Make the Most of Your Time in Chicago
MoneyLIVE North America isn’t just about unbeatable insights and networking — it's your chance to explore the vibrant city of Chicago. While you're here, discover the best sights, sounds, and flavors that the Windy City has to offer with our top recommendations.
What to do near the conference venue
River Boat Architecture Tours
(0.5 mi)
A Chicago must-do, where sleek riverboats glide between towering skyscrapers and historic gems. Expert guides bring the city’s architectural icons to life, turning each bend of the river into a story you can see and feel.
Flight Club Chicago
(0.8 mi)
A modern twist on the classic British pub. With tech-powered darts, craft cocktails, and energetic social spaces, Flight Club brings competitive fun and after-hours buzz under one stylish roof. Ideal for group outings or casual networking with a playful edge.
Millennium Park & Cloud Gate
(0.3 mi)
A cultural and visual icon steps from the Radisson Blu. Wander through landscaped paths, marvel at public art, and experience the mirror-like curves of Cloud Gate. It’s where locals and visitors pause to reflect — literally and figuratively — in the heart of downtown Chicago.
Art Institute of Chicago
(0.5 mi)
World-class masterpieces just a short stroll away. From Monet to Warhol, the Art Institute invites you to step into the pages of art history. Its grand Beaux-Arts architecture, peaceful gardens, and famed Impressionist collection make it a serene yet powerful stop between city adventures.
Zanies Chicago
(1.8 mi)
Nestled in Old Town’s heart, Zanies Chicago is the punchy, 40+ year‑young stand‑up gem where headline comics land and the laughs never stop. Expect tight quarters, top‑tier talent, and a vibe that’s all jokes, no frills. Let me know if you'd like a version focused more on history, visuals, or visitor tips.
Have more time to explore the city?
Check out TimeOut's list of things to this week.
Where to eat near the conference venue
The Radisson Blu stands in the heart of downtown Chicago, steps from the city’s most dynamic dining and entertainment. Surrounded by world-class restaurants, buzzing bars, and iconic attractions, it’s the perfect base to taste, sip, and explore everything the Windy City has to offer — here are some local favorites you won’t want to miss!
Andy’s Jazz Club & Restaurant
(0.1 mi) $$$$
Just steps from the Chicago River, this iconic jazz spot serves up soulful tunes alongside classic American fare. From swinging quartets to sultry late-night sets, Andy’s blends a warm supper-club atmosphere with world-class live music every night. Learn more >>
Shaw’s Crab House
(0.1 mi) $$$$
A Chicago seafood institution where East Coast charm meets Midwestern hospitality. Dive into fresh oysters, buttery crab legs, and a vintage-style oyster bar that hums with energy from lunch through late-night cocktails. Learn more >>
Etta
(0.3 mi) $$-$$$
A wood-fired wonder in the heart of River North, Etta dishes up rustic, flavor-packed plates meant for sharing. With its cozy glow, buzzing bar, and irresistible pasta and pizza, it’s a place that feels like home—only with better bread. Learn more >>
The Purple Pig
(0.4 mi) $$$
A Mediterranean-inspired feast just off Michigan Avenue, where charcuterie boards and small plates overflow with flavor. Bustling and convivial, it’s the kind of place where meals turn into long, laughter-filled evenings. Learn more >>
Mercadito
(0.2 mi) $$$
Vibrant and colorful, this modern Mexican hotspot brings bold flavors and handcrafted cocktails to the heart of River North. From creative tacos to fresh ceviche, every plate bursts with energy and spice. Learn more >>
Cindy’s Rooftop
(0.1 mi) $$$
High atop the Chicago Athletic Association Hotel, Cindy’s serves sweeping lake and park views with a side of elevated comfort food. Whether it’s brunch in the sunshine or cocktails under the stars, it’s always a picture-perfect moment. Learn more >>
Where to drink near the conference venue
River North is packed with sleek lounges, buzzing bars, and cozy hideaways — perfect for unwinding after a busy day at the event. Whether you’re after expertly crafted cocktails, bold local brews, a refined glass of wine, or a refreshing zero-proof option, you’ll find plenty to sip and savor just steps away.
The Redhead Piano Bar
(0.8 mi) $$
Tucked just off the Magnificent Mile, The Redhead Piano Bar offers an old-school Chicago charm with nightly live piano performances and a deep selection of fine spirits and cigars. Its intimate, low-lit atmosphere makes it a memorable spot for a post-conference wind-down or casual conversation over a classic cocktail. Learn more >>
Tiny Tapp
(0.4 mi) $$
A no-frills, old-school dive bar that’s beloved by locals and downtown workers alike. Known for its casual vibe, cheap drinks, and classic Chicago atmosphere, it’s a great spot to relax without the fuss — think bar stools, beer signs, and good conversation. A fun contrast to the flashier lounges nearby. Learn more >>
The Violet Hour
(0.5 mi) $$$
Known for its pioneering approach to cocktail culture in Chicago, The Violet Hour focuses on craft, ambiance, and inventive drinks. If their seasonal pop-up or collab is running near the hotel, it’s well worth checking out for a refined, mixologist-driven experience. Learn more >>
ROOF on theWit
(0.4 mi) $$$
A swanky rooftop bar offering skyline views, stylish seating, and a curated cocktail menu. It’s ideal for conference guests looking for a chic environment to unwind, entertain, or take in the city lights over a handcrafted drink. Learn more >>