$50 Cheap flights to Roosevelt County

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Top places to visit in Roosevelt County

A covered bridge with a sign reading "Cumberland" and a sunset in the background.
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Culbertson

Culbertson

Cheap flights to Roosevelt County from $50 One Way, $100 Round Trip

$100 return flights and $50 one-way flights to Roosevelt County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Jul 14 - Sun, Jul 19
BIL
Billings
OLF
Wolf Point
$100 Roundtrip, found 6 hours ago
$100
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Tue, Jul 14 from Billings to Wolf Point, returning Sun, Jul 19, priced at $100 found 6 hours ago
Thu, Sep 3 - Sun, Sep 6
BIL
Billings
SDY
Sidney
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Cape Air flight, departing Thu, Sep 3 from Billings to Sidney, returning Sun, Sep 6, priced at $100 found 1 day ago
Wed, Aug 26 - Sun, Aug 30
BIL
Billings
SDY
Sidney
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Wed, Aug 26 from Billings to Sidney, returning Sun, Aug 30, priced at $102 found 5 hours ago
Tue, Jul 14 - Sun, Jul 19
BIL
Billings
OLF
Wolf Point
$110 Roundtrip, found 6 hours ago
$110
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Tue, Jul 14 from Billings to Wolf Point, returning Sun, Jul 19, priced at $110 found 6 hours ago
Tue, Jul 14 - Sun, Jul 19
BIL
Billings
OLF
Wolf Point
$120 Roundtrip, found 6 hours ago
$120
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Tue, Jul 14 from Billings to Wolf Point, returning Sun, Jul 19, priced at $120 found 6 hours ago
Thu, Jul 9 - Sun, Jul 12
BIL
Billings
SDY
Sidney
$122 Roundtrip, found 2 hours ago
$122
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Thu, Jul 9 from Billings to Sidney, returning Sun, Jul 12, priced at $122 found 2 hours ago
Thu, Nov 26 - Sun, Nov 29
LAS
Las Vegas
XWA
Williston
$268 Roundtrip, found 5 days ago
$268
Roundtrip
found 5 days ago
Select Sun Country Airlines flight, departing Thu, Nov 26 from Las Vegas to Williston, returning Sun, Nov 29, priced at $268 found 5 days ago
Wed, Aug 12 - Sun, Aug 16
ORD
Chicago
XWA
Williston
$313 Roundtrip, found 6 days ago
$313
Roundtrip
found 6 days ago
Select United flight, departing Wed, Aug 12 from Chicago to Williston, returning Sun, Aug 16, priced at $313 found 6 days ago
Sat, Aug 15 - Sat, Aug 22
ORD
Chicago
XWA
Williston
$376 Roundtrip, found 2 days ago
$376
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Aug 15 from Chicago to Williston, returning Sat, Aug 22, priced at $376 found 2 days ago
Wed, Aug 12 - Sun, Aug 16
ORD
Chicago
XWA
Williston
$381 Roundtrip, found 6 days ago
$381
Roundtrip
found 6 days ago
Select United flight, departing Wed, Aug 12 from Chicago to Williston, returning Sun, Aug 16, priced at $381 found 6 days ago
Thu, Jul 30 - Mon, Aug 3
STL
St. Louis
XWA
Williston
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select United flight, departing Thu, Jul 30 from St. Louis to Williston, returning Mon, Aug 3, priced at $389 found 1 day ago
Wed, Aug 12 - Sun, Aug 16
ORD
Chicago
XWA
Williston
$393 Roundtrip, found 6 days ago
$393
Roundtrip
found 6 days ago
Select United flight, departing Wed, Aug 12 from Chicago to Williston, returning Sun, Aug 16, priced at $393 found 6 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
BILSidneyJuly 10 to July 12$102
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Roosevelt County Accommodation Deals

Homestead Inn Wolf Point Hwy 2

Homestead Inn Wolf Point Hwy 2

2 out of 5
101 Highway East Wolf Point MT
Fully refundable
$150 nightly
The price is $160 total per night from Jul 16 to Jul 17
$160 total
Jul 16 - Jul 17
Total with taxes and fees
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 ...
7.8/10 Good! (367 reviews)
"I arrived at 2:50 the lady was so rude and told me either come back or pay $25 to check in 10 minutes early! We left and came back a few hours later, it was a different person that was nicer than the first, but the room does not look even close to the pictures online. The carpet looked like it had ..."

Reviewed on Jul 6, 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
Fully refundable
$89 nightly
The price is $96 total per night from Jul 10 to Jul 11
$96 total
Jul 10 - Jul 11
Total with taxes and fees
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 ...
8/10 Very Good! (1 review)
"I'm originally from the area. It's been some years since I've been back. I am shocked at the change. I am surprised how clean and quiet this motel was. It was worth the value. I would definitely stay again. I had no problems while staying here. The sink was leaking but I showed the housekeeper. The ..."

