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

Air Canada and United Airlines are the most popular carriers operating from Kelowna to Chicago

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.

C$ 241 Cheap Flights from Kelowna to Chicago in 2026/27

Find the cheapest flights from Kelowna to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:05 a.m. - 4:40 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 35m1 stop Calgary

5:30 p.m. - 11:50 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 20m1 stop Calgary

C$ 324WestJet

Fri, 16 Oct - Fri, 23 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

3:30 p.m. - 7:13 a.m.ORD Chicago O'Hare Intl-YLW Kelowna

17h 43m1 stop Vancouver Intl

C$ 385Air Canada

Thu, 22 Oct - Tue, 27 Oct

9:20 p.m. - 10:07 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

11h 47m2 stops Vancouver Intl Montreal Pierre Elliott Trudeau Intl

3:30 p.m. - 11:28 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 58m1 stop Vancouver Intl

C$ 402Air Canada

Tue, 3 Nov - Tue, 10 Nov

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

3:30 p.m. - 7:13 a.m.ORD Chicago O'Hare Intl-YLW Kelowna

17h 43m1 stop Vancouver Intl

C$ 423Air Canada

Wed, 21 Oct - Wed, 28 Oct

1:47 p.m. - 11:59 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 12m1 stop Seattle/Tacoma Intl

9:00 a.m. - 12:57 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

29h 57m1 stop Seattle/Tacoma Intl

C$ 433Alaska Airlines

Thu, 22 Oct - Tue, 27 Oct

1:47 p.m. - 11:59 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 12m1 stop Seattle/Tacoma Intl

5:46 p.m. - 12:57 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

21h 11m1 stop Seattle/Tacoma Intl

C$ 433Alaska Airlines

Thu, 22 Oct - Tue, 27 Oct

1:47 p.m. - 11:59 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 12m1 stop Seattle/Tacoma Intl

9:00 a.m. - 12:57 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

29h 57m1 stop Seattle/Tacoma Intl

C$ 436Alaska Airlines

Thu, 22 Oct - Tue, 27 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

10:15 a.m. - 7:13 a.m.ORD Chicago O'Hare Intl-YLW Kelowna

22h 58m2 stops Toronto Pearson Intl Vancouver Intl

C$ 440Air Canada

Thu, 22 Oct - Tue, 27 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

3:45 p.m. - 9:52 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 07m1 stop Toronto Pearson Intl

C$ 451Air Canada

Fri, 16 Oct - Fri, 23 Oct

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

2:15 p.m. - 9:52 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 37m1 stop Toronto Pearson Intl

C$ 451Air Canada

Sat, 17 Oct - Wed, 21 Oct

Cheap last-minute flights

Enter your travel dates to find the best prices.

5:05 a.m. - 4:40 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

9h 35m1 stop Calgary

5:30 p.m. - 10:05 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

6h 35m1 stop Calgary

C$ 905WestJet

Thu, 24 Sep - Sun, 27 Sep

10:20 a.m. - 5:38 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

17h 18m2 stops Vancouver Intl Las Vegas Harry Reid Intl

5:30 p.m. - 8:20 a.m.ORD Chicago O'Hare Intl-YLW Kelowna

16h 50m1 stop Calgary

C$ 960Multiple Airlines

Thu, 24 Sep - Sun, 27 Sep

10:50 p.m. - 9:00 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

8h 10m1 stop Toronto Pearson Intl

3:40 p.m. - 11:27 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

9h 47m1 stop Vancouver Intl

C$ 1,201Air Canada

Mon, 28 Sep - Thu, 1 Oct

8:45 p.m. - 11:59 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

25h 14m2 stops Vancouver Intl Seattle/Tacoma Intl

5:30 p.m. - 11:50 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 20m1 stop Calgary

