Top City Vacations

Why You'll Fall In Love With Chicago

By , March 20th, 2014

This week our guest blogger, Max Hartshorne, shares his insights on a city we both adore, Chicago. The Windy City has so much to offer that it’s impossible to sum-up all its awesomeness into just one article, but here’s a start for some of the must sees and dos when visiting Chicago.

Looking for the perfect Chicago hotel? See our post about best places to find shelter from the Chicago winds here


Windy City Trump Tower

Trump Tower

I always trust advice from a local. That’s why I think the information below will be valuable to anyone who is planning a visit to Chicago — and more than 40 million visitors see the city each year. Susan McKee was born and raised in the WindyCity, and below are her top things to do there.  Whether you’re on business or just traveling for fun, check these out!

Neighborhoods are what Chicago is made up of — there are 77 distinct neighborhoods here and each has its own flavor and charms. There is an ornate red and gold gate over Wentworth Ave at Cernak Road that marks Chinatown’s beginning. Here you can sample the taste treats of more than 59 restaurants. If you’re looking for a great taco, visit Pilsen, where Mexican-Americans have replaced a generation of Czechs who once called this home. Or how about some curry?  You’ll find this in the city’s Indo-Pakistani neighborhood, where the Patel Brothers have a famous neighborhood market of Indian specialties.

Chicago Pilsen Neighborhood

Pilsen Neighborhood. Photo by David_Hilowitz CC BY

Festivals are what many cities brag about.  And in Chicago, the Taste of Chicago brings hundreds of restaurants together on the lakefront to feed as many as three million diners who descend on the festival grounds each summer. The Chicago Jazz Fest is another tradition, taking place each Labor Day weekend.  There is a Celtic Festival in May in MillenniumPark and many other ethnic fests throughout the year.

Millennial park chicago

Universities: Chicago is blessed with lots of colleges and universities, and these campuses all have great amenities like art galleries, sports facilities, and other places to enjoy. McKee singles out the University of Chicago’s Oriental Institute as a great place to see its vast collection of ancient art from Mesopotamia (modern day Iraq).  You can also see our current President, Barack Obama’s Chicago home, located nearby at 5046 South Greenwood Avenue.  At Northwestern University, there is a 90-year-old Shakespeare Garden and here visitors flock to see a very special 70 x 100 plot of land, where there are the same trees and herbs that the Bard mentions in his plays.

Sports are another Chicago specialty, and historically too–you can choose either American or National League teams, the Cubbies and the White Sox in Baseball, or take in a professional basketball, NFL, or football game, There’s even a major league soccer team, the Chicago Fire, for those who are coming from out of the country and want that kind of football.


The original Chicago Cubs, 1913. Photo by The Library of Congress CC BY

Museums: If you’re a culture vulture, then you’re in the right place because Chicago has over four dozen museums! The Art Institute of Chicago holds the largest collection of impressionist paintings outside of the Louvre in Paris! There is also the National Museum of Mexican Art, for those looking for another ethnic take on things or the Museum of Modern Art.  There are also more than 200 theaters and 200 art galleries in Chicago. But McKee recommends that if you can only take in one museum, which is the Museum of Science and Industry. This classic repository of the city’s industrial past was opened in 1933, and contains a WWII German submarine, a replica of an Illinois coalmine, and many other intriguing exhibits.

Face statue outside museum modern art chicago

Architecture: If you want to see what the city looks like from a bird’s eye view, visit the Skydeck on the Tower that used to be called the Sears Tower. It’s now the Willis Tower and affords a commanding view of the entire city from its towering perch. The Wrigley building, famous for its namesake chewing gum and Wrigley Field, is across the street from the Tribune Tower, which is famous for its exterior walls that are embedded with actual bits of other famous buildings including Westminster Abbey, The Taj Mahal and the Arc de Triomphe.

Feature image courtesy of Sawyer Bengtson, Unsplash