What are the cheapest airlines flying from Kelowna to Chicago round-trip?

Cheapflights users have booked flights from Kelowna to Chicago round-trip from C$ 443. Other airlines that can offer you cheap pricing are Delta, from C$ 454, and Air Canada, from C$ 466. WestJet is currently priced 31% below the average price you’ll pay for this route.

What are the cheapest airlines to fly from Kelowna to Chicago one-way?

One-way options have recently been found by users for as low as C$ 202 on Air Canada. Other airlines that offer cheap prices include United Airlines from C$ 216 and WestJet from C$ 255 one-way.

What is the cheapest month to book a flight from Kelowna to Chicago?

Currently, January is the cheapest month in which you can book a flight from Kelowna to Chicago (average of C$ 261). Flying from Kelowna to Chicago in March is currently the most expensive (average of C$ 353). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest day to fly from Kelowna to Chicago?

Travelers seeking maximum savings on their Kelowna to Chicago flight should consider departing on Tuesday evenings when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What is the cheapest day to fly round-trip from Kelowna to Chicago?

Departing on a Wednesday is a good option for securing a great price. You can expect to save up to 24% when planning your travel around this day of the week.

What is the cheapest month to fly from Kelowna to Chicago?

The best pricing can be found in the month of October. Prices to Chicago from Kelowna average C$ 648. You can even find prices in October for less than C$ 648, as users have found deals to Chicago from as low as C$ 221. The month of March appears to be one of the more expensive times to travel to Chicago from Kelowna. Flying in the targeted month can save you up to 31%.

What is the cheapest time of day to fly from YLW to CHI?

It’s typically best to fly out from Kelowna to Chicago in the afternoon. Doing so could potentially save you 8% on the flight price compared to flying at noon, which is usually more expensive.

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

Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago from Kelowna. Booking flights from Kelowna (YLW) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 1 airline.

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

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

How can I find direct flights from Kelowna to Chicago?

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

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

Yes. Cheapflights offers flight deals from Kelowna to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

C$ 202+ Flights from Kelowna to Chicago - Compare & Save Big

Cheap flight deals from Kelowna to Chicago

Round-trip from	C$ 443
One-way from	C$ 202
Popular in	March
Cheapest in	October
Average price	C$ 529

WestJet
29/8-2/9
2 total stops
15h 03m total
Kelowna to Chicago

Search Deals

Air Canada
13/6
1 total stop
8h 29m total
Kelowna to Chicago

Search Deals

Highest demand for flights based on searches. 9% potential increase in price (C$ 90 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease (C$ 28 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 2025

Search Deals

Find flight deals from Kelowna to Chicago

Cheapest flights from Kelowna to Chicago
Explore the most affordable flight options available from Kelowna to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.

Fri 29/88:00 a.m.YLW - ORD

1 stop6h 44mWestJet

Tue 2/95:30 p.m.ORD - YLW

1 stop8h 19mWestJet

Deal found 29/4C$ 443

Mon 9/61:05 p.m.YLW - ORD

1 stop8h 58mDelta

Sat 14/67:40 a.m.ORD - YLW

2 stops11h 03mDelta

Deal found 29/4C$ 454

Mon 9/68:35 p.m.YLW - ORD

1 stop7h 03mAir Canada

Sat 14/68:48 a.m.ORD - YLW

1 stop10h 09mAir Canada

Deal found 29/4C$ 466

Mon 9/65:45 a.m.YLW - ORD

2 stops15h 19mUnited Airlines

Sat 14/65:02 a.m.ORD - YLW

2 stops16h 55mUnited Airlines

Deal found 29/4C$ 497

Fri 13/66:00 a.m.YLW - ORD

2 stops25h 26mMultiple Airlines

Fri 20/66:17 p.m.ORD - YLW

3 stops24h 13mMultiple Airlines

Deal found 29/4C$ 620

Fri 13/62:36 p.m.YLW - ORD

1 stop7h 23mAlaska Airlines

Thu 19/612:59 a.m.ORD - YLW

2 stops14h 47mAlaska Airlines

Deal found 29/4C$ 998

Mon 9/65:55 a.m.YLW - MDW

2 stops10h 46mDelta

Sat 14/69:24 a.m.MDW - YLW

2 stops9h 19mDelta

Deal found 29/4C$ 1,251

Best flights from Kelowna to Chicago
Discover carefully curated flight deals from Kelowna to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 30 April 2025.

