Best Things to Do in Chicago

Places to visit in Chicago

Are you going to travel to Chicago soon and don't know where to start planning? We hope to make it much easier for you after reading these 40 things to see and do in Chicago plus some tips to enjoy the city 100%. Chicago is the third largest city in the United States, also known as the windy city, it is the city where the mythical route 66 begins, where Michelle Obama, Walt Disney and Harrison Ford were born, and is known for its "Deep dish" pizzas. The truth is that it was one of the surprises on our trip along Route 66, we liked it much more than we expected and it seemed like a brutal city. Today we tell you all the things to see and do in Chicago to fully enjoy the windy city.

Things to See And Do in Chicago

Millennium Park

Millennium Park and the most famous beans in the world. It may be one of the most famous and photographed places in Chicago, it was the first place we visited and we did very well because in the afternoon you couldn't even walk because of the number of tourists there. The Cloud Gate better known as The Bean (The Bean) for its shape, is made up of 168 steel plates and weighs no more and no less than 98 tons. No tourist leaves Chicago without their photo with the bean, one of the most famous things to see in Chicago without a doubt. Mini-advice to visit the Millennium Park: Go first thing in the morning to be able to see everything in a relaxed way and to be able to take cool photos with almost no people.

Crown Fountain

Almost next to the giant bean is the Crown Fountain built by the Spanish artist Jaume Plensa. It is a huge LED screen on which the faces of people from Chicago appear and from time to time streams of water fall that seem to come from their mouths. In the morning there was no one but in the afternoon it was overflowing with children impatient for him to open his mouth and get under the stream.

Buckingham Fountain

Very close to the previous point is the Buckingham Fountain, the most important source to see in Chicago, they say it is one of the largest in the world. From 8 in the morning to 11 at night there is a water show every hour that lasts about 20 minutes. Due to the weather the fountain is only in operation from May to October.

The Agora

The Agora, a group of 106 headless, armless sculptures also found in Grant Park, are the work of Polish artist Magdalena Abakanowicz, each measuring nearly 10 feet.

Statues of Abraham Lincoln

Visit the two statues of Abraham Lincoln, one of the most important men in the history of the United States, in Chicago. One is in Grant Park, near the Buckingham Fountain, and the other is in front of the History Museum in Lincoln Park.

Chicago Theater

Pay a visit to the Chicago Theater, built over 100 years ago, it had to close its doors in the 1970s but later reopened with a spectacular concert by Frank Sinatra. The architecture is inspired by the Versailles building, spectacular both its facade and the interior, you can take a guided tour in English. You can also check and book one of their shows.

Live Blues Music

Enjoy live Blues music at Buddy Guy's Legends, one of Chicago's mythical venues opened in 1989 by the musician Buddy Guy who is still the owner of the venue and makes regular appearances.

Magnificent Mile

The Magnificent Mile is the honorary title given to a section of Michigan Avenue, undoubtedly the best-known and most luxurious avenue to see in Chicago, a style like 5th Avenue in New York or Gynza in Tokyo, so you can make a idea.

Chicago Water Taxi

Get on the Chicago Water Taxi and travel the Chicago River in the most economical way. There are many tourist boats that go through the Chicago River but the cheapest option is to take the Chicago Water Taxi, it is not a tourist boat but it travels the entire river making several stops. The two tickets cost us about $20 and they are valid for the whole day, you can go up as many times as you want, 100% recommended!

Chicago Guided Boat Ride

Book a boat trip with a guide in Spanish as well as English, where they tell you all the curiosities of the most important places to see in Chicago.

Swim on the beach of Lake Michigan

Go for a swim on the beach of Lake Michigan (if you go in summer!), it has several beaches that are covered in snow in winter but in summer they become a perfect place for a swim, some of the most central ones are Ohio Street Beach and Oak Street Beach. Lake Michigan is one of the five great lakes in the United States, one of the important points to see in Chicago during your visit.

Chicago-style hot dog

Of course you have to try the Chicago-style hot dog, the sausage is beef, it has mustard, green sauce and onion, it doesn't have ketchup! Two traditional places to try it is Portillo's or Gene & Jude's, the latter on the outskirts of Chicago.

Chinatown neighborhood in Chicago

Visit the Chinatown neighborhood in Chicago, the arch that welcomes the neighborhood is located at the intersection of Cermak Road and Wentworth Avenue. Here you will find shops, cafes, tea houses and restaurants specializing in Asian food. We recommend the MingHin Cuisine restaurant. Do not miss the Wall of the Nine Dragons, it is a reproduction of the 15th century mural found in Beijing. You have the exact location on the map at the end of the post.

