Creative small plates from Top Chef winner Stephanie Izard
Bold flavors, packed house nightly
West Loop staple
Famous for caramelized crust deep-dish
Casual, old-school setting
A local go-to for Chicago-style pies
Modernist tasting menu with a global reputation
Three Michelin stars
Dining as theater in Lincoln Park
Soul food with a modern touch
Shrimp & grits, gumbo, fried chicken
Friendly and unpretentious in Lincoln Square
Farm-driven fine dining with a rustic vibe
Intimate space, deeply seasonal menus
Michelin-starred, low-key feel
Mediterranean small plates
Long communal tables, minimalist aesthetic
Located in the heart of the West Loop
Scenic path along the Chicago River
Cafés, art installations, and skyline views
Great for daytime exploring
Masterpieces from Monet to Warhol
Renzo Piano-designed modern wing
One of the oldest and most respected U.S. museums
Deep dive into the city’s skyline story
Runs along the river with expert guides
A must-do even for locals
Home to “The Bean” and open-air art
Music pavilion and seasonal skating
Central, walkable, always active
Indie shops, cafés, record stores
Street art and murals on nearly every block
Hip without being forced
Carnival-style rides, views of Lake Michigan
Boat cruises, food halls, and fireworks in summer
Family-friendly and photo-friendly
High-concept cocktail lab from the Alinea team
Multi-sensory drinks served like works of art
Futuristic, exclusive, unforgettable
Tropical bar with deep tiki vibes
Creative rum-based cocktails
Cozy, colorful, and just a little wild
Speakeasy behind an ever-changing mural
Dim lighting, classic cocktails, strict phone rules
Sophisticated without being stiff
Underground tiki bar with big energy
Dramatic presentations, exotic ingredients
Hidden entrance in an alley
Gin-focused bar in Logan Square
Neighborhood favorite with late-night snacks
Great for date nights or relaxed hangs
Inside the ACME Hotel
“Dealer’s Choice” menu built to your taste
Stylish but approachable
West Loop boutique stay with rooftop vibes
In-house dining, coworking, great location
Young, stylish, and buzzing
Set in a 1920s art deco building in Wicker Park
Rooftop views, sleek rooms
Blends old Chicago with modern edge
Housed in the Carbide & Carbon Building
Glamour without flash
Central and upscale without trying too hard
Members club feel with hotel access
Industrial-chic rooms, rooftop pool
Built for creative travelers
Towering riverfront elegance
Sleek design, full spa, luxury service
Business meets pleasure in style
Budget-friendly but cool
Private rooms and shared spaces
Social, artsy, and central
You get the skyline and the swagger—but people still hold the door.
Deep-dish, high-concept tasting menus, taco trucks—it’s all here, and it’s all serious.
Architecture, art, music, sports—Chicago doesn’t play small.
Maximize your time by avoiding the traps and hitting the real highlights.
Early morning picks from River North to Wicker Park.
Markets, museums, and where to end the day with a drink.
Chicago for First-Timers: What to Skip and What to See
You don’t need to do everything—just do the right things.
Skip Navy Pier if you’re short on time. Go for the Riverwalk instead.
See Millennium Park early before the crowd shows.
Don’t sleep on neighborhood exploring. Logan Square and Pilsen offer real flavor.
Start your day right—whether it’s slow or on the run.
Sawada Coffee (West Loop) – Matcha and espresso in one bold space.
Do-Rite Donuts (Downtown) – Fried fresh, with killer breakfast sandwiches.
Lula Café (Logan Square) – Slow brunch that’s worth the wait.
Here’s a full-day plan that delivers without overdoing it.
Morning: Coffee + Riverwalk stroll.
Midday: Art Institute or shopping on Milwaukee Ave.
Evening: Dinner in the West Loop, then cocktails at Violet Hour.