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Chicago Hot Spots
15
items Discover the best things to do in Chicago! From iconic landmarks and skyline views to world-class museums and local neighborhoods, this list covers must-see attractions and hidden gems. Perfect for first-time visitors or locals wanting to explore the...
Sections
5
Touristy But Worth It
Food & Drinks
Date Night Ideas
Hidden Gems
Things to Do
Touristy But Worth It
Chicago’s famous attractions are popular for a reason. These iconic spots deliver unforgettable experiences that even locals love to revisit.
An iconic Chicago landmark with stunning lake views, restaurants, shops, and seasonal events. Great for family outings or date nights with endless things to do in one spot.
Navy Pier - Chicago's Lakefront Playground
Whether you're an art lover or not, this museum is jaw-dropping. From Grant Wood’s American Gothic to Monet’s dreamy water lilies, it’s a cultural deep dive that never feels boring. Pro tip: enter through the Modern Wing and walk your way back in tim...
The Art Institute of Chicago
Yes, it's super touristy — but stepping out onto The Ledge, a glass box 1,353 feet in the air, is an adrenaline rush you don’t forget. Go right before sunset for dreamy skyline views and fewer crowds.
Skydeck Chicago
Food & Drinks
From cozy brunch nooks to sleek cocktail bars, these Chicago favorites are perfect for satisfying your cravings and sipping in style.
A Mediterranean-inspired staple that’s cozy, stylish, and consistently delicious. The chorizo-stuffed dates and signature focaccia are must-orders. Bonus: perfect for solo dining at the bar, too.
avec Restaurant (West Loop)
A Michelin-starred Filipino bakery and restaurant in East Ukrainian Village. Come for the croissants and lattes in the morning, stay for the mind-blowing tasting menu at night. Casual vibes, serious flavor.
Kasama Bakery
An award-winning Italian restaurant in the West Loop where handmade pastas steal the show. Cozy, lively, and perfect for a memorable dinner — don’t skip the cacio e pepe or the burrata-filled ravioli.
Monteverde (West Loop)
Date Night Ideas
Whether it’s a first date or a weekly ritual, these romantic Chicago spots set the scene for memorable nights out.
Think live jazz, hidden rooms, and vintage cocktails. It’s romantic without trying too hard — the perfect spot when you want to dress up a little and impress.
The Darling (West Loop)
Live classical music in candlelit venues like churches or theaters? It’s as dreamy as it sounds. Check the rotating schedule — there’s something for every taste, from Vivaldi to Beyoncé covers.
Candlelight Concert Series
Stunning views of Millennium Park and Lake Michigan, especially at golden hour. Grab a craft cocktail and feel like you're in a movie.
Drinks at Cindy's Rooftop
Hidden Gems
Step off the beaten path and explore Chicago’s lesser-known treasures — unique spots you’ll want to keep all to yourself.
A mind-blowing, intimate magic show inside the Palmer House Hilton. Not many tourists know about it, but it books up fast — reserve early.
The Magic Parlour with Dennis Watkins
Discover a treasure trove of carefully curated vintage clothing and accessories at Very Best Vintage. This charming boutique offers unique, high-quality pieces spanning decades, perfect for fashion lovers who want to stand out with authentic retro st...
Very Best Vintage
Step into Dovetail, a cozy and stylish shop known for its handcrafted goods, home décor, and local artisan products. This hidden gem champions creativity and quality, offering everything from thoughtfully designed ceramics to chic lifestyle accessori...
Dovetail Vintage Shop
Things to Do
Fun, engaging activities that let you experience Chicago like a local — perfect for weekends, visitors, or a little “me time.”
The best way to take in the city’s legendary skyline. Cruise along the Chicago River while learning about the history, design, and drama behind some of the most iconic buildings from knowledgeable guides. It’s touristy, sure — but absolutely unforget...
River Boat Architecture Tour
A summer night staple — enjoy cocktails and live jazz while wandering the aquarium after hours. Views of the skyline from the terrace are unmatched.
Jazzin' at the Shedd Aquarium
An outdoor farmers market that’s part local culture, part Instagram moment. Pick up fresh flowers, artisanal snacks, and vibe with locals.
Green City Market (Lincoln Park)