More things to see in Chicago

Skydeck of the Willis Tower

Go up to the Skydeck of the Willis Tower, this impressive viewpoint is more than 410 meters high. From above you get one of the best views to see in Chicago. The building in which it is located measures 442 meters, it is the second tallest tower in the United States after One World in New York, You can see prices and book on the Skydeck website, if you have the Go Explorer Pass tourist card you will have access included.

The Hancock Tower

The Hancock Tower with 100 floors and 344 meters high is the fifth tallest building in Chicago and undoubtedly one of the essential places to see in Chicago. Inside the building there are three floors that we can visit, each one is a different experience:

  • Floor 94: The 360º Observatory with incredible views of the entire city of Chicago. The entrance costs about €25 and we can also add the TILT attraction that costs about €8.
  • Floor 95: Signature Room, a pretty VIP restaurant where you can dine with unbeatable views of Chicago.
  • Floor 96: Signature Lounge, just above the restaurant, is more casual but with the same views, this was the one we chose.

The 360º Observatory is the most popular viewpoint to see in Chicago, they say that if the day is clear you can see up to four states, you can book your ticket before going to save queues. The Tilt glass pod tilts forward for an impressive downward view - not for people with vertigo! We went to the Signature Lounge in the late afternoon, there is no entrance fee, you only pay what you ask for. We were able to enjoy the views day and night and it was a success, don't forget to write it down on your list of things to do in Chicago.

We recommend you take a card that does not charge commissions for currency exchange, we have used the N26 card for years that does not charge us anything to pay in a currency other than the euro.

Outdoor Concert at the Jay Pritzker Pavilion

See a free outdoor concert at the Jay Pritzker Pavilion, a huge outdoor concert pavilion with an amazing structure, the work of architect Frank Gehry, you can check the events at Jay Pritzker Pavilion.

Live NBA game

NBA game live, a show that we recommend 100%! As you probably already know, the local team is the Chicago Bulls. The excitement of the game, the music, the speaker, the breaks with the t-shirt launchers, the kissing camera... don't miss the opportunity!

Statue of Michael Jordan

Visit the statue of Michael Jordan, although it is located inside the Chicago Stadium, admission is free. By the way, Michael Jordan has his own steakhouse in the city, you have the exact location on the map at the end of the post.

Cheddar Cheese Popcorn

Try the cheddar cheese popcorn, it is a tradition in Chicago, Garrett Popcorn Shops has several locations in the city and since 1949 they have been selling popcorn of various flavors, the most famous being the Garrett Mix.

Romantic Things To Do Chicago

Chicago Riverwalk

Relax along the Chicago Riverwalk This walk borders the river and is ideal for a walk, you will also see many places to have a drink or eat. The Riverwalk is several kilometers long and it takes several hours to cover it completely . We recommend the section between the Battan and William bridges, it is about 700 meters long enough to enjoy the height of the buildings and their architecture.

The Du Sable Bridge

The Du Sable Bridge, is one of the most important bridges to see in Chicago with the characteristic that it is drawbridge, it unites The Loop area with the north of Chicago, it was built more than a hundred years ago.

BridgeHouse Museum

In the southern part of the bridge is the BridgeHouse Museum, a small museum where you can learn about how the rivers transformed Chicago. Admission is free on Sundays.


In the northern part of the bridge is Ghirardelli, one of the most famous chocolate shops in the United States, take the opportunity to try their sweets! Taking a free guided tour is the best way to get to know all the things to see and do in Chicago from the hand of a person who knows the city perfectly and for a small price.

Chicago Beaches

The beaches in Chicago are located along the shoreline of Lake Michigan. The windy city has more than thirty beaches. They can be used free of charge from the last weekend of May to the first weekend of September.

The main beaches in Chicago

  • North Avenue Beach (the biggest and most popular)
  • Montrose Beach.
  • Ohio Street Beach (good option on visit)
  • Kathy Osterman Beach.
  • Foster Beach.
  • Oak Street Beach, Olive park beach (the most accessible)
  • South Shore Beach.

Beginning of ROUTE 66

Take a picture with the sign at the beginning of ROUTE 66, of course this is an essential thing to see in Chicago and even more so if you plan to do Route 66 like us. Here the adventure begins!

