10 musts for Chicago

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Spending a few days or a week in Chicago means having your pick of a seemingly endless variety of things to see and do. From museums and music, to shopping and food, here are 10 things not to miss in the Windy City.

Catch a game at Wrigley Field

Top 10: Bucket list for Chicago
Wrigley Field (Image: urban.houstonian)

If you’re a baseball fan and it’s baseball season, make sure to grab tickets for a game at the legendary Wrigley Field. If it’s not baseball season, you can still get a guided behind-the-scenes tour to the home of the Chicago Cubs baseball team.

Listen to some jazz at Green Mill

Top 10: Bucket list for Chicago
Green Mill (Image: Keith Cooper)

Opened in 1907, Green Mill is a Chicago institution known for hosting many big names in jazz over the decades. In the 1920’s it was a favourite hangout for mobsters, and has been featured in several movies, such as High Fidelity. Now, it’s simply a great place to have a cocktail and listen to some great jazz music. Go early though as it can fill up fast.

Visit Millenium Park

Top 10: Bucket list for Chicago
Cloud Gate, otherwise known as “the Bean” (Image: Chris Stevenson used under a Creative Commons Attribution-ShareAlike license)

Millennium Park is known as Chicago’s premier green space, but it’s more than just a spot to sit and relax outdoors. The 25 acre park made its debut in 2004 and is full of interesting things to see and do. In particular, several pieces of iconic public art reside here – sculptor Anish Kapoor’s 110-ton Cloud Gate (most often called “the Bean”), Frank Gehry’s Pritzker Pavilion and Jaume Plensa’s Crown Fountain (which you can splash around in).

Explore Navy Pier

Top 10: Bucket list for Chicago
Navy Pier (Image: Ed Bierman)

You won’t be bored with a visit to Navy Pier. This Chicago landmark features shops, restaurants, an IMAX theatre, museums, rides, sightseeing boat cruises, an 18-hole mini golf course and special events. The area is ideal for families since there’s so much to do in an easy-to-navigate area.

Take an architecture cruise

Top 10: Bucket list for Chicago
Architecture cruise (Image: JetpacApp)

Chicago is a city known for its architecture, which you can see via a Chicago Architecture Foundation boat cruise. On board, you’ll get to hear about 50 buildings along the Chicago River and learn about their importance, as well as some historical background on how Chicago became the city it is today.

Visit a museum

Top 10: Bucket list for Chicago
Museum of Science and Industry (Image: Brent Newhall)

Chicago is home to many museums so if you’re craving a culture fix while you’re there, it’s easy to find an interesting place to spend a few hours. Depending on what your interests are, make a point of seeking out the Field Museum, Museum of Science and Industry, Chicago History Museum and Museum of Contemporary Art.

Eat some deep dish pizza

Top 10: Bucket list for Chicago
Deep dish pizza (Image: musicisentropy used under a Creative Commons Attribution-ShareAlike license)

You can’t leave Chicago without sitting down to an ooey, gooey deep dish pie. A thick, often crumbly crust gets a thick layer of mozzarella, toppings and then sauce, creating a filling, messy, yet unforgettable meal. Try some at Pizano’s, Art of Pizza, Gino’s East and Bacino’s.

Check out the views from the Skydeck

Top 10: Bucket list for Chicago
Entrance to the Skydeck (Image: daveynin)
10 musts for Chicago
The Ledge (Image: Charlotte)

The eighth tallest building in the world, Willis Tower, is 443 metres, meaning there are great views to be had over all of Chicago and beyond from the building’s Skydeck at 412 meters. If you’re feeling adventurous, go out on the Ledge, glass boxes that extends more than a meter from the Skydeck on the 103rd floor. Look down – but only if you dare.

Try a Chicago-style hot dog

Top 10: Bucket list for Chicago
CHicago-style hot dog (Image: Arnold Gatilao)

Chicago-style hot dogs are another iconic food item to try when you visit the city. While combinations of toppings do vary, the classic Chicago style dog involves an all-beef hot dog on a poppy seed bun, topped with yellow mustard, bright green relish, pickles, tomatoes, sport peppers, onions and celery salt. Try one at Gene & Jude’s, Hot Doug’s or Superdawg.

Shop along the Magnificent Mile

Top 10: Bucket list for Chicago
Magnificent Mile (Image: Ray_from_LA)

If you’re in the mood to shop, you can do so along the Magnificent Mile, a 13 block stretch of North Michigan Avenue. Widely known for its shopping, you can browse more than 460 stores. Magnificent Mile is also home to 275 restaurants and 60 hotels, as well as museums, galleries and other attractions.

Lead photo: Mike Warot

10 musts for Chicago was last modified: June 26th, 2019 by Jessica Padykula
Author: Jessica Padykula (292 posts)

Jessica Padykula is a Toronto-based writer and editor who regularly covers travel and lifestyle trends. When she’s not writing or researching a story she can be found planning trips to places near and far in a never-ending quest to travel the world.