Posted: 5/13/2024 | May 13th, 2024
Famously known as “the Second City” (meaning second in population to New York), I feel like Chicago is often overlooked by travelers. It sees a fraction of the visitors LA and NYC receive, which is a shame, as it’s one of my favorite cities in the world.
Chicago is chock-full of world-class institutions, Michelin-starred restaurants, awe-inducing architecture, and verdant parks. There is a lot to do here and the city has a really rich history. I think more people should visit.
Sure, the winters are brutal. But, come spring, Chicago blossoms into a dynamic urban landscape of street life, outdoor cafés, and sunny parks when locals take over the outdoors to enjoy the few months of nice weather. (I don’t think you can really beat Chicago in the summer.)
To help you plan your visit, here’s my list of the best things to do in Chicago:
1. Take a Walking Tour
One of the first things I do when I arrive in a city is take a walking tour. They’re a great way to see the main sights, get the lay of the land, and connect with an expert local guide who can answer all my questions. Free Chicago Walking Tours hosts regular free tours that can introduce you to the city. You’ll get to see many of the coolest buildings in the city while also learning about the history of Chicago. The tour lasts a few hours. Be sure to tip the guide at the end!
For a more unique tour, try the Gangsters and Ghosts Tour. You’ll learn all about Chicago’s dark side and creepy past as you explore the Chicago Loop. The tour lasts two hours and really talks about one of the pivotal times in Chicago’s history. Even if you’re not a history buff like me, you’ll get a lot out of it.
2. Relax in Grant and Millennium Parks
Located downtown, these gigantic parks provide a great place to hang out, have a picnic, or go for a run. People play chess here when the weather is nice and, during the summer, there are a lot of free concerts and events here. The larger Grant Park stretches along Chicago’s waterfront, while Millennium Park is the subsection where the famous “Chicago Bean” sculpture is located. This iconic work of public art is a must-see. And, starting at noon on the first and third Saturdays from April through November, the Chicago Cultural Center hosts walking tours focusing on the art of Millennium Park. It’s really interesting. I love strolling through the park or just chilling here with a good book on a nice day.
3. Take in some art at the Art Institute of Chicago
Since 1879, the Art Institute of Chicago has been wowing visitors with its excellent collection of works from around the world. Located in Grant Park, the museum has a few immediately recognizable pieces, including “American Gothic” by Grant Wood, Edward Hopper’s “Nighthawks,” and “A Sunday Afternoon on the Island of Grande Jatte” by Georges Seurat. The vast collection also includes works by Picasso, Monet, Renoir, Van Gogh, Jasper Johns, and Jackson Pollock. There are also wings devoted to African, Asian, and American indigenous art. If you’re going to go to one museum in Chicago, this should be it. Expect to spend a few hours because the collection is so big.
To beat the crowds, skip a weekend visit as the place gets packed. Instead, go on a Monday or Thursday evening (they’re open late on Thursdays). You’ll have the place virtually to yourself.
111 S Michigan Ave, (312) 443-3600, artic.edu. Open Thursday-Monday 11am-5pm (8pm on Thursdays). Admission is $32 USD ($40 USD for advance skip-the-line entry). Daily tours (included in the price of your ticket) are offered at 1pm and 3pm.
4. Admire amazing architecture on a river cruise
Chicago is an architecture lover’s dream. The very best way to take in its famed buildings is via a river cruise. This way, you can sit back and cruise down the canals while an expert guide provides context for what you’re looking at. The guides will give you a detailed history of the architecture. Some of the buildings you’ll see on the boat ride include the Tribune Tower, 333 West Wacker, Navy Pier, the Willis Tower, the Wrigley Building, and Marina City, among others. All in all, there are about 50 structures to see on this fascinating tour, and I promise, it’s much more interesting than it sounds!
5. Stroll down the Magnificent Mile
Often nicknamed “Mag Mile,” this stretch along Michigan Avenue from the Chicago River to Oak Street is known for its upscale designer boutiques. In fact, rent here is the third highest in the US (after Fifth Avenue in New York City and Rodeo Drive in Beverly Hills). Even if you don’t want to blow your budget shopping, it’s still an experience to stroll along the avenue and take in the sights and the people, and enjoy the view of the Chicago River. There are several landmarks and attractions along the way too, including the 360 Chicago Observation Deck for expansive views over the city (more on this below).
