The Best Guide to The Windy City of Chicago

The Best Guide to The Windy City of Chicago

The Windy City will blow you away with its beauty. Our guide to making the most out of a vacation here

Chicago may be the third largest city in the United States but it has a way of welcoming you in a way you don’t expect from a big city. The people are, indeed, as friendly as they made out to be, the architecture is stellar, its food scene boasts cozy, low-key joints that are just as enjoyable as the city’s Michelin-starred restaurants, and Chitown’s distinct lively neighbourhoods make it a joy to discover by foot. This Midwest charmer is well worth packing up your carry-on for a weekend (or more, there’s plenty to explore).

The comfy rooms at The James Hotel

Booking an Airbnb will allow you to immerse yourself into a neighbourhood and feel like a local, but for the first-time visitor, you’d be best served staying centrally. Book a room at The James on for its convenient River North location. This boutique hotel is modern and inviting (pop into the lobby for its daily wine and cheese happy hour) and you’ll be not only steps away from shopping the Magnificent Mile but also close to the red subway line (In fact, take the “el” train around the Loop—it’s an affordable and fun way to see the downtown core as the train winds its way around the buildings).

The artful lobby at The James Hotel.

For bacon that will be life-changing, head to Publican on the weekend for brunch (brunching is practically a hobby all to itself in Chitown). Lovers of Mexican cuisine will want to try out a Rick Bayless restaurant (Obama has dined at Topolobampo so you may very well sit at the same table as the former pres) and also try out Mi Tocaya in Logan Square for their tacos campechano and draft cocktails (the El Serrano is delightfully spicy). And while you’ll see droves of people lining up for Shake Shack, we say skip it (you can get that in many cities now, after all), and go for the hefty,  juicy cheeseburger at Au Cheval (it’s been named the best in America by Bon Appetit). For a souvenir for your foodie friend and yourself, save room in your luggage for a couple of bags of sweet and savoury Chicago Mix popcorn from Garrett’s—it is worth the cheesy orange fingers.

As one of the Midwest’s metropolises since the 1850s, Chicago’s skyline boasts stunning buildings such as the Carbine and Carbon Building, circa 1929, and the Wrigley Building, circa 1925, a glorious sight with its crisp white tiles and 14th floor skywalk, along with Mies Van der Rohe’s minimalist towers. The best way to see and learn about all the noteworthy buildings is on the Chicago Architectural Foundation River Cruise. If the weather proves just too windy or rainy, hide out instead in the impressive Shedd Aquarium (where you’ll find more than 1,500 species) and the expansive Art Institute of Chicago (key paintings to see include Grant Wood’s American Gothic, and pieces from Warhol, Van Gogh and Lichtenstein. And no matter what the weather, a stop into Millennium Park for a photo with Cloud Gate is a tourist essential.


Tip: Both the Aquarium and the Art Institute are part of the Chicago Citypass, which is worth buying if you’re planning on seeing the Chitown’s popular attractions.

Finding gems at Vintage Charm

The wealth of shiny shops along Magnificent Mile and its expansive sidewalks (more room for all of your shopping bags you have in tow!)  is enough to make even a non-shopper giddy about prospect of consumerism. You’ll find flagships from the likes of brands such as Chanel and Nike, along with department stores Saks Fifth Avenue.and Nordstrom. But take your credit card to the neighbourhoods as well: in Bucktown, peruse boutiques such as Diptyque, Aesop and Vintage Charm, a contemporary women’s clothing shop with jewelry and cute trinkets, whereas in Wicker Park, you’ll find more of a boho vibe with stores including John Fluevog, Free People and Adidas mixed in with used-book peddlers and vintage shops such as Kokorokoko.

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