Ahhh Chicago… It’s a city that is full of heart, Midwestern charm and spunk that can entertain any traveler for months — no joke! Since that kind of vacation time isn’t realistic, you just need to know the highlights and can’t-miss experiences. So, here are 11 of the best things to do in Chicago, both indoors and outside, so you can enjoy the best that the city has to offer, whether you visit in the sunshine or snow.
1. Promontory Point
Take the scenic route down Lake Shore Drive to Promontory Point, which offers a great spot to gaze and walk off brunch with stunning views of the azure waters of Lake Michigan. It’s located on the eastern edge of Hyde Park, a historic and beautiful neighborhood famous for its restaurants, the University of Chicago and two notable former residents, Barack and Michelle Obama.
2. North Avenue Beach
You may not be going to Chicago for a beach vacation, but if you’re in town when it’s hot outside, then North Avenue Beach is definitely among the best things to do in Chicago. The official beach season, with lifeguards on duty in designated swim areas, runs from the Friday before Memorial Day through Labor Day. If you’re in town outside of those three-ish months, then North Avenue Beach is still a must-visit if you want a unique spot from which to see the city’s skyline.
3. Chicago Botanic Garden
Located north of the city in Glencoe, IL, the Chicago Botanic Garden boasts 385 acres of colorful landscapes, as well as art exhibitions inside the Regenstein Learning Campus. While you can certainly opt to surpass your daily steps goal by seeing it all on foot, you may consider taking a break for a 2.3-mile narrated tram tour, which is included in your admission ticket. And speaking of admission, check to see if your visit falls on one of the Garden’s free entry days so you can save a bit of money.
4. Pequod’s Pizza
Chicago serves up unique, hearty and eclectic food and drink, from Chicago-style hot dogs to acclaimed fine dining, but don’t skip Pequod’s Pizza in Lincoln Park. This pizza joint is every local’s favorite spot for deep dish. Pequod’s is as Chicago as they come, with an herbed butter crust and heaps of sauce and cheese. Pequod’s never fails to impress, and somehow still avoids the tourist hype of Lou Malnati’s, Giordano’s and Gino’s East. Go during the week or skip lunch for an early dinner on Friday or Saturday to get seated faster. You’ll definitely want an empty stomach when you go to Pequod’s.
5. Art Institute of Chicago
Did you know that the Art Institute of Chicago is one of the world’s oldest and largest art museums? It was founded in 1879 and has thousands of pieces of artwork in its collection, ranging from paintings to ancient artifacts to handcrafted furniture. While you’re there, join a guided gallery tour or a drop-in sketching workshop. There are also activities and programs geared toward families, and kids under 14 get free entrance to the museum.
6. Kayak the Chicago River
Want more fun stuff to do in Chicago for families? Kayaking on the Chicago River will give you a unique perspective of the city’s streets and buildings. Rent a single or double kayak and explore on your own or join a guided tour. The night paddle tour is a magical experience, with Chicago’s towering buildings lit up against the dark sky and their glowing reflections dancing on the water around you.
7. Lake Shore Drive
Hop on Lake Shore Drive for an iconic Chicago experience. You can cruise up and down the Lake Michigan coastline and get a good overview of the entire city in about 30-45 minutes. Take detours to go by some of the better-known Chicago landmarks, like Wrigley Field, the Shedd Aquarium, The Bean (a.k.a. Cloud Gate), the Art Institute of Chicago and Millennium Park.
8. Museum of Science and Industry
Although locals recommend the Museum of Science and Industry as one of the best things to do in Chicago with kids, curious adults can easily pass the hours here too. You can step inside the U-505 German submarine, take a journey through the cosmos in a domed theater, understand how vision works by dissecting a cow eye and experience what it would’ve felt like to be on different aircraft from throughout history in a motion simulator. And that’s just the tip of the iceberg!
9. Ping Tom Memorial Park
This 17-acre park along the south branch of the Chicago River is a quiet place for a stroll if you want to escape the crowds at larger spaces like Grant Park or Millennium Park. You can rent kayaks in the summer, let your kids run free on the playground and enjoy a picnic under a pagoda-style pavilion. Local’s tip: Take the water taxi from downtown for a picturesque way to reach Ping Tom Memorial Park.
10. Robie House
Designed by iconic architect Frank Lloyd Wright, the Robie House is recognized as a masterpiece for its display of American Prairie House Architecture. Building buffs will love Chicago for its diverse styles of modern architecture on parade in both small neighborhoods and on skyscrapers like the Willis Tower and Hancock Tower downtown.
11. Go on an Italian Beef tour
As you can tell by now, one of the best things to do in Chicago is delight your taste buds. The Italian Beef sandwich was a local treat even before Hulu’s “The Bear” TV series piqued international interest and drew more attention to the Chicago food scene. So what is an Italian Beef exactly? This is an oversimplification of the dish, but its core components are thin slices of seasoned beef (the cut used varies by chef), au jus and a French roll. It can be topped with giardiniera and/or roasted green peppers. You really can’t say you’ve “done Chicago” until you’ve gotten your hands on an Italian Beef.
Getting around Chicago
The best way to see the heart of the city is on foot, but if you want to cruise down Lake Shore Drive or break away for a day trip to Indiana Dunes National Park, then a car is a must. Make your life easy by booking with Avail car sharing. We have dozens of locations in neighborhoods all around Chicago so you don’t have to travel far to get your rental. Each location is equipped for self-service pick-up and drop-off, so you don’t have to wait in a single line. Just grab the keys and go enjoy all the fun stuff there is to do in Chicago.