As a Midwestern girl, born and raised, it’s no surprise that post-college I ended up here in Chicago. Now, after having lived in this wonderful city for nearly two years, I feel well-equipped to share my knowledge for any travelers passing through or for anyone considering making Chicago their home.
This city has a distinct feel, characterized by a beautiful architectural aesthetic with friendly, down-to-earth people. You’ll never be lacking for things to do, no matter the season, as Chicago is known for its food, sports, nightlife, festivals, restaurants, and museums.
If you’re looking to spend some time in the Windy City, this guide will give you all you need to know.
Chicago is made up of many neighborhoods, each with its own character. The city is laid out from south to north, hugging Lake Michigan to the east. This is good to know, because realizing that the lake is always east no matter where you are in the city will help you get your bearings right away.
The best way to explain each of Chicago’s prominent neighborhoods would be to start south and work our way north…
The South Side
Chicago’s infamous South Side is often recognized for its intense poverty and street violence, but truly it is much more than that. Go visit Hyde Park, The Museum of Science and Industry, and the University of Chicago, or go see a White Sox game, the set where the hit show Shameless was filmed, or the Pilsen and Chinatown neighborhoods, which are nearby.
Just north of the South Side is Chicago’s Loop neighborhood, which can be considered the true “downtown” of the City. This is where you’ll find Millennium Park and some of the best shopping and restaurants in Chicago. West of the river is referred to as the West Loop, which is an up-and-coming area known for its chic restaurant and nightlife scene.
Moving north, you’ll come to the River North neighborhood, named this way because it’s the neighborhood just north of the Chicago River! Here you’ll discover the Magnificent Mile, Water Tower Place shopping mall, and the Chicago Riverwalk, which is especially beautiful at night. River North is also a hub for Chicago nightlife, and this is where you’ll find some of the most notorious nightclubs, bars, and restaurants in the city.
Chicago’s Gold Coast neighborhood is a wealthy residential neighborhood, as its name would imply, just north of River North. It’s characterized by larger homes and high-rise apartment buildings which offer fantastic views of the lake. This area is known for upscale restaurants and shopping as well.
Moving north and a bit west, you’ll come across Chicago’s historic Old Town neighborhood. Old Town is one of my favorites, as its picturesque, tree-lined streets are beautiful year round. This is where you’ll find plenty of cute boutiques, restaurants, pubs and bars. Wells Street is Old Town’s main strip, and it’s the heart of the area’s nightlife. Old Town is one of the most popular neighborhoods to live in in the city.
Lincoln Park is my absolute favorite neighborhood in Chicago, as it’s the neighborhood that I call home! Lincoln Park houses the Chicago Zoo and plant conservatory, which are both completely free to the public. It is very near to the lake and is filled with picturesque cafes, coffee shops, boutiques, and restaurants. Popular with families, Lincoln Park is a relaxed place to live and is definitely worth a visit if you’re in the area.
Just barely north of Lincoln Park, you’ll come to Lakeview. Lakeview is one of the more lively and fun neighborhoods in the city, typically attracting a younger crowd. It is also home to Chicago’s Boystown which is especially exciting during the Pride Parade in the summer. This neighborhood has lots of funky restaurants, bars, comedy clubs, and shopping, and if you don’t stop for late night macaroni-stuffed grilled cheese at Cheesie’s, you’re missing out!
Continuing north past Lakeview, you’ll come to Wrigleyville, named for the Wrigley stadium which is home to the Chicago Cubs! The neighborhood is mainly characterized by sports bars, nightclubs, and restaurants relating to the team, and is an absolute blast for a night out or during a Cubs game. If you’re looking for cheap hot dogs and beer, this is the place.
Logan Square, Bucktown, and Wicker Park
Paralleling the lake-hugging neighborhoods I’ve just mentioned, Chicago’s west side has a several up-and-coming neighborhoods as well. Logan Square, Bucktown, and Wicker Park are all becoming more and more gentrified, which tends to attract a more hipster and artsy crowd. In these neighborhoods, there is no shortage of quirky bookshops, art galleries, speakeasies, and local theaters. In Wicker Park especially, you’ll find some great trendy bars and restaurants, such as Big Star and Paradise Park. All three areas have a variety of patios, craft cocktail and rooftop bars as well.
One of the best and worst things about Chicago is its seasons. Winter can be bone-chillingly cold, as exhibited by the Polar Vortex we’ve experienced this winter, but there is a silver lining. The city has plenty of fun winter activities that will help you forget how absolutely freezing you are! For example, ice skating in Millennium Park or Wrigleyville, drinking hot chocolate (or spiked hot chocolate) in one of the many bars and cafes, and visiting the wintertime Christkindlmarket downtown. It also helps that the city covered in snow is an incredibly beautiful sight.
