4 Day Itinerary Suggestions in June 2025

Question

Looking for itinerary for our trip to Chicago in June. We are in our 40s with three teenage boys. We are staying at The Londonhouse in Riverwalk. The only plans we have so far is catching a Cubs game. Thanks in advance!

Answer

It sounds like you have an exciting trip ahead! Chicago offers a wide range of activities that are perfect for both adults and teenagers. With your stay at The Londonhouse in Riverwalk, you'll be in a great location to explore many of the city's top attractions. Here's a suggested 4-day itinerary for your family, based on your interests and the fact that you'll be attending a Cubs game:

Day 1: Arrival & Downtown Exploration

Start your trip by familiarizing yourselves with the city and its most iconic landmarks:

Millennium Park & Cloud Gate (The Bean) – Kick off your visit with a trip to Millennium Park, home to the famous Cloud Gate sculpture (The Bean). The park is a fun spot for photos and enjoying the open space, especially with teens who can appreciate the interactive elements and the beautiful views of the Chicago skyline.
Art Institute of Chicago – Just a short walk from Millennium Park, the Art Institute of Chicago offers a world-class collection of art that can captivate both adults and teens. Highlights include the modern art collection, the impressionist paintings, and the Armoury collection (which might appeal to the boys!).
Chicago Riverwalk – Since you're staying at The Londonhouse, you're already near the Chicago Riverwalk. Take a leisurely stroll along the river, rent bikes, or hop on a boat tour. There are lots of bars and cafes along the way for a relaxed lunch or snack.

Day 2: Sports & Shopping

Make this day a mix of sports and shopping activities that both adults and teens will enjoy:

Cubs Game at Wrigley Field – Depending on the time of your game, head over to Wrigley Field in the afternoon. Even if you're not a baseball fan, the atmosphere at this historic ballpark is unmatched. If your teens are into sports, they'll enjoy the energy and the experience.
Lincoln Park Zoo & Conservatory – If time permits, after the game, head over to the Lincoln Park Zoo (which is free!) or visit the Lincoln Park Conservatory. It's a great option for families with teens who want to explore nature and wildlife, and it's located in a beautiful neighborhood.
Magnificent Mile Shopping – Spend some time walking along the Magnificent Mile (Michigan Avenue) for shopping. You'll find everything from high-end stores to popular brands. It's also a great place for lunch or to stop for a break at one of the city's famous cafés.

Day 3: Museum Day & Navy Pier

Dedicate this day to learning and exploring Chicago's world-class museums, as well as some fun activities at Navy Pier:

Field Museum – Start the day at the Field Museum, where you'll find amazing exhibits on everything from ancient civilizations to the famous T. rex named Sue. It's a great place for teens to learn while exploring the interactive displays.
Shedd Aquarium – After the Field Museum, walk to the nearby Shedd Aquarium. It’s one of the largest indoor aquariums in the world and offers tons of fascinating marine life exhibits that teens will find both educational and exciting.
Navy Pier – In the afternoon, head over to Navy Pier for some fun activities. The Ferris wheel offers stunning views of the lake and city skyline. You can also enjoy the amusement park, or rent a boat for a quick tour of Lake Michigan. Navy Pier has plenty of restaurants and shops, so you can grab a bite to eat there as well.

Day 4: Chicago Architecture & Parks

For your final day, enjoy some scenic views and iconic Chicago architecture:

Architectural Boat Tour – Take a boat tour along the Chicago River to learn about the city's incredible architecture. This is a must-do activity in Chicago, especially if you're interested in the history and design of the buildings. Teens will appreciate the city’s iconic skyscrapers and modern buildings.
360 Chicago Observation Deck (John Hancock Center) – Visit the 360 Chicago Observation Deck for an amazing panoramic view of the city. You can take in views of Lake Michigan, the Gold Coast, and the Loop, or if you're feeling adventurous, try the TILT experience that lets you lean out over the city for an unforgettable thrill.
Millennium Park or Grant Park – Finish your trip with a visit to either Millennium Park or Grant Park, where you can relax, enjoy the open space, and take a final stroll around the city. If you're in Grant Park, be sure to check out Buckingham Fountain, which is a Chicago icon.

By combining sports, shopping, museums, and scenic attractions, this itinerary gives you a great mix of things to do in Chicago, and you’ll have plenty of opportunities to explore and create lasting memories with your family. Enjoy your trip to Chicago!

4 Day Itinerary Suggestions in June 2025

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