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Chicago Bucket List

Someone holds a Cubs cap in front of a baseball pitch.

There is no best time to visit Chicago because there are endless activities and experiences to keep you entertained year-round. To help you decide between the best Chicago architecture boat tours, spectacular city views, and must-try snack joints we’ve narrowed down our favorite activities to create our very own Chicago Bucket List.

Head to the River

If you truly want to appreciate the city’s architecture, a group or private Chicago boat tour is the best way to do it. Float down the Chicago River, gazing up at the impressive structures as you go. Tours & Boats offers one of the best Chicago Architecture Boat Tours, covering all three branches of the river. Our expert guides will enlighten you with interesting facts and history such as how the city was rebuilt after the 1871 Great Chicago Fire. What’s more, the 360-degree views will give you endless photo opportunities.

Get Up High

Get your adrenaline fix or challenge your fears by braving The Ledge Skydeck at Willis Tower. The glass boxes extend out 4.3 feet from the building at a height of 1,353 feet. As the second tallest building in the Western Hemisphere, stepping out onto The Ledge is one of the city’s most unique experiences. The views across Chicago are sure to leave you breathless, and we recommend going at sunset to catch the golden hour!

Another great spot for panoramic views of the Windy City skyline is 360 Chicago. However, there is more to this observation deck than just the views. If the height of the building isn’t enough for you, the location is home to Chicago’s highest thrill ride, TILT. There is also a bar and cafe where you can watch the sun set while sipping on a cocktail.

Get Outside & Explore Nature

The Millenium Park is considered to be the top tourist destination in both Chicago and the Midwest, meaning it definitely deserves a spot on our Chicago Bucket List. Take a photo under Anish Kapoor’s ‘The Bean’ (Cloud Gate), one of the most popular Chicago selfie spots. Take some time to relax and take in the tranquility of the Lurie Garden. This oasis in the bustling city is peppered with perennials, bulbs, grasses, shrubs, and trees that form dense hedges and bursts of vibrant colors. Or, if you’ve got the energy to burn, harness up and take a shot at the climbing wall in Maggie Daley Park. It’s suitable for all levels, from beginners to pros – and best of all, it’s free!

Enjoy lush flora and fauna and tropical temperatures in the Garfield Park Conservatory. The conservatory consists of eight indoor display gardens as well as 10 acres of outdoor gardens. The vibrant Tropical Room is a good way to escape the cold on winter days. In summer, be transported to another country as you enter the humid jungle or enjoy the water lily ponds in the outdoor gardens. Entry to the park is free and it’s a great place to visit with kids or friends.

The Lakefront Trail runs 18 miles along Chicago’s shoreline. Choose your mode of transport (bike, foot, rollerblades) and enjoy the track with Lake Michigan situated on one side and the green parks and skyscrapers on the other. This is a great way to get to know the city and appreciate the immensity of Lake Michigan.

Grab a Chicago Bite

Food is a massive part of Chicago culture, and if you’re a foodie passing through our city, you’re in for a real treat.

Stroll through the second-largest Chinatown in the US and soak up the architecture, history, and, of course, the food. To avoid the crowds, we suggest heading to Emperor’s Choice Restaurant, a traditional Cantonese restaurant that serves up some killer seafood dishes.

Love it or hate it, you can’t come to Chicago and not try deep dish pizza. This divisive dish is the perfect antidote to a cold day with a bitter wind blowing off the lake. The famous caramelized crust on Pequod’s pizzas makes it one of our go-to pizza joints. It developed a cult following by cooking mozzarella cheese along the edge of a cast-iron pan and creating the golden crust we love.

Get Your Art & Culture Dose

As a city with over 60 museums, getting your dose of culture is an easy feat here. The Field Museum is an impressive natural history museum that has 350,000 square feet of permanent exhibitions. It was originally founded to house the pioneering Columbian Exhibition of 1893 and continues to attract visitors from all over the world.

Explore paintings, sculptures, photos, and drawings at the Art Institute of Chicago. The world-renowned museum offers pieces across many styles including Impressionist and Post-Impressionist painting, early twentieth-century European painting and sculpture, as well as contemporary art, Japanese prints, and photography.

If traditional museums aren’t for you, check out the Museum of Illusions. Challenge your perceptions and see the world differently in this weird and wonderful place. It’s great fun for adults and kids alike with around 80 exhibits to keep you entertained.

For those looking to take in some art outside, the outdoor gallery of murals known as 16th Street Murals is home to works of art by internationally renowned artists. The old railroad embankment has been transformed into a cultural hub of vibrant colors and ideas. One of the murals is Belgian artist ROA’s infamous depiction of a severed possum – beware, it’s not for the faint-hearted!

Catch a Game or Enjoy an Evening of Live Music

The Green Mill is an institution in the jazz world. With previous clientele including Charlie Chaplin and Al Capone, it is widely considered one of the best places to see live jazz in the US. The venue that has played host to jazz greats such as Von Freeman and Kurt Elling, was named in reaction to the Moulin Rouge (Red Mill) in Paris. Travel back in time with its 1940s décor and enjoy shows from some of the modern-day jazz geniuses.

If you’re a sports fan, you won’t be short of games to catch. Our city is home to the Chicago Bulls (basketball), the Chicago Bears (football), the Cubs (baseball), Chicago Fire FC (soccer), and for ice hockey fans, the Blackhawks. Choose your sport and soak up the crowd atmosphere in Chicago!

There’s plenty more we could add to our Chicago Bucket List, it’s a city with so much to offer. Our architecture boat tours run from May to October and they are the best Chicago architecture boat tours around, so be sure to get in touch and book your spot with plenty of notice!

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