Chicago
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Chicago may not be Illinois’ capital, but it’s one of the state’s major cities where people come together for business, culture, and food. Also referred to as “The Windy City,” Chicago is a great place to see world-class architecture, eat Chicago-style hotdogs and deep dish pizza, as well as watch a Cubs game. If you’re planning a road trip, Historic Route 66 begins at Grant Park in front of the Art Institute of Chicago and ends in California.
Travel tip #1: In recent years, gun violence throughout America has skyrocketed, but has been especially bad in Chicago. Much of the city’s Southside has been ravaged by gun violence and is currently suffering from heightened levels of shootings. Be cautious and aware of your surroundings at all times when traveling, regardless of where you are!
Places of Interest
The Loop: The Loop is the central business district and Chicago’s downtown area. It is home to Chicago’s commercial core and City Hall, as well as numerous buildings and well-known companies. Take a self-guided architecture tour to witness some of the city’s finest designs.
Millennium Park: This large public park is centrally located in the Loop area and sits near Lake Michigan’s shoreline. It was built with the original intent of celebrating the third millennium, hence the park’s name. There are community events held here throughout the year, with locals and tourists alike enjoying the public space.
Cloud Gate: Commonly known as “The Bean” due to its appearance, this sculpture sits in AT&T Plaza at Millennium Park. It was constructed between 2004 and 2006 and is made up of 168 stainless steel plates which have been welded together. The design was inspired by liquid mercury and its surface reflects the Chicago skyline.
Crown Fountain: This interactive art display also calls Millennium Park home. The fountain is composed of a black pool in between two 50-foot glass brick towers that display digital videos. The water operates in the warmer months, from May to October specifically.
Willis Tower: The Willis Tower, formerly known as the Sears Tower, was previously named one of the tallest buildings in the world. It is the second tallest building in America after the One World Trade Center in New York. The 110-story building is in the heart of Chicago’s downtown area and peaks above every other skyscraper in the city.
The Skydeck: While at the Willis Tower, you can appreciate the view from the Skydeck on the 103rd floor. Step out on The Ledge’s glass boxes that extend 4.3 feet out from the Skydeck—1,353 feet in the air! Tickets are a little pricey, starting at $24 USD for adults.
Logan Square: On the northwest side of Chicago is the community of Logan Square. The neighborhood is known for bike-friendly streets lined with ample coffee shops, fun bars + breweries, and cocktail lounges. In its heart is the actual “square” of Logan Square, which comes together at the intersection of Kedzie and Logan Boulevard. The city’s Blue Rail Line conveniently runs through here and connects to the O’Hare Airport.
Lincoln Square: Lincoln Square is an enclave with old-fashioned shops and cobblestone streets that boasts a collection of restaurants, bars, and boutiques. Music, arts and crafts are the highlight of this community, as well as a fair amount of international cuisine. During the warmer months, check out the Farmers’ Market.
Travel tip #2: If the Cubs are playing at their home stadium of Wrigley Field, be sure to get some tickets and catch a game. If you’re not around for baseball season and happen to be in the city during St. Patrick’s Day, head down to the banks of the Chicago River. It’s dyed green every year and is quite the sight to see.
Food
Colectivo Coffee: With one location of several in Logan Square, this cafe features a hip, colorful interior. They serve some awesome espresso, coffees, and teas. There is also a full cafe menu as well as Colectivo Keg Co. beers and Nitro Cold Brew on tap. Their coffee is available at other shops and restaurants throughout Chicago, too.
Cafe Tola: Breakfast tacos and burritos are delicious ways to start your day, and Cafe Tola is the place to grab them. With two locations, this Mexican restaurant serves tasty food all day long–including empanadas–in a fun, quirky atmosphere. Their “Salsa Buena” is incredibly spicy and is not for the faint of heart, but really brings together their food’s flavors.
Batter and Berries: If you’re into brunch, Batter and Berries is the place to go for a cozy, homestyle meal made with love, centered around community. The atmosphere is friendly and their service is amazing. Ask about their specials or stick to some fan favorites: the French Toast Flight, the sweet potato waffle with fried chicken plate (“Cluck-N-Gaufre”), or the biscuits and chicken sausage gravy with eggs (“Cluck & Gravy”). This place is BYOB, too!
