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

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

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.

Mon, Dec 14 - Mon, Dec 14
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$94 Roundtrip, found 4 days ago
$94
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Dec 14 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Dec 14, priced at $94 found 4 days ago
Mon, Sep 21 - Mon, Sep 21
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$96 Roundtrip, found 6 days ago
$96
Roundtrip
found 6 days ago
Select Cape Air flight, departing Mon, Sep 21 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Sep 21, priced at $96 found 6 days ago
Sun, Sep 6 - Thu, Oct 8
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sun, Sep 6 from Logan Intl. to Sidney-Richland Municipal, returning Thu, Oct 8, priced at $100 found 6 hours ago
Sun, Sep 6 - Thu, Oct 8
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$101 Roundtrip, found 6 hours ago
$101
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sun, Sep 6 from Logan Intl. to Sidney-Richland Municipal, returning Thu, Oct 8, priced at $101 found 6 hours ago
Sat, Sep 19 - Wed, Sep 23
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$110 Roundtrip, found 1 day ago
$110
Roundtrip
found 1 day ago
Select Cape Air flight, departing Sat, Sep 19 from Logan Intl. to Sidney-Richland Municipal, returning Wed, Sep 23, priced at $110 found 1 day ago
Thu, Sep 10 - Fri, Sep 11
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, Sep 10 from Logan Intl. to Sidney-Richland Municipal, returning Fri, Sep 11, priced at $111 found 2 days ago
Mon, Sep 21 - Mon, Sep 21
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$116 Roundtrip, found 6 days ago
$116
Roundtrip
found 6 days ago
Select Cape Air flight, departing Mon, Sep 21 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Sep 21, priced at $116 found 6 days ago
Sun, Sep 6 - Thu, Oct 8
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$121 Roundtrip, found 6 hours ago
$121
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sun, Sep 6 from Logan Intl. to Sidney-Richland Municipal, returning Thu, Oct 8, priced at $121 found 6 hours ago
OriginDestinationTravel DatesFlights From*
BILSidneyDecember 14 to December 14$94
BILWolf PointSeptember 28 to September 30$101
SFOWillistonOctober 15 to October 18$768
BILWillistonOctober 22 to October 26$868
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BILSidneySeptember 12 to September 13$101
BILWillistonSeptember 13 to September 15$1,380
*Prices include taxes and fees

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! (387 reviews)
"Hallway wasn’t clean Room was ok clean. Beds were not very good"

Reviewed on Sep 1, 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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 $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 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 December 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 $1,380 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.