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Things to do in Chicago

A lakefront Midwestern city known for skyscraper architecture, deep-dish pizza, blues and jazz, and the Art Institute.

4 of the most-booked tours in Chicago are listed below, rated 4.5 to 4.8 stars from more than 23,000 traveler reviews on GetYourGuide.

📺 Watch the Chicago story

Updated October 18, 2026. Prices and availability come live from the partners when you click; ratings are re-checked on the date shown in the note at the end of the page.

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Top sights in Chicago

  1. Millennium Park – Public park in Chicago, Illinois, USA
  2. Cloud Gate – Public art sculpture in Chicago, Illinois, United States
  3. Navy Pier – Amusement pier in Chicago
  4. Art Institute of Chicago – Art museum and school in Chicago, United States
  5. Willis Tower – Skyscraper in Chicago, Illinois, USA
  6. Magnificent Mile – Section of Michigan Avenue in Chicago, United States
  7. Wrigley Field

Well-known landmarks, each checked against Wikidata (CC0), which also supplies the one-line descriptions. The bookable tours below are the second layer: guided ways to see them.

Top-rated tours in Chicago

See all things to do in Chicago → More tours on Viator →

Planning your trip to Chicago

Best time to visit

Late spring to early autumn is the best, with festivals and lake weather. Winters are very cold and windy, and spring can be changeable.

How many days you need

Three to four days covers the main architecture, a big museum or two, the lakefront and several neighborhoods. Add an evening of live music.

Getting around

The elevated and underground train system covers the main areas, and downtown is walkable. Buses fill in the gaps. Layer up for the wind off the lake.

What to skip

Restaurants clustered on the busiest tourist pier and shopping street are aimed at visitors. Neighborhoods just outside the center have a wider range of places to eat.

Where to stay in Chicago

Hotels and vacation rentals around Chicago with live prices from the big booking sites. Pick your dates on the map to compare.

Hotel map by our partner Stay22. If you book through it we may earn a commission, at no extra cost to you.

Best time to visit Chicago

By temperature and rainfall alone, the most comfortable months in Chicago are June to September, with average daytime highs of 76 to 82°F (24 to 28°C) and 10 to 12 rainy days a month. This is a weather-data pick that has not yet been checked against crowds, closures or local seasons. July is the hottest month, averaging 82°F (28°C), and January the coolest at 33°F (1°C). April sees the most rain, around 14 days, while November is the driest with about 7.

Jump to a month: Jan Feb Mar Apr May Jun Jul Aug Sep Oct Nov Dec

MonthAvg highAvg lowRain (about, mm)Rainy daysVerdict
January33°F (1°C)21°F (-6°C)5010Avoid: cold, 33°F (1°C)
February37°F (3°C)21°F (-6°C)509Avoid: cold, 37°F (3°C)
March48°F (9°C)32°F (0°C)6011Shoulder: 48°F (9°C), 11 rainy days
April58°F (14°C)40°F (4°C)9014Avoid: among the wettest, 14 rainy days
May67°F (19°C)51°F (11°C)12013Avoid: among the wettest, 13 rainy days
June79°F (26°C)62°F (17°C)10012Comfortable: 12 rainy days
July82°F (28°C)67°F (19°C)10012Comfortable: 12 rainy days
August81°F (27°C)66°F (19°C)10011Comfortable: 11 rainy days
September76°F (24°C)61°F (16°C)9010Comfortable: 10 rainy days
October63°F (17°C)49°F (9°C)10013Avoid: among the wettest, 13 rainy days
November49°F (9°C)36°F (2°C)607Shoulder: 49°F (9°C), 7 rainy days
December41°F (5°C)29°F (-2°C)608Shoulder: 41°F (5°C), 8 rainy days

Average daily high and low, and days with rain (a day with at least 1 mm), from Open-Meteo ERA5 records for 2019-2024. Highlighted rows are the pick above. Verdicts use only these numbers.

Rainfall: NASA POWER monthly normals. Sea temperature: NOAA daily satellite data.

