Welcome to my curated guide to exploring Chicago: a city where skyline views meet deep-dish cravings, lakefront walks, and a vibrant arts scene. Whether you’re a local looking for hidden gems or visiting for the first time, this list highlights the b...
Sections
5
Outdoor Activities
Restaurants
Other Food + Drinks
Arts + Entertainment
Local Favorites
Outdoor Activities
From lakefront walks to skyline views, Chicago’s outdoor spaces are unmatched. Explore scenic spots like Millennium Park, the Riverwalk, and the Lakefront Trail, or unwind with a picnic at a local park. Whether you’re into biking, kayaking, or simply...
get a unique skyline view from the water
Urban Kayaks | Chicago Kayak Tours & Lakefront rentals
run north–south along the lake, passing beaches, parks, and lagoons
Divvy Bike Rental
see the city’s famous buildings from its waterways
Chicago Architecture Center River Cruise aboard First Lady
for a treetop adventure just outside downtown
Chicago Ziplining & Ropes Course | All Ages Obstacle Course - Go Ape
seeing the bean is a must! stroll through gardens and open-air art spaces; a classic mix of nature and city design
Cloud Gate in Millennium Park
Restaurants
Chicago’s food scene is a world of its own; from deep-dish pizza and hot dogs to upscale dining and fusion favorites. This section highlights must-visit restaurants that capture the city’s flavor, whether you’re after comfort food, date-night ambianc...
local favorite for brisket and smoked meats
Smoque BBQ
Neapolitan-style pizza that some say rivals what you’d find in Italy.
Spacca Napoli Pizzeria
upscale, vintage steakhouse vibes and standout food
Bavette's
Mediterranean tapas-style, with a nice rooftop patio
Aba Restaurants
fun, lively spot (in Pilsen) with BBQ, live music, and Southern-influenced eats
Honky Tonk BBQ / The Tonk
Other Food + Drinks
Coffee shops, dessert bars, and hidden cocktail lounges; this is where you’ll find Chicago’s best spots to sip, snack, and unwind. Perfect for a casual catch-up, a solo reading session, or a late-night treat. Expect cozy atmospheres, aesthetic interi...
a Wicker Park favorite with retro/vintage vibes
The Wormhole Coffee (@thewormholecoffee) · Chicago, IL
Lakeview spot known for in-house syrups and creative drinks
Coffee Lab & Roasters
more than a Starbucks…a whole experience
Starbucks Reserve Roastery
aesthetic café in the city’s museum / historic district area
3 Arts Club Cafe at RH Chicago
community-forward café with a cozy, local feel
Kusanya Cafe
Arts + Entertainment
Chicago’s creative side shines through its museums, theaters, galleries, and live events. Here you’ll find must-see attractions, cultural exhibits, and entertainment that defines the city’s vibrant energy; from improv shows and street art to immersiv...
world-class collections and rotating exhibits
The Art Institute of Chicago
natural history and immersive exhibits
Field Museum
fun, interactive and Instagram-worthy illusions
Museum of Illusions Chicago
dive into the city’s story and culture
Chicago History Museum
space, stars, astronomy in a gorgeous lakeside setting
Adler Planetarium
Local Favorites
These are the hidden gems and community-loved spots that make Chicago feel like home. Think thrift stores, local boutiques, indie bookstores, cozy nooks, and neighborhood hangouts; the places locals keep coming back to and visitors fall in love with.
an offbeat bar/music venue tucked away but beloved by locals
Hideout Chicago | Live Music and Events | Chicago, IL
family-owned Mexican spot with authentic vibes
La Casa De Samuel
unique cafe that provides delicious food and cool art; also perfect for Instagram photos
2d restaurant - Mochi Donuts and Fried Chicken
local favorite for scratch cooking and warm service