6. Visit the Shedd Aquarium
If you’re visiting the city with kids (or you’re a kid at heart), head to the massive Shedd Aquarium. It’s the third-largest aquarium in the Western hemisphere and home to over 32,000 animals. They have turtles, penguins, sea otters, snakes, sharks, and more. They really emphasize education here so you’ll learn a ton while you roam the different exhibitions. You can even pay extra to do things like feed penguins and sharks, and they also host all kinds of fun evening events (such as live music after hours). I absolutely love coming here. Just make sure to book your ticket in advance as they do get busy and sell out!
To beat the crowds, skip the weekend and visit during the week instead. Also, try and visit right when it opens (especially Wednesday-Friday). It’s usually quieter then.
1200 S DuSable Lake Shore Dr, (312) 939-2438, sheddaquarium.org. Open 9am-5pm Monday-Friday (9pm on Tuesdays), 9am-6pm Saturday, and 11am-6pm on Sundays. Tickets start at $37 USD. Admission can also be included with the Chicago CityPASS.
7. Take in some natural history at the Field Museum
In 1893, the World’s Columbian Exposition (also known as the Chicago World’s Fair) took place in the Windy City to celebrate the 400th anniversary of Christopher Columbus’ arrival in 1492. The fair displayed some incredible artifacts from around the world, notably in the Columbian Museum of Chicago, which showcased anthropological and biological collections. After the fair was over, organizers wondered what to do with it all. So, the Columbian Museum became the Field Museum, named after benefactor Marshall Field, a department store mogul, and everything remained on display.
One of the biggest museums in the world, the Field houses extensive collections spanning anthropology, geology, botany, and zoology. Some important collections include the displays of taxidermied animals, a wing dedicated to astronomy, and fascinating artifacts from ancient Egypt. I recommend planning to spend at least 3-4 hours to really take it all in.
1400 S. Dusable Lake Shore Drive, (312) 922-9410, fieldmuseum.org. Open daily 9am-5pm (last admission is at 4pm). Basic admission is $30 USD. Special exhibitions are an additional charge (which varies), though you can get an all-access pass for $43 USD.
8. Get a stunning view at 360 Chicago Observation Deck
Chicago is a skyscraper city, including a few rather iconic towers. Located atop what was formerly known as the John Hancock Building and now (uninspiringly) called 875 N. Michigan, the 360-degree viewing deck a thousand feet up and allows visitors to get the best view of the Windy City and Lake Michigan. You can even grab a pint at the Cloud Bar, which serves beer from Moody Tongue, a local brewery.
If you’re a thrill seeker and want more than just the view, sign up for Tilt. This part of the observation deck is where you can stand in front of a glass window, which then tilts forward, until it appears you’re looking directly down at the street, 94 floors below.
Just make sure to check the weather before you go so you will actually have a view to enjoy. Additionally, if you want to beat the crowds, come early (before 10am).
875 N Michigan Ave, (888) 875-8439, 360chicago.com. Open daily 9am-11pm (the last entry is at 10pm). Admission starts at $30 USD (get your tickets in advance for skip-the-line access).
9. Feast on deep-dish pizza
If there’s one food Chicago has become synonymous with, it is deep-dish pizza. It was invented in 1943 by Pizzeria Uno, which is now a national restaurant chain. For something more local, Chicagoans swear by Lou Malnati’s. Personally, I’m not usually a huge fan of deep-dish (I like NYC pizza better), but it’s something you have to try while you’re here.
If you really want to indulge, hop on a Chicago Pizza Tour, on which you’ll get to sample all the varieties on offer in town. Tours start at $49 USD.
10. Stroll the Chicago Riverwalk
Stretching from Lake Michigan to Lake Street, the 1.25-mile Riverwalk along the Chicago River makes for a fun stroll. Along the way, you’ll not only get fantastic views of the river and city, but you’ll encounter a legion of waterfront restaurants, cafés, and bars. There’s a ton of public art and green space too (great for picnicking and people-watching). It’s the perfect place to slow down and enjoy the moment in this Midwestern metropolis, but if you prefer a more active experience, there are also lots of aquatic activities here too (such as kayaking or taking a river cruise).
11. Eat your way through the Mexican eateries in Pilsen
The neighborhood of Pilsen was founded in 1878 by Czech immigrants, who named the area after the fourth-largest city in the Czech Republic, where pilsner beer was born. The Czechs may be gone now, but today Pilsen is Chicago’s main Latino neighborhood, particularly Mexicans from the Michoacán region. Today you can wander the area, eating some of the best tacos while taking in the vibrant street art.
