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February 27.2025
3 Minutes Read

Discover What to Do in Chicago This Weekend Like a Local

Iconic Chicago theater at night with bright lights in cityscape.

Discover What to Do in Chicago This Weekend Like a Local

Chicago, known for its vibrant culture, stunning architecture, and hearty cuisine, transforms into a playground for weekend adventurers regardless of the unpredictable weather. Whether you're a local or visiting for the first time, this weekend invites you to explore its eclectic neighborhoods, make culinary memories, and engage in activities that epitomize the distinctive Chicago charm.

Explore Neighborhood Gems Beyond the Tourist Trail

While iconic landmarks like the Willis Tower and Millennium Park are must-sees, don’t miss out on the lesser-known neighborhoods, each offering a unique slice of Chicago life. Hyde Park, for instance, is enriched with history and a sense of community, making it a perfect weekend retreat. Check out Promontory Point for spectacular views of the skyline – it’s an ideal spot for a scenic run or a leisurely picnic. In the winter months, soak in the festive spirit with ice skating at Midway Plaisance.

As you wander through Hyde Park, fuel your day at the Dawn A.M. Eatery with a delightful southern-style brunch, which serves as a great introduction to the city’s culinary scene. For those who love to explore, the Museum of Science and Industry and the DuSable Museum are perfect places to immerse yourself in engaging exhibits and historical narratives.

Cultural Hotspots Awaiting Your Discovery

Greg Robbins, a fitness coach at Feast Fitness, recommends a weekend itinerary on the North Side that starts with a memorable dinner at Bayan Ko, a Filipino-Cuban eatery that artfully blends cultural flavors. After a satisfying meal, sip hand-crafted spirits at Koval Distillery in the Ravenswood Corridor, known for its unique distilling processes.

For a lazy Sunday, indulge in a specialty coffee at Side Practice Coffee and journey through local boutiques that celebrate female entrepreneurship. Shops like Bon Femmes and Ponnopozz not only offer beautiful goods but also support the community's vibrant commercial fabric.

Don’t Miss the Hottest Events This Weekend

This weekend is packed with exciting events that showcase Chicago's talent and social scene. From live music at The Promontory to art exhibitions across local galleries, there’s no shortage of entertainment. The bustling theater scene also beckons, with numerous shows scheduled to capture your imagination. Make it a night out with friends, sipping cocktails and enjoying a performance that touches the heart.

Arts and culture in Chicago come alive in the winter through various ongoing exhibits. Catch the latest at the Museum of Contemporary Art, or take a trip back in time at the Chicago History Museum to appreciate the city’s rich heritage.

Make Lasting Memories While Nourishing Your Soul

Each weekend is an opportunity for making unforgettable memories and exploring your own passions and interests. Imagine discovering a new passion for ice skating or unraveling the magic of live theater. The warmth of Chicago’s communities shines brightest in the colder months as locals come together to enjoy festive activities and support one another.

As the weekend approaches, take the initiative to gather your friends and family and dive into all that Chicago has to offer. From sipping a warm drink in a neighborhood café to exploring the bustling markets, your weekend is primed for adventure!

Take the Leap: Experience Chicago Like Never Before

Don’t stay cooped up this weekend! Embrace Chicago's array of activities that promise exploration, fun, and connection. Whether you're skating, dining, or savoring art, take each moment to heart as these experiences build cherished memories. Ready to dive in? Make your plan and seize this chance to discover Chicago’s rich offerings.

Check out local listings for events and updates, and don’t hesitate to explore the city’s vibrant neighborhoods where delicious food and dynamic culture await. Let the weekend adventure begin!

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01.29.2026

Don’t Miss These Key Sessions at Inman Connect New York!

Update Unlock Your Potential at Inman Connect New York As the curtain lifts on Inman Connect New York (ICNY), real estate professionals from around the globe prepare for what is often deemed the industry’s biggest moment of the year. The excitement around this coveted event is palpable, as every session promises not just insight, but also a chance to redefine one’s approach to business. Troy Palmquist is among those excited about ICNY, sharing a curated list of sessions that are destined to be game-changers for attendees. Why Attending Inman Connect is Essential For many, the mere thought of sifting through an exhaustive agenda can be overwhelming. Instead of targeting names and buzzwords, attendees should zero in on substantive sessions that promise real value. Like sipping a shot of espresso, selecting the right sessions can invigorate your approach to real estate, transforming your strategies away from conventional thinking. Top Sessions Not to Miss Troy enthusiastically highlights a few key sessions that are must-attends: The Inman Interview: Robert Reffkin - A conversation with the CEO of Compass, this session is sure to delve into the pressing issues confronting the market, with tough questions posed by industry leader Brad Inman. The Leader’s Playbook: Turning Strategy Into Relentless Execution - Sean Soderstrom’s first-time moderation speaks of not just talking about strategies but implementing them effectively, drawing from his rich experience at McKinsey and Compass. Recruiting and Retention in the Age of Consolidation - Stacie Staub shares her journey, providing insights into keeping a brokerage appealing in a rapidly consolidating industry. Networking: The Heartbeat of ICNY Networking can sometimes feel overwhelming, but it doesn’t have to be. Before even stepping into the first session, make time to wander the venue, soak in the atmosphere, and connect with fellow attendees at casual meetups. Troy suggests the Bridges Bar at the Midtown Hilton for a laid-back environment where attendees can mingle, exchange ideas, and foster connections that may last long past the event. Making the Most Out of Your Experience Jet-lagged or not, the key to maximizing your time at ICNY is to approach it with a well-thought-out game plan. This means having your content lined up, whether that involves penning down insightful notes during sessions or capturing content that can resonate with your audience. Following expert advice, like insights from video content specialist Ransome Tucker, can help amplify your post-event visibility. Your Roadmap to Success Attending ICNY isn’t just about the talks; it’s about the moments that you carve out for yourself. Make sure to attend side events, such as Troy's upcoming pizza party at a local gaming lounge, where business talks can blend with fun, fostering an informal atmosphere encouraging rich exchanges of ideas. These additional layers are just as significant in transforming your ICNY experience. Final Thoughts Taking in all of ICNY’s potential can feel daunting, yet by strategically selecting sessions and networking opportunities, attendees are bound to leave the conference feeling not just inspired, but equipped to elevate their businesses. Embrace the chance to learn, connect, and grow—and don’t miss the chance to attend those pivotal sessions!

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