BEST Things to Do, See and Eat in Chicago

Looking for the best things to do in Chicago? As a Chicagoan, here are the top things to do, see and eat in the Windy City that cannot be missed!

Famous Chicago Attractions Not To Miss

Cloud Gate (The Bean)

The Bean, Chicago's most famous tourist attraction

If you have seen photos of Chicago on instagram or facebook, chances are you have seen photos of Cloud Gate (which most people call The Bean), the famous mirrored sculpture in Millenium Park.

Although it is very touristy, the Bean is a must see attraction.  Millennium Park is free and one the best spots to take photos for instagram to remember your trip to Chicago.

Tip:  Millennium Park is usually crowded (especially in the summer and on weekends) so to avoid the crowds visit early in the morning or later in the day.  If you are visiting Chicago with children, you might want to also visit Maggie Daley Park, a large public park connected to Millennium Park that has play areas for kids of various ages.

Navy Pier

Chicago is famous for Navy Pier

Some locals consider Navy Pier a bit of a tourist trap, but it is a not to missed attraction if you are visiting Chicago with kids.  Navy Pier is full of fun things to do including a Ferris wheel, restaurants, shops, an IMAX theatre, the Chicago Children’s Museum and the Chicago Shakespeare Theater.  Navy Pier is also the starting point for various sightseeing cruises and boat rides. Navy Pier is free although you have to pay for the attractions and restaurants.

Tip: If visiting Chicago in the summer, you might want to come back in the evening to see the free fireworks at Navy Pier every Wednesday and Saturday night.

Great Museums

Chicago has many great museums which are well known and worth visiting. Depending how much you enjoy museums, you might want to spend some time in one of more of them when visiting Chicago.

The Art Institute of Chicago is my top pick and is conveniently located next to Millennium Park. It is one of the oldest and largest art museums in the United States and is frequently found on lists of the top museums in the world.

Other good museums include the Adler Planetarium, the Shedd Aquarium, and the Field Museum of Natural History – all located near each other on The Museum Campus. The Museum of Science and Industry in Hyde Park is a bit out of the way from downtown Chicago but it is a really fun museum with hands-on activities and interactive exhibits.

Tip:  To save money on entrance fees and skip long lines if you are visiting several museums,consider purchasing a Chicago CityPASS. Take advantage of free museum days. Some of the best Chicago museums offer free admission on the first weekend of every month to Bank of America credit or debit cardholders under the Bank of America Museums on Us program.


Chicago is known for its great architecture

Chicago has amazing architecture and the best way to see it is by taking an architecture river cruise.  There are several companies that offer tours but the best one is the one from the Chicago Architecture Foundation (CAF). The 90 minutes cruises are run by CAF-certified volunteer tour guides. Because the water sometimes freezes in the winter, river cruises only operate part of the year.

Chicago Riverwalk

The Chicago Riverwalk is a famous attraction

The Chicago Riverwalk, a pedestrian promenade along the river, is another must see Chicago attraction especially in the summer. The Riverwalk is one of the best spots in Chicago for people watching and it has restaurants, bars and places to sit along the way.


Chicago skyline wih some of Chicago's famous skyscrapers

Chicago is famous for its tall skyscrapers especially the Willis Tower (formerly known as the Sears Tower and what locals still call it) which used to be the tallest building in the world from 1974 until 1998. One of the best ways to see Chicago is to check out the view from one of its two tallest buildings. Chicago has two famous skyscrapers with observation decks:

The Skydeck at Willis Tower (formerly known as the Sears Tower) is famous for The Ledge, a glass balcony extending four feet outside the 103rd floor.

360 CHICAGO (formerly John Hancock Observatory) on the 94th floor of the 875 North Michigan Avenue (the building formerly known as the John Hancock Center) has TILT an enclosed moving platform that tilts you out over Michigan Avenue.

Lake Michigan

Lake Michigan with a view of some of Chicago's famous attractions including Sears Tower and Navy Pier

Another famous must see attraction in Chicago is Lake Michigan which is one of the five Great Lakes of North America.  Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan and it is a great spot to people watch and get some exercise.  In the summer and weekends, the lakefront is packed with locals and visitors walking, running and riding bikes. There are many beaches along the lake.  The most popular beaches are located downtown (Oak Street and North Avenue) but they are also the busiest.

Go on a Gangsters Tour
Chicago has a long history of organized crime and is famous for being the home of mafia figure Al Capone. There are many mob tours for those that want to learn more about the history of organized crime.

Best Chicago Food

Chicago is one of the best cities in the world for food lovers! Although Chicago is famous for certain dishes – there is so much more great food in Chicago. Don’t limit yourself to just these iconic Chicago dishes, but you should definitely try these once!

Chicago-style hot dog

famous chicago food specialties

A Chicago-style hot dog or Chicago dog is one of the two foods that Chicago is most famous for. The classic version of the Chicago dog is an all-beef hot dog served on a poppy seed bun and topped with yellow mustard, pickle, relish, sliced tomato, onions, sport peppers and celery salt. Ketchup is famously not allowed.

If you are visiting Chicago these are the best places to try a Chicago hot dog:

Portillos is a convenient restaurant to try the Chicago hot dog as it has outposts all over Chicago.

Downtown Dogs is my favorite understated spot to grab a Chicago dog and I love that it has photos of dogs taped on the walls. It is a tiny restaurant convenient located close to some major Chicago attractions.

Deep dish pizza

Chicago is famous for Chicago-style deep-dish pizza. The main difference between deep-dish pizza and most other forms of pizza is that the crust is very deep, creating a very thick pizza that resembles a pie more than a flatbread.

There is a lot of debate which restaurant in Chicago serves the best deep dish pizza but you can’t go wrong with either Lou Malnati’s or Giordano’s, two of the most popular and famous pizza places with several locations in downtown Chicago. If you do eat at one of these keep in mind that they are usually busy especially on weekends and in the summer (during peak times you will often see people waiting outside on the sidewalk).

Most locals prefer Pequods in the Lincoln Park neighborhood of Chicago which is said to have the best deep dish pizza in Chicago and is famous for its caramelized crust.

Italian beef sandwich

Although not as well known as deep dish pizza and Chicago style hot dogs, Italian beef is another dish Chicago is famous for.  Al’s Italian Beef is the best and most famous place in Chicago to try an Italian beef sandwich. Another good spot is Portillos if you are there for a Chicago hot dog.

These things are the top things to do, see and eat in Chicago.  They are are food and attractions that Chicago is most famous for and should not be missed whether you only have a day in Chicago or are visiting for a long weekend.

Planning a trip to Chicago? Check out my Chicago guides and itineraries:

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Best Things to Do in Chicago Famous Must See Attractions Chicago is Known For
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