Cheap Flights to Roosevelt County from $51 (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.

Thu, Feb 4 - Thu, Feb 4
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$94 Roundtrip, found 3 days ago
$94
Roundtrip
found 3 days ago
Select Cape Air flight, departing Thu, Feb 4 from Logan Intl. to Sidney-Richland Municipal, returning Thu, Feb 4, priced at $94 found 3 days ago
Sat, Oct 3 - Sat, Oct 3
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$96 Roundtrip, found 3 days ago
$96
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Oct 3 from Logan Intl. to Sidney-Richland Municipal, returning Sat, Oct 3, priced at $96 found 3 days ago
Thu, Feb 4 - Fri, Feb 5
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$100 Roundtrip, found 3 days ago
$100
Roundtrip
found 3 days ago
Select Cape Air flight, departing Thu, Feb 4 from Logan Intl. to Sidney-Richland Municipal, returning Fri, Feb 5, priced at $100 found 3 days ago
Wed, Oct 7 - Thu, Oct 8
BIL
Logan Intl.
OLF
L. M. Clayton
$101 Roundtrip, found 10 hours ago
$101
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Wed, Oct 7 from Logan Intl. to L. M. Clayton, returning Thu, Oct 8, priced at $101 found 10 hours ago
Sat, Oct 3 - Sat, Oct 3
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$101 Roundtrip, found 3 days ago
$101
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Oct 3 from Logan Intl. to Sidney-Richland Municipal, returning Sat, Oct 3, priced at $101 found 3 days ago
Fri, Nov 27 - Fri, Nov 27
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$104 Roundtrip, found 4 days ago
$104
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Nov 27 from Logan Intl. to Sidney-Richland Municipal, returning Fri, Nov 27, priced at $104 found 4 days ago
Sat, Oct 3 - Sat, Oct 3
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$106 Roundtrip, found 3 days ago
$106
Roundtrip
found 3 days ago
Select Cape Air flight, departing Sat, Oct 3 from Logan Intl. to Sidney-Richland Municipal, returning Sat, Oct 3, priced at $106 found 3 days ago
Fri, Nov 27 - Tue, Dec 1
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$110 Roundtrip, found 4 days ago
$110
Roundtrip
found 4 days ago
Select Cape Air flight, departing Fri, Nov 27 from Logan Intl. to Sidney-Richland Municipal, returning Tue, Dec 1, priced at $110 found 4 days ago
Thu, Oct 8 - Sun, Oct 11
MSP
Minneapolis - St. Paul Intl.
XWA
Basin Intl.
$422 Roundtrip, found 1 day ago
$422
Roundtrip
found 1 day ago
Select United flight, departing Thu, Oct 8 from Minneapolis - St. Paul Intl. to Basin Intl., returning Sun, Oct 11, priced at $422 found 1 day ago
Thu, Oct 22 - Mon, Oct 26
DFW
Dallas-Fort Worth Intl.
XWA
Basin Intl.
$438 Roundtrip, found 2 days ago
$438
Roundtrip
found 2 days ago
Select United flight, departing Thu, Oct 22 from Dallas-Fort Worth Intl. to Basin Intl., returning Mon, Oct 26, priced at $438 found 2 days ago
Fri, Feb 19 - Mon, Feb 22
JAX
Jacksonville Intl.
XWA
Basin Intl.
$665 Roundtrip, found 1 day ago
$665
Roundtrip
found 1 day ago
Select United flight, departing Fri, Feb 19 from Jacksonville Intl. to Basin Intl., returning Mon, Feb 22, priced at $665 found 1 day ago
OriginDestinationTravel DatesFlights From*
BILSidneyNovember 27 to November 27$94
BILWolf PointNovember 13 to November 20$101
SFOSidneyOctober 17 to October 21$904
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BILSidneyOctober 9 to October 11$101
BILWolf PointOctober 10 to October 11$101
GEGWolf PointOctober 11 to October 15$897
SFOSidneyOctober 11 to October 15$1,005
*Prices include taxes and fees

Best Roosevelt County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
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

Dec 21 - Dec 25

4 night stay

Minneapolis (MSP) to Sidney (SDY)

United • Non-stop roundtrip • Coach
Price was $1,113, price is now $1,033 per person
$1,033
per person
found 1 day ago
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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! (391 reviews)
"Terrible Internet, poor bed, poor breakfast."

Reviewed on Sep 29, 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.
6/10 (5 reviews)
"Be nice to have a shower that worked and that was at the long stay area- would not go back here"

Reviewed on Aug 17, 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.
5/10 (4 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.
9.8/10 Exceptional! (11 reviews)
"Great property and very clean. Would definitely recommend."

Reviewed on Sep 7, 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 $94 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 20 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 February 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. $94 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 $94 and $1,005 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.