C$ 1,204Multiple Airlines

Mon, 28 Sep - Thu, 1 Oct

3:07 p.m. - 11:59 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

6h 52m1 stop Seattle/Tacoma Intl

5:30 p.m. - 9:40 a.m.ORD Chicago O'Hare Intl-YLW Kelowna

18h 10m1 stop Calgary

C$ 1,273Multiple Airlines

Thu, 24 Sep - Sun, 27 Sep

3:10 p.m. - 6:20 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

13h 10m2 stops Vancouver Intl Seattle/Tacoma Intl

6:00 a.m. - 6:00 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

14h 00m2 stops Seattle/Tacoma Intl Vancouver Intl

C$ 1,298Multiple Airlines

Mon, 28 Sep - Thu, 1 Oct

3:07 p.m. - 1:26 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

20h 19m2 stops Seattle/Tacoma Intl Portland

2:22 p.m. - 2:17 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

25h 55m2 stops Portland Seattle/Tacoma Intl

C$ 1,350Alaska Airlines

Thu, 24 Sep - Sun, 27 Sep

6:05 a.m. - 6:26 p.m.YLW Kelowna-ORD Chicago O'Hare Intl

10h 21m2 stops Calgary Detroit Metropolitan Wayne County

5:30 p.m. - 11:50 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

8h 20m1 stop Calgary

C$ 1,439WestJet

Thu, 24 Sep - Sun, 27 Sep

5:55 a.m. - 12:55 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

17h 00m2 stops Vancouver Intl Guadalajara Miguel Hidal

7:09 a.m. - 9:45 a.m.ORD Chicago O'Hare Intl-YLW Kelowna

28h 36m3 stops Santiago de Querétaro Guadalajara Miguel Hidal Vancouver Intl

C$ 1,472Multiple Airlines

Thu, 24 Sep - Sun, 27 Sep

10:55 a.m. - 5:38 a.m.YLW Kelowna-ORD Chicago O'Hare Intl

16h 43m3 stops Calgary Phoenix Sky Harbor Intl Las Vegas Harry Reid Intl

8:55 p.m. - 11:50 p.m.ORD Chicago O'Hare Intl-YLW Kelowna

28h 55m3 stops Las Vegas Harry Reid Intl Phoenix Sky Harbor Intl Calgary

C$ 1,516Multiple Airlines

Mon, 28 Sep - Thu, 1 Oct

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

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

Trusted and free

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

Price Alerts

Not ready to book? to track prices.

Search flight deals

Delta flights from Kelowna to Chicago

Our best Delta deals on Kelowna to Chicago flight tickets

Delta

17 Oct

YLW10:20 a.m.Kelowna

9h 45m

2 stops

ORD10:05 p.m.Chicago O'Hare Intl

21 Oct

ORD6:20 a.m.Chicago O'Hare Intl

10h 15m

2 stops

YLW2:35 p.m.Kelowna

C$ 484

Delta

22 Oct

YLW7:50 a.m.Kelowna

6h 50m

1 stop

ORD4:40 p.m.Chicago O'Hare Intl

27 Oct

ORD6:20 a.m.Chicago O'Hare Intl

10h 10m

2 stops

YLW2:30 p.m.Kelowna

C$ 517

Delta

21 Oct

YLW6:05 a.m.Kelowna

12h 25m

2 stops

ORD8:30 p.m.Chicago O'Hare Intl

28 Oct

ORD6:20 a.m.Chicago O'Hare Intl

10h 10m

2 stops

YLW2:30 p.m.Kelowna

C$ 526

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

Air Canada

22 Oct

YLW10:50 p.m.Kelowna

8h 10m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

27 Oct

ORD3:30 p.m.Chicago O'Hare Intl

17h 43m

1 stop

YLW7:13 a.m.Kelowna

C$ 385

Air Canada

3 Nov

YLW9:20 p.m.Kelowna

11h 47m

2 stops

ORD10:07 a.m.Chicago O'Hare Intl

10 Nov

ORD3:30 p.m.Chicago O'Hare Intl

8h 58m

1 stop

YLW11:28 p.m.Kelowna

C$ 402

Air Canada

21 Oct

YLW10:50 p.m.Kelowna

8h 10m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

28 Oct

ORD3:30 p.m.Chicago O'Hare Intl

17h 43m

1 stop

YLW7:13 a.m.Kelowna

C$ 423

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 16/10

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

1 stop8h 35m

Chicago O'Hare Intl

Fri 23/10

5:30 p.m.-11:50 p.m.

