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A trip to the United States is not complete without a trip to Chicago, the “most American of big cities.” It is the birthplace of jazz and home to more than 250 theaters, 200 dance companies, 125 art galleries, 56 museums, and over 5,000 restaurants. It is where the world’s first skyscraper was built in 1885 and where the tallest building in the Western Hemisphere still stands today.  Whatever your background or interests, you will find something in Chicago to enjoy and to love during your visit and for many years to come. Even after living in Chicago for 8+ years, I am still constantly finding new and fun things to do here. Use this local’s guide to visiting Chicago for the first time to help you plan your first trip to the Windy City.

What to do in Chicago

The Willis (Sears) Tower

The Willis Tower, formerly called the Sears Tower and still commonly referred to as such, is a 110 story, 1,450 feet (443 meter) tall skyscraper located in the heart of Chicago. It is the tallest building in the Western Hemisphere and the 8th tallest in the world.

When you visit, head up to the 103rd floor to stand in the glass boxes at The Ledge and look down onto Chicago from 103 floors (1,353 feet) high. Even if you’re afraid of heights, I challenge you to muster up the courage to step out into one of the glass boxes, which extends 4.3 feet out from the skydeck. When else can you say you’ve seen a city from 103 floors in the air?

For the best experience possible, plan your visit for a clear day, and head over to the Willis Tower early in the day or later in the afternoon/evening right before it closes, so you can avoid the lines.

And one final local’s tip for you: do NOT refer to the Willis Tower as the Willis Tower to locals, unless you want some mean stares thrown your way. It will forever be the Sears Tower in our hearts.

Millennium Park and The Bean (Cloud Gate)

Millennium Park is a 25-acre public park in the middle of the city that contains beautiful landscapes, architecture, green space, and public art. The biggest attraction in Millennium Park is Cloud Gate, more commonly known as “The Bean.” As far as Chicago attractions go, The Bean may be the most photographed, followed closely by Navy Pier. The Bean is a large stainless steel structure with a mirror-like surface that not only provides good entertainment for you to see your own reflection, but also a great medium on which to take photos of the skyline. If you are really dedicated to filling up your camera roll on your upcoming trip to Chicago, make sure you check out this list of the 25 most Instagrammable restaurants, bars, and cafes in Chicago as well.

In the summer, head over to Pritzker Pavilion in Millennium Park for one of the many free shows and a picnic with your loved ones. In the winter, lace up your boots and slide onto the ice rink in front of The Bean to ready yourself for a big holiday feast or have some good laughs.

Navy Pier

Navy Pier is a 3,300 feet (1,006 meter) long pier sitting on 50 acres that juts out onto Lake Michigan. Here you can find plenty of entertainment, activities, museums, restaurants, and shops. While certain attractions come with an entrance fee, walking around Navy Pier and taking in the breathtaking views is completely free. And if free is your jam, don’t forget to check out this list of 35 free things to do in Chicago.

On a clear day, hop onto the 150-foot (46-meter) ferris wheel at Navy Pier for some great views of the city and Lake Michigan. Or, get off the shore on one of the many dining and sightseeing cruises that leave from the pier for even more stunning views of the skyline.

For those of you traveling with kids, enjoy a game of mini golf, remote controlled boats, or go for a ride in the carousel or lift-and-twirl. Then, head on over to the Chicago Children’s Museum, where you and your kids can get hands-on with interactive exhibits.

Navy Pier is open year-round and hosts special events regularly at one of its many venues. Make sure you check online before you visit to see if there are any fun events going on when you’re in town!

Art Institute of Chicago

The Art Institute of Chicago (AIC) is one of the oldest and largest art museums in the United States. It was rated the #1 museum on TripAdvisor for consecutive years recently and hosts approximately 1.5 million guests each year. One of my favorite things about being a local in Chicago is being able to visit the AIC whenever I want – and never getting bored of the exhibits. 

One interesting fact about the AIC is that it is also a research institution and an art school in one. In fact, it is one of the few remaining unified art institutions in the United States.

Whether you’re an art enthusiast or not, the AIC offers a large variety of exhibits that are sure to keep you entertained. If you are a resident of Illinois, you’ll be happy to know that admission is free for you every Thursday from 5:00 to 8:00 p.m. year round. The AIC is typically open to the public from 10:30 a.m. to 5:30 p.m. daily.

Wrigley Field

Wrigley Field is a baseball park located on the north side of Chicago and one of the oldest ballparks in the United States. Home to the 2016 World Series Champions, Wrigley Field has become an even more popular landmark since then.

If you’re fortunate to travel to Chicago during baseball season, try to catch a game at Wrigley Field. Otherwise, ballpark tours are offered regularly and provide visitors with an insider’s look at this ballpark’s 100+ years of history.

Street Art

Chicago isn’t necessarily known for its street art, but there are lots of fun and interesting street art scattered throughout the city if you know where to look (cue my next local’s tip). Head north on Milwaukee Avenue through the Wicker Park, Bucktown, and Logan Square neighborhoods, and you’ll find more than your fair share of murals. Or, venture out to the other side of town and check out the Pilsen neighborhood. Not only will you find plenty of street art there, you’ll also find some of the city’s best Mexican food (my personal favorite: Canton Reggio).

Comedy

Chicago is home to many well known comedians such as Seth Meyers, John Belushi, Joan Cusack, Melissa McCarthy, Beck Bennett, Cecily Strong, and many more. Many of these comedians graduated from Chicago’s Second City Improvisational Theatre, so what better way to get a good laugh and glimpse the next generation of comedians than to attend a comedy show at Chicago’s Second City? I have been to many shows at Second City in my last 8+ years of living in Chicago, and they have all been fantastic. Tickets are reasonably priced, and you typically do not have to book too far in advance.

For even more fun and awesome things to do in Chicago, check out this post on seven of my favorite things to do in Chicago.

Where to eat and drink in Chicago

In recent years, Chicago has risen to become one of the world’s hottest food cities. With celebrity chefs like Stephanie Izard, Rick Bayless, and Grant Achatz, Chicago is far past its days of being known for just pizza and hot dogs and is now home to sophisticated, diverse cuisines that cater to any audience. The list below contains essentials for a first time visitor to Chicago, but if you are more interested in eating where the locals eat, check out my local’s guide to the 35 best restaurants in Chicago, and if you do all things for the ‘gram, don’t miss this list of the 25 most Instagrammable restaurants, bars, and cafes in Chicago.

Gino’s East

A trip to Chicago is incomplete for many until they’ve had some of Chicago’s signature deep dish pizza. Although Giordano’s and Lou Malnati’s get the most hype around here, my favorite deep dish joint to take friends and family to is Gino’s East. With several locations in and around the city, Gino’s East is a Chicago classic. Not only do they serve delicious deep dish pizza, they also brew their own beer and serve decadent desserts like their super moist and delicious deep dish brownie. If deep dish pizza is on your list, you would be remiss to skip Gino’s East.

Side note: Another deep dish favorite amongst locals in Chicago is Pequod’s, so make sure you check them out as well!

Au Cheval

If you’re looking for the best burgers in town, head on over to Au Cheval and order a cheeseburger with bacon and a fried egg on top. It may sound basic, but this is one of the best burgers I’ve had in Chicago. The bacon served by Au Cheval is a thick cut of pork belly and not the bacon you’re used to getting with your breakfast plate. Be warned that there will almost undoubtedly be a line at Au Cheval, but I hardly mind waiting as they make the wait process as convenient for you as possible. All you have to do is give them your name and number, and they’ll text you when your table is ready. While you wait, head to any of the excellent bars nearby for a drink.

Girl and the Goat

Girl and the Goat is a Chicago classic. In fact, it may actually be a crime for anyone who’s lived in the city for more than a few years to have never experienced a meal at Girl and the Goat. Food here is served family style, and the rotating menu features fresh ingredients that come together in bold, globally inspired flavors.

I would highly recommend making a reservation here as far in advance as possible, as the demand here is high. If you are unable to make a reservation, I would recommend walking in at 4:30 p.m. when the restaurant opens and trying to grab a seat at the bar or lounge area.

Ramen Takeya

Chicago isn’t the most well known for Asian food (compared to cities like New York or San Francisco), but we can hold our own. I am almost always craving ramen, and one of my favorite ramen joints in the city is Ramen Takeya in the Fulton Market District. The ramen here is light yet filling, and I’ve brought people here who have lived in Japan before and vouched for the authenticity of the ramen here. So if you don’t feel like waiting hours in line for High Five Ramen down the street, head on over to Ramen Takeya.

Cindy’s Rooftop Restaurant at Chicago Athletic Association Hotel

Chicago has a number of rooftop bars that offer beautiful views of the city, but one of my favorites is Cindy’s Rooftop at Chicago Athletic Association (CAA). CAA is located right off of Michigan Avenue and close to Lake Michigan. From the rooftop, you can glimpse beautiful views of the cityscapes and the lake, and there is even a fireplace on the roof to keep guests warm while they enjoy the beautiful Chicago skyline. If you’re looking for a place to do some work while enjoying a cocktail, check out the dining area on the first floor of CAA, where an old school library meets a bar.

How to get around Chicago

Chicago public transportation will get you everywhere you need to be, so there’s no need to rent a car. The downtown area is very walkable, and if you want to check out other areas of the city, you can hop on a train, bus, bike share, or Uber.

To use the train or bus, you’ll need to purchase a Ventra card, which you can use to access the trains and busses and continue to load money onto throughout your stay. A ride on the train costs $2.25 (rides from O’Hare Airport cost $5.00), a ride on the bus costs $2.00, and transfers (up to two additional rides within a two hour period) cost only $0.25. 

If you are only staying in Chicago for a short time and want to try and see everything in one day, it may be worthwhile for you to purchase a 1-day pass for $10 or a 3-day pass for $20. You’ll get your best value if you stay for a week or longer and purchase the 7-day pass for $28.

Another convenient way to get around the city is by Uber or Lyft. There are several options for Uber and Lyft rides in Chicago. The cheapest option is Uber pool or Lyft shared, which means your driver may pick up additional riders on the way to your destination. Although this option might take you longer to reach your destination, it can be significantly cheaper than the other options.

Where to stay in Chicago

It’s always hard for locals to give hotel recommendations, since I’ve never had the need to stay in one (except that one time my power went out for days in the middle of winter and I had to temporarily move into a hotel but that’s a story for another day). However, I have recommended hotels to friends and family, and these are a few Chicago hotels that have come back with good reviews.

Budget: Freehand Hostel

For a budget option, try the Freehand Hostel. I always recommend this hostel because of its prime location to visiting many of the major sites in the city. It is also in the center of plenty of nightlife and restaurants, so you can enjoy yourself in the evenings right outside your doorstep.

Mid-Range: Kimpton Hotels

For a mid-range option, check out one of the four boutique Kimpton hotels downtown. Out of the four, the lower end options are the Monaco and the Allegro, which you should be able to find in the $100-$200s range depending on the season and how far out you book. I love the Kimpton Hotels again because of their prime locations and also because of their unique boutique designs.

Luxury: The Peninsula

If you are really looking to treat yourself, check yourself into The Peninsula. This 5-star hotel will give you the royal treatment you’ve always dreamed of. The Peninsula was recognized as part of the “2017 Travel + Leisure World’s Best Awards” and I’m sure that will be of no surprise to you when you experience it for yourself. This hotel is the definition of luxury and elegance.

This guide is perfect for someone wondering what to do in Chicago for first timers but will hopefully also inspire you to come back and visit again so that you can dig deeper into the history and culture of Chicago. As someone who has traveled to over 60 countries on four continents and has still chosen to live in Chicago, I can say that Chicago is my favorite city in the world! Hopefully you can understand why when you visit!

Looking for more fun things to do in Chicago? Check out these posts to read more:

• 35 Free Things to do in Chicago
• A Local’s Guide to the 35 Best Restaurants in Chicago
• 7 Awesome Things to do in Chicago
• Kayaking in Chicago With REI
• 25 Most Instagrammable Restaurants, Bars, and Cafes in Chicago

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