Chicago is one of the major cultural hotspots of the world. For a relatively young city, it’s been incredibly influential in the history of Western music, cuisine, civil rights, and more. The cuisine and culture aficionado will be spoiled for choice in Chicago, which is why it helps to have some idea of what to see and do before you touch down in the Windy City. Use this guide to help find the rhythm of Chicago and uncover the best music, food, and landmarks it has to offer.
Set the stage with good accommodation
Your accommodation can make a big difference to your cultural experience of Chicago. Start by looking for good Chicago hotel deals that will get you comfortable, affordable accommodation in the heart of the action. Think about the kind of neighborhood you want to spend the most time in. If you’re looking for gleaming skyline views then downtown neighborhoods have plenty of sleek skyscraper hotels with incredible views. For a more artsy, boutique experience, look for accommodation in neighborhoods like Wicker Park and Logan Square.
If you’re planning on spending long nights at clubs and concerts, think about the logistics of getting home. The red and blue L Train lines run 24 hours, but other lines are more restricted. So think about how you’re going to get back to your accommodation safely after a few drinks at night.
Pick the right time of year
Chicago’s weather is always unpredictable, but every season offers its own unique experience. If you want to spend a lot of time sightseeing outdoors, summer and fall are best, as they don’t have the icy chill of winter and early spring, and the fall foliage is incredible. That being said, winter - although very cold - has a charm all of its own, especially around the festive season when the city lights up for Christmas and winter markets pop up in the parks.
If you’re looking for good deals on flights and hotels, early spring and late fall often see price dips. The flipside of this is that some tourist attractions only open for the tourist season, which runs roughly from May to September.
Experience the soundtrack of the city
Chicago is one of the best cities in the world to visit for music. Chicago shaped the musical soul of the USA - it’s the crucible where jazz, blues, and soul were shaped into the globally popular genres we know today.
Music is ever-present in Chicago. There are plenty of big concerts in stadiums and theaters throughout the city, but you can also get up close and personal with Chicago’s musical heart in one of the cocktail bars and music lounges. Enjoy a traditional jazz night in former speakeasy Green Mill Cocktail Lounge, drop in for the nightly blues show at Blue Chicago, rock out at Reggies, or follow your ears to one of Chicago’s many, many live music venues.
If what you’ve heard gives you an urge to learn more, the Blues Heaven Foundation, the Chicago Hip Hop Heritage Museum, and the Museum of Post Punk and Industrial Music all offer absorbing (and often interactive) insights into Chicago’s musical history. You can also find music-focused exhibitions alongside other artefacts and cultural points of interest in the Chicago History Museum.
Feed your body and your soul
Music may be the food of love, but it’s at its best when it’s paired with actual food. Chicago has a legendary food scene, with a huge diversity of cuisines available throughout the city.
Of course, when people think ‘Chicago food’ they think of the famous deep dish Chicago-style pizza. You can find this iconic city staple all over the city, but some places are famous for their version. Chains like Giordano’s, Lou Malnati’s, and Gino’s East all serve rich, flavour-filled and unapologetically indulgent deep dish pizzas to suit every taste.
If you’ve had enough of cheese and carbs and feel like something a little lighter, Greektown offers a mouthwatering array of Mediterranean restaurants and tavernas. Or, if you’re in the mood for more carbs, head over to Little Italy for the unique Chicago take on Italian cuisine.
There are food stalls, stands, and trucks all over the city, so do yourself a favor and grab some food on the go. Chicago is famous for its hot dog stands, but hot dogs aren’t all that’s on offer. You’ll find everything from tacos to cakes lining the streets, especially in parks and popular areas.
Drink in some iconic sights
No trip to Chicago is complete without taking in some of its landmarks. ‘The Bean’ is a famous sculpture in Millennium Park that’s been amusing and delighting Chicagoans for 20 years, and it’s quite fascinating up close - especially on a sunny day, when it gleams and reflects the city’s skyline.
For the best view of the city’s historic architecture, take a cruise down the Chicago River. You’ll get an unparalleled look at the city’s skyline, and knowledgeable guides will tell you about points of interest. There are specialised cruises which focus on things like architecture, historical sites, and even urban folklore. For a stunning view of the city lit up, book a night cruise - just remember to wrap up warm! Even during the summer, Chicago nights can get chilly.
The Museum Campus is not only fascinating on the inside of the museums, but it’s also home to some famous historical landmarks. The Adler Planetarium is the oldest planetarium in the Western world, and the neoclassical Field Museum is as architecturally impressive today as it was when it first opened its doors over a century ago.
Find the soul of Chicago through music, food, and landmarks
Chicago is a big city with an even bigger heart. Dedicate your time there to feeding your soul through music, your body with delicious Chicago food, and your mind with historical landmarks. You won’t regret it!
