Build your Chicago itinerary with this bucket list of things to eat, drink, see and do. These are the classics. The essentials. But by no means does our bucket list cover all that the city has going on. You could stay here for days, weeks, months...and STILL not get to everything.
Any shopping adventure in Chicago should begin with the granddaddy of all Chicago retail: The Magnificent Mile. This cosmopolitan, history-packed section of Michigan Avenue teems with shopping, dining, and entertainment treasures that make any vacation unforgettable.
An endless number of events fill every minute of the day in Chicago... our calendar is the place to start. Take part in our featured festivals — Chicago is where Lollapalooza and Pitchfork crank it up each summer, and where locals treat you like neighbors at weekend street fests. Each night at the theater is an event — see a pre-Broadway premiere or watch a novel come to life at one of 200+ theaters. From comedy to concerts, an exhibit opening at the museum to a home opener at the ballpark, do any and all of it.
Find food and drink specials and happy hours in Chicago restaurants and bars. Going out is much cheaper when you visit places that offer Happy Hour specials or feature food and drink specials all day. Use our interactive search tool to find today's Chicago drink specials and discounted food near you, or select a day of the week if you're planning ahead.
It’s no surprise that Chicago is one of the biggest tourist destinations: we have miles of beaches, world-class museums, and some of the friendliest city-dwellers out there. But in such a gigantic city, it can be tough for visitors to know what’s really worth visiting. So whether you’re an out-of-towner or a Chicagoan planning a staycation, we’ve assembled the 25 must-see sites and attractions.
"It is hopeless for the occasional visitor to try to keep up with Chicago. She outgrows his prophecies faster than he can make them." - Mark Twain, 1883 Chicago was only 46 years old when Mark Twain wrote those words, but it had already grown more than 100-fold, from a small trading post at the mouth of the Chicago River into one of the nation’s largest cities, and it wasn’t about to stop.
The best places to stay are in the Loop District in downtown Chicago, where you’ll find most of the major sights and attractions. Chicago is a large city, however, and offers much more than just a bustling downtown district. For a spot of tranquillity and seclusion, you may prefer to stay within the lush scenery surrounding the Chicago O’Hare Airport.
The beauty of Chicago lies not only in its magnificent downtown architecture, but also in the city's vast preserved green space. Chicagoans and locals have over 580 parks, dozens of gardens and 8,300 acres of grass, flowers and trees at their disposal. With beaches, ice rinks and an 18.5-mile long bike path, there's no shortage of options for Chicago's active visitors and locals.
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