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Which fun things to do in Chicago to remember this city for the whole life

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I am Yura Matskevich, traveled around 74 countries, travel is my passion, on pages I share useful information.

ChicagoThe city Сhicago has many names: Chi-town, Windy City, Second City, City of Big Shoulders – without doubt it is one of the most fascinating localities of America. The city was founded in 1833, in a very good location – among the Great Lakes, near the Mississippi River. Chicago is one of the key transport and telecommunications nodes of the country, and simultaneously it is the detonating cocktail of different traditions and cultures. All this, as well as many other advantages of the city, make it an extremely interesting destination for tourists. So which fun things to do in Chicago if a man wants to preserve impressions of Chicago for a lifetime?


Thing to do number 1: Have fun at the popular beaches

North Avenue BeachAt North Avenue Beach (Lincoln Park), you can:

  • join a volleyball game
  • ride on the bike path along Lake Shore Drive

Montrose Beach (Uptown) attracts tourists not only because of its sport activities but also as it is a comfortable area for having a family BBQ or a friendly picnic. This place is unpretentious, but quite original and cozy. Enjoy the pleasures of the beach-lying vacation at the Ohio Street Beach (Streeterville) which is just near the central hills and cafes with palm roofs and drinks. Don’t you have a photo on a background of the skyscrapers of Chicago? It is time to visit the 31st Street Beach (Burnham Park), where, you will have an opportunity to go fishing.

Interesting: Beaches of Chicago are for those who are looking for the combination of the “lazy” and active rest sunbathing and playing beach games.


Thing to do number 2:Don’t miss famous Chicago’s festivals and shows.

Chicago’s festivalsEach of the city’s festivals is very popular among the local people who may have the list of festivals to visit on Facebook or somewhere where they will see it and not miss any of them. Even if you have the excuse that you need to go somewhere, in your neighborhood there will be what to visit and how to pamper yourself with ribs, popcorn and other typical dishes of the festival.

Here we have prepared the Top-5 of the most popular shows that all guests of Chicago should visit as there is something special in these festivities:

  • music,
  • people,
  • goodies,
  • traders.

Roscoe Village Burger Fest (Belmont & Damen, Roscoe Village)

On the 11th- 12 July – there is a presentation of the best burgers of the local restaurants. It seems that the air is being heated not only by the scorching sun, but also by the dozens of incandescent grills. Add to this:

  • rock music,
  • art-tents,
  • children’s area.
  • the opportunity to vote for the best burger.

Interesting: This entertainment is available for 10$!

Chinatown Summer Fair

It takes place on July 19 with an ethnic flavor in the open air. Every year this event attracts more than 40,000 visitors. This celebration of beauty and culture of the Far East with all sorts of entertainment:

  • the traditional procession of Lion Dance Procession,
  • classical Chinese dance,
  • martial arts demonstration.

Interesting:  The entrance is free!

Randolph Street Market Festival (1350 W Randolph St.)

This festival is held year round. In the summer months: on July 25 and 26 as well as 29th and 30th  August. The festival is a home to:

  • the Chicago Antique Market,
  • Indie Designer Market,
  • Modern Vintage Chicago,
  • Holiday Market.

According to Travel & Leisure, NY Times, Lucky Magazine and others, Randolph Street Market Festival is considered to be a “Mecca” for lovers of antiques, the best place for admiring the objects of art and purchase something sensible. Perhaps this is where you will find the next inspiration, because there are more than two hundred stalls with amazing finds:

  • furniture,
  • vintage clothing,
  • jewelry,
  • collectibles.

All is in one place for any creative experiments!

Interesting: The entrance fee is $ 8 and up!

Chicago Hot Dog Fest

Try not to miss the following dates when the festival is going to be held on the 7th -9th of August. This is a great opportunity to participate in the age-old Chicago tradition of “hunting” for the hot- dogs with all sorts of variations and unusual ingredients. Since 2014 you have been offered 2 full days of entertainment. What could be better than combining the two “classics of the genre”:

  • the American fast food,
  • green space – the venue of the festival.

Interesting: the entrance is free of charge!

