Best Things to Do in Chicago – Chicago Travel Guide

Home of the blues and the truth of jazz, the heart of American comedy and the first American builder of the skyscraper. There are many beautiful places, so let’s have a look at the best things to do in Chicago!

Chicago Travel Guide

One of the world’s spectacular cities, one with a swagger, but without the surliness or the fake smiles, it will welcome you with its magnitude of theater, shopping, and fine dining activities!

A must-visit for anyone exploring the USA.



Chicago is a city that is divided into ten various districts. Each one takes a unique side of Chicago and presents you with a different feel of this amazing city.

The Downtown is the center of Chicago for work and play. Major corporate headquarters, skyscrapers, shopping, big theaters, parks, museums, beaches, and the city’s most famous sites find the Downtown as their home.

The North Side is home to upscale neighborhoods and entertainment, for anyone seeking club and bar entertainment.

The South Side is the sight of the historic Black Metropolis, soul food, and the real Chicago blues. It is also the home of the University of Chicago.

The West Side hosts ethnic enclaves, dive bars, and hipsters on what is considered the fashionably rough side of town.

The Far North Side contains miles of beaches and is a vibrant and ultra-hip part of town. It contains the Uptown, Lincoln Square, and Rogers Park.

The Far West Side is definitely off the beaten tourist track but contains all the amazing food, a couple of top blues clubs in the city, and enormous parks.

The Southwest Side is home to huge Polish and Mexican neighborhoods.

The Far Northwest Side contains historic homes and theaters, apart from which it hosts a few undiscovered gems in the neighborhoods near O’Hare International Airport – if you are interested in something off the beaten path.

The Far Southeast Side is popularly considered the industrial underbelly of Chicago and is home to a popular tourist destination: the historic Pullman District.

The Far Southwest Side is essentially Ireland in Chicago, with authentic Irish pubs, brogues, galleries, and the strange haunted castle.

The Trump tower - Chicago
The Trump tower – Chicago

A Little History

Chicago is a city rich with history and names, which capture its different facets. It originated as a swampy area incorporated as a town in 1833.

It was completely destroyed by the Great Chicago Fire after a cow knocked over a lantern in crowded immigrant quarters.

At the pinnacle of its rebirth, Chicago was known as The White City. Cream of Wheat, soft drinks, streetlights, and safe electricity, the fax machine, and the Ferris Wheel bespoke the colossus that grew to greatness by the 1890s.

During the early 20th century, the city’s names reflect its massive growth. It was called the Hog Butcher for the World for its enormous cattle stockyards. It was also called the City of the Big Shoulders, noting the tall buildings in the birthplace of the skyscraper.

To this day, it is also known as The Second City, referring to its rebuilding after the fire.

Sights to See

There are two popular tours of Chicago.

One is “Along the Magnificent Mile” which is a one day and night in Chicago tour, with skyscrapers, shopping, food, parks, and amazing views of the city from high and low.

The second is the “Loop Art Tour” which is a 2 to 4-hour walking tour of downtown Chicago’s magnificent collection of modern sculptures.


Chicago boasts a set of museums and cultural institutions that are among the best in the world.

Three are located on what is known as the Museum Campus, in the Near South: Adler Planetarium, with all sorts of cool hands-on space exhibits and astronomy show; the Field Museum of Natural History, and the Shedd Aquarium. A short distance away, is what the Chicago-area grammar school students know as the “best field trip ever”: Museum of Science and Industry.

Additional museum and exhibitions hosted by Chicago are Art Institute of Chicago, Lincoln Park Zoo, International Museum of Surgical Science, Chicago History Museum, DuSable Museum of African American History, National Museum of Mexican Art, the Polish Museum of America, the Museum of Photography, and the Driehaus Museum.

Discount packages like the Chicago CityPASS can be purchased before you arrive, which cover admission to some museums and other attractions, allowing you to cut to the front of lines.

A Walk around Lincoln Park Zoo. Chicago
A Walk around Lincoln Park Zoo. Picture: Jess R.

Great Lakes and Parks

The Chicagoans enjoy flocking to the beaches of Lake Michigan, one of the five Great Lakes. The water is quite warm in the summer, with the Chicago shore being called the second cleanest urban waterfront in the world.

There are also great waterfront parks, as well as inland parks. These include the Grant Park which hosts music festivals throughout the year, the Millennium Park which is a fun destination for all ages, the Midway Park which offers skating in the winter, as well as the Washington Park which is great for community sports.

Chicago also hosts a few famous events attended by millions. The largest outdoor food festival in the world, Taste of Chicago occurs in Grant Park in July. There are four major music festivals: the Blues Fest, the Gospel Fest, the Lollapalooza, and the Jazz Fest. All but Lollapalooza are free.

Taste of Chicago
Taste of Chicago

Chicago offers a ton of things to do, whether you admire the skyline, go to the beach, or visit one of the many extremely famous museums, one thing is – you will have an absolutely unforgettable experience.

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