Your Perfect 3-Day Itinerary for Chicago

Discover the best landmarks, where to eat, and where to stay in Chicago.

Best Time to Visit Chicago

Spring

Mar - May

15°C / 6°C

Crisp, unpredictable, and often windy

Summer

Jun - Aug

28°C / 19°C

Warm and lively, perfect for lakefront activities

Fall

Sep - Nov

17°C / 8°C

Cool and colorful, great for walking

Winter

Dec - Feb

2°C / -6°C

Freezing, snowy, and famously windy

Day 1

Cloud Gate (The Bean)

Morning activity: Cloud Gate (The Bean).

Lou Malnati's Pizzeria

Lunch nearby: Lou Malnati's Pizzeria.

Art Institute of Chicago

Afternoon sightseeing: Art Institute of Chicago.

Girl & The Goat

Dinner in the area: Girl & The Goat.

Architecture River Cruise

Evening experience: Architecture River Cruise.

Day 2

Willis Tower Skydeck

Morning activity: Willis Tower Skydeck.

Portillo's Hot Dogs

Lunch nearby: Portillo's Hot Dogs.

Navy Pier

Afternoon sightseeing: Navy Pier.

Alinea

Dinner in the area: Alinea.

The Second City

Evening experience: The Second City.

Day 3

Field Museum

Morning activity: Field Museum.

Au Cheval

Lunch nearby: Au Cheval.

The Magnificent Mile

Afternoon sightseeing: The Magnificent Mile.

Bavette's Bar & Boeuf

Dinner in the area: Bavette's Bar & Boeuf.

360 Chicago Observation Deck

Evening experience: 360 Chicago Observation Deck.

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