Chicago Air and Water Show

This event takes place on the 15th -16th of August. Without this summer in Chicago is not the real summer! Even if you have already seen everything, you won’t be tired of watching over bends of the intrepid pilots and other flying machines in the sky. Be prepared to fight for a place for a better view of the show as there are always many people there.  Take with you the following things:

  • beach cushions,
  • parasols,
  • water.

Interesting: It is better to watch from Fullerton to Oak Streets along the line of the lake, as well as on the way to North Beach.


Thing to do number 3:  Go to the farmers’ markets

farmers’ marketsThis place is for those who care about what they eat. If you are keeping to the healthy diet, then don’t miss an opportunity to visit the farmers’ markets.  They present their products in the best possible ways.

There is the list of those places which can be recommended to the tourists who are in Chicago for the first time:

  • Portage Park,
  • Green city,
  • Logan Square and,
  • a traditional market on Thursdays at Daley Plaza.

Interesting: If the downtown merchants are clearly focused on the commercial part of the project, the other areas of the city offer you a chance to become the best friends with the sellers of fruits and vegetables, pasta and honey at these markets.


Thing to do number 4: Go for a walk to Millenium Park.

Millenium ParkAll the roads take you here. You can choose whatever you like:

  • the orchestra,
  • cinema,
  • concerts.

If you wonder how to spend time here, then use the chance to carry a picnic with friends, relax in the open air, to fall asleep listening to Tchaikovsky or to watch the classic of 80’s “Dirty Dancing”.

Interesting: Here you can feel the atmosphere of Chicago and have a rest from everything.


Thing to do number 5: Visit Shedd Aquarium

Shedd AquariumMany interesting stories can be told about one of the oldest and largest public aquariums in the world. Shedd Aquarium, donated to the city president of multi-million dollar company «Marshall Field & Company» John Shedden and which cost is $ 3 million, welcomed its first guests at the end of May 1930. Since then, the flow of the ocean depths lovers not faded away, for example, only in 1933 the aquarium was visited by over 4 million people. And no wonder: in the realm of water, performed in the style of ancient Greek buildings 5 exhibitions are constantly working. One of them, Amazon Rising, sends in an amazing journey through the deep river Amazon.

Here more than 250 species of river creatures have been collected, including:

  • giant anacondas,
  • Piranhas,
  • bloodthirsty crocodiles,
  • spiders.

Another popular exhibition is a true Caribbean reef dwellers for which are gathered by the own research vessel of Shedd Aquarium. Waters of the World represents the diversity of marine life, on the Wild Reef – Filipino fishing village in miniature, and on Jellies there are hundreds of Atlantic, Japanese and striped jellyfish.

Interesting: In Chicago marine paradise that has become home to 25,000 sea creatures, the performances of sea lions, dolphins, belugas and penguins are held.


Thing to do number 6: Visit Chicago Academy of Arts

Chicago Academy of ArtsThis place is perfect for those who like to find out some new facts from the history of the Chicago. Here you will have such an opportunity in the Academy of Design, which successfully has combined the functions of the university and the museum since 1866. Thanks to the frequent private donations the exposition of the main cultural attractions of the city on Lake Michigan has evolved from a modest collection of reproductions of European works of art in one of the richest museums in the United States.

Those who do not understand the modern trends of the bohemian world are always welcomed to the:

  • exhibition of weapons and armor, storing vintage chain mail,
  • photographic exhibition,
  • the gallery which covered the whole long history of Asian art.

The museum also presents a huge collection of works of the Impressionists and Post-Impressionists, containing paintings by Paul Cezanne, Claude Monet and Auguste Renoir.

Interesting: In addition to the permanent exhibitions, the Chicago Cultural Center conducts interesting temporary exhibitions.


Thing to do number 7: Go to the Willis Tower

Willis TowerThe area of ​​the largest US skyscraper, built in 1973, is equal to 57 football fields, and the roof height reaches 443 meters. And if to cheat a little and add the height of the television antennas installed at the top, you can reach the heaven as the highest point of Willis Tower is located at 527 meters above the ground. The huge tower of steel and glass has 16,000 windows and a telephone cable laid inside the structure. Huge spire is tilted by 10 cm to the west, and even swinging during high winds. However, you hardly notice it from the ground as the lightning strikes, beating in Willis Tower up to 600 times a year. In order to appreciate the magnitude of the 110-story skyscraper, go up to the observation deck, located at an altitude of 412 meters.

