Updated: 04/01/2018 | April 1st, 2018
I first visited Chicago at the end of my U.S. road trip in 2006. I spent three days there before leaving to explore the rest of the world. I’d always heard a lot about Chicago and was excited to finally see the Windy City (named because of the politicians who blow hot air, not for the climate).
Incorporated in 1833, Chicago has played an important role in the country’s history ever since. In 1840, Chicago was the 92nd most populous city in the United States, but it grew so rapidly that, 20 years later, it was the ninth-largest city in the country. By 1900, Chicago had 1.7 million residents.
Chicago was the rail link between the west and the east, and its meatpacking industry was the biggest in the country. Beef from the plains and Texas came in and was then cut, packed, and shipped to the rest of the world from Chicago. (However, the notoriously unsanitary conditions of the industry led to the publication of Upton Sinclair’s The Jungle, and the founding of the Food and Drug Administration.)
In 1871, most of the city burned down in the Great Chicago Fire. Over 300 people died, 18,000 buildings were destroyed, and a third of the city’s residents were left homeless. One of the factors contributing to the fire’s spread was the abundance of wooden buildings and narrow streets. The fire led to strict fire-safety codes that included a strong preference for masonry construction, which helped contribute to the architectural tradition that has emerged in the city.
Today, Chicago is a cosmopolitan city. From food to parks to shopping, Chicago has it all. If you like to shop, there are the upscale stores along the Magnificent Mile, where you can buy from all the top designers. For architectural lovers, Chicago provides a plethora of buildings to see and examine. Chicago is filled with amazing turn-of-the-century buildings mixed with modern architecture. There’s the famous Willis Tower (though it will always be the Sears Tower to me), the Chicago Building, the Tribune Tower, the Hancock Tower, and the old Water Tower, one of the few buildings to survive the great fire. The infamous Loop is a great way to see old buildings in the Chicago Style. For those looking for something more relaxing and entertaining, there’s Navy Pier by Lake Michigan, which has shops, restaurants, museums, exhibition halls and auditoriums, and a Ferris wheel. It’s one of the most visited landmarks in the Midwest.
Then there is Millennium Park. The huge park has a lot of green space, concert halls, and some serious chess players who will beat you for one dollar. The park includes the reflective Cloud Gate sculpture (“The Bean”), which reflects the Chicago skyline and makes for great photos! Millennium Park also has an outdoor restaurant and two tall glass sculptures that make up the Crown Fountain. The fountain’s two towers display images of local residents with water spouting from their lips. The park is active year-round and was one of the highlights of my time in the city.
Chicago is simply one of the best cities in the country so how would I spend the perfect Saturday? Here’s how:
Relax in Grant and Millennium Park
Located right downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. You can also find people playing chess out here and during the summer they have a lot of free concerts. This is also where you will find the famous “Chicago Bean” sculpture. This is one of the best spots to hang out on a warm, sunny day as you stare out into Like Michigan.
Experience St. Patrick’s Day
Next to Ireland, Chicago is the best place to be on March 17th. With a large Irish-American population, St. Patrick’s day is a celebration of Ireland’s patron saint Patrick who drove all the snakes out of Ireland. To celebrate, everyone – Irish or not – gets incredibly drunk and wears green. The city even dyes their river green, the streets are filled with tons of people, and there’s a big parade.
Be a kid at Navy Pier
(Location: 600 E Grand Ave, navypier.org)
Navy Pier is sort of like a carnival in a city. It contains some rides, a Ferris wheel, lots of restaurants, a Shakespeare theater, boat tours, an oddly large number of beer gardens, and even miniature golf. Navy Pier is open year-round (closed on Thanksgiving and Christmas) and general operating hours vary depending on the seasons and may be subject to change. There is no admission fee to enter Navy Pier. However, attractions within Navy Pier may have admission prices.
Visit Robie House
(Location: 5757 S Woodlawn Ave, website)
This Frank Lloyd Wright masterpiece, completed in 1909, is a premier example of his Prairie School design. Wright helped make Chicago architecture famous and this house is one of his best-known buildings. It’s one of the most famous buildings in all the city and should not be missed. Don’t miss his other houses too! Open: Thursday to Monday, 10:30 am to 3 pm. Tickets are $18 with discounts for students, seniors, military, and children.
Visit the Shedd Aquarium
(1200 S Lake Shore Drive, sheddaquarium.org)
Shedd is one of my favorite aquariums in the world, holding more than 32,000 different species and giving you an intense and detailed look at all the fish in the oceans. The tanks are massive and there’s a lot of educational displaces on animal care, environments, and interpretation. Don’t miss it! Open: daily from 9 am to 5 pm (6 pm on the weekends and in the summer). Tickets are $39.95.
See the Cubs play
Locals are fanatical about their baseball team. Get in the spirit and head out to a game. It gets really intense when the Cubs play Chicago’s other team, the White Sox. Ticket prices vary. If you don’t get a chance to get tickets, head to one of the bars near the stadium and just drink beer, eat food, and cheer with the locals. They love to turn out of towners into fans!
Catch an improv show
Chicago is the birthplace of improv comedy and a visit to the city wouldn’t be complete without catching a show. There are tons of companies here – many of which have given birth to comedy greats like Tina Fey, Amy Poehler, Stephen Colbert, Mike Myers, Steve Carell, Eugene Levy, Bill Murray, and a ton of others. Some of the most popular companies are Second City, Improv Olympic, and ComedySportz.
Eat the famous pizza
Chicago developed the deep dish pizza, as well as the stuffed crust pizza, and no trip is complete without trying at least one. The deep dish pizza was invented by Pizzeria Uno, which is now a national restaurant chain, and not the best place to get pizza these days. Many Chicagoans swear by Lou Malnati’s so eat there!
Chicago is one of the best cities in the world, especially during the summer when the weather is nice. There is a ton of things to do here, incredible food thanks to the variety of cultures and gastronomy influences in the city, great art museums, parks, and everything in between. And, on a beautiful day, there’s also baseball or just sitting outside with a glass of wine. Don’t breeze through Chicago. Stay for a while and enjoy everything this Saturday city has to offer.
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Note: This article was originally published in 2008.