Flights To Osage County - Cheap Flights Starting at CA $509

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How Much Does it Cost To Fly To Osage County?

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Oct 29 - Sat, Oct 31
YYZ
Pearson Intl.
COU
Columbia Regional
CA $892 Roundtrip, found 2 days ago
CA $892
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 29 from Pearson Intl. to Columbia Regional, returning Sat, Oct 31, priced at CA $892 found 2 days ago
Thu, Oct 29 - Sat, Oct 31
YYZ
Pearson Intl.
COU
Columbia Regional
CA $892 Roundtrip, found 2 days ago
CA $892
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 29 from Pearson Intl. to Columbia Regional, returning Sat, Oct 31, priced at CA $892 found 2 days ago
Thu, Oct 29 - Sat, Oct 31
YYZ
Pearson Intl.
COU
Columbia Regional
CA $995 Roundtrip, found 2 days ago
CA $995
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 29 from Pearson Intl. to Columbia Regional, returning Sat, Oct 31, priced at CA $995 found 2 days ago
Tue, Dec 15 - Sun, Dec 20
YYZ
Pearson Intl.
COU
Columbia Regional
CA $995 Roundtrip, found 12 hours ago
CA $995
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Dec 15 from Pearson Intl. to Columbia Regional, returning Sun, Dec 20, priced at CA $995 found 12 hours ago
Thu, Oct 29 - Sat, Oct 31
YYZ
Pearson Intl.
COU
Columbia Regional
CA $997 Roundtrip, found 2 days ago
CA $997
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 29 from Pearson Intl. to Columbia Regional, returning Sat, Oct 31, priced at CA $997 found 2 days ago
Thu, Oct 29 - Sat, Oct 31
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,035 Roundtrip, found 2 days ago
CA $1,035
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 29 from Pearson Intl. to Columbia Regional, returning Sat, Oct 31, priced at CA $1,035 found 2 days ago
Tue, Dec 15 - Sun, Dec 20
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,035 Roundtrip, found 12 hours ago
CA $1,035
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Dec 15 from Pearson Intl. to Columbia Regional, returning Sun, Dec 20, priced at CA $1,035 found 12 hours ago
Thu, Oct 29 - Sat, Oct 31
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,067 Roundtrip, found 2 days ago
CA $1,067
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Oct 29 from Pearson Intl. to Columbia Regional, returning Sat, Oct 31, priced at CA $1,067 found 2 days ago
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Kingdom City
2.0-star property

Days Inn by Wyndham Kingdom City

Dec 26 - Dec 29

3 night stay

Toronto (YYZ) to Columbia (COU)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,107, price is now CA $1,076 per person
CA $1,076
per person
found 1 day ago
Capital O Amerihost Inn and Suites Fulton Hwy 54 MO
2.5-star property

Capital O Amerihost Inn and Suites Fulton Hwy 54 MO

Nov 2 - Nov 9

7 night stay

Kelowna (YLW) to Columbia (COU)

United • Roundtrip • Coach
Price was CA $2,331, price is now CA $2,082 per person
CA $2,082
per person
found 10 hours ago
Capital O Amerihost Inn and Suites Mexico Hwy 54 MO
2.5-star property

Capital O Amerihost Inn and Suites Mexico Hwy 54 MO

Nov 2 - Nov 9

7 night stay

Kelowna (YLW) to Columbia (COU)

United • Roundtrip • Coach
Price was CA $2,213, price is now CA $2,015 per person
CA $2,015
per person
found 10 hours ago
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Travelers ❤️ These Osage County 🏨

Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

Scenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace

Belle MO
Book a stay at this family-friendly vacation home in Belle. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews.
10/10 Exceptional! (242 reviews)
"This property is amazing . We had very good time there . It is equipped with everything you will need to have a great time there. We will definitely come back."

Reviewed on Oct 12, 2026

Opens in a new windowScenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace
Days Inn by Wyndham Jefferson City

Days Inn by Wyndham Jefferson City

2 out of 5
2100 Jefferson St Jefferson City MO
Book a stay at this business-friendly hotel in Jefferson City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions McKay Park and Rolling Hills Neighborhood Park are located nearby.
8/10 Very good! (1,003 reviews)
"Basic hotel at a nicer hotel price (maybe because the Missouri football game was in the area). Very basic breakfast with only one juice offering, hot tub out of order, no automatic front entrance and no benches on the property to rest/hang out"

Reviewed on Oct 12, 2026

Opens in a new windowDays Inn by Wyndham Jefferson City
Baymont by Wyndham Jefferson City

Baymont by Wyndham Jefferson City

2.5 out of 5
319 W. Miller Street Jefferson City MO
Book a stay at this business-friendly hotel in Jefferson City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Miller Performing Arts Center and Carnahan Memorial Garden are located nearby.
8.4/10 Very good! (1,013 reviews)
"The staff were very helpful and friendly. Having laundry was very handy as we were biking the Katy Trail. The breakfast was the best one of the trip. The room was clean, spacious, and comfortable. We were very pleased."

Reviewed on Oct 13, 2026

Opens in a new windowBaymont by Wyndham Jefferson City
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Capitol Plaza Hotel Jefferson City

Capitol Plaza Hotel Jefferson City

3.5 out of 5
Jefferson City 415 W. McCarty St Jefferson City MO
Book a stay at this business-friendly hotel in Jefferson City. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Carnahan Memorial Garden and Rotary Centennial Park are located nearby.
6.8/10 (1,042 reviews)
"HVAC definitely had mold in system. Pool had exposed wires, toilet stopped up. No fridge no microwave. No breakfast but said it had free breakfast. Literally everything in hotel was old out dated and need replacing. Do yourself a favor and pay a few dollars more and stay somewhere else. Pictures ..."

Reviewed on Oct 12, 2026

Opens in a new windowCapitol Plaza Hotel Jefferson City
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Osage County?
A roundtrip flight to Osage County cost as little as CA $892 within the last seven days. When you're ready to book, we'll help you score a top deal. This price was available on Travelocity for flights to Osage County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Osage County?
According to Travelocity's direct return flight demand between January and December last year, October is the cheapest time to journey to Osage County. Search for flights during this month and snap up a bargain today.
How can I check my flight status to Osage County?
"Trips" will clue you in when it comes to details about your flight to Osage County. This handy customer portal allows you to manage everything from one place, from checking the status of your flight to making changes to your booking. Click on Trips at the top right of the Travelocity homepage and then create a free account. Alternatively, download the Travelocity app and access your travel itinerary while you're on the go. Whether you have the family flying with you or you're riding solo, all your travel plans are right there in your grasp.
How do I find the best deals on flights to Osage County?
You'll always find an epic deal with Travelocity — our "Flexible dates" search tool makes it super simple. Enter your desired dates, then select the flexible dates box above your results to compare prices with the surrounding days. CA $892 was the best price for a return flight to Osage County in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Osage County with Travelocity?
Where to begin! With cheap flights to Osage County, accommodations and activities, you'll find all you need to create your perfect trip with Travelocity. Secure your cheap family flights and take advantage of our 24/7 customer assistance and free cancellations on most hotels if you need. Our goal is to offer stress-free travel when you book with us so that you can spend less time on the nitty-gritty and more time making memories with your family and friends.
How much is a flight to Osage County on average?
In the last seven days, roundtrip flights to Osage County cost between CA $892 and CA $1,067. No matter what type of fare you're after, we've got some great deals to help you keep within budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.