two nights in

Chicago

Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. Wikivoyage

Population 2,746,388 (Wikidata)

Live guide From your hotel

Before you go

Emergency numbers in United States

Visas and entry What your passport needs for United States

Getting there

Remembered in this browser only, with the last few you used.

Still gathering the markets around Chicago. I'll let you know here when it's all in — or open the live guide.

Best-documented sights

All of them in the guide

Within a kilometre of the centre, ordered by how well documented each is — not by a "best" anyone decided. Each opens on the map in the guide. Photos from Wikimedia Commons, credited there.

Through the year

  1. Chicago International Children's Film Festival

    October

    In 1983, Facets Multi-Media founded the Chicago International Children's Film Festival (CICFF), the first competitive festival of films for children in the U.S.

    Official site Wikipedia

  2. Chicago International Film Festival

    October

    The Chicago International Film Festival is an annual film festival held every fall. Founded in 1964 by filmmaker and graphic artist Michael Kutza, it is the longest-running competitive film festival in North America.

    Official site Wikipedia

  3. Christkindlmarket

    November

    Christkindlmarket is a Christmas market held annually at Daley Plaza in Chicago, Illinois, United States. The festival attracts more than 1 million visitors each year.

    Wikipedia

Annual events from Wikidata and Wikivoyage; descriptions from Wikipedia where it has one, photos from Wikimedia Commons. Dates move year to year — check before you plan around one.

Eating nearby

All 79 places to eat

Somewhere to run

Getting around

More train stations: Van Buren Street 420 m, Museum Campus/11th Street 880 m, Chicago Union Station 1.0 km, Millennium Station 1.0 km, Ogilvie Transportation Center 1.4 km, 18th Street 2.2 km, Halsted Street 2.3 km, McCormick Place 2.8 km, 27th Street 3.7 km, 35th Street 4.9 km, Western Avenue 5.2 km, Clybourn 5.7 km

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Places © OpenStreetMap contributors, as of 9 October 2026. Description from Wikivoyage (CC BY-SA). Events from Wikidata and Wikivoyage, population from Wikidata.