City Guide to Chicago, Illinois

By Lauren Elizabeth Campbell, Editor-in-Chief

Known for its art, architecture, and deepdish pizza, the “Windy City” of Chicago lies on the western end of Lake Michigan. It’s the third largest city by population in the United States, however the city's Midwestern charm makes it feel like a small town with all the perks of a big city, such as its phenomenal restaurant scene and worldrenowned museums. And due to its relatively low housing costs, it’s a great city to call home.

Chicago is an inspiring city filled with many of the country’s prime hidden gems. This guide will help you find them and experience the best places to eat, stay, consume music, and find the cultural treasures in this inspiring town.

Eats

Chicago’s diverse and lively culture makes for its unique food scene. From its most iconic dishes and street fare, such as the iconic deep-dish pizza and Vienna beef sausages to make what’s known as the Chicago-style hot dog, to more cuisine from all around the world, such as pierogis and sushi. Chicago has it all - just don't put ketchup on your hot dog. Sugar in ketchup smothers the flavor of the dog, and is highly recognized in Chicago as a sin. Here is your guide on everything else ok to eat:

Giordano’s vs. Lou Malnati's

Every Chicagoan has their favorite deepdish pizza, but it generally comes down to a debate between the two local franchises Giordano’s and Lou Malnati’s. Whether you are Team Giordano’s or Team Lou Malnati’s will most likely depend on what you appreciate most in a pizza.

Giordano’s serves stuffed deep dish pizza with an additional layer of dough separating the cheese from the toppings, however there is undoubtably more cheese than crust in a Giordano’s pizza. If you appreciate cheese more than crust, Giordano’s is most likely for you.

Lou Malnati’s does not have as much cheese as Giordano’s, however its crust comes from a secret family recipe that makes it flaky on the outside and soft in the middle. If you appreciate crust more than cheese, Lou Malnati's is most likely for you. I recommend you try both to make your own decision.

Portillo's

Portillo’s Chicago-style hot dog is a musthave when visiting the Windy City. A Chicago-style dog consists of a Vienna Beef wiener dragged through the garden with mustard, neon green relish, raw or grilled onions, tomatoes, and celery salt with optional sport peppers, and, of course, never ketchup. Their crinkle-cut fries are also a must.

Podhalanka

Chicago is home to a huge Polish and Eastern European population, whose heritage plays a major part of the city ’s food presence. The no-frills Podhalanka serves some of the best Polish food in the city, including: golabki (stuffed cabbage), placki ziemniaczane (potato pancakes), and pierogi ruskie (potato and cheese dumplings). Helena, Podhalanka’s owner, came to the United States from Poland in 1983 via Pan Am Air and has been cooking traditional Polish dishes ever since.

Sushi-San

Chief Kaze Chan came to Chicago in 1995 to become the original chef at Mirai. After opening his own restaurants with his brother, Macku: Heat, Kaze, and Macku, he started another venture becoming the chef at SushiSan. The best way to experience Sushi-San is at the “hand roll bar, ” where sushi masters behind the counter roll and serve sushi directly to you. Chan says this experience and sushi should be eaten as soon as it is served, as even a 30-second delay in service could hurt the tasting experience.

Stays

If you’re traveling to Chicago for the first time, the best area to stay in is "The Loop, " the downtown area of Chicago, that borders the Chicago River. The neighborhood got its name because of the elevated Chicago Transit Authority (CTA) tracks that "loop" around a rectangle in the area. This is the perfect location because of the easy access to downtown attractions and public transportation. Here are some of the best places to stay in The Loop:

Chicago Athletic Association

The Chicago Athletic Association boutique hotel sits in a 1890s Gothic building that once was home to an exclusive sportsmen's club. Each of its 241 rooms feature unique flourishes to remind guests of the hotel’s past. Rooms feature views of Millennium Park and Lake Michigan, and allow guests access to an expansive game room with bocce and shuffleboard. The Chicago Athletic Association has been temporary closed due to COVID, but will be reopening its doors this April.

The Publishing House Bed and Breakfast

Stay in the former Free Methodist Publishing House, built in 1909. With 11 unique rooms and a delicious breakfast cooked by its owners every morning, The Publishing House is the perfect Chicago retreat for fans of literature and/or Instagramable spaces. This bed and breakfast provides guests with a retreat within the city.

Staypineapple

Those who are visiting Chicago for the architecture will enjoy Staypineapple. Within Chicago’s Reliance Building, built in 1895 and on the National Register of Historic Places, guests can awe at the hotel’s industrious, yet charming interior. A small West Coast hotel chain, Pineapple Hospitality, bought the hotel in 2016, as it was known as Hotel Burnham from 1999 to 2016. Designed by architects Daniel Burnham, Charles Atwood and John Root, the building still features the original ornate grillwork on the elevators.

Music

Chicagoans take their music very seriously. From iconic listening rooms to full-blown music festivals, there is music in Chicago for everyone’s taste. Innovative blues musicians who traveled to Chicago in the 1940s helped define the Chicago Blues sound. Here are the best ways to get a sense of the Chicago music scene:

Lollapalooza

Lollapalooza, a four-day music festival in Chicago’s Grant Park draws over 400,000 attendees each year. Artists from every genre wow crowds each year. In 2020, due to the pandemic, the festival was held virtually, but the festival’s founder, Perry Ferrell, said in a video posted to his social media accounts on March 20th, “I will see you at Lollapalooza –soon. ”

Green Mill Cocktail Lounge

The Green Mill, a former speakeasy that opened in 1907, is the longest continuously running jazz club in the country. Big-name artists, such as Billie Holiday and Al Jolson have graced the stage at the Green Mill, which also hosts local artists for late-night jam sessions.

Culture

Chicagoans embrace their city known for its arts, comedy, and architectural history. Going on one of Chicago's many architecture tours is a must, as well as visiting these beloved Chicago institutions:

Wrigley Field

Wrigley Field, the baseball park home to the Chicago Cubs, is beloved to Chicagoans and baseball fans alike. Whether or not you are a sports fan, a trip to Wrigley is essential.

The Art Institute of Chicago

As seen in "Ferris Bueller’s Day Off, " The Art Institute of Chicago is one of the oldest and largest art museums in the United States. It is home to "American Gothic, " "Nighthawks, " and "A Sunday Afternoon on the Island of La Grande Jatte. "

The Second City

See an improvisational comedy show at the famed Second City, where comedians like Bill Murray, Tina Fey, Catherine O’Hara, and Stephen Colbert got their start. You never know which comedian may someday star on Saturday Night Live or what alumnus may come back for a visit.