Falling in love with the Windy City

Chicago’s Riverwalk is a popular place for locals and visitors to hang out; you can eat, drink, explore and play right by the water’s edge, running along the south bank of the Chicago River. Photo: Choose Chicago.

By Loukia Zigoumis

Chicago—one of the largest cities in America and a short flight from Ottawa—offers something special for every traveller. Whether you’re a theatre lover, a fan of incredible architecture, a historian, a shopaholic, or a foodie, (hello, deep dish pizza!) the Windy City on Lake Michigan should be your destination of choice. Once you arrive, you’ll understand why travellers all over the world love it so much—and keep coming back for more.

Last year, Chicago welcomed more than 57 million visitors, and this year, even more people will check this city off their bucket list. After all, it has been designated the “Year of Chicago Theatre,” an initiative that includes theatre performances for the public at venues throughout the city. The focus on theatre combined with the fact that the James Beard Awards (an annual event honouring the best in the food and restaurant industry) will call Chicago home until 2020, are two big reasons people are flocking to this city.

The Blackstone Hotel, a historic hotel in Chicago, close to Grant Park, and their beautiful lobby filled with antique art and furniture.


There are many places to stay in Chicago; from luxury to boutique hotels, you can easily find a place that’s right for you. A popular hotel is The Blackstone Hotel, also known as the “Hotel of Presidents”. This historic, luxurious hotel first opened its doors in 1910, and has played host to many former American Presidents, including JFK. (He happened to be eating Boston Clam Chowder in the 10th floor suite when he heard the news of the Cuban Missile Crisis). The term ‘smoke-filled’ room actually originated at The Blackstone Hotel, in the infamous smoke-filled suite, after a group of United States Senators gathered to arrange the nomination of Warren G. Harding as the republican candidate for President in 1920. The hotel was also a favourite hangout of Al Capone.

The Blackstone Hotel is filled with beautiful pieces of antique furniture, art, (and has a fifth-floor art gallery, too) and other historical pieces, and the lobby—where President Truman liked to hang out, playing the piano and drinking bourbon late into the night—is where you’ll find the bar, Timothy’s Hutch, serving up craft cocktails of all kinds. You can dine at top-notch restaurant Mercat a la Planxa, too.

The spacious guest rooms and suites are modern, comfortable, and clean, many with stunning views of Lake Michigan. The hotel is a short walk from Grant Park, Millennium Park, and the Art Institute of Chicago, and the service is exceptional, from check-in to check-out.


Chicago’s First Lady Architecture River Cruise: An excellent way to see the city is by going on a river cruise, where you’ll learn about the architectural landscape surrounding you, and the history of the many skyscrapers that make the city so famous. This is considered the top tour in Chicago and one of the top ten tours in the United States, so it’s not to be missed, especially if it’s your first time in the city.

Riverwalk, breathtaking views in Chicago no matter the season.

The Chicago Riverwalk: Located on the south bank of the Chicago River, the pedestrian-friendly Riverwalk is a great way to explore the city on foot, while discovering cafés, wineries, bars, and museums. It’s become a popular recreational destination for everyone, bringing people close to the waterfront for a beautiful experience.

Millennium Park and Cloud Gate: Cloud Gate, Chicago’s most recognizable structure, is the official name of the famous ‘bean’ sculpture, designed by artist Anish Kapoor. Inspired by liquid mercury, and meant to reflect the city’s skyline, it’s one the largest pieces of art of its kind in the world, and a definite attraction for both tourists and locals alike. Millennium Park, where Cloud Gate is located, is a beautiful large outdoor space within Chicago’s Grant Park. It’s now one of the biggest attractions in the city, because of the open space, and the variety of things to do for families. Not only is Millennium Park a great place to snap some photos, it’s the perfect place to relax or have a picnic after a day of sight-seeing and shopping.

The Chicago skyline.
Photos: Choose Chicago.