On the flip side of that, Chicago’s summertime is unlike anything else you have ever, and probably will ever experience. There is a buzz in the air, an excitement, and everyone in the city feels it. When summer comes, we don’t waste a minute of it. From sunbathing at North Avenue Beach to drinking craft cocktails at rooftop bars and patios, watching outdoor movies in the park, going to free outdoor concerts, strolling through farmer’s markets, and of course, attending acclaimed music festivals such as Mamby on the Beach and Lollapalooza, Chicago is the absolute best place to be during summer.
If you’re a sports fan, Chicago is a great place to be year round, and especially in the fall if you’re into college sports. Chicagoans pull from many of the surrounding states and the city is a huge draw for many Big 10 university graduates. The city is such a magnet for Big 10 grads that many neighborhood bars throughout the city are specifically university-themed, such as a University of Michigan bar or an Ohio State or Wisconsin bar, showing that school’s big games and bringing out tons of alumni as a result.
Things To Do:
I touched on it briefly before, but if you’re in Chicago during any time of year, here are some highlights of the best activities the city has to offer:
Go check out The Bean and several other of Chicago’s most famous sculptures, go ice skating during winter, and attend free outdoor concerts and movies in the park during summer.
Go see a Cubs game at Wrigley Field, or if you don’t have tickets, watch at one of the many sports bars in the area. Though Chicago’s other sports arenas aren’t located in Wrigleyville, stop by a Chicago Blackhawks, Bears, or Bulls game to get a taste of the city’s sports scene.
Chicago is known for being home to some of the best museums in the country. Be sure to check out The Field Museum, the Museum of Science and Industry, The Art Institute of Chicago, The Adler Planetarium, the Shedd Aquarium, and many more.
The Magnificent Mile is the city’s primary commercial and shopping district, with upscale restaurants, hotels, and shops. Here you’ll find Chicago’s Water Tower Place shopping mall and can also access Chicago’s Riverwalk to enjoy an architectural boat tour, rent kayaks, or walk along the river, stopping at various bars and restaurants along the way. One of the area’s main attractions is the 360 Chicago Observation Deck at the John Hancock Center, which offers panoramic views of the entire city.
No trip to Chicago would be complete without taking in the city’s wild nightlife! Experience some of Chicago’s many pubs, live-music, speakeasy, patio, and rooftop bars all over the city. For trendy nightclubs, the River North neighborhood will be your best bet.
North Avenue Beach
During the summer especially, North Avenue Beach is a can’t-miss destination. Sunbathe at the beach, play volleyball, go swimming in the lake, and walk or rent a Divvy bike and ride along the boardwalk.
As a tourist, you’re required to stop by Chicago’s Navy Pier. Take a ride on the iconic ferris wheel and watch the fireworks Wednesday and Saturday nights during the summer.
Other great things to do in the city are going to see a comedy show at the world-renowned Second City theatre, a Broadway show or a local theatre show, The Chicago Theatre for rotating stand-up comedians, concerts, and speakers, or the free Chicago zoo, which hosts ZooLights during the winter.
Classic Chicago Food and Restaurants
No matter what brings you to the city, you absolutely cannot leave without trying some of the foods and restaurants Chicago is famous for. Possibly the most famous and most important Chicago food to try is our Deep Dish pizza. Love it or hate it, Lou Malnati’s or Giordano’s are the two best places to give it a try.
You’ll also need to make sure to try a classic Chicago hot dog, preferably at The Wiener’s Circle, which is open late and has several locations throughout the city. Garrett Popcorn Shops gourmet popcorn is another must-try while in the city, and I would definitely recommend trying the traditional Garrett Mix, which combines their popular cheesecorn and caramel corn. Other notable restaurants to try are Chicago Pizza and Oven Grinder Company, Au Cheval for incredible burgers, BIG & Little’s for some of the city’s best tacos, and Sweet Mandy B’s if you have a sweet tooth.
If you’re looking for a beautiful American city with something for everyone, Chicago should definitely be high on your list. From food, to sports, to music, to nightlife, you’ll never be lacking for something exciting to do. Come check out Chicago and see what the Windy City is all about!
My name is Sophie Mendel, and I’m an American wanderluster currently residing in Chicago, Illinois, USA. I have traveled to 42 countries and lived in 5, am fluent in English and Spanish (and always in the process of learning more languages), and love lugging my guitar around the world with me! Follow my travels on Instagram @theunboundedtraveler!