The 3 Best Destinations for an Epic Weekend Trip

We feel you, Lenny Kravitz: sometimes, you just want to get away. Problem is, you don’t always have ample time for a long-term escape. Here in workaholic North America, you get two weeks a year, the occasional holiday, and other than that, a criminally short weekend. It’s all good, though — you need not be a business casualty. Just because your time is limited doesn’t mean you can’t make a break for it once in a while. With a bit of preparation, you can have the kind of weekend getaway you’ll be bragging about all year long. (And no, business trips don’t count.) All it takes is a bit of planning — that’s what we’re here for.


“My kind of town, Chicago is,” Frank Sinatra once famously crooned. As that lyric’s oddly Yoda-esque phrasing implies, Ol’ Blue Eyes was wise. Certainly wise enough to realize there’s much more to the Windy City than broad shoulders and Kanye and deep-dish pizza. (Although, if we’re being real, the pizza is actually pretty damn delicious.)



Chicago is considered one of America’s culinary destinations, and no, it’s not just because of their pizza and hot dogs. It’s a bona fide steakhouse town. Gibsons is the OG of the bunch — their steak is so good, the USDA gave them their own certification: USDA Gibsons Prime Angus beef. So yeah, a safe bet. If you’re looking for something more modern, however, try Boeufhaus. It’s less a steakhouse and more a hip, underground, meat-centric club, but its five-day dry-aged bone-in rib eye is sublime.

And alright, fine, we’ll talk about the pizza too. Go to Pequod’s. They stand out for their inimitable caramelized crust — thick, crispy, black edges as tall as The Wall of the Seven Kingdoms, barricading a thick lake of cheese, Italian beef, spinach, giardiniera, and more.



In recent years, Chicago’s had a full-on boozy renaissance, making it one of America’s best drinking cities. Bars everywhere. Especially cocktail bars, like Violet Hour — the first, and still the best, pre-prohibition-style cocktail speakeasy in town. If gin is more your jam, Scofflaw is your joint. It’s got immaculate cocktails made from an impressive collection of 40-plus gins, plus a behemoth of a secret menu sandwich called the Guapichosa.

Given this is the land of Billy Corgan, Wilco, and Chance the Rapper, you may want to peep the local music scene. You can catch a show just about any night of the week at The Metro or the Empty Bottle. Or, if you’re up for the trek, check out Madame Zuzus, Corgan’s own tea shop, where the Smashing Pumpkins frontman is known to drop in for eight-hour impromptu jams and such.



The Sheraton Grand Chicago. It’s smack downtown, overlooking the Chicago River and just a stone’s throw from Michigan Avenue’s shops and Navy Pier’s dining and nightlife. It’s also got ample rooms and a robust fitness centre — trust us, you’ll need it after all that pizza.


Vegas North? Pfft. Montreal’s better than that. With world-class restaurants and an unrivalled nightlife scene, Sin City — as it was known in the Prohibition days — offers up the wickedest of weekends. There’s a reason all those bachelor parties happen here.



If it’s good enough for the heads of state, it’s probably good enough for you. Liverpool House is where Justin Trudeau and Barack Obama dined, to much fanfare, earlier this year. Less crowded than its sister restaurant Joe Beef, it’s got a killer wine list and remains the city’s top spot for seafood and oysters. (Get the lobster spaghetti — Obama was apparently nuts about it.) You’ll also want to eat at Europa, a French dining joint that often winds up near the top of world-best lists. Get the signature 12-course tasting menu, which includes a braised beef sundae in béarnaise sauce, cornish hen cooked in breakable clay, and more nom-worthy goodness.

And yes, chances are that later at night, perhaps after a few drinks, you’ll be jonesing for some poutine. Head to La Baquise. This classic greasy spoon, open 24/7, boasts 30 varieties of the trashy fave, including La T-Rex: a monstrous number topped with ground beef, pepperoni, and bacon.



Stumped on what to do in the hours prior to your dinner reservations? If there aren’t any Habs games happening, then enrich yourself at the Musée d’art contemporain de Montréal, which features art collections that rival that of any city in the world. Post-dinner, kick back at Montreal’s best secret speakeasy: Big in Japan Bar. Since it is, you know, a secret, you’ll need to look for a big grey door with two small Japanese symbols on the window. Inside, an elegantly dressed staff, rows of ambient tea candles, and columns of Japanese whiskey bottles will be there to greet you.

And if gentlemen’s clubs are your thing (this is Sin City, after all), Chez Parée is the classiest, most famous joint in town. (And please do keep it classy, guys).



Le Méridien Versailles. This stylish boutique hotel sits right in the middle of downtown, with elegant, spacious rooms and an excellent Mediterranean restaurant, Branzino. It’s also got a nifty bike rental program (with suggested routes) that allows you to unlock the hidden nooks of the city.


It’s no secret at all that Austin is one of the best cities to get rowdy in. Hell, it’s one of the best cities for just about anything, routinely landing on year-end “best of” list for everything from its restaurants to its music scene. The only thing uncool about the city is its weather, and it’s got copious watering holes to compensate for that.



East Austin has been having a moment as of late, and few eateries capture that moment quite like Kemuri Tatsu-ya. What happens when rock star chefs Tatsy Aikwawa and Takuya Matsumoto combine a boisterous izakaya with a smoky Texas barbecue joint? Brisket-filled ramen. That’s what.

The Texas capital boasts an embarrassment of choice smokey meats, and Franklin Barbecue may be the city’s — and for that matter, the world’s — most talked-about barbecue destinations. There will definitely be a line and it will definitely be worth it. Best ribs in the country. Afterwards, press on for dessert at Cow Tipping Creamery, which has the best soft serve in Austin made even better with layers of treats like cake balls and honey dust.



If you’re in Austin during South by Southwest, then, duh, obviously go to that. If not, start off with one of the nightly alt-bluegrass sets at The White Horse, an old-fashioned, hipster-approved honky-tonk known for its lively crowd, draft beer, and bomb tacos. Post-show, forge ahead to Fine Foods, a Zagat-rated ’60s-mod patio bar where the people watching in unrivalled and the cocktails are unimpeachable (try the Cold Fashioned; it’s — you guessed it — a frozen Old Fashioned). Pass on that third Tom Collins, and continue on to Lazarus Brewing Co., a funky brewery with well-curated, cozy décor and exquisitely crafted beers. For $1,000 USD, you can become a Patron Saint of Lazarus by taking home one of only 300 hand-blown, gold leaf chalices. Hang on to it — it gets you free Lazarus beer for life.



W Austin. Most of the places to stay near Austin’s bustling downtown area are drab business hotels that disregard the city’s vibe. This sleek glass tower livens things up with a sprawling ground floor of bars, colourful mid-century décor, and many amenities. Its Pets Are Welcome program lets you bring Buddy along for the trip, providing everything from pet beds to food bowls to special treats.

Insider Tip

You’d be wise to get yourself a Starwood Preferred Guest Credit Card from American Express. It lets you earn Starpoints faster, which you can redeem for free nights (sans any blackout dates) at over 1,300 hotels and resorts (including all the ones mentioned above — see what we did there?). You’ll snag a limited time Welcome bonus of 25,000 Starpoints if you get one before October 18, 2017. Now that we’ve stoked your wanderlust, you’ll be racking these bad boys up like nobody’s business.