The Ledge at Skydeck: The Ledge at Skydeck, on top of the Willis Tower, (formerly Sears Tower), is one of the best experiences the city offers. People can stand on one of the ‘ledges’ from the 103rd floor of the building, for endless city views—you can even see four different states from that height. The glass balconies extend four feet outside and the views, during the day or at sunset, are breathtaking. Skydeck attracts more than 1.7 million visitors a year.

Shopping: When in Chicago, make some time for shopping along The Magnificent Mile, where you’ll find all the stores you love, from department stores to designer boutiques. The shopping is incredible, but make sure to wear comfortable shoes because you’ll be walking for, well… miles. Don’t forget to stop by Chicago’s famous Garrett Popcorn Shop, for their delicious cheddar-caramel mix.

Dining: Chicago is known for its architecture, culture, and, of course—food! Bon Appetit Magazine named Chicago the restaurant city of the year in 2017, and it is definitely the place to be if you’re a foodie at heart, because there are literally countless dining options. You’ll find plenty of tasty classics throughout the city, like Chicagostyle hot dogs and delicious, mouth-watering deep-dish pizza (Pizzaria Uno, Giordano’s, and Lou Malnati’s are some of the most popular pizza joints). If you’re looking to dine in a popular neighbourhood, head to the West Loop; it’s earned a top spot in the food world, and it’s where you’ll find some of the trendiest (and tastiest!) restaurants, like The Publican.

Theatre: With over 200 theatre companies to entertain visitors, deciding on which show you want to watch will be the only difficult decision you’ll have to make in Chicago— along with where to dine. You can celebrate The Year of Chicago Theatre by attending an improv show, the opera, and various musicals. Of course, the hottest ticket in town is Hamilton: The Musical. This incredibly popular musical created by Lin-Manuel Miranda is about the American Founding Father, Alexander Hamilton. The show received a record-settng 16 Tony nominations in 2016, winning 11 awards, including Best Musical. Hamilton runs in Chicago until January, 2020. It’s an incredible show, and worth the hype. Get your tickets before you arrive—you’ll be thankful you did!

Navy Pier: The Navy Pier—the Midwest’s number one attraction— is a go-to destination when in Chicago. The lakefront playground has over 50 acres of parks, shops, restaurants, and entertainment for everyone, including rides, like the famous Ferris Wheel and the musical carousel. In addition to the shops and restaurants, families can enjoy the miniature golf course, Chicago’s Children’s Museum, the Chicago Shakespeare Theatre, and the Navy Pier IMAX.

The famous Bean sculpture in Chicago, a popular tourist attraction.

Museums and Art Galleries: Chicago, like New York City, is home to many great museums and art galleries. The Chicago Architecture Center is a must-visit—it offers interactive exhibits and tours of architectural treasures, and it’s the perfect place to learn more about the history and architecture of Chicago. Stop by The Museum of Contemporary Art (MCA) for lunch at Marisol, a beautiful restaurant and bar featuring food from Chicago chef Jason Hammel. The food is delicious, and being surrounded by art makes it an even more memorable experience. The MCA is one of the largest museums dedicated to art since 1945, and exhibits new and experimental work from artists across all media, paired with educational programs. The Art Institute of Chicago is one of the city’s most well-known cultural institutions, which houses over 300,000 pieces of art, and is home to the delicious Italian restaurant, Terzo Piano-another great stop during a day of sight-seeing in the city. For the science lover, check out the Museum of Science and Technology, where you can stand in a tornado, inside a U-boat, or deep down in a coal mine. The hands-on museum is a great place to have fun while learning.

To maximize your time in Chicago and to save money, pick up a Chicago CityPASS. The CityPASS provides great deals on shopping, and VIP admission to attractions like Shedd Aquarium, Skydeck Chicago, Field Museum, the Art Institute of Chicago, and the Museum of Science and Industry Chicago. The CityPASS is valid for nine consecutive days, and can be purchased online at, or at CityPASS attraction.

For details about all you can see and do, check out