Ideas for my Teen Sons While I’m Working?

Question

I will have to travel to Chicago soon for a work event. Im thinking of letting my two teen sons (ages 18 and 15) tag along. I’ll be at work from the morning until late afternoon on the weekdays in mid-July. We’ve never been. We’ll be staying in the Chinatown area. What are safe, easy things for them to do and see? They love to eat, explore-one likes museums and such so are there any can’t miss museums or things to do and see (we are coming in from Austin, TX). Also, on the last day we may try to go see a Chicago Cubs game but we would do it as our last activity…game is at 1pm and the flight I’m looking at is at 7:45p from OHare. Is this doable? Anywhere we could store our luggage-hotel would be in the opposite location…do I have to rent a car to be able to have a place to keep our stuff while at the game?

Aside from their solo adventures while I’m at work: what are somethings we can do together-well have one full day that I’ll have no work/taking the day off.

Answer

Hi there,

It sounds like you're planning a great trip to Chicago with your sons! There’s so much to see and do, and while you're working, your teens will have plenty of opportunities to explore and enjoy the city. Here are some ideas for both solo activities for your teens and things you can do together on your day off.

For your sons while you’re working, here are some fun and safe activities they can enjoy around the Chinatown area and beyond:

Chinatown Exploration: Since you'll be staying in Chinatown, they can start by exploring the local shops, restaurants, and culture. A visit to the Chinese-American Museum of Chicago could be interesting, and they might enjoy trying some authentic Chinese food at places like Ed's Potsticker or Triple Crown for lunch.
Millennium Park: Just a short train ride from Chinatown, Millennium Park is a must-see with its iconic Cloud Gate ("The Bean") and the Jay Pritzker Pavilion. They can enjoy walking around the park, checking out the free outdoor events, or taking photos in front of the Bean.
Art Institute of Chicago: For the son who loves museums, the Art Institute is a top spot. It’s home to amazing collections of art from around the world, and it's just a short distance from Millennium Park. They can explore the Impressionist and Modern Art galleries, and check out the famous American Gothic painting by Grant Wood.
Museum of Science and Industry: This is a perfect spot for teens, with hands-on exhibits covering everything from space exploration to transportation. They can explore the U-505 Submarine exhibit or the Science Storms exhibit, which is interactive and fun.
Lincoln Park Zoo: Located in Lincoln Park, this zoo is free to visit and has a variety of animals and exhibits. It’s a great place to explore without needing to rush. It’s also close to the Lincoln Park Conservatory and the Chicago History Museum if they want to add more to the visit.
Shoreline Sightseeing: If they enjoy being on the water, they could take a Lake Michigan architecture cruise to see the famous skyline and some of Chicago’s iconic architecture from the water. The boats are easy to access from Navy Pier, and this could be a relaxing way for them to enjoy the afternoon.

For your final day, attending a Chicago Cubs game sounds like a fantastic way to cap off your trip. With a 1:00 PM game and a 7:45 PM flight, it is definitely doable, but you'll need to be mindful of timing.

Luggage Storage: Since your hotel is in a different area, you can store your luggage at the game or in the city. Many hotels offer luggage storage even after check-out, so it’s worth asking your hotel about that. Alternatively, you can use a service like LuggageHero or Vertoe, which allows you to store your bags at various locations around the city, including near Wrigley Field.
Getting to O'Hare from Wrigley Field: Keep in mind that Wrigley Field is about a 40-45 minute drive from O'Hare. With the Cubs game ending around 4 PM, you should have enough time to head straight to the airport. However, it’s a good idea to leave the game a little early to avoid any last-minute rush, especially with traffic.

For your full day together with your sons, here are a few ideas for activities that can be a mix of adventure, relaxation, and fun:

Chicago Architecture Tour: You can take a guided boat tour along the Chicago River to explore the city’s incredible architecture. It's a great way to relax together, learn about the city's history, and get some great photos. The architecture river cruise is a perfect option for families.
Skydeck Chicago or 360 Chicago: For an amazing view of the city, take a trip up to one of the observation decks. The Skydeck at Willis Tower has the famous "Ledge" where you can step out onto a glass box 1,353 feet above the city, and 360 Chicago offers a unique tilt experience for a more thrilling experience.
Food Tour: Since your sons love to eat, consider booking a food tour. Chicago is known for its deep-dish pizza, hot dogs, and other local specialties. You could join a food tour to sample some of the best bites around the city, from pizza to Italian beef sandwiches and more!
Millennium Park and Maggie Daley Park: Spend a day outside with a visit to Maggie Daley Park where you can rent bikes or ride the park's famous ice-skating ribbon (weather permitting). You could also relax at Millennium Park and take in some outdoor performances or events.

There’s no shortage of things to do in Chicago, so your teens will be well-entertained while you're at work, and you'll have a fantastic time together when you have a free day. Have an amazing trip!

Ideas for my Teen Sons While I’m Working?

More Chicago Travel Questions

The attractions mentioned in this question

Popular Destinations

Popular Travel Questions