Reviewed on Oct 1, 2025

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.
Get rates
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
$385 nightly
The price is $416 total per night from Jul 12 to Jul 13
$416 total
Jul 12 - Jul 13
Total with taxes and fees
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 ...
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Roosevelt County

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Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Roosevelt County flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Roosevelt County again.

Earn with Your Frequent Flyer Program and Orbitz

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Low Prices for Roosevelt County Flights

Orbitz has the scoop on cheap tickets and bargain airfare for flights to Roosevelt County. You can research the best flights for your trip and make your reservations all on our website with the confidence that you’re getting a great price.

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Frequently asked questions

What is the best airport to fly to in Roosevelt County?
L. M. Clayton Airport (OLF) is the major gateway for this popular destination. Once you've stepped out of the arrivals area, the possibilities are endless when it comes to exploring Roosevelt County.
How much is a flight to Roosevelt County?
Travelers from far and wide snapped up round-trip flight deals ranging between $100 and $393 this week to Roosevelt County. Starting your trip from Billings (BIL)? The cheapest one-way prices were just $50.
How to book the cheapest flight to Roosevelt County?
With some of the most impressive flight deals around, you're guaranteed value for money with Orbitz. The following handy hints will help you score cheap flights to Roosevelt County — and leave you with extra cash in your wallet:

  • Depending on where you're leaving from, click on the 'Nearby airports' function (located under the departure and arrival options). Occasionally, alternative departure points offer more value for money.
  • Similarly, click on the 'Show flexible dates' option and you'll see the prices for days around your selected departure. It's possible to score cheaper flight deals if you're flexible with your plans.
  • Select 'Show options' to narrow down your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even select whether you'd like to fly in the morning, afternoon or evening.
  • The early bird gets the most rewarding savings, so purchase your seats once you've settled on your travel dates. The most affordable fares sell fast and prices increase as the departure date gets closer.
  • Save even more on your vacation by combining your flights, hotels and car rentals into one convenient package deal. Your bank account will thank you.
  • If you can, avoid traveling in high seasons. Airfares surge during school breaks, summer and other vacation periods like Thanksgiving and Christmas.

What is the best time to book a flight to Roosevelt County?
Reserve your tickets to Roosevelt County in January. This is the ideal time of the year for bargain airfares, followed by February and August. Snap up cheap flights and make your dream vacation a reality with Orbitz.
What day of the week is the cheapest to book a flight to Roosevelt County?
If you're after inexpensive fares to Roosevelt County, the best days of the week to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a superb flight deal will be all yours.
What is the cheapest day of the week to fly to Roosevelt County?
You can score cheap flights to Roosevelt County by taking off on a Monday, according to Orbitz data from 2020. Tuesday is the next cheapest day, while Saturday has the most costly airfares. Whether you prefer to stretch your travel budget or take off on whichever day is convenient, you'll always get a rewarding deal with Orbitz.
What is the cheapest month to fly to Roosevelt County?
We won't keep you guessing — according to Orbitz data, August is generally the most inexpensive month to fly. Perfect for those who need a weekend getaway or just an escape from it all before the weather turns. Be aware that the costliest time to fly is the height of summer, with airfares at their highest in June.
Which airlines allow free cancellation?
Things change, and we think your flight should be able to do the same. That's why Orbitz makes it easy to search for flights with free cancellation and no change fees. Simply enter your departure and arrival points and then choose "Filter by flexible change policies." That's what we call peace of mind!
What do I need for the flight to Roosevelt County?
There is so much to plan for any big adventure, so it's great to get a little help along the way. Here are a few suggestions to make sure you're organized for take off:

  • Check that you've packed your travel paperwork and identification. For international trips, you'll require your passport. When reserving your seats, always use the exact details stated on your current ID.
  • A well-packed carry-on bag is the key to flying in comfort. Given this journey to Roosevelt County is no short hop, take enough snacks and activities to keep you happy. Something to read will help pass the time.
  • Aeroplane cabins are often chilly. If you decide to travel during the height of the Roosevelt County summer, be sure to take some extra layers of clothing just in case.

How do I get cheap first-class/business deals to Roosevelt County?
There are ways of booking business or first-class fares to Roosevelt County that won't burn a hole through your wallet. Grab a seat at the front of the plane for less with these practical tips:

  • Flexibility is key. By being open to various travel dates, you'll have more chances of landing a deal on first or business-class airfares.
  • A lot of low-cost carriers these days have excellent business-class seating that doesn't cost the earth.
  • Take advantage of your airline's frequent flyer program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

What is the best time to go to Roosevelt County?
If you want to soak up the culture of Roosevelt County in peak season, July, August and October are the best months to visit. June 20 marks the first day of summertime in the Northern Hemisphere and is a fantastic time to travel if you're hooked on the great outdoors. During this time of year, average daily temperatures usually range from 60 ºF to 80 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.