It offers the best in Chicago:

  • panoramic views of Lake Michigan,
  • view of the wide plains of Illinois,
  • in the clear cloudless days – beauty and the neighboring state.

By the way, this is a great opportunity to tickle nerves: fast climb to the observation deck is performed with the four glass balcony cabins that can withstand up to 5 tons.

Interesting: In order to have the better chance to look at the neighborhood, even in transparent elevators there are monitors showing scenes of the rapidly receding land.


Thing to do number 8: Go to the Navy Pier

Navy PierPierce – the easternmost point of the city. The main attraction of Chicago, each year attracting more than eight million visitors, stands in Lake Michigan on one kilometer. The construction of the impressive structures, designed to become a major logistics center in the Chicago River, which flows through the city, was completed in 1916. For many years there was severe discipline like in army: Navy Pier was used for training of the recruits. But in less than a hundred years, all has changed dramatically. In 2012, a secret facility, though by magic, turned into “pumpkin into a carriage.” If to be more exact, it has transformed from the army entertainment complex in the Pier “for the people”. Warehouses, designed to provide transportation on the Chicago River, became exhibition halls and cafes, and the place of military cruisers was taken by the pleasure boats and steamers.

Now you can find at Navy Pier of Chicago:

  • Botanic Garden,
  • theater,
  • wonderful Children’s Museum,
  • the Museum of stained glass,
  • the main local attraction – a Ferris wheel, at the height of which the whole city can be seen.

Interesting: Be sure to check out here on holidays and weekends: on-site live shows, concerts, festivals and fireworks illuminating the sky with all the colors of the rainbow.


Thing to do number 9: Go for a walk to the Lincoln Park

 the Lincoln ParkThe most northern point of interest in the city is waiting for you at the north of Chicago city. It will take you an hour to get to it by public transport. You can drive along the North Shore Lake, turn onto West Fullerton Avenue and drive a couple of kilometers.

The largest public park’s area is about 5 square kilometers. Lincoln Park is an ideal place for recreation and entertainment. On its territory there are:

  • 15 baseball fields,
  • 6 playgrounds for basketball,
  • 35 tennis courts,
  • over 160 volleyball courts,
  • golf courses,
  • parking for yachts,
  • seven beaches.

Until 1850 the “green lung” of the city was a small cemetery, where the dead with infectious diseases – smallpox and cholera were buried. And then the men of the city, guided by a clear logic, have transformed the burial ground in the recreation area Lake Park, after the killing of 16th US President became Lincoln Park. Improvement of green areas in the city cost 10 thousand dollars.

During the years of existence on its territory, a lot of memorable places have appeared here:

  • one of the oldest and most famous zoos in America,
  • a greenhouse,
  • a water theater,
  • rowing canal,
  • a monument dedicated to General Grant,
  • several museums, the most famous of which are the Chicago History Museum and Museum of Nature.

 Interesting: By the number of visitors, Lincoln Park is second only to Central Park of New York: during the year it is visited by about 20 million people.


Thing to do number 10: Become closer to nature in the Brookfield Zoo

the Brookfield ZooZoo, which is situated on 87 acres of land, is home to more than 6,000 animals. The main exposition of the zoo – Great Bear Wilderness exhibit, which occupies 3 hectares, is the natural habitat of North America:

  • polar bears,
  • grizzly bears,
  • Mexican gray wolves,
  • bison,
  • eagles.

Of particular note there is a pavilion dedicated to the tropics – an enclosed space with artificial climate of the rainforest. Once there, you will be able to see how the primates swing on vines and over your head strange birds fly and sing.

Interesting: You will see really ideal conditions for the life of animals, in which some representatives of fauna often produce offspring.


Thing to do number 11: Go to the Museum of African American History of Dusable

Museum of African American History of DusableThe museum dates back to 1961, when the doctor, writer and historian Margaret Taylor Burroughs collected a small collection of artifacts relating to the history of African-American people. Since then the collection has evolved into the largest and oldest museum of:

  • African American history,
  • culture,
  • art in the United States.

