On a scale of 1 to 10, how would you rate the amount of fun Chicago brings you? I’ll give you a few seconds to think about your rating. Meanwhile, apparently, our beloved Windy City is among the Top 10 most fun cities in America this year (yet again!), according to Wallethub. In this report, Wallethub compared more than 180 U.S. cities based on 65 key metrics, such as fitness center density, movie costs, average open hours, etc.

Eat & Drink

Our culinary scene is probably the most famous aspect when people ask what’s so fun about Chicago. From unique cuisines, fine dining restaurants, to more innovative dining concepts, pop ups, and underrated neighborhood spots, Chicago can satisfy every human being. Honestly, there are only food you have yet thought of, but never something Chicago cannot offer.

If you’re looking for something to get your feet wet with Chicago’s food scene, check out these articles we have:


The ultimate guide to the best ramens in Chicago
Underrated hidden gems in every Chicago neighborhood
Speakeasies and underground bars that redefine drinking experience
The best heated rooftops in Chicago

Music & Art

Chicago’s entertainment world is at least 60% art. From our vibrant performers, dancers, jazz musicians, and musicians of other genres, to a diverse and multidisciplinary art scene, Chicago is truly a heaven on earth for those who sees the beauty beyond this mundane reality. There are plenty of bars and restaurants with live music, comedy clubs, established high-end galleries, and artist-run organizations in Chicago. You’ll also find museums of all sorts (science, installation, sculpture, ethnic art…) throughout the city!


In the meantime, don’t forget to check out the many theaters in town. The Chicago Danztheatre had just announced their 2023 programming, and the Marriott Theater is presenting A Christmas Story: The Musical, followed by the all-time classic, Little Woman. Other independent theaters, Broadway Chicago, and Chicago Shakes have also announced their new programming for the upcoming year.

Entertainment & Experience

From WNDR Museum’s infinity room to MOIC’s latest Pinkmas remake, Chicago’s entertainment is all about building an unforgettable experience. For example, the many holiday pop-ups are here to bring holiday festivities to the peak. Meanwhile, children and adults alike will have an unforgettable time at iconic Chicago locations such as the Children’s Museum, Shedd Aquarium, and Lincoln Park Zoo.

At the same time, Chicago has plenty of classic experience and tour routes for those new to the city, or, if you want to remind yourself of the profound culture and history, our lovely Windy City beholds. Some of the all time favorites are the Chicago Architecture Tour, Chicago Culture Center Building Tour, the Skydeck, the Bean (and right now, the tree at Millenium Park), and of course, the Art Institute!


You’ll never have trouble treating yourself and your loved one to wonderful gifts if you are in Chicago. And let’s admit it: shopping makes life fun because it gives meaning to our daily grind. What’s the point of busting our butts off if we don’t get to spend, right? Naturally, plenty of name brands are lined up along the lake, let alone the malls and outlets in the adjacent burbs. However, Chicago is also a treasure island for those with unique tastes. Explore the many farmer’s markets, street fairs, and neighborhood markets, or check out the countless artisan and independent shops. If you need help getting started, below are a few shopping guides we’ve published:

Best thrift shops for a vintage hunt
The best independent bookstores in Chicago
The best craft candle shops in Chicago
Boutique clothing stores we love for wardrobe upgrades
Your guide to the best stocking stuffers from Chicago small businesses

Nature & Outdoors

If you ever thought Chicago is all about skyscrapers and busy traffic, you’re so wrong. The Windy City is never short of beautiful outdoors and peaceful nature, even within the booming city area! Here, explore some hidden parks and trails when you need some me time, or even take a short drive to the closest forest preserve. For those who enjoy outdoor activities, the 606 Trail is deeply loved by cyclists and roller skaters. And now that winter is here, so are the many ice rinks across the city. Even if you don’t like sports, the heated patios and rooftops will still let you enjoy the outdoors without getting sweaty or having to deal with the cold!

Love Life

Ahem, ahem. We’re finally at this topic. Honestly, if you live in Chicago but can’t figure romance out…you know what, Imma drop this line of conversation. The point is, Chicago is the perfect place for a perfect date, regardless of your date’s interests and personality! Our neighborhoods are so diverse and full of characters: some focus on history and culture, others are known for the popping night life.

If you want some advice, check out our Chicago dating guides: Lakeview, Lincoln Park, West Loop, Pilsen, Logan Sqaure, Ravenswood. If you didn’t find the one your date lives in, no worries. We’re working on more neighborhood dating guides!

Featured Image: Unsplash

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