Cheap Flights to Roosevelt County from $50 (2026/2027)

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Jet to one of Roosevelt County's top cities

A mountainous landscape with snow-capped peaks, a field with grazing cattle, and a cloudy sky.

Wolf Point

Flights
Wolf Point
A covered bridge with a sign reading "Cumberland" and a sunset in the background.

Culbertson

Flights
Culbertson

How Much Does it Cost To Fly To Roosevelt County?

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

Fri, Sep 4 - Fri, Sep 4
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$96 Roundtrip, found 7 hours ago
$96
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Sidney-Richland Municipal, returning Fri, Sep 4, priced at $96 found 7 hours ago
Mon, Aug 10 - Mon, Aug 10
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$97 Roundtrip, found 2 days ago
$97
Roundtrip
found 2 days ago
Select Cape Air flight, departing Mon, Aug 10 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Aug 10, priced at $97 found 2 days ago
Thu, Aug 6 - Mon, Aug 10
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, Aug 6 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Aug 10, priced at $100 found 2 days ago
Fri, Sep 4 - Fri, Sep 4
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$101 Roundtrip, found 7 hours ago
$101
Roundtrip
found 7 hours ago
Select Cape Air flight, departing Fri, Sep 4 from Logan Intl. to Sidney-Richland Municipal, returning Fri, Sep 4, priced at $101 found 7 hours ago
Tue, Aug 4 - Sat, Aug 8
BIL
Logan Intl.
OLF
L. M. Clayton
$102 Roundtrip, found 4 days ago
$102
Roundtrip
found 4 days ago
Select Cape Air flight, departing Tue, Aug 4 from Logan Intl. to L. M. Clayton, returning Sat, Aug 8, priced at $102 found 4 days ago
Sat, Aug 29 - Sat, Sep 5
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sat, Aug 29 from Logan Intl. to Sidney-Richland Municipal, returning Sat, Sep 5, priced at $102 found 1 day ago
Sat, Aug 29 - Sat, Sep 5
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$113 Roundtrip, found 1 day ago
$113
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sat, Aug 29 from Logan Intl. to Sidney-Richland Municipal, returning Sat, Sep 5, priced at $113 found 1 day ago
Sat, Aug 1 - Sun, Aug 2
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sat, Aug 1 from Logan Intl. to Sidney-Richland Municipal, returning Sun, Aug 2, priced at $120 found 2 days ago
OriginDestinationTravel DatesFlights From*
BILSidneySeptember 4 to September 4$96
*Prices include taxes and fees

Best Roosevelt County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Microtel Inn & Suites by Wyndham Sidney
2.5-star property

Microtel Inn & Suites by Wyndham Sidney

Aug 20 - Aug 23

3 night stay

Columbus (CMH) to Sidney (SDY)

United • Roundtrip • Coach
Price was $794, price is now $767 per person
$767
per person
found 1 day ago
Homestead Inn Wolf Point Hwy 2
2.0-star property

Homestead Inn Wolf Point Hwy 2

Aug 20 - Aug 23

3 night stay

Columbus (CMH) to Wolf Point (OLF)

United • Roundtrip • Coach
Price was $996, price is now $886 per person
$886
per person
found 1 day ago
The Roosevelt Hotel & RV Park Gateway to Theodore Roosevelt National Park-Medora-on i-94
2.5-star property

The Roosevelt Hotel & RV Park Gateway to Theodore Roosevelt National Park-Medora-on i-94

Aug 20 - Aug 23

3 night stay

Columbus (CMH) to Sidney (SDY)

United • Roundtrip • Coach
Price was $856, price is now $819 per person
$819
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Columbus to Roosevelt County
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Travelers ❤️ These Roosevelt County 🏨

Homestead Inn Wolf Point Hwy 2

Homestead Inn Wolf Point Hwy 2

2 out of 5
101 Highway East Wolf Point MT
Stay at this motel in Wolf Point. Enjoy free WiFi, free parking, and free train station pick-up. Our guests praise the helpful staff in our reviews. Popular attractions Nellie’s Park and Northern Lights Casino are located nearby.
7.8/10 Good! (372 reviews)
"Just keep driving! We stopped here on our way to Glacier to break up the drive, but wish we hadn't. This hotel is so old and run down it is like stepping back into the 80's. I cannot imagine that our brown shag carpet was sanitary. It has that old hotel mixed with smoke smell. Before we even got ..."

