Where to Go From Here

Three-Day Weekends from Chicago

by Daniel Schwartz
Spyhouse Photo courtesy of Spyhouse Coffee.

You've done literally nothing but tear through Netflix this winter. Make up for adventures missed like a true weekend warrior with these three-day trips from Chicago.

CHICAGO – Winter is almost over in the Windy City. It's time to unfurl from the blanket burrito and channel your pent-up cabin fever into weekends away in America's northern country. Whether the weather blooms balmy or surprises with a snowy spell, you're covered for options. Adrenaline, art, booze, and farm-to-table bounty are all a weekend away from Chicago.


If you're in the mood for: history, silence, and solid slopes.

Route to take: Drive three hours west on US-20.

On your agenda: Stroll the cobblestone streets, note that most of the beautiful brick buildings are included in the National Register of Historic Places, then tour the home of Ulysses S. Grant. Ski on Chestnut Mountain, defrost at Otto's Place, and toast at Blaum Bros. Distilling Co. Fall asleep by the fireplace in your lakeside cottage at Le Fevre Inn. You came to the country. Keep it simple.

Avoid the Sunday blues: Hit the slopes early and have lunch on Chestnut Mountain at Sunset Grille as you gaze off at the Mississippi River Valley. Think of the rush and the views as souvenirs.

The Bachelor Farmer, Minneapolis, Minnesota

The dining room. Photo courtesy of The Bachelor Farmer.

Dish from The Bachelor Farmer, Minneapolis, Minnesota

Vegetables from the rooftop farm. Photo courtesy of The Bachelor Farmer.


If you're in the mood for: eye candy, hipster shopping, and a farm-fresh food coma.

Route to take: Fly O'Hare International (ORD) to Minneapolis-Saint Paul (MSP). The hour-and-a-half flight is roughly $100 roundtrip and lands in the middle of the Twin Cities metropolitan area so you can hit the ground running.

On your agenda: Taste the terroir at Spoon and Stable, experiment with new Nordic cuisine at The Bachelor Farmer, suit up for reservations at Borough, or skip downstairs to Parlor for fancy cocktails and epic burgers. (Instagram at least once from each.) Pack on pastrami at Ideal Diner if the selfie-taking set grows old. Shop at Wilson & Willy's and Askov Finlayson for the north country look and The Foundry Home Goods for dreamy kitchenware. Grab a growler from Able Seedhouse and Brewery before retiring to The Commons Hotel by the river.

Avoid the Sunday blues: Chances are, you'll wake up dazed from the salt and booze that kept you going Saturday night. Revive with massage therapy from Jeromeo and an espresso from Spyhouse Coffee before leaving town with local stationary from Angel Bomb.

Aga Khan Museum, Toronto

Geometry. Photo courtesy of Aga Khan Museum.

Mjolk, Toronto

Design envy. Photo courtesy of Mjolk.

Big Crow, Toronto

A carnivore's delight. Photo courtesy of Big Crow.


If you're in the mood for: art and booze.

Route to take: Fly Porter Airlines to Billy Bishop Toronto City Airport (YTZ). The hour-and-a-half flight costs around $350 and lands 1.5 miles from downtown Toronto.

On your agenda: Toronto is a hotspot for high-culture and emerging artists and there are weekends' worth of treasure at the city's best art museums — Aga Khan Museum for Islamic art, Art Gallery of Ontario for big-name collections, and Design Exchange for high fashion. But better for short agendas are the avant-garde galleries in Junction, namely Clint Roenisch Gallery, Daniel Faria Gallery, and ESP. Combat fatigue with caffeine from Balzac's Coffee Roasters or another kind of buzz from Indie Ale House. For lunch, go healthy at The Beet or go home and sleep after barbecue at Big Crow. After sunset, head to no-reservations tapas hot spot Bar Raval and nearby Track and Field for brews and bocce ball.

Avoid the Sunday blues: After check-out from The Drake Hotel, shop 'till you drop at Drake General Store or buy something your design friends will really envy from home decor store Mjolk. A more masculine memory is the bourbon, cigar, and haircut experience at Rod, Gun, & Barbers.


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