Chicago Pedway

Stroll the Chicago Pedway, a network of underground tunnels and overpasses that connect more than 50 buildings in downtown Chicago, great for the colder months! We can go from Millennium Park to the Chicago City Hall, which is about seven blocks without going out into the street. These tunnels are usually open Monday through Friday from 7 in the morning to 5 in the afternoon.

Eating in Little Italy

Eating in Little Italy, In the surroundings of Taylor Street you will find one of the best-known Italian neighborhoods in the United States next to New York, ideal for going to eat a good plate of Italian pasta. Tuscany Taylor or Pompei are two restaurants where you will be sure to hit the mark! Although little remains of its golden age, we can see Piazza Dimaggio and the Church of Our Lady of Pompeii that will take us to Italy for a moment. Curiosity! This is where the Italian mafia settled in the 1920s and Al Capone began his criminal career.

Greetings From Chicago Mural

One of the best known murals to see in Chicago is the "Greetings from Chicago" a whole sample of street art, it is the work of the New Yorker Victor Ving, each of the letters of the mural shows different aspects of the city, such as pizza, the skyscrapers and the bean. At 500 meters is the mural in honor of Robin Williams surrounded by blue geniuses from the Aladdin movie to which he put the voice in the original version. The two murals are located on Milwaukee Avenue, very close to the California and Western subway stop.

Trying the deep dish pizza

Trying the deep dish pizza is one of the things to do in Chicago yes or yes! It may be the star dish in the city, it's like a pizza pie and the cheese wears it down, the most famous is Giordano's restaurant, don't miss it!

Chicago Water Tower

You can't miss the Historic Water Tower, one of the most historic buildings to see in Chicago, located on the Magnificent Mile. It is the second oldest water tower in the United States and was used to extract water from Lake Michigan, now it is an art gallery. It is one of the few buildings left standing after the Great Chicago Fire.

Museum of Contemporary Art

Visit the Museum of Contemporary Art (MCA), with works by Andy Warhol and other important artists, located near the Water Tower. If you like contemporary art you have to visit it.

Field Museum

One of the most curious things to see in Chicago is the largest and most complete tyrannosaurus in the world at the Field Museum of Natural History, visitors can see through glass windows how the museum's paleontologists work.

Chicago Museum of Science and Industry

If you go with children, the Chicago Museum of Science and Industry is surely a very fun plan, it is an interactive museum with exhibitions on science designed for the little ones.

Stan's Donuts

Try the donuts at Stan's, which has several locations throughout the city. Although they have only been open since 2014, they have become an iconic place to have breakfast and try their donuts.

The latest things to see and do in Chicago

Wrightley Field stadium

Going to see a baseball game at the Wrightley Field stadium with more than a hundred years of history, it is the second oldest in the United States Major League. Here the local team Chicago Cubs plays, a curiosity is that the scoreboard is manual unlike most that are digital.

Navy Pier Ferris wheel

Relax at Navy Pier, one of the liveliest places in Chicago, the walk is full of restaurants, there are also many food stalls with tables and benches where you can sit and contemplate Lake Michigan while you eat a hot dog or have a drink something. We took a break here and stayed for a long time watching the boats arrive and leave with the Chicago skyline in the background. Of all the areas to see in Chicago, this is possibly the one we liked the most. Climb the Navy Pier Ferris wheel, it reminded us of the Santa Monica pier, because it was located on the pier next to a small amusement park, but this one is taller and more modern. Opened in 2016, it measures 61 meters and has some very cool views of Chicago. Admission is included in the Go Explorer Pass tourist card. See Chicago from above, the L subway line runs on an overpass through the center of the city, it is an affordable way to see the city at any time of the year. Save when you visit the different attractions with the Chicago Go Explorer Pass, the tourist card that gives access to different attractions for a cheaper price than buying them separately. Attractions included in the Go Explorer Pass:

  • SkyDeck Chicago
  • Field Museum
  • Navy Pier Centennial Wheel
  • Legoland Discovery Center
  • Adler Planetarium
  • Frigate ride on Lake Michigan
  • Cruise to admire the main monuments of Chicago
  • Bicycle rental to tour the city at your leisure
  • Chicago Sightseeing Bus (Big Bus)

The garden area of the Adler Planetarium. It is very pretty and from here you get wonderful views of Lake Michigan and the Chicago skyline, both day and night. Visiting Legoland on the outskirts of the city, another great plan to do in Chicago if you go with children (or without them), you will surely have a fun time. It is also all covered, great if the weather is bad. Fun fact: Chicago's Adler Planetarium is the first planetarium in the United States.