Your Perfect 3-Day Itinerary for Chicago
Admire the bold architecture of Chicago, a major lakeside metropolis known for its deep-dish pizza, renowned museums, and vibrant arts community.
Chicago is served by O’Hare and Midway airports and is a major rail hub. The L (elevated train) and buses make getting around straightforward; the Loop and lakefront are walkable. Summer and fall are the most pleasant; winter is cold and snowy but has its own charm. Book architecture cruises, museum tickets, and popular restaurants in advance. Allow time for the Art Institute, Millennium Park, neighbourhoods like Wicker Park and Logan Square, and deep-dish and hot dogs. The lakefront and river walks are highlights.
Discover the best landmarks, where to eat, and where to stay in Chicago.
Best Time to Visit Chicago
Spring
15°C / 6°C
Crisp, unpredictable, and often windy
Summer
28°C / 19°C
Warm and lively, perfect for lakefront activities
Fall
17°C / 8°C
Cool and colorful, great for walking
Winter
2°C / -6°C
Freezing, snowy, and famously windy
Day 1
Cloud Gate (The Bean)
Huge outdoor sculpture shaped like a bean & allowing for views from its many mirrored sides.
Morning activity: Cloud Gate (The Bean).
Lou Malnati's Pizzeria
Family-owned local chain for Italian classics & Chicago-style, deep-dish pizzas with buttery crusts.
Lunch nearby: Lou Malnati's Pizzeria.
Art Institute of Chicago
Renowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
Afternoon sightseeing: Art Institute of Chicago.
Girl & The Goat
Hot spot where Stephanie Izard serves up innovative small plates from a dramatic open kitchen.
Dinner in the area: Girl & The Goat.
Architecture River Cruise
Evening experience: Architecture River Cruise.
Day 2
Willis Tower Skydeck
103rd floor of the Willis Tower with clear observation boxes & views extending to four states.
Morning activity: Willis Tower Skydeck.
Portillo's Hot Dogs
Chicago-born chain for hot dogs, Italian beef sandwiches & more, plus beer & wine, in retro digs.
Lunch nearby: Portillo's Hot Dogs.
Navy Pier
Former Navy training center draws crowds with carnival rides, restaurants, shops & fireworks.
Afternoon sightseeing: Navy Pier.
Alinea
Chef Grant Achatz draws foodies with New American tasting menus featuring highly creative plates.
Dinner in the area: Alinea.
The Second City
Known for its many famous alums, this storied spot hosts popular sketch shows & improv classes.
Evening experience: The Second City.
Day 3
Field Museum
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
Morning activity: Field Museum.
Au Cheval
Diner with an open kitchen using ingredients ranging from bologna to foie gras.
Lunch nearby: Au Cheval.
The Magnificent Mile
Afternoon sightseeing: The Magnificent Mile.
Bavette's Bar & Boeuf
Upscale steakhouse with a New American menu in an ornate, dimly lit wood & brick setting.
Dinner in the area: Bavette's Bar & Boeuf.
360 Chicago Observation Deck
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
Evening experience: 360 Chicago Observation Deck.