12. Watch an improv show
The Second City is one of the most popular and well-known improv troupes in the country. It’s where greats like Bill Murray, John Candy, Catherine O’Hara, Steve Carell, Tina Fey, and Amy Poehler all cut their teeth. They put on regular performances and also host all kinds of special events. They even host workshops and classes if you want to give improv a try yourself. Just be sure to get your tickets in advance as the most popular shows sell out fast.
230 W North Ave, (312) 337-3992, secondcity.com. Performances are held daily so check the website for what’s on. Tickets start at $35 USD.
This 3,300-foot-long (1,010-meter) pier on the shore of Lake Michigan started off as a shipping site, but it has also been a prison for draft dodgers during World War II, a Naval training center, and a temporary university campus. Since 1995, it has reopened to the public in its current form and has become a sort of carnival. It’s Chicago’s second-most visited tourist attraction (after “The Bean”) and contains some rides, a Ferris wheel, lots of restaurants, a Shakespeare theater, boat tours, a large number of beer gardens, mini-golf, and more! It’s a good place to have some silly fun (especially if you have kids).
600 E Grand Ave, (312) 595-7437, navypier.org. Open Sunday-Thursday 11am-8pm and Friday-Saturday 11am-9pm (individual attractions and restaurants may have separate hours). Admission to the pier is free, though attractions charge their own fees (the Centennial wheel is $21.30 USD, for example).
14. Catch a game at Wrigley Field
Home of the Cubs, Wrigley Field, on Chicago’s North Side, is smack in the middle of town. It also happens to be one of the oldest baseball stadiums in the United States (it opened in 1914). If you’re in Chicago during the baseball seasons (April to October) and the Cubs are in town, do yourself a favor and go to a game. It’s one of the most intimate and atmospheric baseball stadiums in the country. If the Cubs are not in town, you can also take a 90-minute behind-the-scenes tour of the stadium.
1060 W Addison St, (773) 404-2827, mlb.com/cubs/ballpark. Tour dates and times vary depending on the season (check the website for availability). Tour admission is $30 USD. Tickets to see a game vary greatly but start at just $10 USD (for better seats at a popular game, expect to spend closer to $80-125 USD).
15. Feast in Chinatown
Bring your appetite to Chinatown, where you can feast on cheap dim dum, do karaoke, or relax at one of the many tea houses. One of the oldest Chinatown’s in the country, over a third of Chicago’s Chinese population lives in Chinatown, making it one of the largest concentrations of Chinese-Americans in the USA. Don’t miss Ping Tom Memorial Park, and keep an eye out for colorful murals around the neighborhood. Some of my favorite places here are Hing Kee, MCCB Chicago, and Phoenix.
 
16. Experience St. Patrick’s Day
Next to Ireland, Chicago is one of the best places to be on March 17th, St. Patrick’s Day. To honor its large Irish-American population, the city dyes the Chicago River green, hosts a huge parade, and parties until the sun comes up (complete with copious amounts of green beer).
The tradition began in 1843, when Chicago’s first Irish parade was held, but it wasn’t until 1962 that the dyeing of the river started, at the suggestion of a plumber’s union, which is still responsible for the green river each year, though it won’t divulge its secrets about what’s used (it’s environmentally friendly, though). Take a river cruise on the emerald waters or snap a pic from the sidelines and enjoy. This is one of the biggest days of the year here!
17. Explore Oz Park
This whimsical little park, located in the Lincoln Park area, was created to honor L. Frank Baum, the author of The Wizard of Oz. He lived in the area at the end of the 19th century, and when the city wanted to renovate the park they decided to do so in a way that honored Baum’s popular book.
There’s a playground named after Dorothy, a green space called the “Emerald Gardens,” and numerous life-size statues of popular characters from the musical adaptation, including the Dorothy, Toto, the Tin Man, the Cowardly Lion, and the Scarecrow.
Open daily 6am-11pm. Admission to the park is free.
Chicago doesn’t get the attention it deserves. I think it’s fun and perfect for a weekend getaway. And you really can’t beat the summers here either. With lots of interesting museums, plenty of green space, and some great eats, Chicago should be on every traveler’s list!
Book Your Trip to Chicago: Logistical Tips and Tricks
Book Your Flight
Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe so you always know no stone is left unturned.
Book Your Accommodation
You can book your hostel with Hostelworld as they have the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as they consistently return the cheapest rates for guesthouses and cheap hotels.
Don’t Forget Travel Insurance
Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:
Looking for the Best Companies to Save Money With?
Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road. They will save you money when you travel too.
Want More Information on Chicago?
Be sure to visit our robust destination guide on Chicago for even more planning tips!
