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Cheap flights from Kelowna to Chicago from C$ 224

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kelowna to Chicago departing on 10/6. 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

Find the cheapest flights from Kelowna to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
6:05 a.m. - 4:40 p.m.
YLW
-
ORD
8h 35m
1 stop
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
C$ 512WestJet
Mon, 17 Aug - Fri, 28 Aug
Multiple Airlines Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
Multiple Airlines Logo
7:40 a.m. - 2:46 p.m.
ORD
-
YLW
9h 06m
1 stop
C$ 589Multiple Airlines
Fri, 5 Jun - Sun, 7 Jun
Multiple Airlines Logo
10:50 p.m. - 9:00 a.m.
YLW
-
ORD
8h 10m
1 stop
Multiple Airlines Logo
5:10 a.m. - 2:35 p.m.
ORD
-
YLW
35h 25m
3 stops
C$ 621Multiple Airlines
Thu, 11 Jun - Thu, 18 Jun
Multiple Airlines Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
Multiple Airlines Logo
7:49 p.m. - 2:46 p.m.
ORD
-
YLW
20h 57m
1 stop
C$ 640Multiple Airlines
Mon, 25 May - Mon, 1 Jun
WestJet Logo
6:00 a.m. - 4:40 p.m.
YLW
-
ORD
8h 40m
2 stops
WestJet Logo
5:30 p.m. - 10:05 p.m.
ORD
-
YLW
6h 35m
1 stop
C$ 643WestJet
Mon, 17 Aug - Fri, 28 Aug
Multiple Airlines Logo
7:50 a.m. - 4:40 p.m.
YLW
-
ORD
6h 50m
1 stop
Multiple Airlines Logo
7:15 a.m. - 9:45 a.m.
ORD
-
YLW
28h 30m
3 stops
C$ 644Multiple Airlines
Fri, 5 Jun - Sun, 7 Jun
United Airlines Logo
8:30 p.m. - 5:40 a.m.
YLW
-
ORD
7h 10m
1 stop
United Airlines Logo
6:00 a.m. - 11:28 p.m.
ORD
-
YLW
19h 28m
2 stops
C$ 647United Airlines
Mon, 25 May - Mon, 1 Jun
Air Canada Logo
10:50 p.m. - 9:00 a.m.
YLW
-
ORD
8h 10m
1 stop
Air Canada Logo
7:40 p.m. - 10:29 a.m.
ORD
-
YLW
16h 49m
1 stop
C$ 651Air Canada
Thu, 11 Jun - Thu, 18 Jun
United Airlines Logo
2:50 p.m. - 9:43 a.m.
YLW
-
ORD
16h 53m
2 stops
United Airlines Logo
9:40 p.m. - 2:14 p.m.
ORD
-
YLW
18h 34m
2 stops
C$ 663United Airlines
Mon, 17 Aug - Fri, 28 Aug
Porter Airlines Logo
12:50 p.m. - 2:35 p.m.
YLW
-
MDW
23h 45m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:55 a.m.
MDW
-
YLW
22h 35m
2 stops
C$ 1,168Porter Airlines
Thu, 11 Jun - Thu, 18 Jun

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Alaska Airlines flights from Kelowna to Chicago

Our best Alaska Airlines deals on Kelowna to Chicago flight tickets
Alaska Airlines
1 Jul
YLW1:46 p.m.Kelowna
8h 13m
1 stop
ORD11:59 p.m.Chicago O'Hare Intl
8 Jul
ORD8:02 a.m.Chicago O'Hare Intl
6h 54m
1 stop
YLW12:56 p.m.Kelowna
C$ 1,022
Alaska Airlines
4 May
YLW3:37 p.m.Kelowna
13h 03m
1 stop
ORD6:40 a.m.Chicago O'Hare Intl
7 May
ORD8:48 p.m.Chicago O'Hare Intl
19h 59m
1 stop
YLW2:47 p.m.Kelowna
C$ 2,069
Alaska Airlines
4 May
YLW3:37 p.m.Kelowna
13h 03m
1 stop
ORD6:40 a.m.Chicago O'Hare Intl
7 May
ORD2:13 p.m.Chicago O'Hare Intl
26h 34m
2 stops
YLW2:47 p.m.Kelowna
C$ 2,083

