Last Updated on October 7, 2022 by JaimeSays
Many thanks to Explore Whitefish, Glacier Country, and Discover Kalispell for arranging my stay. All opinions are my own.
When you think of the best weekend trips from Chicago, you may be considering something driveable, like Ludington or Destination Kohler. While the millions of people and traffic are enough to make you move to the suburbs, the direct flights to amazing places make it bearable. Consider heading to Northwest Montana on your next trip. With places like Glacier National Park, Whitefish, Flathead Lake, and Kalispell, you won’t be disappointed.
Direct flights to Northwest Montana from Chicago O’Hare in Under 4 Hours

A seasonal direct flight for both winter and summer is available from Chicago O’Hare to Glacier International Airport (Code: FCA). These flights are operated by both American Airlines and United Airlines, depending on the season. With only one hour time difference and under four hours each way, these flights allow for minimal disruptions for weekend trips from Chicago.
Luxurious Hotel Stays in Northwest Montana

Head to a major city, and you’ll have to spend quite a bit of money to stay in a one-of-a-kind, luxurious hotel. The same can be said of Northwest Montana in peak summer season, but visit September through early June, and you’ll find incredibly luxurious hotels at reasonable prices.

I had the pleasure of staying at Grouse Mountain Lodge while I was in Whitefish, Montana. Situated along the 18th hole of Whitefish Lake Golf Course, you can hit balls right outside of Grouse Mountain Lodge. While some 18th holes can get rowdy, Grouse Mountain Lodge was exceptionally quiet.
Speaking of rooms, I don’t know about everywhere in Northwest Montana, but the bathrooms at Grouse Mountain Lodge room were enormous! A double sink and double vanity were ideal, especially with one separate from the shower/toilet area. From my days living in a 630 square foot Chicago apartment, I am paranoid about dropping things in the toilet. The separate vanity completely eliminated that now irrational fear.

I also spent some time at the Lodge at Whitefish Lake. Situated on the water, this hotel has a certain breathtaking appeal that is hard to replicate. For the summer season, the hotel offers boat and personal watercraft rentals.

There are many places to stay in Northwest Montana, but these are ones that I would recommend:
- Lodge at Whitefish Lake (Luxury, Family Friendly, Good for Couples)
- Grouse Mountain Lodge (Family Friendly, Good for Golfers, Rustic)
- Snow Bear Chalets (Ski-in Ski-out, Luxury, Good for Families)
- Country Inn and Suites (Business travelers, Luxury, Family Friendly)
- Kalispell Grand Hotel (Historic, Good for Solo Travelers) *Request for room with “Large Bathroom”
Hiking and Biking for all Levels in Northwest Montana

When my husband and I were on our honeymoon, I discovered that he is a quick, half- or quarter-day hike person. Personally, I prefer long, all day hikes. While the prospect of visiting a mountainous place like Glacier National Park seemed daunting to this Illinoisian, I found out that there are plenty of more novice accessible hikes at one of the 10 state parks in the area. One such hike is The Reservoir Trail, a short loop that is part of Whitefish Trail.
A fairly easy hike, the trail starts with multiple switchbacks but eases up after that. In May, the trail was littered with some of the most beautiful wildflowers, like Indian Paintbrush, and Beargrass. The reward of course, is the lookout point at the top of the loop. The intermittent dense tree cover of this trail make it a manageable hike during a rainstorm or intense sun. The periodic areas of ancient forest provide a vast canopy from both the sun and the rain.

Depending on the time of year you visit, you may be lucky enough to bike the Going to the Sun Road at Glacier National Park without encountering vehicle traffic. Cars are able to traverse only when all snow and debris is cleared from the road, usually in late June/early July through late September. Whether there are vehicles or not, this 50 mile road that winds up and over the Continental Divide won’t disappoint. With just about 6,500 feet of elevation, layers, bear spray, snacks, and plenty of water are a must.

Because tour operators are rigorously vetted in the National Park, Glacier Guides and Montana Raft are the only tour company with concessionaires that are allowed to lead hikes and tours within Glacier. When we visited, I enjoyed the pace, expertise, and flora and fauna information that the guides provided. If you would like to go deeper into the park, but don’t feel like you are capable enough to go on your own, Glacier Guides lead single- and multi-day treks and ovenights.
Fun in Any Season in Northwest Montana
If you know me, I’m an off-season travel kind of girl. Mainly because there are fewer crowds and it’s less expensive. For people with kids in school or limited vacation, off-season travel may not be possible. Luckily, no matter the season, Northwest Montana offers loads of possibilities for fun and affordability.
Summer in Northwest Montana

Of the 11 million visitors to Montana each year, 50% come during the summer season. Planning in advance with reservations at attractions, restaurants, and lodging make it more manageable. Long days and warm weather mean more time spent outside camping, hiking, biking, swimming, and picking huckleberries. If you need to rest your haunches, consider taking in a play at the outdoor Bigfork Summer Playhouse.
Fall and Spring Shoulder Seasons
Shoulder season is a sweet spot for visitors to Northwest Montana. The spring brings milder weather and also a booming art scene. The Whitefish Theatre Company operates late September through early June, and the Glacier Symphony operates both an orchestral and choral arm. Places like Northern Michigan and Vermont are known for their beautiful fall colors, but did you know that in Northwest Montana you get two chances to experience the changing colors? There is the color change for the deciduous trees that happens in late September into October. Then, the Tamarack Evergreens change their color in late October into November. Do you think the people of Montana know how lucky they are to get this twofer? There are so many reasons to love fall around Glacier National Park!
Winter in Northwest Montana
Visiting Kalispell, Whitefish, or Northwest Montana in the winter? Head to Whitefish Mountain Resort or local favorite, Blacktail Mountain Ski Area. Colloquially known as “Big Mountain,” Whitefish Mountain Resort is SKI Magazine’s 2019 top rated resort for overall satisfaction. Visitors can expect 300 inches of snow, and great deals like $99/night ski in, ski out accommodations. The best way to arrange lodging is to speak with a concierge from Ski Whitefish.
A Delicious Food and Beer Scene

In my experience, the variety of restaurants in resort towns is somewhat wanting. This is not the case in Northwest Montana. They have everything! In my five days in the area, I didn’t eat the same cuisine twice. Not only that, but I drank some of the most memorable beverages of my 30-something years on this planet. You can read all about the best Whitefish Montana restaurants in this other post, but here are some of the highlights:
- The Smoked Trout at Casey’s Skybar is only second to the rooftop views of the newly historic building.
- Spotted Bear Spirits‘ female owned distillery and bar uses local mixers to make seasonal spirits.
- The Habanero Ginger Beer at Huck’s Place Glacier Ginger Brew is the white whale of ginger beers.
- Big Mountain Pale Ale by Great Northern Brewery is also a Safely Check out multiple breweries by booking a tour with Big Sky Brews Cruise!
- Check out this post about where to grab a drink in Whitefish, Montana.
I fell for Montana so hard that I’ll be heading back again next month. I plan on picking up some of my favorite lotions, beers, and trinkets, and giving even more reasons to visit this great state.
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I LOVE Whitefish so much. I HAVEN’T been back in years but spent 3 weeks there every summer for 3 years when I was a nanny. Such a BEAUTIFUL aRea and so much to do year-round.
Oh I do too! It was my favorite spot when I was there. It reminded me a lot of another favorite, Sandpoint Idaho.