9 of the Best Things to do in Chicago

If you’re planning a trip to Chicago, here are 9 top things to do in one of the USA’s largest cities.

The Chicago skyline overlooking Lake Michigan

Today’s guest post is written by Nausheen Farishta from Globe Gazers. She is a part-time traveller and full-time desk jockey. Her blog inspires readers to use all of their annual leave, eat deliciously well and take care of their physical and mental well-being.

Heading to Chicago? You’re sure to love it.

Twice named ‘Best Big City’ by Condé Nast Traveler (yes, beating New York), it’s no doubt that it deserves a spot on your must-visit list. The streets are clean, the architecture stunning and the food scene enviable.

My two top tips before you go? Chicago winters are infamous so, if possible, I recommend a summertime visit to help you truly appreciate all the city has to offer. And there’s no need to rent a car, as our public transportation is some of the best around.

Once you’re in Chicago you’ll find there’s plenty to do. Here are some of the best Chicago activities everyone can enjoy!

Indulge in the food scene

Chicago’s food scene is well-known. Whether you’re after Michelin-starred experiences or something simpler Chicago does food well.

Of course, you should not miss trying the famous deep dish pizza. See here for recommendations on where to get a slice.

Other highlights to try include: Chicago style hot dog at Portillo’s, Italian beef sandwich at Al’s Beef, gourmet donut from The Doughnut Vault (get the popular Old Fashioned), and burgers at Au Cheval.

Pro tip: to avoid long wait times, visit Small Cheval in Three Greens Market instead for the same burger in a different setting.

Additional iconic restaurants to try include the popular Alinea, Frontera Grill and Publican just to name a few. For more foodie insights, check out Eater’s extensive guide to Chicago.

Catch a movie or music performance at Millennium Park

Of course, you’ll want to check out Chicago’s Millennium Park and snap a few photos with the iconic Cloud Gate sculpture (lovingly nicknamed, The Bean).

Why not take it a step further by bringing wine, snacks and picnic blanket out to the park’s Jay Pritzker Pavilion? You’ll be able to enjoy an outdoor movie night or concert on the lawn.

Locals flock to the Pavilion after work to unwind with this fun summer date night idea.

And after the show, you can stroll around the park and surrounding areas, to appreciate the city lights with the night sky as your backdrop .

Grab drinks at a rooftop bar

Chicago’s got some great views and you’ll want to grab a great cocktail and take it all in from above.

So head to Cindy’s Rooftop for views of Millennium Park and the lake. Or, make your way to the Signature Lounge atop the John Hancock Building right around sunset, for a drink with a view on the 96th floor.

(Ladies, be sure to snap some pictures from the women’s bathroom window. The view from there is said to be one of the best in the city!)

Window shop along the Magnificent Mile

The Mag Mile runs along Michigan Avenue and is home to one upscale shop after another.

Spend some time popping in and out of shops or simply taking in the crowds and window displays. You may even be reminded of Paris’ Champs-Elysees!

There are various eateries scattered along Mag Mile as well, so you can certainly stop for a bite if the shopping becomes overwhelming.

Admire the architecture

It doesn’t take much looking around to realize that Chicago’s got some truly special architecture.

The best way to take in the city’s unique architectural styles is through a river cruise. Alternatively, if you’re in Chicago during the month of October, check to see whether Open House Chicago is ongoing.

This annual event is put on by the Chicago Architecture Foundation and allows free access to a multitude of unique buildings throughout the city. It’s the perfect opportunity to get up close and personal with the city’s architecture.

Venture beyond downtown

There’s so much more to Chicago than the Loop or downtown neighbourhood. The various neighbourhoods of Chicago each offer a vibrant culture all their own.

See here for a snapshot of neighbourhoods worth a visit while you’re in town.

Wrigley Field, home of the Cubs
Wrigley Field, home of the Cubs

Check out Wrigley Field

You don’t have to be a baseball fan to respect the Cubs! Tour the stadium or simply take a can’t-miss photo with it from the outside.

The area around Wrigley Field has birthed a variety of new restaurants and it’s worth your while to spend some time exploring. Though, beware, Wrigleyville is a favourite haunt for usually rowdy, younger 20-somethings.

Explore the Museum Campus

Chicago’s Museum Campus is a park that holds some of the cities’ best museums: Adler Planetarium and Field Museum. Spend a day museum hopping and enjoy a lunch in the beautiful park with some fantastic views of Chicago’s skyline.

Not part of the museum campus but equally worth a visit are the Museum of Science and Industry and the Art Institute.

Bike the lakefront trail

Consider renting a Divvy bike (the stands are all around the city) and going for a picturesque ride.

A nearly 20-mile path runs along the beach for cyclists, joggers and walkers. Biking the lakefront trail toward the loop means the beach and lake sprawl out to your left and majestic skyline views beckon to you from straight ahead.

Have you visited Chicago? What’s your favourite thing to do there?

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