1 stop8h 20m

C$ 324

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

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

1 stop8h 10m

Chicago O'Hare Intl

Tue 27/10

3:30 p.m.-7:13 a.m.

1 stop17h 43m

C$ 385

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Tue 3/11

9:20 p.m.-10:07 a.m.

2 stops11h 47m

Chicago O'Hare Intl

Tue 10/11

3:30 p.m.-11:28 p.m.

1 stop8h 58m

C$ 402

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Wed 21/10

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

1 stop8h 10m

Chicago O'Hare Intl

Wed 28/10

3:30 p.m.-7:13 a.m.

1 stop17h 43m

C$ 423

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

1:47 p.m.-11:59 p.m.

1 stop8h 12m

Chicago O'Hare Intl

Tue 27/10

9:00 a.m.-12:57 p.m.

1 stop29h 57m

C$ 433

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

1:47 p.m.-11:59 p.m.

1 stop8h 12m

Chicago O'Hare Intl

Tue 27/10

5:46 p.m.-12:57 p.m.

1 stop21h 11m

C$ 433

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

1:47 p.m.-11:59 p.m.

1 stop8h 12m

Chicago O'Hare Intl

Tue 27/10

9:00 a.m.-12:57 p.m.

1 stop29h 57m

C$ 436

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Thu 22/10

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

1 stop8h 10m

Chicago O'Hare Intl

Tue 27/10

10:15 a.m.-7:13 a.m.

2 stops22h 58m

C$ 440

Quickest round-trip

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Fri 16/10

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

1 stop8h 10m

Chicago O'Hare Intl

Fri 23/10

3:45 p.m.-9:52 p.m.

1 stop8h 07m

C$ 451

KelownaChicago

YLW Kelowna - ORD Chicago O'Hare Intl

YLWORD

Kelowna

Sat 17/10

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

1 stop8h 10m

Chicago O'Hare Intl

Wed 21/10

2:15 p.m.-9:52 p.m.

1 stop9h 37m

C$ 451

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest month to fly to Chicago?

The month of May is another great option to travel to Chicago, with average flight prices from Kelowna averaging around C$ 443.

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

Best price found	C$ 241
Fastest flight time	6h 42m
Direct flights	None

The best one-way flight to Chicago from Kelowna in the past 72 hours is C$ 241. The best round-trip flight deal from Kelowna to Chicago found on momondo in the last 72 hours is C$ 324.

The fastest flight from Kelowna to Chicago takes 6h 42m

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 42m.
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?
Based on momondo bookings for flights between Kelowna and Chicago, the leading airline is WestJet, making up 100% of the total bookings.

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

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

Thu 22/10

Thu 29/10

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Cabin classes

Other United States destinations

Other flights from Kelowna

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Kelowna to Chicago from C$ 241

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 29/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Kelowna to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Delta flights from Kelowna to Chicago

Our best Delta deals on Kelowna to Chicago flight tickets

Air Canada flights from Kelowna to Chicago

Our best Air Canada deals on Kelowna to Chicago flight tickets

momondo Fare Finder

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

See travel insights to Chicago from

How to get the cheapest flight ticket from Kelowna to Chicago

What is the cheapest month to fly to Chicago?

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

When to book flights from Kelowna to Chicago

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

Best price found

Fastest flight time

Direct flights

Frequently asked questions about flying from Kelowna to Chicago

Travelling to a place near Chicago?

Why use momondo?

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.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Kelowna

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year