2026 Chicago Travel Guide: must-see attractions, popular food, hotels, transport & travel experiences (updated in January)

What do you want from an unforgettable city vacation? Iconic monuments, diverse culture, exciting food scene, serious shopping, all wrapped up in a beautiful setting? Chicago has it all and more.Chicago is ranked as the third-largest metropolitan area in the United States and the most populous city in the Midwestern. This city by the lake, also known as the windy city, is situated in the Great Lakes region of northeastern Illinois. Beyond the City of Chicago, the greater Chicagoland area extends into the neighboring states of Wisconsin and Indiana. The windy city is also culturally diverse with approximately 2.7 million residents. There are 50 districts or 77 designated community areas in the City of Chicago, the Loop is the central business district and home to the tallest skyscrapers, top attractions, and shopping areas.Situated near the southern tip of Lake Michigan, Chicago started as a small trading post at the mouth of the Chicago River. Its ideal geographical location made it a vital link in the great waterway, and later on, with the expansion of railways, Chicago was transformed into the country’s railway hub. The rise of the city was not all smooth sailing, as in the Great Fire of 1871 about one-third of Chicago was destroyed. But it rose from the ashes like a phoenix and made itself a global center for finance, commerce, industry, transportation, and tourism.Chicago boasts a diverse variety of tourist attractions, for example, every year tens of thousands of visitors come to the city just to marvel at its impressive and iconic buildings in postmodernist and gothic revival architectural styles. But it is not just the architecture that attracts people to the city by the lake. There are endless unique and fun experiences to be had here, such as enjoying the classic rides at Navy Pier, overcoming your vertigo at 360 Chicago Observation Deck, getting to know the urban art scene on a street art tour, and soaking in the sun and skyline on a cruise. If after all that excitement you want to escape to nature, Garfield Park Conservatory, Chicago Botanic Garden, and the Morton Arboretum are your best bet.