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A Cheapskate's Guide to Visiting Chicago—Part One

August 24, 2017

The Windy City, Second City, City in a Garden; whatever you prefer to call it, Chicago boasts world-renowned architecture, exquisite food options, and some of the friendliest people you’ll meet anywhere. Now that we’re in the middle of the dog days of summer, there’s no better time to take advantage of the numerous festivals, free outdoor concerts, and the many public parks and beaches along beautiful Lake Michigan.


Contrary to popular belief, savvy travelers know that exploring Chicago doesn’t necessary have to cost a lot of money. If you are only interested in participating in the overly-priced tourist traps, this guide is not for you. However, if you’re looking to experience Chicago like a local, you’ve come to the right place. To help you get started planning your next urban adventure, I’ve compiled an insider’s list of the most exciting, fun, and entertaining options available to budget-minded visitors.


Visiting for 1-3 Days

If you’re staying for one to three days in Chicago, my advice is to try to explore as much of downtown and the nearby surrounding areas as much as possible. Downtown Chicago boasts some of its most famous architectural wonders such as the Sears Tower (Chicagoans refuse to call it by the titular Willis Tower), Aqua Tower, and the Marina Towers.



Navigating around downtown is simple and affordable thanks to the Chicago Transit Authority (CTA). Most trains operate between 4am-1am. Both the blue line and the red line run twenty-four hours a day, every day. For specific hours and times, visit the CTA’s website. I suggest that you purchase a Ventra Card upon arrival, which you can find at any El Station and select gas stations, Cash Exchanges and grocery stores. To search for specific locations that sell the CTA passes, visit Ventra’s website. Although they can be used to ride any CTA bus, you cannot purchase a Ventra card on the bus.


What to Do

Art Institute of Chicago ($25/Adults; Free/Children under 14)



I know I promised not to include the typical activities found in every humdrum tour guide on the web, but this museum deserves a pardon to that rule. The Art Institute of Chicago has been showcasing world-renowned fine art and sculptures since opening its doors at the current location in 1893. Among its many collections, some of the museum’s most notable exhibits include Grant Wood’s American Gothic, Georges Seurat’s A Sunday on La Grande Jatte—1884, Edward Hopper’s Nighthawks, Georgia O’Keeffe’s Cow’s Skull with Calico Roses, and Pablo Picasso’s The Old Guitarist.


Millennium Park (Free)



Nestled in the heart of the loop, this verdant landscape serves as Chicago’s outdoor crowning jewel. In this modern-day town square, you’ll be dazzled by the vibrant beauty of the 3.5 acre Lurie Garden, the massive arcuate stainless steel sculpture Cloud Gate (fondly nicknamed “the bean”), and the state-of-the-art outdoor Jay Pritzker Pavilion, where you can catch free concerts, theater performances, and movies throughout the entire summer. For a comprehensive list of showtimes, visit the City of Chicago’s website.


Chicago Cultural Center (Free)



The original home of the Chicago Public Library, the Chicago Cultural Center now serves as a space for art exhibitions, musical concerts, and countless programs that connect visitors to the vast array of cultural experiences that make up the fabric of Chicago. The Beaux-Arts Classical façade displays eye-catching features like its enormous window arches and Ionic columns, standing out in stark contrast to its modern architectural neighbors. Noteworthy features of the interior include the world’s largest Tiffany glass dome, which gives the impression of gazing up into an enormous kaleidoscope, and the breathtaking detail of millions of mosaic tiles that spell out sagacious quotes from Western Civilization’s greatest thinkers. A truly transcendental experience is to be had by all whole walk through this landmark building.


Chicago Riverwalk (Free)



Having been given a facelift in recent years, this expansive pedestrian walkway stretches along the Chicago River from downtown to Lake Shore Drive. Along the way, you’ll find plenty of photo-worthy views of some of Chicago’s most iconic skyscrapers. You’ll also see the zero-depth fountain, a place to rent kayaks and canoes, a tiki bar, and a boardwalk that grants access to Lake Street.


Bike Along Lake Michigan ($9.95)



One of Chicago greatest visual assets is its location along the azure waters of Lake Michigan. On a clear, bright summer day, there is nothing better than biking along the trail that expands the entire lakefront from the south side all the way north to Evanston. With the recent installation of bike share stations across the city, enjoying the resplendent scenery has never been easier for visitors and residents alike. You’ll find Divvy docking stations intermittently along the entire stretch of the lake shore path. Bike rentals cost just $9.95 per day, which grants you unlimited 30-minute rides in that 24-hour period. It’s important to remember to dock your bike at one of the stations before your half-hour is over, otherwise you will be slapped with a small fee. This is to ensure that the bikes are evenly distributed and readily available for others. Visit Divvy’s website for more information about their bike sharing program.


