Must-Dos for Day Trips to Chicago


chicago river cruise

Being in any city for just a day can feel overwhelming. This is especially true with a city like Chicago that has a rich history. Don’t fret. We’ll be discussing the must-dos for day trips to Chicago to help you make the most of your visit. 

Visit “The Bean” at Millennium Park

Colloquially known as “The Bean,” Cloud Gate is a sculpture that has become a must-see in Chicago. Anish Kapoor created a timeless piece of art for Chicagoans and tourists to admire. Since its unveiling in 2004, Cloud Gate has become one of the most recognizable landmarks of Chicagoland. The stainless steel exterior reflects the city’s famous skyline and the lush greenery of Millenium Park. It is the perfect place to take pictures of you and your travel group, considering the mirrored effect of the sculpture. So, with limited time in the area, this is certainly a must-do on your day trip to Chicago. 

the bean chicago

Explore the Lakefront Museum Campus

If you’re looking for great group activities in Chicago, exploring the lakefront will allow you to capture the true beauty of Lake Michigan. Doing so on the Lakefront Museum Campus will allow you access to stunning views. You can also appreciate some of the museums central to the city’s cultural programming. Let’s take a look at some of the favorites:

  • Shedd Aquarium: The Shedd Aquarium was one of the first inland aquariums in the world. With more than 100 animal species within the building, this Aquarium has become a hub of education and conservation efforts. 
  • Field Museum: The Field Museum’s exhibits prioritize natural wonders. You can experience nearly 40 million artifacts, including SUE – the city’s favorite T. Rex. Beyond this, the museum is a massive hub for research and conservation of ecosystems in Chicago and abroad. No day trips to Chicago are complete without a visit.
  • Adler Planetarium: The Adler Planetarium is a beloved spot in downtown Chicago. With a series of amazing shows, the Planetarium renders images of the starry sky and other phenomena of the universe. 

Immerse Yourself in the Art Institute of Chicago

Speaking of outstanding museums to visit, the Art Institute of Chicago offers a deep cultural venture for all who visit. The exhibitions explore centuries of art from across the globe. They hold events offered both in-person and virtually. In terms of group activities in Chicago, these programs help individuals at any level of artistic knowledge understand the importance of the collections. 

Witness the Fantastic View at Skydeck Chicago

Located at Willis Tower, the SkyDeck is an excellent place to get a full view of Chicago. The viewing tower is on the 103rd floor of the tallest building in the city. And, if you’re brave enough to experience The Ledge, you can stand on a glass balcony and look down 1,353 feet below. In addition to witnessing the gorgeous environment from above, you can also explore the interactive exhibits that SkyDeck has to offer. It is guaranteed to be a humbling and educational experience for visitors of all ages. 

chicago river cruise

Wade Through History on an Architecture River Cruise

Chicago’s architecture has a rich and fascinating history. This is especially true considering Chicago went from a small settlement to one of the largest cities in the country in less than a century. The Architecture River Cruise is a 90-minute spectacle that explores history and deepens your understanding of the area.  The experience is open both during the day and in the evening, with the setting sun reflected in the skyline. This makes it easy to fit into your schedule for your day trip to Chicago. The cruise is also available in five languages – English, French, Spanish, Japanese, and Korean – making it accessible to a diverse crowd. 

Catch a Game at Wrigley Field

Second only to Boston’s Fenway Park, Wrigley Field is one of the oldest baseball fields in America’s major league. The ballpark, built in 1914, is the home field of the Chicago Cubs. The MLB typically runs 6 months, which gives you plenty of opportunity to catch a game. For fans, this can be one of the best group activities in Chicago. Not interested in baseball? No worries. The Wrigley Field campus includes 20 unique venues to visit!

arcade in chicago

Get To Know Your Playful Side at Wintrust

If you’re looking for an arcade in downtown Chicago, Wintrust is minutes away in Bedford Park. Wintrust has a collection of popular arcade games, as well as access to other invigorating activities! Let’s take a look at all they have to offer.

Popular Arcade Games

Wintrust is a hub for all your favorite arcade games. Want to be a pinball wizard? We’ve got you covered. Ready to beat the high score of Pacman or Space Invaders? We have those too. You can play all the best arcade games and challenge your friends along the way. 


Popular arcade games are one thing. But what about e-sports? Competitive video gaming has become increasingly popular, so we adapted with our e-sports lounge. Conquer some multiplayer games with your travel party or enjoy the challenge with new connections you make in the lounge. 

Laser Tag

If you’d prefer something a little more active, we can help you out with that. Not all arcades in downtown Chicago offer the fast-paced fun of laser tag, but we do! Laser tag is an amazing way to get your blood pumping, have some laughs with friends, and get into the competitive spirit!

Station Grille

When looking for arcades in Chicago, you may also be searching for a place to grab a bite in between games. Well, Wintrust is also home to the best bar in Bedford Park: Station Grille. Who doesn’t want to have the perfect mix of fun and food? Fuel up with a delicious meal and get back to the enjoyment of gaming! 

The Perfect Day

As you plan out any day trips to Chicago, you want to make sure you have a well-rounded experience. Enjoy the leisure of the Architecture River Cruise alongside the exhilaration of The Ledge. But no matter what, make sure to visit us at Wintrust to add a dynamic layer of fun to your day. 

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