Heading to Chicago for the first time promises to be a great adventure! To make sure you maximize your time there, whether it is a few days or longer, here are five fun activities to do. First, though, let’s talk about why Chicago is a must-visit destination.
Key Takeaways
- Head to one of the many parks! Grant Park is one of the top-visited parks in Chicago
- Enjoy a sightseeing cruise along the Chicago River on a luxury boat, taking in the amazing skyline with your travel companions
Why Visit Chicago Soon?

This city is on many people’s bucket lists, and there’s good reasons for it. There are many attractions, dining options, and things to do. What’s great for families, in particular, are the kid-friendly activities.
Plus, if you like walking, then downtown is going to be a great way for you to get your steps in as you go around “The Loop.” On a walking tour, you can find out more about the history and culture of the place.
Tips for a Good Chicago Visit

By following these tips, you’ll make the most of your Chicago adventure and experience the city like a pro!
- Pack for the Weather – Chicago’s weather can be unpredictable, so bring layers, especially if you’re visiting in spring or fall. Winters can be harsh, while summers are warm and perfect for exploring.
- Use Public Transportation – The “L” train system is a convenient way to get around the city without dealing with traffic or expensive parking.
- Drop Off Your Bags – If you arrive early or have a late departure, lighten your load by storing your bags at a luggage storage in Chicago. This way, you can explore comfortably without carrying heavy suitcases.
- Explore the Neighborhoods – Beyond downtown, check out neighborhoods like Wicker Park for trendy shops, Pilsen for vibrant murals, and Hyde Park for history and culture.
- Try the Local Food – Don’t leave without trying deep-dish pizza, a Chicago-style hot dog, and Italian beef. These iconic eats are a must!
- Plan for Museum Visits – The Art Institute, Field Museum, and Museum of Science and Industry are worth a visit. Buy tickets in advance to save time.
- Enjoy the Lakefront – Walk or bike along Lake Michigan, visit Navy Pier, or relax at one of the city’s beaches for stunning views and a fresh breeze.
Check out these other tips:
1. Visit an Amazing Art Museum

Visiting an art museum in Chicago is a must for anyone looking to experience the city’s rich cultural scene. Museums like the Art Institute of Chicago house world-renowned collections, featuring everything from classic masterpieces to contemporary works.
Walking through the galleries, you can admire famous pieces like Grant Wood’s American Gothic or Georges Seurat’s A Sunday on La Grande Jatte, all while gaining a deeper appreciation for artistic expression. Whether you’re a seasoned art enthusiast or just looking for an inspiring way to spend the day, these museums offer an immersive and thought-provoking experience.
2. Water Fun and Relaxation

Boat cruises are among the highlights of the trip! Enjoy a sightseeing cruise along the Chicago River on a luxury boat, taking in the amazing skyline with your travel companions.
It’s a one-of-a kind way to see the city, and there’s likely a guide who provides commentary on the top sights as you pass by them. You’re sure to see amazing landmarks like Willis Tower and enjoy food served on board, too. A kayak tour is another fun idea for adventurous travelers.
3. See Wildlife in a Historic Location

For families, a great destination is the Lincoln Park Zoo. Dating back to 1868, this historic location is where you and your little ones can have a wildlife adventure. Your kids might not yet have seen many of the animals anywhere other than on TV or movies.
Seeing them now in this inclusive environment, your children can see cows, goats, birds, seals, apes, and more. There is also a 28-passenger train to ride together on-site. This zoo is one of the only free ones in the US, so the outing fits into the vacation budget easily. Hopefully, the weather will be nice as you walk around.
4. Enjoy Green Space: Park Fun

Head to one of the many parks! Grant Park is one of the top-visited parks in Chicago. You will have been there when you went to the Art Institute of Chicago mentioned earlier. This public park is where you can look forward to seeing more than 300 acres of greenery. It’s in The Loop, so try to get there early in the day to avoid crowds.
There is a lot to do at Grant Park, including seeing one of the festivals there if you go at the same time one is happening live. While you’re there, take time to walk along the Lakefront Trail, looking out at Lake Michigan as you enjoy the 1.5-mile trail. Along the way, look forward to passing the famous Buckingham Fountain.
5. Have a Laugh during a Night Out

Enjoy a fun evening out at The Second City comedy club! This activity isn’t something you usually get to do as you’re so busy working, so it’s fun to be able to let loose and laugh at a night out on the town while staying safe.
The Second City is where a lot of comedians got their first break and later became very famous. This club has seven stages and is affordable for two-hour shows. An improv show is unlike any other, and it’s a great experience you can enjoy from the audience.
If you were downtown earlier in the day, The Second City is a short cab away. Make it an amazing night by having dinner out before the show. Then, at the end of the night, head back to the hotel for a relaxing rest of your evening. Try to get your tickets in advance to make sure you don’t miss the show you want while you’re in town.
For Your First Trip to Chicago, There’s So Much to Enjoy

During your first trip there, you might not see everything you want to, depending on how much time you have. Other great sightseeing spots include The Chicago Theatre and Wrigley Field, both of which are famous worldwide.
Of course, there are also terrific places to shop, including the upscale Magnificent Mile. Don’t forget about the great music venues either, as well as the summertime outdoor festivals with live performers.
It’s no wonder that Chicago has been named the Best Big City in the US so often. There are great things to see and experiences to have there. The cultural experiences to be had here are also amazing as you explore neighborhoods.
Don’t forget the great restaurants too, which will make for a yummy part of the trip. There are many Michelin-starred eateries there, as well as amazing street food, including the famous Chicago-style hot dog. In other words, there’s something for every budget food-wise. You might just find yourself dining at the next restaurant that makes it big and you can say you ate there before it got famous.
Final Word
If you haven’t seen everything by the time your vacation is over, be sure to head back a second time (and third). That way you’ll get to see more and keep the fun adventures going!
Be sure to take photos and videos along the way as you explore the city. This experience is one you will remember for a long time, and you want to be able to share the memories with others when you get back home. As you show them pics, they may just want to be your next travel companion!