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.

Mon, Nov 9 - Mon, Nov 16
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$100 Roundtrip, just found
$100
Roundtrip
just found
Select Cape Air flight, departing Mon, Nov 9 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Nov 16, priced at $100 just found
Mon, Nov 9 - Mon, Nov 16
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$110 Roundtrip, just found
$110
Roundtrip
just found
Select Cape Air flight, departing Mon, Nov 9 from Logan Intl. to Sidney-Richland Municipal, returning Mon, Nov 16, priced at $110 just found
Fri, Oct 23 - Sun, Oct 25
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$120 Roundtrip, found 10 hours ago
$120
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Fri, Oct 23 from Logan Intl. to Sidney-Richland Municipal, returning Sun, Oct 25, priced at $120 found 10 hours ago
Fri, Oct 23 - Sun, Oct 25
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$130 Roundtrip, found 10 hours ago
$130
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Fri, Oct 23 from Logan Intl. to Sidney-Richland Municipal, returning Sun, Oct 25, priced at $130 found 10 hours ago
Fri, Oct 23 - Sun, Oct 25
BIL
Logan Intl.
SDY
Sidney-Richland Municipal
$140 Roundtrip, found 10 hours ago
$140
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Fri, Oct 23 from Logan Intl. to Sidney-Richland Municipal, returning Sun, Oct 25, priced at $140 found 10 hours ago
Fri, Dec 18 - Fri, Jan 1
DFW
Dallas-Fort Worth Intl.
XWA
Basin Intl.
$488 Roundtrip, found 1 day ago
$488
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 18 from Dallas-Fort Worth Intl. to Basin Intl., returning Fri, Jan 1, priced at $488 found 1 day ago
Fri, Dec 18 - Fri, Jan 1
DFW
Dallas-Fort Worth Intl.
XWA
Basin Intl.
$600 Roundtrip, found 1 day ago
$600
Roundtrip
found 1 day ago
Select United flight, departing Fri, Dec 18 from Dallas-Fort Worth Intl. to Basin Intl., returning Fri, Jan 1, priced at $600 found 1 day ago
Tue, Dec 15 - Wed, Jan 6
PSC
Tri-Cities
SDY
Sidney-Richland Municipal
$622 Roundtrip, found 5 days ago
$622
Roundtrip
found 5 days ago
Select United flight, departing Tue, Dec 15 from Tri-Cities to Sidney-Richland Municipal, returning Wed, Jan 6, priced at $622 found 5 days ago
Tue, Nov 3 - Sat, Nov 7
PHX
Sky Harbor Intl.
OLF
L. M. Clayton
$636 Roundtrip, found 2 days ago
$636
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Tue, Nov 3 from Sky Harbor Intl. to L. M. Clayton, returning Sat, Nov 7, priced at $636 found 2 days ago
OriginDestinationTravel DatesFlights From*
BILSidneyNovember 4 to November 8$100
BILWolf PointNovember 14 to November 19$100
SFOWillistonNovember 5 to November 8$448
BUFWillistonNovember 11 to November 17$709
GEGSidneyNovember 4 to November 8$789
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BILSidneyOctober 23 to October 25$100
*Prices include taxes and fees

Best Roosevelt County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Richland Inn & Suites
2.0-star property

Richland Inn & Suites

Dec 9 - Dec 13

4 night stay

Tampa (TPA) to Sidney (SDY)

United • Non-stop roundtrip • Coach
Price was $653, price is now $585 per person
$585
per person
found 1 day ago
Microtel Inn & Suites by Wyndham Sidney
2.5-star property

Microtel Inn & Suites by Wyndham Sidney

Dec 25 - Jan 1

7 night stay

Miami (MIA) to Sidney (SDY)

United • Non-stop roundtrip • Coach
Price was $1,274, price is now $1,122 per person
$1,122
per person
found 1 day ago
Candlewood Suites Sidney by IHG
2.5-star property

Candlewood Suites Sidney by IHG

Dec 25 - Jan 1

7 night stay

Miami (MIA) to Sidney (SDY)

United • Non-stop roundtrip • Coach
Price was $1,305, price is now $1,178 per person
$1,178
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.
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 $100 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 16 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 November 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. $100 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 $100 and $789 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.