Plan the rest of your trip to Chicago

🏨Hotels in ChicagoCompare hotels and apartments through our partner RateHawk. 🚗Car rental in ChicagoCompare car rental prices in Chicago with Discover Cars. 🎟️What’s on in ChicagoSee upcoming concerts, sports and shows from Ticketmaster. 🏨Hotels in ChicagoHotels and vacation rentals with free-cancellation filters, from ZenHotels. 🎫Go City pass for ChicagoOne pass for many top attractions, so you save on entry to the sights you want. 🎟️Museum and attraction ticketsSkip-the-line tickets for top sights in Chicago, from Tiqets. 🧭Guided tours of ChicagoExpert-led small-group and private tours from ExperienceFirst. 🛋️Private luxury ground travelLandJet for 50 to 400 mile trips in the central U.S. 👻Ghost tours in ChicagoHaunted history walks, pub crawls and ghost hunts after dark, from US Ghost Adventures. EVASIM eSIM for the USA: 5% off with code VOYAGGORA ✈️Flights to ChicagoCompare airfares on Trip.com and search your route. 🛎️Hotels in Chicago on Trip.comCompare hotels and homes in Chicago for your dates. 🏩Hotels in Chicago on ExpediaCompare hotel prices and reviews on Expedia for your dates. 🎫Is a city pass worth it?How to tell if a sightseeing pass will save you money in Chicago, before you buy. 🍝Eating near the big sightsHow to avoid tourist-trap restaurants near Chicago’s landmarks and find a better meal nearby. 🎡Things to do in Chicago on ExpediaTours, tickets and activities you can book on Expedia. 🏡Vacation rentals in Chicago on VrboWhole homes, villas and apartments with room for everyone. 🚖Airport transfer in ChicagoPre-book a driver who meets you at arrivals, from Welcome Pickups. 🧭Transfer, taxi or rideshare?Our guide to choosing the best ride from the airport into Chicago. 🧳Luggage storage in ChicagoDrop your bags at a nearby shop or hotel and explore hands-free, with Radical Storage. 🙋Private local guideCustomizable private tours with vetted local guides from GoWithGuide. 📱eSIM data planGet mobile data before you land, with Airalo. 📶eSIM, roaming or local SIM?Our guide to staying connected on a short trip to Chicago. 🛡️Travel insuranceCompare travel medical and cancellation cover with HelloSafe. ⏱️Flight delayed or cancelled?Check if you are owed compensation, with AirHelp. ✦Ask our AI conciergeTell us how many days you have and what you enjoy, and get a plan for Chicago. 🏨Hotels in Chicago on AgodaCompare hotel prices and reviews on Agoda, via our partner Stay22.🔎Compare hotels in Chicago on KAYAKSearch and compare hundreds of hotel sites at once, via our partner Stay22.🛂Do you need a visa for Chicago, United States?Check entry requirements and apply online with eVisas.com, a private visa service (service fee applies).🚗Car rental in Chicago on VIP CarsCompare car rental prices from 800+ suppliers.✈️Package holidays to Chicago (German site)Flights and hotels from Eurowings Holidays.

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Closest guides to Chicago

Planning guides

Is it safe to travel to United States right now?

Official US, UK and Canada travel advice for United States, side by side, with each source and the time it was checked. See today's advisory for United States

Chicago: common questions

When is the best time to visit Chicago?
By temperature and rainfall alone, the most comfortable months in Chicago are June to September, when average highs run 76 to 82°F (24 to 28°C) with 10 to 12 rainy days a month. This is a weather-data pick, not yet checked against crowds, closures or local seasons. July is the hottest month at 82°F (28°C) on average, and January the coolest at 33°F (1°C).
What is the rainiest month in Chicago?
April, with roughly 14 days of rain. The driest is November, with about 7. A rainy day is a day with at least 1 mm of rain; figures are averages from 2019-2024 records.
How warm does it get in Chicago?
July is the warmest month, averaging 82°F (28°C) by day and 67°F (19°C) at night. January is the coolest, at 33°F (1°C) by day and 21°F (-6°C) at night.
What is the rainy season in Chicago?
The wettest months in Chicago are March to August and October, with 11 to 14 rainy days a month. November is the driest.
How many days do you need in Chicago?
Three days covers the Loop and Millennium Park, an architecture river cruise, a museum or two on the Museum Campus and a Wrigleyville or neighborhood evening. Add a day for the lakefront trail, Lincoln Park and a second neighborhood such as Pilsen or Wicker Park.
How do I get around Chicago?
The L train system reaches most visitor areas and connects both airports with downtown. The Loop and the Magnificent Mile are walkable, and buses cover routes the trains miss. Divvy bike share is good along the lakefront. A car is unnecessary downtown and parking is costly.
Is it safe to travel to United States right now?
Voyaggora shows the official US, UK and Canada travel advisories for United States on one page, with the source and the time each was last checked. Open the live advisory for United States before you book.
What other places are near Chicago?
The closest Voyaggora guides to Chicago are Nashville (400 miles), Toronto (440 miles), Niagara Falls (450 miles).

Some links on this page are sponsored: if you book through them we may earn a commission at no extra cost to you. Ratings and review counts come from GetYourGuide and were last checked on September 28, 2026. Prices, availability and rules are set by the providers and change often. See our affiliate disclosure.