Top 10 Things To Do in Chicago

Chicago was my first home as a “real adult.” It was the first time I was not a student, but a full-fledged working #girlboss. I had a job, friends, met my boyfriend, and truly fell in love with the city. As a kid, I envisioned myself living in New York City: being a subway pro, jogging in central park, and grabbing coffee on a big orange couch everyday (I watched a lot of Friends). But I found that Chicago, unexpectedly, fulfilled my big city dreams. It’s definitely a more laid back, down to earth city compared to NYC, and I love it for that! You NEED to have Chicago on your travel bucket list! Here are my favorite things to do in Chicago for a first time visitor.

things to do in chicago

The Essentials

Best time to visit? Summer

Summer in Chicago is what gets everyone through the winter. There are so many activities, festivals every week, and great weather. You can definitely go in the winter, but it’s going to be cold. Like REALLY cold. But hey, the snow and ice are also really pretty!

Transportation? The ‘El’

The public transportation in Chicago is great. The subway is better know as the El, due to the elevated tracks around the Loop (Chicago’s downtown area). Don’t bother renting a car; parking is a nightmare. Chicago’s two airports, O’hare and Midway, have direct lines into the city.

Is it safe? YES.

If you watch the news, you know about the gun violence in Chicago. It’s mostly gang related in certain parts of the city. If you’re a tourist sticking to the main tourist areas, you will be fine. It’s like any other big city, so keep your wits about you. Don’t leave your purse wide open; don’t wander around at 3am in dark alleys. But as we’ve seen in past weeks, bad things can happen anywhere. Don’t let the ‘what if’s’ stop you from visiting a great city like Chicago!

chicago sign

Things To Do In Chicago

The Bean and Millennium Park

This is my favorite part of the city. Cloud Gate, or more commonly referred to as The Bean, is a sculpture in Millennium Park with a great view of the city skyscrapers. The hustle and bustle is great for people watching. There’s even an ice skating rink in the winter. While some may argue it’s fairly touristy, it was the first place that made me feel like I was really in the big city (as a small town girl), and I loved visiting it every time I was in the Loop!

chicago bean

The Art Institute of Chicago

Just steps from the Bean is a building flanked by two lions. Inside you’ll find an amazing array of art, from Monet to Picasso and much more.

Fun Fact: I did a competition in elementary school called Picture Memory, where I was shown a painting and had to identify the title and artist. So it’s always fun for me wandering through art museums and vaguely remembering a painting from my childhood (I was a weird kid, ha).

art institute of chicago

Buckingham Fountain

Keep walking south within Grant Park and you’ll soon find one of the world’s largest fountains. It sits in a large public square with a great view of both the city and Lake Michigan. This is also the area where the biggest music festival occurs in late summer, Lollapalooza!

buckingham fountain

Museum Campus

This park sits to the south of the Loop and houses a few other big museums. You could spend a whole day here museum-hopping. Choices include Adler Planetarium, Shedd Aquarium, Field Museum of Natural History, or if da Bears are playing – Soldier Field. And you guessed it; there are sweeping views of the city along the lake here.

adler planetarium
Fun at Adler Planetarium
field museum
Sue the T-Rex at the Field Museum
View from Museum Campus

Views From Above

In a city of skyscrapers, you would be amiss to not travel upwards. You have two options – the infamous Sears Tower (aka Willis Tower) or the John Hancock Center. Both give great views of the city but are expensive (~$20 per person).

Main difference? Sears has the Glass Deck, and Hancock has the Tilt Deck. My preference is the John Hancock Center, but not the observation deck. The Signature Lounge is a bar on the 95th floor that is free of admission and has the same great views. Cocktails are around $15 but if you are going to pay regardless, why not enjoy the view with a drink in hand?

Sears Tower
Sears Tower
hancock center
Hancock Center
chicago skyline
View from the Signature Lounge

Lincoln Park Zoo

For a break from the concrete jungle, head over to Lincoln Park where you’ll find one of the country’s oldest zoos. And it’s free admission! This open-air zoo makes for a great day out with the family, date night, or even a solo stroll through the park!

lincoln park zoo

lincoln park

Navy Pier

Navy Pier is one of the top attractions in Chicago, especially for families. There are amusement park rides including the iconic Centennial Wheel (a large Ferris wheel). Even in the dead of winter when most things are closed, you can get a great view of the skyline sans hordes of people.

navy pier winter
Navy Pier in winter
navy pier summer
Navy Pier in summer

Architecture Tour

While you’re at Navy Pier, hop on a boat tour along the Chicago River for a lesson on the city’s impressive architecture. Boring, you think? Absolutely not! The history is simply fascinating, you get a different perspective of the city along the river, and of course, there’s a bar. What’s better than drinking on a boat in Chicago?

boat tour

chicago flag

chicago river

Wrigley Field

To delve deeper into Chicago history and culture, you’ll need to head north to Wrigleyville and catch Cubs game. Even if you don’t like baseball (and I don’t), the experience itself is very fun. Take a picture with the iconic Wrigley Field sign, eat a Chicago dog, drink some beer, and cheer on the city’s beloved Cubs.

wrigley field

cubs game

Lake Michigan

And last but not least, enjoy Lake Michigan! The lake that looks more like an ocean is a centerpiece of fun and leisure in Chicago. The Lakefront Trail offers miles of paths all along the lake.   Numerous beaches (Oak Street Beach, North Avenue Beach) let you soak up the sun, play volleyball, or even let your dog run free (Montrose Dog Beach). My advice is to rent a bike (Divvy is a good option), enjoy a day along the lake, and fall in love with Chicago!

lakefront trail

northerly island
Amazing sculptures at Northerly Island


Tell me your favorite things to do in Chicago!

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