One of the largest cities in the U.S. and biggest hubs in all of North America, Chicago is a must stop for any visitor. The Windy City (nickname possibly taken due to the breeze coming from Lake Michigan or from the bid of the 1893 World Fair which is disputed) feels far less crowded and overwhelming than many other big cities and includes a large beautiful skyline. It's also much greener and friendlier than other mega cities in North America, which adds to its allure.
We were adventurous enough to take a 13 hour drive from Montreal to Chicago and we couldn't be any happier with what we saw. Chicago is filled with rich culture and has many neighbourhoods to explore. We fell in love with the city as it reminded us of our hometown. It's a perfect place to visit if you're a foodie or love beautiful architecture and artifacts. And Chicagoans sure do love their sports teams! I'm not sure if it's because of the Lake that separates the city in two, but you sense the hustle and bustle of the downtown area filled with tourists, while the other side of town can make you feel relaxed and at ease. We spent an entire week here and time passed rather quickly as our days were filled with much to do.
Willis Tower Skydeck
Conquer your fear of heights by taking the quick elevators and zoom up to the 103rd floor of the former Sears Tower, we know we did. This building once stood as the tallest skyscraper in the world for over 40 years. Tiptoe onto the glass cube structure, as you're suspended 1,353 feet off the ground. Some pose for pictures and others hurry off the platform that stares at the abyss below. Also, there are large windows throughout the floor that allow you to get a glimpse at 360 degrees of the entire city.
Take a selfie or battle your way to take a picture of your own reflection with the Cloud Gate, otherwise known as the Bean. It’s definitely a Chicago landmark and it can’t be missed. Millennium Park is great in the summertime for festivals and concerts. In the winter, the park fills with tourists heading for the skating rink and the large Christmas tree. The park is well-kept with gorgeous gardens, the Crown fountain and an interesting pedestrian bridge for a nice stroll. Please note that parking is found below the park, but is rather expensive.
Another suggestion you should note is by walking further down to Buckingham Fountain in Grant Park. Located in the center of the park, this massive landmark showcases beautiful water shows every hour. It's inspired by the Palace of Versailles fountain in France.
This long stretch of road is a must visit in Chicago. There’s no better place to fulfill your shopping needs than going to visit this long stretch of department stores on Michigan Avenue. There are lots of stores and clothing boutiques all found on one street. We must add that many fabulous restaurants and historical landmarks can be found here as well. You will definitely enjoy a walk down this lane.
360 Chicago Observation Deck
Remember the movie Ferris Bueller’s Day Off? Well, the classic Chicago-themed movie included a scene of this tower. Tilt off the Observatory on the 94th floor of the previously-known John Hancock Building. You can lean against the glass pane and get beautiful views of Chicago from 1000 feet high as it begins to tilt forward. It’s quite an experience.
The Art Institute of Chicago
Located in Chicago’s Grant Park, the Art Institute includes over 300 000 collections of art. It’s been ranked the top art museum in the world and kids under 14 can visit for free. If that's not enough, the large museum has over 30 exhibits and two hours are simply not enough to complete the entire tour. That's why we suggest you take your time when coming here or select certain sectors to visit. Enjoy modern art like Picasso and Warhol as well as some famous impressionist art like Van Gogh and Monet paintings. The museum is a work of art itself with contemporary decor such as glass windows and an elegant spiral staircase that make it even more impressive.
Ride the subway
Riding the “L” (which stands for “elevated”) is an inexpensive way to find your way around town by subway. You will fall in love as the train maneuvers in between buildings when riding outdoors. Certain trains provide 24 hour service as well. The one downfall is it requires climbing some long stairs to the platform at certain stations. However, escalators or elevators are available to ease passengers. This is a great way to see Chicago and its beautiful architecture.
Chicago Cultural Center
Take the time to wander at probably the most overlooked part of the city. It definitely deserves more recognition than it actually gets. The art is lovely inside and we would highly advise seeing the stunning Tiffany dome on the second floor. Admission is free to the exhibits. In fact, many events here are free, such as classical concerts on Mondays, Wednesdays and Sundays and many theatrical performances.
This is probably Chicago's top tourist attraction to spend a day. There’s the beautiful Centennial Wheel that illuminates at night brightening up the city, which is impossible to miss. The new 200-foot Ferris Wheel marks the 100th anniversary of the Pier, but beware as it’s a bit pricey. Also, there are many other carnival rides, a movie theater, the Children’s museum, souvenir shop and a beer garden to visit. From Harry Caray’s Tavern to Bubba Gump’s Shrimp Co., indulge at some iconic restaurants or grab a quick bite to eat at the large food court. In addition, many outdoor shows are hosted here year-round.
Lincoln Park Zoo
One of the most remarkable elements of the city is having year-round access to the Lincoln Park Zoo. What's even better is that it's one of the only zoos in the U.S. with free admission for all and it's located very close to the heart of Chicago. This is the perfect tour to come as a family and view the large variety of animals like lions, polar bears and monkeys. Enjoy all the exhibits and we recommend taking a stroll on the boardwalk too.
The Chicago Cubs finally broke the Curse of the Billy Goat after Billy Goat Tavern owner William Sianis put the curse on the team in 1945. Now the team are finally 2016 champions and what better place to go visit than this historic baseball park. Buy a ticket for a game or take the tour to the second oldest ballpark. Wrigley Field is made famous for its ivy-covered outfield wall and hand-turned scoreboard as it remains the most lovable among fans.
This was a dream come true coming here and we absolutely loved the rooftop seats that are no longer a freebie, but definitely offer a different view and perspective of the game. For all you sports fans, don't forget that the Blackhawks, Bulls, White Sox and Da Bears are all in proximity as well.
Donuts, popcorn (Garrett's) and deep-dish pizza (@ Lou Malnati's)!! Not exactly the biggest health foods, but they all have become a city staple. A culinary tour in Chicago is of epic proportions filled with many neighbourhoods, making it a rich ethnic food scene. You can never get enough, since there's enough eateries here to feed the hungriest of hearts. If you're in need of a quick bite, stop off at one of the city's many hot dog stands.
Chicago Riverwalk and Boat tours
This is a great way to see the city through the waterways including many iconic buildings and bridges. Take a stroll along the Chicago Riverwalk and enjoy the city from a different perspective.
Taking the boat tour is fun, entertaining and educational.
Visit different neighbourhoods
There's a large diversity of communities in Chicago and there's no better way, if time allows you, to go and visit some of the following neighbourhoods. We were fortunate enough to explore these areas and got a real good sense of the rich ethnic diversity of Chicago.
-Greek Town: visit also Little Italy and Chinatown further south