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Chicago is a city buzzing with boundless excitement and energy, but its friendly people and welcoming atmosphere are what really set it apart from other destinations. You feel at home in Chicago from the second you arrive until the moment you leave, whether you're looking for a low-key weekend with friends or an activity-packed week of exhilaration and adventures. With an endless number of world-class restaurants, sightseeing, architecture, shopping, live music, theatre—you name it, Chicago has everything you need to plan your dream vacation.

Rest assured, with so much to do, the most difficult part of your trip will be finding the time to see everything on your list! To help with your planning, we've outlined a few of our favorite summer "bucket list" activities, from timeless Chicago essentials to seasonal events and shows.

1. Millennium Park and the Chicago Cultural Mile: Explore Michigan avenue and cover downtown Chicago's highlights, including Millennium Park (named one of the six Great Places in America by the APA) and the Art Institute of Chicago. Snap a picture of your reflection in Cloud Gate, a.k.a. the giant bean (because, let's be honest, a #BeanSelfie is basically a requirement when visiting Chicago). Tip: Be sure to exit Millennium Park along the BP Bridge, a pedestrian walkway with some of the city's best skyline views.
2. Summer Food Festivals: Satisfy your inner foodie and taste an endless variety of eats and treats at one of Chicago's many food festivals. From Taste of Chicago on the lakefront (highlighting the city's diverse, world-class cuisine) to Ribfest in North Center or the Taste of Randolph Street festival, there's something for everyone.
3. Chicago Friday Night Flights: Discover Chicago's robust craft beer scene at these new bi-monthly events running June–August. Taste an array of beers from various Chicago neighborhoods while enjoying live music from local bands and discovering neighborhood eats. Tip: Avoid lines and save $5 by buying your tasting pass in advance online.
4. Kayak the Chicago River: Enjoy the great outdoors while taking in views of the river, architectural masterpieces, the Chicago skyline, and the Riverwalk. Rent kayaks to explore solo, or take a guided tour to hear more about the city. Tip: Take a sunset kayak tour for majestic sunset views of Chicago.
5. Summer Music Showcases: Take advantage of the numerous outdoor concerts under the stars in Millennium Park (many of them are free!) or experience one of the city's many music festivals, from Lollapalooza to the Chicago Blues Festival.

These activities barely even scratch the surface of all that Chicago has to offer, but they're a great place to start planning your summer escape!