Flights To Osage County - Cheap Flights Starting at

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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.

Wed, Sep 30 - Thu, Oct 1
YYZ
Pearson Intl.
COU
Columbia Regional
CA $744 Roundtrip, found 6 days ago
CA $744
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 30 from Pearson Intl. to Columbia Regional, returning Thu, Oct 1, priced at CA $744 found 6 days ago
Thu, Jul 23 - Mon, Jul 27
YYZ
Pearson Intl.
COU
Columbia Regional
CA $829 Roundtrip, found 5 hours ago
CA $829
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Jul 23 from Pearson Intl. to Columbia Regional, returning Mon, Jul 27, priced at CA $829 found 5 hours ago
Wed, Sep 30 - Thu, Oct 1
YYZ
Pearson Intl.
COU
Columbia Regional
CA $844 Roundtrip, found 6 days ago
CA $844
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 30 from Pearson Intl. to Columbia Regional, returning Thu, Oct 1, priced at CA $844 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $858 Roundtrip, found 6 days ago
CA $858
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $858 found 6 days ago
Wed, Sep 30 - Thu, Oct 1
YYZ
Pearson Intl.
COU
Columbia Regional
CA $887 Roundtrip, found 6 days ago
CA $887
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 30 from Pearson Intl. to Columbia Regional, returning Thu, Oct 1, priced at CA $887 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $898 Roundtrip, found 6 days ago
CA $898
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $898 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $925 Roundtrip, found 6 days ago
CA $925
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $925 found 6 days ago
Thu, Jul 23 - Mon, Jul 27
YYZ
Pearson Intl.
COU
Columbia Regional
CA $934 Roundtrip, found 5 hours ago
CA $934
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Jul 23 from Pearson Intl. to Columbia Regional, returning Mon, Jul 27, priced at CA $934 found 5 hours ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $964 Roundtrip, found 6 days ago
CA $964
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $964 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $966 Roundtrip, found 6 days ago
CA $966
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $966 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $981 Roundtrip, found 6 days ago
CA $981
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $981 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,000 Roundtrip, found 6 days ago
CA $1,000
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $1,000 found 6 days ago
Thu, Jul 23 - Mon, Jul 27
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,011 Roundtrip, found 5 hours ago
CA $1,011
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Thu, Jul 23 from Pearson Intl. to Columbia Regional, returning Mon, Jul 27, priced at CA $1,011 found 5 hours ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,015 Roundtrip, found 6 days ago
CA $1,015
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $1,015 found 6 days ago
Mon, Sep 7 - Wed, Sep 9
YYZ
Pearson Intl.
COU
Columbia Regional
CA $1,017 Roundtrip, found 6 days ago
CA $1,017
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 7 from Pearson Intl. to Columbia Regional, returning Wed, Sep 9, priced at CA $1,017 found 6 days ago
Price found within the past 48 hours. Click for updated prices.
Finn's 66 Motel
2.5-star property

Finn's 66 Motel

Jul 26 - Jul 28

2 night stay

Calgary (YYC) to Columbia (COU)

WestJet • Non-stop roundtrip • Coach
Price was CA $855, price is now CA $832 per person
CA $832
per person
found 1 day ago
Super 8 by Wyndham Lake of the Ozarks
2.0-star property

Super 8 by Wyndham Lake of the Ozarks

Aug 9 - Aug 13

4 night stay

Winnipeg (YWG) to Columbia (COU)

United • Non-stop roundtrip • Coach
Price was CA $1,105, price is now CA $1,049 per person
CA $1,049
per person
found 2 hours ago
Rock Harbor Resort and Motel
2.0-star property

Rock Harbor Resort and Motel

Aug 9 - Aug 13

4 night stay

Winnipeg (YWG) to Columbia (COU)

United • Non-stop roundtrip • Coach
Price was CA $1,143, price is now CA $1,110 per person
CA $1,110
per person
found 2 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! (230 reviews)
"This property is simply amazing!! Randy , the host was excellent to communicate with!! The house is stocked with everything you can think of!! The pool and outdoor kitchen was top notch!! We will definitely be returning!"

Reviewed on Jul 8, 2026

Opens in a new windowScenic Lakeside Chateau with Heated Pool, Hot Tub & Outdoor Kitchen-TV-Fireplace
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, breakfast (surcharge), and room service. 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.
7/10 Good! (1,025 reviews)
"Looks like it’s from the 70s with nothing but basic maintenance since. There’s a huge water feature in the conference hall that is just one step above being held together with duct tape and baling wire. Desk staff was efficient but personality of rocks. I won’t stay there again."

Reviewed on Jul 10, 2026

Opens in a new windowCapitol Plaza Hotel 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! (1,011 reviews)
"We were passing through Jeff City to visit the Capitol. The room was clean and bed was very comfortable!"

Reviewed on Jul 13, 2026

Opens in a new windowBaymont by Wyndham Jefferson City
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Hermann Crown Suites

Hermann Crown Suites

3.5 out of 5
403 South Market Street Hermann MO
Stay at this inn in Hermann. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Deutschheim State Historic Site and Hermannhof Vineyards are located nearby.
9.4/10 Exceptional! (823 reviews)
"Delightful themed room, special free goodies—breakfast, adult beverages, even ice cream, and fantastic outdoor Biergarten with live music. Within easy walking distance of stores, restaurants, and historic sites. Would definitely stay again."

Reviewed on Jul 14, 2026

Opens in a new windowHermann Crown Suites
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 $744 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, September 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 $744 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 $744 and CA $1,017. 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.