Ah, Chicago. It’s like Toronto, except with a better waterfront, nicer architecture, and way more murders. But as long as you avoid the south side, you can partake in all the great food and culture the Midwest’s’ mecca has to offer.
Where to Sleep
If you’re just in your hotel to change clothes and check your email, go with the Aloft. It’s downtown, affordable, and is what would happen if a Silicon Valley made a hotel—brushed steel and spectrograph patterns everywhere. And there’s free Wi-Fi.
If you’re looking for the boutique touch, look into Longman & Eagle, located in the very hipster Logan Square (about twenty minutes from downtown on the blue line). Longman & Eagle is also a Michelin-starred restaurant with amazing food and over 150 whiskies at their bar, but it’s also a boutique hotel with seven rooms that blend the historic bones of the structure with modern design sensibilities.
Finally, if you’re not going to settle for anything less than complete luxury, book the Peninsula Chicago. Five star? Check. Five diamond? Check. Right on Mag Mile? Check. They also do their own tours of the city.
Where to Eat
Here’s the thing about downtown Chicago: it has forty-three steakhouses. Chicago magazine has it narrowed down to the twenty best, but for our money, go to David Burke’s Primehouse, where you can feast on a 55-day aged rib eye, to be followed by a tour of their aging room.
Hankering for steak taken care of? Well, Chicago has twenty-four restaurants with Michelin stars covering all sorts of cuisines. Leading the pack is Alinea, which is renown for deconstructed plates—but book early. Like, months in advance. Don’t have months? That’s okay, us neither—which is why we also recommend contemporary American at Schwa, Mexican at Mexique, molecular gastronomy at Moto, and, of course, the aforementioned Longman & Eagle, where you can get brunch after a short line-up. Oh, and once more: over 150 whiskies at the bar.
You don’t need awards to have a great restaurant, though. You can enjoy a dozen different types of oyster at the Publican, where a beer sommelier (technically, a beer cicerone) will school you in the over fifty offerings they have. Be sure to visit the Wiener Circle, not just for the hotdogs, but for the unique customer service experience (i.e., they’re brutally rude and hostile). Finally, don’t leave Chicago without ordering a burger at Au Cheval; it’ll be the best burger of your life.
What to Do
So, what to do after you’re done luxury shopping at Mag Mile? There’s plenty of entertainment to be had: check out the waterfront at Navy Pier, take in live music (and a drink) at the Redhead Piano Bar, and feast on improve at Second City. And, of course, there’s the Blackhawks, the Bulls, the Cubs, and the White Sox.
Want something off the beaten path? Too Much Light Makes the Baby Go Blind is a weekly attempt to perform thirty plays in sixty minutes. The Chicago Architecture Foundation does tours of the city’s storied (and jealously-inducing) architecture. Finally, Big Joe’s, a neighbourhood bar in Logan Square, does turtle racing every Thursday. That’s right: turtle racing.