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Must-Visit Places in Chicago

What should you do in the Windy City?

Graphic of a postcard for Chicago showing the city skyline with water in front of it and large snowflakes blowing in the breeze.
Check out Chicago and all it has to offer. Illustration by John Creed

So you planned a trip to Chicago, now what? You most likely have the basics down like shopping and eating out, but there’s so much more to the city. From the famous Bean to a hidden speakeasy, visiting Chicago will be a trip to remember.

Picture yourself weaving through bustling city streets, the wind blowing through your hair. You stop and turn to see your reflection and in front of you is The Bean, Chicago’s biggest tourist attraction.

Intriguing? This might be your sign to book that trip and discover the amazing opportunities that Chicago has to offer.

Chicago – Where urban buzz meets Midwestern friendliness.

Where to eat

Chicagos deep dish style pizza.
The famous Chicago-style deep dish pizza. Credit: Shutterstock/shinyshot

Food can make or break your trip, you could have the most amazing meal of your life or you could end up with food poisoning (been there, done that).

Some of my favorite tried and true restaurants are The Hard Rock Cafe, Smoque BBQ, Superkahana International, Lula Cafe, and Hermosa Restaurant.

A great breakfast or lunch stop that I instantly fell in love with is Corey’s NYC Bagel Deli. Corey’s features a wide range of bagels, sandwiches, salads, pizzas, and more. My favorite item has always been the blueberry bagel with homemade cream cheese. Talk about mouth-watering.

If you’re looking for that world-renowned Chicago-style deep-dish pizza, be sure to check out Lou Malnatis Pizzeria. Not only do Chicago natives love Lou’s pizza, but people all over the states have taken a liking to the fresh, cheesy pizza.

Lou Malnatis now ships coast to coast, sharing that love for deep-dish pizza with the rest of the United States.

Where to stay

Rooftop view from the Best Western River North hotel located in Chicago, Illinois.
View from our stay at the Best Western River North. Credit: Kierah Hietala

On my many adventures in the windy city, I’ve stayed in a variety of hotels. One of my favorite hotels in Chicago is the Kinzie Hotel.

Excellent service, convenient location, friendly staff, historic atmosphere.

Joseph Kim, Google review

As someone who frequents concerts, the Kinzie Hotel is kitty-corner to The House of Blues, a common theater for concerts. With its affordable prices and stunning location, the Kinzie Hotel has become a staple for my visits to Chicago.

Some other great hotels I’ve stayed at include the Courtyard by Marriott in Downtown or River North, The London House, The Best Western River North, and Renaissance Chicago.

A great tip I’ve learned is to use sites like Skyscanner, Expedia, and Tripadvisor to book hotel stays and flights. You can usually find amazing deals on otherwise expensive hotels and earn points for free stays through these sites.

Whether you’re headed to Chicago for business or pleasure, you’re sure to find a place that fits your vibe.

What to do

A picture of Chicagos famous tourist attraction, The Bean.
Chicago’s famous Bean is located in the heart of the city. Credit: Shutterstock/Photo Spirit

There are countless things to do in Chicago, depending on the season. If you’re headed to the city over winter, make sure you check out the McCormick Tribune Ice Rink.

Placed in the center of Chicago, the rink offers amazing views while skating. They also offer hot cocoa, coffee, and other drinks or snacks right at the rink.

If you’re visiting the city through spring or summer, some of my favorite spots have been Navy Pier, Chicago 360, and a walk along the Chicago Riverwalk.

The Chicago 360 tower is open year-round, but I prefer to visit in the summer or even fall. Over winter you will frequently encounter unpredictable, cloudy skies.

The Navy Pier is also a time-honored tradition in Chicago open year-round. If you plan to visit in winter make sure to dress especially warm, being that close to the water really brings out the “windy” in Windy City.

On my most recent visit to the Windy City in December of 2023, the famous Chicago Bean was closed due to construction. Although this rarely happens, I highly recommend checking out the Millenium Park website to make sure you can enjoy this attraction on your trip.

Over the summer there are always concerts and festivals happening. Some popular festivals for the 2024 summer include Lollapalooza Chicago, Windy City Smokeout, and The North Coast Music Festival.

Infamous “local” spots

Oak Street Beach in Chicago, Illinois on a sunny day.
Oak Street Beach in Chicago. Credit: Shutterstock/James Andrews1

Chicago has a large variety of hidden bars and speakeasies, most unknown to tourists and visitors.

One in particular that I had enjoyed was The Press Room. The Press Room is a speakeasy hidden in the west loop. The speakeasy is a classy yet casual bar-style restaurant offering a variety of foods and drinks.

On the topic of pretending to be a local, a great spot to hang out or meet new people is along the lakefront. With tons of parks, walkways, and boating opportunities, there’s always something to do along the lakefront.

On particularly sunny days over the summer, you’ll often find people laid out on the beaches.

Oak Street Beach in Cook County Chicago is known for its amazing, sandy shore and constant action. With the sun hitting your skin and the slight Chicago breeze, Oak Street Beach is the perfect spot to sit back and relax.

For my coffee lovers

Chocolate Croissant from Starbucks in Chicago, Illinois.
Coffee and chocolate croissants from Starbucks. Credit: Kierah Hietala

A cup a day is an understatement when it comes to my love for coffee. Visiting a new city has made no exception when finding great coffee. Some of my favorite coffee stops in Chicago have included:

  1. The world’s largest Starbucks
  2. Metropolis Coffee Company
  3. The Understudy Coffee and Books
  4. Gaslight Coffee Roasters
  5. Ipsento 606

One coffee shop in particular that I’d like to highlight is the Metropolis Coffee Company. Although they’re located on the outskirts of Chicago, I’ve always indulged in the short trip.

With Metropolis’ smooth coffee and distinct flavors, it was love at first sip.

If you are like me and like to indulge in foreign flavors, I would recommend giving Maison Parisienne a try. They offer a variety of French-style beverages and treats that combine the French love for coffee and the unique vibe of Chicago.

Tips from TikTok

@jaznomz Top things to do in Chicago if you’re visiting for the first time! #chicago #downtownchicago #chitown #thingstodoinchicago #traveltiktok #traveltok #fyp ♬ Snooze X We Belong Together – Sped Up – lonely xo

As your typical Gen-Z gal, I usually take to TikTok experts to help find new places. The TikTok community has provided me with many new places to test out and has given me the opportunity to discover new activities.

As mentioned in the video, The Lincon Park Zoo in Chicago is a must-stop entertainment center. With the polar bear and penguin arenas, even my crabbiest of companions enjoyed their time at the zoo.

Whether you are looking for time to kill or need an escape from the windy outdoors, the zoo is perfect for all ages.

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Hello! I am a full time marketing student and content creator based in Wisconsin. Aside from working as a journalist for Trill Mag, I am also a social media and marketing intern for a non profit organization called The Plumery. I am an avid traveler and I love visiting new places!

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