 1,307
Thu 3/910:20 a.m. -
2 stops24h 19m
Mon 7/96:42 p.m. -
2 stops21h 53m
Deal found 26/8C$ 1,308

Find flight deals from Kelowna to Midway

Round-trip from

C$ 489

One-way from

C$ 293

Popular in

October

Cheapest in

May

Average price

C$ 535
Delta
  • Delta
  • 17/10-21/10
  • 4 total stops
  • 20h 33m total
  • Kelowna to Chicago
Search Deals
8/9
  • 8/9
  • 2 total stops
  • 19h 36m total
  • Kelowna to Chicago
Search Deals
Highest demand for flights based on searches. 36% potential increase in price (C$ 512 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 63 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 17/10

6:05 a.m.-6:00 p.m.

2 stops9h 55m

Chicago Midway

Wed 21/10

1:27 p.m.-10:05 p.m.

2 stops10h 38m

C$ 489

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sun 11/10

8:15 p.m.-11:54 a.m.

2 stops13h 39m

Chicago Midway

Sun 18/10

1:27 p.m.-11:50 p.m.

2 stops12h 23m

C$ 838

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sun 11/10

10:45 p.m.-2:35 p.m.

1 stop13h 50m

Chicago Midway

Sun 18/10

11:45 a.m.-9:49 p.m.

1 stop12h 04m

C$ 1,009

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 5/12

5:20 a.m.-3:50 p.m.

2 stops9h 30m

Chicago Midway

Mon 14/12

6:00 a.m.-11:20 p.m.

2 stops18h 20m

C$ 1,047

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Thu 21/1

8:25 p.m.-3:25 p.m.

2 stops18h 00m

Chicago Midway

Wed 27/1

12:30 p.m.-1:15 a.m.

2 stops13h 45m

C$ 1,282

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Fri 9/10

8:15 p.m.-3:17 p.m.

2 stops17h 02m

Chicago Midway

Mon 12/10

9:29 a.m.-11:50 p.m.

2 stops16h 21m

C$ 1,508
Cheapest one-way

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Tue 8/9

8:15 p.m.-5:51 p.m.

2 stops19h 36m

C$ 293

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Wed 9/9

6:30 p.m.-11:44 p.m.

2 stops27h 14m

C$ 342
Quickest one-way

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 5/9

8:15 p.m.-10:10 a.m.

2 stops11h 55m

C$ 672

KelownaChicago

YLW Kelowna - MDW Chicago Midway

YLWMDW

Kelowna

Sat 5/9

12:05 p.m.-2:35 p.m.

3 stops24h 30m

C$ 774

Flights are sorted by cheapest round-trip flights first.

Deals found on 27/8

Sorted by cheapest first

Best time to book a flight from Kelowna to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Kelowna with our price prediction graph.
Estimated round-trip price

Related info for your journey

  • What airport do you fly from for flights from Kelowna to Chicago Midway?

    Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago Midway from Kelowna. Booking flights from Kelowna (YLW) 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 Kelowna to Chicago Midway Airport?

    Departing from Kelowna to Chicago Midway Airport will take you 9h 55m. Airlines will cover a distance of 2586 km.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Kelowna 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

Browse thousands of different options on Cheapflights for your next trip

Fly with Cheapflights

How does Cheapflights help users find flights from Kelowna to Midway?

When you search for this flight from Kelowna to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Kelowna to Midway?

Cheapflights simply makes it quick and affordable to book flights from Kelowna to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Kelowna to Midway with no change fees?

Yes, we can. To see specific flights from Kelowna to Midway with no change fees, users can toggle flexible booking options after using the search form above to find flights.

Can Cheapflights notify me if prices for flights from Kelowna to Midway become cheaper?

Of course! You can now track prices for flights from Kelowna to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.