What to See and Do in Chicago

by  Kristine Hansen | Feb 6, 2020
Chicago / Sean Pavone/iStock

Don’t be fooled: The Windy City is a great destination year-round, in part due to its vibrant four seasons. The city’s green space, shoreline, and street art are stunning visuals on a neighborhood walk, whether you’re on North Michigan Avenue or in Wicker Park, or experiencing Chicago’s version of New York City’s High Line — a former elevated rail line now green space and walkway. This is the Midwest’s hub for performing arts, cultural experiences, and other wow-worthy attractions. Plus, you'll  find some of the country's best museums here, too.

What Chicago Is Known For

Millennium Park

Millennium Park, Chicago / Sean Pavone/iStock

This 25-acre park in the Loop features several distinct areas, from free outdoor concerts and films during the warmer months in the Frank Gehry-designed Jay Pritzker Pavilion to the digitized screens and water works at Crown Fountain. If you’re traveling with small children, take them to the interactive slides on the park’s far east side to work out the wiggles. The Cloud Gate (also known as "the Bean"), is a popular picture-taking spot were you can see your reflection (and the Chicago skyline) within.

Navy Pier

Come summer, Navy Pier — which juts out into Lake Michigan and is just north of downtown Chicago — hosts a weekly fireworks show on select evenings. The pier is also home to the Chicago Shakespeare Theater and the Chicago Children’s Museum and, during the cooler months, an outdoor ice-skating rink. While most of the restaurants and shops cater to tourists, a stroll along the boardwalk offers a fantastic glimpse at Chicago’s skyline.

The Art Institute of Chicago

Art Institute of Chicago / benkrut/iStock

Located along South Michigan Avenue in the Loop and marked by two stone lions out front, The Art Institute of Chicago is one of the country’s premier art institutions. Here, you'll find works Monet, Picasso, and Gaughin, along with a rotating art show that often demands purchasing tickets in advance. Be sure to dedicate at least a half day to truly experience this huge art museum.

The 606

Created in 2015, The 606 is an urban oasis that features street art by local artists as well as a reimagined green space where elevated rail lines used to run. The 606 passes through the neighborhoods of Logan Square, West Town, and Humboldt Park. Bikers, runners, and walkers alike enjoy The 606, which spans almost three miles and is free to enter.

Willis Tower

Adrenaline junkies will love Skydeck Chicago, a cantilevered, glass-bottom ledge at the 110-story Willis Tower — 1,450 feet into the air! This ledge juts out over four feet from the side of the building on the 103rd floor. On a clear day, you can see four states: Illinois, Indiana, Wisconsin, and Michigan. 

Where to Stay in Chicago

St. Jane Hotel - guest room / Courtesy of the property

Stay in the heart of downtown Chicago at the St. Jane, which opened within a glamorous Art Deco skyscraper back in 2018 (rates from $97 per night, depending on the season). Right outside the hotel is Millennium Park and the Art Institute of Chicago.

The West Loop is a favorite neighborhood for locals thanks to its many restaurants with celeb chefs as owners along with art galleries and a more edgy vibe than the Loop. Pick from Ace Hotel Chicago (rates from $125 per night, depending on the season) or Soho House Chicago (rates from $155 per night, depending on the season). In town for a Cubs game? Hotel Zachary (rates from $134 per night, depending on the season) and The Wheelhouse Hotel (rates from $90 per night, depending on the season) are two boutique properties that have opened within the last year. Both offer easy access to Wrigley Field.

Chicago’s South Side is getting a makeover and prepping for the opening of the Obama Library. The 98-room Sophy Hyde Park is an absolute beauty and is home to a trendy restaurant, lounge, and bar called Mesler. Rates from $119 per night, depending on the season. 

Where to Eat in Chicago

Chicago-style hot dog / Kate Marynenko/iStock

You already know about hot dogs and deep-dish pizza but don’t even think about leaving Chicago without trying both. If you’re staying downtown, then Lou Malnati’s and  Giordano’s are both good options for ‘za. For a Chicago-style hot dog (topped with yellow mustard, chopped onions, pickle relish, dill pickle, pickled peppers, tomato slices, and celery salt) head to America’s Dog & Burger — there’s one on Navy Pier — or Chicago’s Dog House in Lincoln Park. The local Portillo’s chain, which can be found in the city and its ‘burbs, is also a classic. 

For trending restaurants, head to the West Loop and Fulton Market district, where Top Chef winner Stephanie Izard runs Girl & the Goat  and Little Goat. Other popular spots nearby include find Grant Achatz’s Alinea, The Aviary, and Au Cheval, a wildly popular, can't-miss burger spot. 

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