The Illinois city has topped Time Out's City Life Index, ranking it the best city in the world, closely followed by Porto, New York, Melbourne and London.
Whilst you're in Chicago, make sure to stop off at Millennium Park, the 24.5 acre park which hosts free concerts and has a number of public art installations. In its centre, the Jay Pritzker Pavilion - which is designed by Frank Gehry - is regularly home to a number of outdoor festivals and concerts and there is also offerings for alfresco dining.
There is also the Art Institute of Chicago, which is adorned by two bronze lions, is home to 300,000 artworks as well as The Field Museum, which houses Egyptian mummies, dinosaur skeletons and even a range of rare jewels.
If you'd rather take in nature, there is a beautiful riverside walk to be had in Chicago, where you can enjoy all the architecture this cosmopolitan city offers.
James Manning, City Life Editor of Time Out, said: "This year's Time Out City Life Index reveals the urban hotspots that are unbeatable right now, and the detailed results provide a fascinating look at how people make the most of city life in 2018. Chicago, Porto, NYC, Melbourne and London are this year's top five - a list that shows how different, diverse and unique great cities can be. They really should be on everyone's travel bucket list for this year, along with many other cities in our global ranking."