1 MINNEAPOLIS

Amtrak has doubled its Twin City service from Chicago.

The rail operator’s new seven-and-a-half-hour Borealis line complements its existing Empire Builder service with a four-hour-earlier departure, at 11:05 a.m. For $41 each way, you get Wi-Fi, wide reclining seats, and daylit views of Midwestern farmland and the Mississippi River as you wind through Wisconsin.
Once there: You’ll arrive at 6:30 p.m., early enough to grab a table at Hai Hai, the Southeast Asian street food restaurant helmed by Christina Nguyen, who won the James Beard Award for best chef in the Midwest this year. During the day, visit Lake of the Isles Park for biking, paddleboarding, and exceptional leaf peeping.

2 KOHLER, WISCONSIN

You can stay in a posh lakeside cabin designed by a trendy artist.

This June, the resort Destination Kohler, two and a half hours away by car, unveiled the Arsham Cabin, created by New York–based artist Daniel Arsham, best known for his Porsche and Pokémon collabs. The two-bedroom, adults-only retreat will set you back a whopping $1,230 a night, but can you really put a price on living in a work of art? The bluff-top cabin overlooking Lake Michigan features furnishings and other touches from the futuristic multimedium artist, including a Zen garden off the back deck dotted with his playful sculptures.
Once there: Autumn is perfect for hiking or canoeing in River Wildlife, a 500-acre wilderness preserve. And the resort’s four golf courses are among the best in the Midwest.

3 MACKINAC ISLAND, MICHIGAN

A historic Edwardian resort just completed a $40 million overhaul.

Perched on the island’s western shore, the Inn at Stonecliffe reopened this summer following a massive two-year renovation. New to the 15-acre property are private three-bedroom cottages offering full kitchens and porches with views overlooking the water, while inside the mansion — built in 1904 for the family of a wealthy Chicago meatpacker — guests will find 16 modernized rooms (starting at $383) and a new suite.
Once there: Strait’s, the resort’s upscale farm-to-table restaurant under the direction of chef Joseph Nardo, who previously worked at the French Laundry, showcases produce from the property’s own garden.

4 SOUTH HAVEN, MICHIGAN

New garden cottages make glamping even more glam.

Posh tents have long been the draw at the Fields of Michigan, a resort on a blueberry farm a two-hour drive from Chicago. But if the notion of sleeping in a tent, even a souped-up one, sounds too rustic, check out the nine modern garden cottages (from $400) that the property debuted in June. Set at the edge of the woods, the bright and airy cabins offer the aesthetics of camping sans canvas.
Once there: Bike the Kal-Haven Trail to the beach. Or drive 20 minutes to Fennville for all things fall, from apple picking at Crane’s Pie Pantry to live music at Virtue Cider.

5 WINNIPEG, CANADA

Direct flights from O’Hare to this northern wonderland have been restored.

Paused during the pandemic, United’s two-and-a-half-hour daily departure — the only nonstop service to Manitoba’s capital — returned in May. This fall is an ideal time to visit the sneakily cosmopolitan city, which mixes rich cultural experiences with easy access to outdoor adventure.
Once there: The Winnipeg Art Gallery, home to the largest collection of Inuit art (sanauganit) in the world, has an exhibition featuring works from 200 BCE to modern times. Winnipeg is also the gateway to Churchill, a two-and-a-half-hour flight north and a destination for polar bear seekers. The blanche bruins are most active in October and November as they await the formation of sea ice on the Hudson Bay.

6 LONG BEACH, WASHINGTON

You no longer have to go to Japan for Japanese-style camping.

Snow Peak Long Beach Campfield opened in June as the first U.S. campsite from the Japanese brand Snow Peak. Boasting 25 acres in the woods of Long Beach Peninsula in southwestern Washington, the property offers 56 sites for bring-your-own campers (from $40), eight fully equipped tents loaded with the brand’s gear (from $120), and 14 Jyubakos, wooden micro cabins with climate control, a private bathroom, and a modern minimalist aesthetic (pictured, from $130).
Once there: In the Pacific Northwest, the fall harvest season means picking cranberries at Cranguyma Farms — or digging into freshly shucked oysters from the estuary at Oysterville Sea Farms.

7 PUNTA MITA, MEXICO

Increased seasonal flights make it easier to get to this exclusive oasis.

There may be no more luxurious hideaway in Mexico than Punta Mita, home to a 1,500-acre private peninsula featuring posh resorts, white sand beaches, and two Jack Nicklaus–designed golf courses. It’s just a 45-minute drive from the Puerto Vallarta Airport. And come November, United and American step up their service to at least daily, through early spring.
Once there: Naviva, a 48-acre beachfront resort from Four Seasons, is priced at a bonkers $3,950 a night for two, but the all-inclusive, one-of-a-kind luxe experience may have you considering cashing out your 401(k). There’s no better way to ball out than in one of the property’s 15 standalone suites (pictured) surrounded by lush jungle and overlooking the Pacific Ocean.

8 MILAN, ITALY

You can now fly nonstop later into the fall.

United Airlines has long provided the only direct flights from Chicago to Milan, typically just through the end of October. But the airline is now operating its daily eight-hour-and-45-minute service through December 2. Fall is ideal for exploring Italy’s suavest city, not just for the weather (highs in the mid-50s) but for the deals: In November, flights and hotel rates drop by some 35 percent from September.
Once there: Just a five-minute walk from the Duomo, Milan’s famed Gothic cathedral, is another architectural landmark: the Palazzo Cordusio Gran Meliá, a new hotel housed in a stunning 18th-century neoclassical building (rooms start at $760 a night).