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
11 Jun
YLW10:50 p.m.Kelowna
8h 10m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
18 Jun
ORD7:40 p.m.Chicago O'Hare Intl
16h 49m
1 stop
YLW10:29 a.m.Kelowna
C$ 651
Air Canada
11 Jun
YLW12:55 p.m.Kelowna
18h 05m
2 stops
ORD9:00 a.m.Chicago O'Hare Intl
18 Jun
ORD7:40 p.m.Chicago O'Hare Intl
16h 49m
1 stop
YLW10:29 a.m.Kelowna
C$ 692
Air Canada
10 Jun
YLW10:50 p.m.Kelowna
8h 10m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
17 Jun
ORD8:25 p.m.Chicago O'Hare Intl
16h 35m
1 stop
YLW11:00 a.m.Kelowna
C$ 704

momondo Fare Finder

 
Customize your flight search to find flights from Kelowna to Chicago 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 30 April 2026.
Use the filters below to find and compare flights from Kelowna to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 17/8

6:05 a.m.-4:40 p.m.

1 stop8h 35m

Chicago O'Hare Intl

Fri 28/8

5:30 p.m.-10:05 p.m.

1 stop6h 35m

C$ 512

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 5/6

7:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Sun 7/6

7:40 a.m.-2:46 p.m.

1 stop9h 06m

C$ 589

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 11/6

10:50 p.m.-9:00 a.m.

1 stop8h 10m

Chicago O'Hare Intl

Thu 18/6

5:10 a.m.-2:35 p.m.

3 stops35h 25m

C$ 621

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 25/5

7:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Mon 1/6

7:49 p.m.-2:46 p.m.

1 stop20h 57m

C$ 640

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 17/8

6:00 a.m.-4:40 p.m.

2 stops8h 40m

Chicago O'Hare Intl

Fri 28/8

5:30 p.m.-10:05 p.m.

1 stop6h 35m

C$ 642

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 5/6

7:50 a.m.-4:40 p.m.

1 stop6h 50m

Chicago O'Hare Intl

Sun 7/6

7:15 a.m.-9:45 a.m.

3 stops28h 30m

C$ 644

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 25/5

8:30 p.m.-5:40 a.m.

1 stop7h 10m

Chicago O'Hare Intl

Mon 1/6

6:00 a.m.-11:28 p.m.

2 stops19h 28m

C$ 647

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Thu 11/6

10:50 p.m.-9:00 a.m.

1 stop8h 10m

Chicago O'Hare Intl

Thu 18/6

7:40 p.m.-10:29 a.m.

1 stop16h 49m

C$ 651

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 17/8

2:50 p.m.-9:43 a.m.

2 stops16h 53m

Chicago O'Hare Intl

Fri 28/8

9:40 p.m.-2:14 p.m.

2 stops18h 34m

C$ 663

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Thu 11/6

12:50 p.m.-2:35 p.m.

2 stops23h 45m

Chicago Midway

Thu 18/6

3:20 p.m.-11:55 a.m.

2 stops22h 35m

C$ 1,168

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Kelowna to Chicago

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 typical price of a round-trip flight between Kelowna and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Kelowna averaging around C$ 0.

When to book flights from Kelowna to Chicago

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

Cheap Kelowna to Chicago (YLW to CHI) flight deals and tips

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

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Kelowna to Chicago takes 6h 50m
There are no direct flights from Kelowna to Chicago. There are no popular flight routes from Kelowna to Chicago.
Search flight deals

Frequently asked questions about flying from Kelowna to Chicago

  • How far is Kelowna to Chicago by plane?

    The straight-line distance from Kelowna to Chicago is 2596.6 km. By plane, this route typically takes 6h 50m.

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

    Prices for flights from Kelowna Airport to Chicago are refreshed on a daily basis.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Kelowna Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago 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 Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Kelowna to Chicago?

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

Why use momondo?

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

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 Kelowna to Chicago for you.

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

Flights from Kelowna to Chicago 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 Kelowna to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Kelowna.

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

Yes momondo offers price alerts on flights to Chicago from Kelowna. 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport