A trip to the United States is not complete without a trip to Chicago, the “most American of big cities.”

There is something for everyone in Chicago. 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.


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 meters) 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 on top of the glass bays at The Ledge and look down onto Chicago from 103 floors high. Even if you’re afraid of heights, I challenge you to muster up the courage to step out onto one of the glass bays. 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 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.” 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.

Millennium Park and The Bean

Millennium Park and The Bean

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 meters) long pier sitting on 50 acres that juts out onto Lake Michigan. Here you can find plenty of entertainment, activities, museums, restaurants, and shops.

On a clear day, hop onto the 150-foot (46-meter) Ferris wheel 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 X (HOW MANY?) consecutive years recently and hosts approximately 1.5 million guests each year.

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.

Art Institute of Chicago

The Art Institute of Chicago

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 in the last year.

Wrigley Field

Wrigley Field, Chicago

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.


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.

Gino’s East

With that said, a trip to Chicago is incomplete for most until they have some of Chicago’s signature deep dish pizza. Although Giordano’s and Lou Malnati’s get most of the 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.

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 the best burger I’ve had in Chicago. The bacon served by Au Cheval much more resembles pork belly than the bacon you get with your breakfast plate. Be warned that there will almost undoubtedly be a line there, but I hardly mind waiting as they make the waiting 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 next door to Lone Wolf or any of the other excellent bar options 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 of years to have never experienced a meal at Girl and the Goat. The 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 who’ve lived in Japan who have attested the ramen tastes truly authentic. So if you don’t feel like waiting the 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 get great 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.


Public transportation in Chicago will get you everywhere you need to be, so there’s no need for 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 buses 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 at $10 or a 3-day pass at $20. You’ll get your best value if you stay for a week or longer and purchase the 7-day pass at $28.

Unlike in many cities around the world, Uber is actually legal in Chicago, so take advantage of it! There are several options for Uber rides in Chicago. The cheapest option is Uber pool, 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 so you may want to plan ahead and take an Uber pool.


Since I’ve lived in the city all six years I’ve been here, I haven’t had the need to stay in hotels. However, I have recommended hotels to friends and family, and these are a few 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 restaurant 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 just 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.


Street Art

Chicago isn’t hugely well-known for its street art, but there is actually loads of super cool and interesting street art scattered throughout the city. 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).

Street Art in Chicago

Street Art in Chicago


Chicago is home to many well known comedians such as Seth Meyers, John Belushi, Joan Cusack, Melissa McCarthy, Beck Bennett (featured in the AT&T “It’s Not Complicated” ads), Cecily Strong (aka “Girl You Wish You Hadn’t Started a Conversation With at a Party”), 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 get a glimpse at the next generation of comedians than to attend a comedy show at Chicago’s Second City? I have been to many shows in my last six years of living here, and they have all been fantastic. Tickets are reasonably priced, and you typically do not have to book too far in advance.

This is just a glimpse into everything you can do in Chicago. As someone who has traveled to close to 50 countries on 4 continents, I can say that Chicago is my favorite city in the world and the reason I have chosen to live here. Hopefully you can understand why when you visit!

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Diana Chen

Diana Chen

FTB Member

Diana is an ex-lawyer from Chicago who recently quit her job to travel the world. She blogs with her sister at MVMT Blog, where they show people how to travel the world with a full-time job or while in education. Diana’s next big adventure is hiking Mt. Kilimanjaro and checking country #50 off her list.

Follow her on her site MVMT Blog to learn about her travels. You can connect with her on Facebook, Instagram, Twitter and Pinterest here.


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