Deep Dish Pizza: A trip to the Windy City wouldn’t be complete without sampling this speciality dish. Due to its thickness, this pizza is typically enjoyed using a knife and fork. However, be prepared to wait about 30-45 minutes after ordering for your pizza to be expertly crafted. Many places offer individual-sized pies (6-inch pizzas), which are ideal for sharing between two people if you plan on trying multiple deep dish pizzas in a single day.
- Giordano’s: This restaurant is unique because it serves a stuffed deep dish pizza, meaning that there’s an additional layer of dough separating the cheese from the other toppings. Giordano’s ratio of cheese, sauce, and super flaky crust is awesome. Here, we tried the pepperoni in our deep dish pizza, which was mighty tasty.
- Lou Minalti’s Pizzeria: The secret family recipe used to make the crust at Lou Minalti’s includes a lot of butter—that’s obviously from the flavor. Yet, it’s amazingly soft in the middle but crusty on the outside. The sauce is sweeter and also tarter (if that’s possible?) compared to Giordano’s. We tried “The Minalti” pizza that came with a layer of fresh sausage—delicious, flavorful, savory—and definitely a must-try.
Taco in a Bag: Nachos are one of my favorite things to eat no matter what time of the day it is, so I had to try Taco in a Bag while in Chicago. It’s basically a spot that makes gourmet nachos in a bag rather than on a plate. I tried “The Norberto,” which came with soft, savory braised chicken, sauteed peppers and onions, pepper jack cheese, avocado jalapeno sauce, cilantro, and dried cranberries—really good and something to try if you’re in the Lincoln Square neighborhood.
The Signature Lounge at the 96th: This place serves speciality cocktails and offers a swanky menu on the 96th Floor of the building. It features stunning views of the city and the lake, as well. It’s an excellent place to enjoy a classy meal alongside fancy drinks, especially if you’re looking to get more bang for your buck. Opt for The Signature Lounge rather than the Willis Tower if you want a view with fantastic food and drinks.
Travel tip #3: Breweries and bars are generously sprinkled throughout the city, and are certainly the place to soak in Chicago’s vibe. Check out Eater’s list of some of the best bars and breweries in the Windy City. My personal favorite bar was Lost Lake in Logan Square. I also tried the locally crafted Green Line Pale Ale alongside my deep dish pizza, which was crisp and refreshing.
Transportation & Accommodation
Getting around Chicago is fairly easy, but in my opinion is a bit expensive compared to other major cities. All transit systems (subway trains, buses, and Metra Trains) conveniently operate through the same payment method, which is called a Ventra Card. These cards can be purchased at all train and subway stations for a single ride, re-loadable pass, or day pass (a 1-Day Pass is $10 and the 3-Day Pass is $20) and accept cash or credit card. However, the machine I used didn’t give change so exact dollar amounts were needed. Buses take cash (exact change is necessary) or Ventra, but trains and the subway always require a Ventra ticket or card. Uber and Lyft are also widely available and used in Chicago, as parking can be a challenge throughout the city.
While in Chicago, I used Airbnband stayed in the Logan Square neighborhood off of Kedzie. This was a wonderful location, as it was in walkable distance from several bus stops and the Blue Line train. Additionally, our host, Amy, was incredibly chill and helpful. She had two cute kitties that made the stay really fun, too. When booking through Airbnb, make sure to do research on the area you’re staying in as some neighborhoods in Chicago are safer than others. Of course, Chicago offers a number of hotels that range from luxury to budget. Booking.com is a great place to start your accommodation search in the Windy City, and many places offer free cancellation if your stay is arranged through booking.com.
Travel tip #4: The cost of a reloadable Ventra Card is $5 USD, but you can register that card to receive a $5 free ride credit, which technically gives you your money back. It may be more financially savvy to purchase a reloadable Ventra Card compared to a day pass if you’re not going to solely rely on public transportation during your time in Chicago.
Climate
Chicago’s climate includes all four seasons: wet, cool springs; hot and often humid summers; mild autumns; and cold, windy winters. The city’s weather is heavily influenced throughout the year due to its proximity to Lake Michigan. In the winter, cities on the other side of Lake Michigan usually receive more snow than Chicago because of the lake-effect snow, but winds can sometimes bring this weather phenomenon into the Chicago area. It rains throughout the year, with January and February being the driest and May and June experiencing the most rainfall. The best times to visit Chicago are April through May, as well as between September and October. During these times temperatures are comfortable, several festivals take place, and crowds are not as large.