The museum had to go through really tough times, but since the early 90-ies of the last century, it became flourishing and popular among visitors of the city of Chicago.

Interesting: The museum has collected about 15,000 a variety of exhibits – paintings, sculpture, printing and more.


Thing to do number 12: Visit the Nature Museum of Peggy Noutbert

the Nature Museum of Peggy NoutbertSince 1857 in Lincoln park there has been a museum devoted to the wildlife of Illinois, as well as the flora and fauna of the Great Lakes region. 2.5 hectares of the museum incudes the variety of ecosystems and nature in its purest form:

  • more than 15,000 plants,
  • 13,000 birds,
  • 22,000 reptiles and amphibians.

Interactive displays will help children to get acquainted with the surrounding beauty and thousands of butterflies swirling in the pavilion “Paradise butterfly” them.

Interesting: Visitors of all ages will be satisfied with what they will see.


Thing to do number 13: Go to Chicago Cultural Center

Chicago Cultural CenterEarlier it was the public library, and since 1991 the Chicago Cultural Center has offered free concerts of classical music. Events are held on:

  • Mondays,
  • Wednesdays,
  • Friday.

Most concerts are held in the lobby of Preston Bradley, which is located on the second floor, near the entrance to Washington Street.

Interesting: For lovers of unusual -experimental concerts taking place in the theater of Claudia Cassidy.


Thing to do number 14: Visit Museum of Natural History of Field

Museum of Natural History of FieldIt is one of the largest natural history museums in the world. It was founded in 1893 in Illinois. It occupies 28 thousand square meters, the whole block, and stores more than 24 million a variety of artifacts:

  • precious stones,
  • Egyptian artifacts, meteorites,
  • even dinosaur skeletons.

One of the skeletons, solid skeleton of Tyrannosaurus is the main pride of this historic institution, which even came up with a woman’s name – Sue.

Interesting: The museum has 10 permanent exhibitions that help visitors to immerse themselves in the history of the origin and evolution of the planet Earth.


Thing to do number 15: Relax in the café “Green Mill”

café “Green Mill”In the 1920s in the cafe “The Green Mill” the great gangsters rested, headed by Al Capone, but today it is a famous music bar. Here you can enjoy real jazz: traditional bop – modern and improvisation! In the 80’s founder Dave Jamie returned to the bar its former luster, and to this day this place has retained its authenticity.

In the “Green Mill” you can hear local celebrities:

  • Kimber Gordon,
  • Patricia Barber.

Interesting: You will need to book seats in advance as there are many people visiting this place


Thing to do number 16: Visit Museum of Science and Industry

Museum of Science and IndustryIf you are carried away by the exhibitions, where you can see live strange bells, whistles, and other industrial tools, this museum is exactly for you! It is the largest science museum in the Western Hemisphere and this is one of the reasons any tourist must go there.

The permanent exhibitions of the museum:

  • a copy of a coal mine in full size,
  • a German submarine (U-505), which was invaded during the Second World War,
  • the model of the old railway.

Interesting: More than 2000 exhibits and 75 main rooms are waiting for their curious visitors.


Thing to do number 17: Go to the cinema Music Box

True film fans will really like this place, especially, those who prefer to art-house and documentary to the trendy Hollywood blockbusters.  There is no better theater than the Music Box.

This modern theater with two screens offers its visitors:

  • independent films
  • foreign films

The midnight shows of cinema classics are often held in the magnificent main hall of the theater.

Interesting: Here you can relax, watch good movie and eat very tasty popcorn with real butter.

As you can see Chicago is full of fun and exciting free things to do. For example, chocolate tour, during which you will not only have to pass a certain route, but also taste the many varieties of chocolate; cruises, which differ consistently with the delicious food and excellent drinks; midnight tour of the city, revealing all the nuances of the Chicago night life. So go ahead – pack your suitcase and go to Chicago! But remember – this city is not for those who like a quiet and relaxing holiday. It is a paradise for tourists, whose life – the constant movement.



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I am Yura Matskevich, traveled around 74 countries, travel is my passion, on pages I share useful information.

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