Reviewed on Jul 21, 2026

Opens in a new windowHomestead Inn Wolf Point Hwy 2
Homestead Inn Extended Stay - 3 nights minimum

Homestead Inn Extended Stay - 3 nights minimum

3 out of 5
6201 A N 1 Dr Wolf Point MT
Stay at this apartment in Wolf Point. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Nellie’s Park and Montana Cowboy Hall of Fame are located nearby.
7.4/10 Good! (3 reviews)
"The room was clean. New floor. Good comfortable beds. AC kept room cool in 100 degree heat. Price was very reasonable. Shower had lots of hot water. Room was quiet even though located next to highway #2. The unit is isolated but lots of lights made it feel secure. I would stay here again. Met the ..."

Reviewed on Jul 21, 2026

Opens in a new windowHomestead Inn Extended Stay - 3 nights minimum
Homestead Inn Extended Stay - 3 nights minimum

Homestead Inn Extended Stay - 3 nights minimum

Wolf Point MT
Stay at this hotel in Wolf Point. Enjoy air conditioning. Popular attractions Nellie’s Park and Montana Cowboy Hall of Fame are located nearby.
6/10 (3 reviews)
"The mosquitos"

Reviewed on Jul 13, 2026

Opens in a new windowHomestead Inn Extended Stay - 3 nights minimum
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Charming 4-bedroom house. NO ANIMALS.

Charming 4-bedroom house. NO ANIMALS.

Wolf Point MT
Stay at this vacation home in Wolf Point. Enjoy free WiFi, laundry facilities, and air conditioning. Popular attractions Nellie’s Park and Northern Lights Casino are located nearby.
9.6/10 Exceptional! (9 reviews)
"Full family experience nice location"

Reviewed on Jun 24, 2026

Opens in a new windowCharming 4-bedroom house. NO ANIMALS.
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 Roosevelt County?
To help you budget, the cheapest roundtrip flight to Roosevelt County was $96 in the last seven days. A good way to nab a travel bargain is to be flexible with your dates. This price was available on Travelocity for flights to Roosevelt County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Roosevelt County?
There are 15 airline companies that you can fly with to Roosevelt County. If you're thinking about a journey to Wolf Point, go for Cape Air. This highly rated carrier operates 60 flights a month to Roosevelt County's major city.
What is the cheapest month to fly to Roosevelt County?
Leave September empty in your calendar, because it's the most affordable month to travel to Roosevelt County. That's based on Travelocity's direct flight demand from January to December last year. With more money in your wallet, you can go on a shopping binge, go to a concert or whatever else you feel like!
How can I check my flight status to Roosevelt County?
"Trips" should be your first stop when it comes to the details of your flight to Roosevelt County. Our handy portal makes it possible to do everything in the one place, from checking the status of your flight to seeing details about your hotel. Click on Trips at the top of the Travelocity homepage and then sign in. Or, download the Travelocity app and access your itinerary while you're out and about. Whether you've got the family flying with you or you're going solo, all your travel plans are right there in your pocket.
How do I find the best deals on flights to Roosevelt County?
Walk away with an unbeatable deal with Travelocity — our "Flexible dates" search tool makes it super simple. Enter the travel dates you prefer, then click the flexible dates box above your results to compare prices for nearby days. $96 was the cheapest price for a roundtrip flight to Roosevelt 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 Roosevelt County with Travelocity?
If you're on the lookout for cheap flights to Roosevelt County, you'll track down some attractive deals with Travelocity. From cheap family flights with budget air carriers to flexible airfares, we've got you covered. Experience a worry-free break with our 24/7 social media customer support, Price Match Guarantee and free cancellation policies with most hotels. Start packing your bags and get ready to jet off to this exciting destination.
How much is a flight to Roosevelt County on average?
Travelers were scoring roundtrip flights to Roosevelt County for between $96 and $120 with Travelocity in the last seven days. Whether you're looking to fly budget or first class, we'll help you get an incredible deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Roosevelt County?
What you can expect largely depends on your carrier and where you're departing from. Most airlines provide food, drinks and entertainment on long-haul services. Whether you're seeking business class flights to Roosevelt County or cheap flights for family vacations, you'll be looked after from the moment your plane leaves the runway to touchdown.