Field Museum ($22/adult, $15/child)



Okay, you got me. This is the only other popular tourist attraction you’ll find on this list. I promise. But first, let me explain my reasons for including the Field Museum among the, otherwise, more obscure and subtle joys of the downtown area. For starters, this museum marks the final resting place of the world-famous fossil known as Sue the T. Rex. Measuring 40.5 feet long from snout to tail, she is the largest, best-preserved, and most complete Tyrannosaurus Rex ever discovered. And that’s just the first of many awe-inspiring exhibits you’ll see when you walk through the museum. Some of my favorite permanent exhibits include the Egyptian mummies and artifacts, the gem vault, and hundreds of additional dinosaur fossils. An experience as unique as this is definitely worth the price of admission in my opinion.


Summer Festivals (Most are free; some suggest a small donation)



What would summer be without the smells of food grilling in the open air? I guess you could say it would be like summer without thunderstorms or lightning bugs. There are just some things that define the season.


Picnic Near Adler Planetarium (Free)



Venture out to the furthest part of Northerly Island to get a view of the city in all its photogenic glory. Spend an afternoon to enjoy a picnic on the grassy slopes while watching the boats sailing along the glassy surface of Lake Michigan. Even better, stay until the sun sets to watch the city skyline transform into a spectral show of neon and halogen lights.


Buckingham Fountain (Free)



Located in the heart of Grant Park, Buckingham Fountain is one of the largest fountains in the world. Water shows are displayed on the hour every hour from mid-April to mid-October, shooting jets of water vertically 150 feet into the air. For added ambiance, visit the fountain in the evening to see the water choreographed to bright lights and music.


Maggie Daily Playground (Free-$12)



Rediscover what it feels like to be a kid again in this giant 20-acre playground located in Millennium Park, adjacent to the Jay Pritzker Pavilion. Enjoy a day of outdoor fun with activities that include rock climbing, a play garden for children under 12 years old, tennis courts, picnic groves, and mini golf. Roller blades and scooters can be rented from the park fieldhouse for 30 minute intervals ($12 for rollerblades, $8 for scooters).


Once you’ve trekked around the city’s downtown area and played in the numerous park areas, I guarantee that you’ll have built up an appetite worthy of a deep dish pizza. Of course, Chicago has more to offer than just pizza. If you’re looking for something to eat that is distinctly Chicagoan, then you’ll find a list of some of the tastiest and most affordable (two descriptions that don’t often coincide) dining establishments in the city.


Where to Eat


Wildberry Cafe ($10-$15/person; 130 E. Randolph Street)



Hands-down the best breakfast and brunch spot in downtown Chicago. Featured on Chicago’s Best, you’ll be dazzled by the variety of pancakes and other breakfast offerings ranging from eggs benedicts to Belgian waffles. Take note that on any given day you’ll likely encounter a thirty minute to one hour wait, so plan your visit accordingly.


Lou Malnati’s Pizzeria ($10-$20/person; 805 S. State Street)



Most Chicagoans have pledged their allegiance to one of the many deep dish dynasties that have sprouted up over the years, the two most popular being Lou Malnati’s and Giordano’s. Despite the inevitable backlash of taking sides, I’m willing to go on record when I say that Lou Malnati’s has won my devotion for Chicago-style deep dish pizza.


With the perfect ratio of sauce and cheese made from locally-sourced ingredients, Lou Malnati’s will defy all expectations of the ultimate pizza-dining experience. Needless to say, once you’ve dived into the flaky, buttery crust you might never think of pizza the same way again.


And, of course, the restaurant has been featured on a variety of culinary shows including Food Network’s On the Road, Throwdown with Bobby Flay, Travel Channel’s Food Wars and a whole slew of other media programs. After one bite and you’ll understand why the restaurant has become a Chicago institution.


Wao Bao ($8-$12/person; 225 N. Michigan Avenue)



Featured on Time Out Chicago, Gourmet Magazine, Esquire, and The Washington Times. Wao Bao is a fast food restaurant that serves traditional Asian flavors in a casual setting. Menu items range from their eponymous steamed buns to potstickers and dumplings. A word of caution: their buns can become highly addictive and can cause unexpected sensory daydreams.


Portillo’s ($5-$10/person; 100 W. Ontario Street)



If you’re looking for the best Chicago-style hotdog, you’ll find it at Portillo’s. Established in 1963 and featuring nostalgic 1950s-era decorum, Portillo’s specializes in classic all-American fare, serving up delectable lunch and dinner options such as grilled hotdogs and hamburgers, beef and sausage sandwiches, and BBQ ribs. Believe me, you will not be disappointed with anything on this menu.

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