Fri 29/88:00 a.m.YLW - ORD

1 stop6h 44mWestJet

Tue 2/95:30 p.m.ORD - YLW

1 stop8h 19mWestJet

Deal found 29/4C$ 443

Mon 9/61:05 p.m.YLW - ORD

1 stop8h 58mDelta

Sat 14/67:40 a.m.ORD - YLW

2 stops11h 03mDelta

Deal found 29/4C$ 454

Mon 9/68:35 p.m.YLW - ORD

1 stop7h 03mAir Canada

Sat 14/68:48 a.m.ORD - YLW

1 stop10h 09mAir Canada

Deal found 29/4C$ 466

Mon 9/65:45 a.m.YLW - ORD

2 stops15h 19mUnited Airlines

Sat 14/65:02 a.m.ORD - YLW

2 stops16h 55mUnited Airlines

Deal found 29/4C$ 497

Fri 13/66:00 a.m.YLW - ORD

2 stops25h 26mMultiple Airlines

Fri 20/66:17 p.m.ORD - YLW

3 stops24h 13mMultiple Airlines

Deal found 29/4C$ 620

Fri 13/62:36 p.m.YLW - ORD

1 stop7h 23mAlaska Airlines

Thu 19/612:59 a.m.ORD - YLW

2 stops14h 47mAlaska Airlines

Deal found 29/4C$ 998

Mon 9/65:55 a.m.YLW - MDW

2 stops10h 46mDelta

Sat 14/69:24 a.m.MDW - YLW

2 stops9h 19mDelta

Deal found 29/4C$ 1,251

Last-minute flights from Kelowna to Chicago
Discover last-minute flight deals from Kelowna to Chicago. Data last updated 30 April 2025 and is based on user searches.

Sun 4/55:45 a.m.YLW - ORD

1 stop6h 58mAir Canada

Thu 8/58:52 a.m.ORD - YLW

1 stop10h 08mAir Canada

Deal found 29/4C$ 979

Sun 4/51:34 p.m.YLW - ORD

1 stop8h 25mAlaska Airlines

Thu 8/56:58 p.m.ORD - YLW

2 stops19h 46mAlaska Airlines

Deal found 29/4C$ 1,103

Sun 4/55:45 a.m.YLW - ORD

2 stops15h 22mUnited Airlines

Thu 8/59:02 a.m.ORD - YLW

2 stops12h 55mUnited Airlines

Deal found 29/4C$ 1,134

Thu 15/57:30 p.m.YLW - ORD

1 stop8h 16mAir Canada

Mon 19/55:05 a.m.ORD - YLW

2 stops13h 52mAir Canada

Deal found 29/4C$ 576

Thu 15/55:45 a.m.YLW - ORD

2 stops16h 44mUnited Airlines

Mon 19/55:05 a.m.ORD - YLW

2 stops19h 27mUnited Airlines

Deal found 29/4C$ 756

One-way flights from Kelowna to Chicago
Search for one-way flight options from Kelowna to Chicago. Find affordable one-way fares based on user searches. Data last updated 30 April 2025.

Fri 13/611:30 p.m.YLW - ORD

1 stop8h 29mAir Canada

Deal found 29/4C$ 202

Fri 13/65:45 a.m.YLW - ORD

2 stops16h 14mUnited Airlines

Deal found 29/4C$ 216

Sun 19/107:00 a.m.YLW - ORD

1 stop7h 43mWestJet

Deal found 28/4C$ 255

Fri 13/611:30 p.m.YLW - MDW

2 stops10h 59mDelta

Deal found 29/4C$ 269

Fri 13/68:45 p.m.YLW - MDW

3 stops22h 08mMultiple Airlines

Deal found 29/4C$ 439

Tue 3/61:05 p.m.YLW - ORD

1 stop8h 54mDelta

Deal found 29/4C$ 825

Cheapflights Fare Finder

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

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 29/8

8:00 a.m.-4:44 p.m.

1 stop6h 44m

Chicago O'Hare Intl

Tue 2/9

5:30 p.m.-11:49 p.m.

1 stop8h 19m

C$ 443

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 9/6

1:05 p.m.-12:03 a.m.

1 stop8h 58m

Chicago O'Hare Intl

Sat 14/6

7:40 a.m.-4:43 p.m.

2 stops11h 03m

C$ 454

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 9/6

8:35 p.m.-5:38 a.m.

1 stop7h 03m

Chicago O'Hare Intl

Sat 14/6

8:48 a.m.-4:57 p.m.

1 stop10h 09m

C$ 466

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Mon 9/6

5:45 a.m.-11:04 p.m.

2 stops15h 19m

Chicago O'Hare Intl

Sat 14/6

5:02 a.m.-7:57 p.m.

2 stops16h 55m

C$ 497

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 13/6

6:00 a.m.-9:26 a.m.

2 stops25h 26m

Chicago O'Hare Intl

Fri 20/6

6:17 p.m.-4:30 p.m.

