Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Kelowna to Chicago from C$ 257

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 30/9. 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 Kelowna to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
Air Canada Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
C$ 505Air Canada
Mon, 19 Oct - Tue, 20 Oct
Air Canada Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
Air Canada Logo
3:40 p.m. - 11:12 p.m.
ORD
-
YLW
9h 32m
1 stop
C$ 507Air Canada
Mon, 19 Oct - Tue, 20 Oct
Air Canada Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
Air Canada Logo
2:15 p.m. - 10:27 p.m.
ORD
-
YLW
10h 12m
1 stop
C$ 517Air Canada
Mon, 19 Oct - Tue, 20 Oct
Delta Logo
6:05 a.m. - 6:33 p.m.
YLW
-
MDW
10h 28m
2 stops
Delta Logo
1:28 p.m. - 10:05 p.m.
MDW
-
YLW
10h 37m
2 stops
C$ 579Delta
Fri, 2 Oct - Tue, 6 Oct
Delta Logo
6:05 a.m. - 6:33 p.m.
YLW
-
MDW
10h 28m
2 stops
Delta Logo
1:28 p.m. - 10:05 p.m.
MDW
-
YLW
10h 37m
2 stops
C$ 581Delta
Fri, 2 Oct - Tue, 6 Oct
United Airlines Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
United Airlines Logo
1:30 p.m. - 11:12 p.m.
ORD
-
YLW
11h 42m
2 stops
C$ 589United Airlines
Mon, 19 Oct - Tue, 20 Oct
United Airlines Logo
11:30 p.m. - 9:00 a.m.
YLW
-
ORD
7h 30m
1 stop
United Airlines Logo
1:30 p.m. - 11:12 p.m.
ORD
-
YLW
11h 42m
2 stops
C$ 591United Airlines
Mon, 19 Oct - Tue, 20 Oct
Multiple Airlines Logo
5:05 a.m. - 2:35 p.m.
YLW
-
MDW
31h 30m
3 stops
Multiple Airlines Logo
3:20 p.m. - 11:15 a.m.
MDW
-
YLW
21h 55m
3 stops
C$ 1,018Multiple Airlines
Tue, 21 Jul - Sun, 26 Jul
Multiple Airlines Logo
12:50 p.m. - 9:40 a.m.
YLW
-
MDW
18h 50m
2 stops
Multiple Airlines Logo
10:25 a.m. - 8:20 a.m.
MDW
-
YLW
23h 55m
3 stops
C$ 1,033Multiple Airlines
Tue, 21 Jul - Sun, 26 Jul
WestJet Logo
6:05 a.m. - 6:18 p.m.
YLW
-
MDW
10h 13m
2 stops
WestJet Logo
9:54 a.m. - 11:50 p.m.
MDW
-
YLW
15h 56m
2 stops
C$ 1,837WestJet
Tue, 21 Jul - Sun, 26 Jul

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets
Air Canada
19 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
20 Oct
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
C$ 505
Air Canada
19 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
20 Oct
ORD3:40 p.m.Chicago O'Hare Intl
9h 32m
1 stop
YLW11:12 p.m.Kelowna
C$ 507
Air Canada
19 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
20 Oct
ORD2:15 p.m.Chicago O'Hare Intl
10h 12m
1 stop
YLW10:27 p.m.Kelowna
C$ 517

United Airlines flights from Kelowna to Chicago

Our best United Airlines deals on Kelowna to Chicago flight tickets
United Airlines
19 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
20 Oct
ORD1:30 p.m.Chicago O'Hare Intl
11h 42m
2 stops
YLW11:12 p.m.Kelowna
C$ 589
United Airlines
19 Oct
YLW11:30 p.m.Kelowna
7h 30m
1 stop
ORD9:00 a.m.Chicago O'Hare Intl
20 Oct
ORD1:30 p.m.Chicago O'Hare Intl
11h 42m
2 stops
YLW11:12 p.m.Kelowna
C$ 591
United Airlines
16 Jul
YLW11:00 p.m.Kelowna
8h 45m
1 stop
ORD9:45 a.m.Chicago O'Hare Intl
19 Jul
ORD7:45 p.m.Chicago O'Hare Intl
16h 44m
1 stop
YLW10:29 a.m.Kelowna
C$ 657

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 3 July 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 19/10

11:30 p.m.-9:00 a.m.

1 stop7h 30m

Chicago O'Hare Intl

Tue 20/10

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 505

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 19/10

11:30 p.m.-9:00 a.m.

1 stop7h 30m

Chicago O'Hare Intl

Tue 20/10

3:40 p.m.-11:12 p.m.

1 stop9h 32m

C$ 507

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 19/10

11:30 p.m.-9:00 a.m.

1 stop7h 30m

Chicago O'Hare Intl

Tue 20/10

2:15 p.m.-10:27 p.m.

1 stop10h 12m

C$ 517

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 2/10

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

2 stops10h 28m

Chicago Midway

Tue 6/10

1:28 p.m.-10:05 p.m.

2 stops10h 37m

C$ 579

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Fri 2/10

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

2 stops10h 28m

Chicago Midway

Tue 6/10

1:28 p.m.-10:05 p.m.

2 stops10h 37m

C$ 581

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 19/10

11:30 p.m.-9:00 a.m.

1 stop7h 30m

Chicago O'Hare Intl

Tue 20/10

1:30 p.m.-11:12 p.m.

2 stops11h 42m

C$ 589

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 19/10

11:30 p.m.-9:00 a.m.

1 stop7h 30m

Chicago O'Hare Intl

Tue 20/10

1:30 p.m.-11:12 p.m.

2 stops11h 42m

C$ 591

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 21/7

5:05 a.m.-2:35 p.m.

3 stops31h 30m

Chicago Midway

Sun 26/7

3:20 p.m.-11:15 a.m.

3 stops21h 55m

C$ 1,018

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 21/7

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

2 stops18h 50m

Chicago Midway

Sun 26/7

10:25 a.m.-8:20 a.m.

3 stops23h 55m

C$ 1,033

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Tue 21/7

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

2 stops10h 13m

Chicago Midway

Sun 26/7

9:54 a.m.-11:50 p.m.

2 stops15h 56m

C$ 1,837

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 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

7h 30m

Direct flights

None
The fastest flight from Kelowna to Chicago takes 7h 30m
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 7h 30m.

  • 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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sun 2/8
Sun 9/8
By creating a price alert you accept our terms of use and privacy policy.

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