Things to do in Chicago: sights, day-by-day itinerary and weather

Things to do in Chicago (United States): Pillar of Fire, Comiskey Park Home Plate, Stearns Quarry, Chess Studio, Jane Addams Hull-House Museum, 1 day-by-day itinerary, month-by-month weather, the best time to go and hotels.

Travel itineraries in Chicago

Hotels in Chicago

Frequently asked questions about Chicago

When is the best time to visit Chicago?

According to real weather data (2023-2024 averages), the months with 18–33 °C daytime highs and under 100 mm of rain in Chicago are: May, June, August, October.

How many days do you need in Chicago?

Our 1 day-by-day plans for Chicago last 4 days.

How much does a trip to Chicago cost?

On site (flights excluded), our plans start at €1100–1600 per person for 4 days, including lodging, meals, visits and transport.

What to do in Chicago in 4 days?

Our “Chicago, Capital of Architecture” plan: Day 1 — Arrival & Millennium Park; Day 2 — Architecture & Willis Tower; Day 3 — Museums & Navy Pier; Day 4 — Departure.

Where to stay in Chicago?

Close to the tourist centre: Jaslin Hotel (1.3 km), Benedictine Bed and Breakfast (1.4 km), SpringHill Suites Chicago Chinatown (1.5 km). Our directory lists 228 hotels in Chicago, to contact directly.

What to see in Chicago?

Some places to see in the centre: Pillar of Fire, Comiskey Park Home Plate, Stearns Quarry, Chicago Skyline, Chess Studio, Jane Addams Hull-House Museum.

Sights in Chicago

Museums in Chicago

Parks and gardens in Chicago

Where to eat in Chicago