3 stops24h 13m

C$ 620

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 13/6

2:36 p.m.-11:59 p.m.

1 stop7h 23m

Chicago O'Hare Intl

Thu 19/6

12:59 a.m.-1:46 p.m.

2 stops14h 47m

C$ 998

KelownaChicago

YLW - MDW

YLWMDW

Kelowna

Mon 9/6

5:55 a.m.-6:41 p.m.

2 stops10h 46m

Chicago Midway

Sat 14/6

9:24 a.m.-4:43 p.m.

2 stops9h 19m

C$ 1,251

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 13/6

11:30 p.m.-9:59 a.m.

1 stop8h 29m

C$ 202

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Fri 13/6

5:45 a.m.-11:59 p.m.

2 stops16h 14m

C$ 216

KelownaChicago

YLW - ORD

YLWORD

Kelowna

Sun 19/10

7:00 a.m.-4:43 p.m.

1 stop7h 43m

C$ 255

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/4

Showing 1-10 of 13 results

Best time to book a flight from Kelowna to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kelowna with our price prediction graph.

Estimated round-trip price

Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Kelowna to Chicago

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

To help decide which airline to fly from Kelowna to Chicago, see what other customers have to say about Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Alaska Airlines

8.0

Very good

9,961 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Alaska Airlines

8.0

Very good

9,961 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Delta

8.0

Very good

7,929 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

United Airlines

7.4

Good

8,696 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

WestJet

7.2

Good

2,826 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Air Canada

7.0

Good

9,244 reviews

Alaska Airlines

8.0

Very good

9,961 reviews

Check prices

Reviews

1 / 20

10.0

Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Related info for your journey

What airport do you fly from for flights from Kelowna to Chicago?
Located just 11.2 km from the city centre, Kelowna is the airport most travellers will use when flying to Chicago from Kelowna. Booking flights from Kelowna (YLW) to Chicago should be relatively easy as there are 0 daily outbound flights to Chicago from 1 airline.
What are the cheapest airlines flying from Kelowna to Chicago round-trip?
Cheapflights users have booked flights from Kelowna to Chicago round-trip from C$ 443. Other airlines that can offer you cheap pricing are Delta, from C$ 454, and Air Canada, from C$ 466. WestJet is currently priced 31% below the average price you’ll pay for this route.
What are the cheapest airlines to fly from Kelowna to Chicago one-way?
One-way options have recently been found by users for as low as C$ 202 on Air Canada. Other airlines that offer cheap prices include United Airlines from C$ 216 and WestJet from C$ 255 one-way.
Can I find deals for flights from Kelowna to Chicago that include hotel bookings?
Yes. In addition to deals on Kelowna to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Kelowna to Chicago?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kelowna to Chicago.
Can I find deals for business class flights from Kelowna to Chicago?
Yes. Cheapflights offers flight deals from Kelowna to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.
What is the cheapest month to book a flight from Kelowna to Chicago?
Currently, January is the cheapest month in which you can book a flight from Kelowna to Chicago (average of C$ 261). Flying from Kelowna to Chicago in March is currently the most expensive (average of C$ 353). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Kelowna to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Air Canada	CheapestC$ 384	AverageC$ 510	FlexibilityNo cancel fee	On-time67%	Search Air Canada flights

Fly with Cheapflights

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

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Kelowna to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights simply makes it quick and affordable to book flights from Kelowna to Chicago 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 Chicago with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights from Kelowna to Chicago flexibly with Cheapflights today.

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

Yes, and it’s super simple to set up. Click the bell icon next to the flight deals above and provide a valid email address to enable Price Alerts. That’s it!

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Cheap flights from Kelowna to Chicago from C$ 202

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 13/6. Fares are subject to change and may not be available on all flights or dates of travel.

Cheap flight deals from Kelowna to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Kelowna to Chicago

Cheapest flights from Kelowna to ChicagoExplore the most affordable flight options available from Kelowna to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.

Explore the most affordable flight options available from Kelowna to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.

Cheapflights Fare Finder

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

Best time to book a flight from Kelowna to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Kelowna with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Kelowna to Chicago

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

To help decide which airline to fly from Kelowna to Chicago, see what other customers have to say about Alaska Airlines, Delta and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Kelowna to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

What are the cheapest airlines flying from Kelowna to Chicago round-trip?

What are the cheapest airlines to fly from Kelowna to Chicago one-way?

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

How can I find direct flights from Kelowna to Chicago?

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

What is the cheapest month to book a flight from Kelowna to Chicago?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Kelowna to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Kelowna to Chicago

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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

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

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

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

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Cheapest flights from Kelowna to Chicago
Explore the most affordable flight options available from Kelowna to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 April 2025.