A city filled with magnificent architecture, world-class museums, inspiring chefs, a massive brewing scene, and 77 unique neighborhoods to explore from Bridgeport to Logan Square, Chicago is also home to that midwestern charm that you just can’t find anywhere else. With easy-to-use public transportation, it’s not hard to get around the city to experience the different pockets, each so distinctive and worth visiting that it will almost be an impossible task to narrow down what to see and do. We’ve put together a curated list of our favorites to help inspire you while visiting the windy city.
Eat & Drink
Centennial Crafted Beer & Eatery
Conveniently located in the River North neighborhood, a short walk or drive from Level River North, this local gathering spot offers 56 taps with a selection of 36 rotating craft beers as well as a curated wine and spirits list. When ready to pair your brews, have a look at their chef-driven menu which focuses on beer pairings in addition to incorporating beer as part of many of the dishes offered. Learn more.
Beatnik On the River
This riverfront boho-chic oasis transports you to a time of bohemian freethinkers of the 1950’s. Come here for the breathtaking views of the Chicago River but also for the colorful tiles, ethnic daybeds and fringe umbrella style decor that dominates the space. The menu is worldly and Executive Chef Marcos Campos takes guests on a journey without borders, playing with flavors from places like Spain to South America, Asia and the Middle East. Learn more.
Located on a rooftop patio in Chicago’s historic Fulton Market District, Aba brings Chef CJ Jacobson’s lighter style of cooking with influences from the Mediterranean, including Israel, Lebanon, Turkey and Greece. Their exceptional bar program is crafted by Liz Pearce and showcases rare Mediterranean-inspired wines and spirits. Learn more.
Ken Kee Restaurant
With decor and neon accents inspired by the streets and markets of 1950’s Hong Kong, Ken Kee is famous for it’s noodle cart offerings (there is a traditional menu as well). Guests can customize their noodle bowl to their liking, picking the broth, noodles and all the toppings from a generously long list of options. Learn more.
Pre-COVID times, Giant operated as a teeny tiny restaurant with a not so tiny reservation waitlist. During the pandemic, Giant took it’s food to the streets via their food truck, and today, they are back to indoor dining, serving simple, delicious food. Menu items not to miss include their saffron tagliatelle, pizzas and burroti (a burrito wrapped in roti bread), and of course their dark chocolate microwave cake served with banana ice cream and halva. Learn more.
A two-minute stroll from Level River North you’ll find a rooftop patio inspired by the leisurely style of dining found in coastal towns along the Iberian Peninsula. Take in sweeping views of the Chicago skyline while you sip on their line-up of crafted cocktails and nosh on classic Spanish cuisine inspired by seaside diners. Be sure to try their bacon-wrapped chorizo stuffed dates and their salt cod brandade – two bar avec fan-favourites. Learn more.
Play & Explore
Tap your toes at this late-night jazz club
Green Mill is an uptown institution that was frequented by infamous Chicago gangster, Al Capone. But since Prohibition is a thing of the past, the club has made a name for itself for hosting live jazz. Take photos under the green glimmering marquee and step inside for an evening unlike no other (minus the gangsters).
Level Up at 360 CHICAGO
Take the elevator to the 94th floor to 360 CHICAGO Observation Deck, atop the building formerly known as the John Hancock Center for views of the city (and surrounding states) from 1,030 feet above the streets. Enjoy a cocktail at their bar and explore the interactive exhibits detailing the history of Chicago. But before you go, board a glass-enclosed platform that slowly tilts over the side of the building at a 30-degree angle (TILT tickets are available for purchase).
Spend the afternoon on the Chicago Riverwalk
The 1.25-mile long Chicago Riverwalk path includes four distinct districts: The Confluence, The Arcade, The Civic and the Esplanade. The Riverwalk is a treasured natural amenity that allows a close proximity to the waterway while strolling past famous architecture. Grab a glass of wine at City Winery or a cold beer at Chicago Brewhouse. Boat and kayak rentals are also available for those wanting to get out on the water.
Check out the public art in Millennium Park
Millennium Park is home to iconic public art installations such as Cloud Gate, also known as “the bean”, this 25-acre park is popular with everyone. Depending on the time of year, the park hosts all sorts of community events, arts programming and even has a 3.5-acre urban sanctuary, the Lurie Garden.
Wicker Park / Bucktown
The bustling “six corners” area (the intersection of Milwaukee, Damen and North Avenues) is dotted with trendy boutiques and hip vintage shops. Shop everything from locally inspired gifts to trendy vinyl, vintage couture, unusual jewelry and endless cups of excellent coffee in this mish mash neighborhood that offers a bit of everything. The main shopping area is along Milwaukee and Damen Avenues. Neighborhood favorites include Myopic Books, Una Mae’s and Eskell, all of which have enough to keep pretty much anyone preoccupied as they meander throughout searching for treasures to take home.
Lakeview encompasses a bunch of smaller areas — East Lakeview, the Southport Corridor, Wrigleyville, and Northalsted (also known as Boystown), Chicago’s LGBTQ+ neighborhood. Head to Southport Avenue for popular chains mixed in with trendy boutiques. And along bustling Belmont Avenue, Lincoln Avenue, Clark Street, Halsted Street, and Broadway Street, you can hunt for both vintage feels as well as the latest designer clothes. If you are hunting Chicago Cubs gear or souvenirs, you’ll find lots of stores and stalls all around Wrigley Field. Also for a unique way to remember the city, visit Waxman Candles with candles and fragrances inspired by Chicago’s neighborhoods.
Come here for the charming streets lined with both Victorian row houses but also local boutiques. The area around Armitage Avenue and Halsted Street is home to some of the city’s most popular shops. Check out All She Wrote, a charming stationary shop with thoughtful gifts, and also make a stop at Laudi Vidni (“individual” spelled backwards) for custom leather bags and accessories that are handcrafted and then shipped directly to you.
Old Town today has most of the unique qualities of its former self. Because of this, the neighborhood has been able to keep its charm and uniqueness while still embracing change and development. Here you will find both bohemian chic paired with timeless charm. Luxury high-rises set among brownstones and historic Victorians. Small businesses dominate here in addition to small grocers like Fox Trot Market and Marianos, both of which make it easy to grab and go so you can prepare delicious home-cooked meals from the comfort of your suite at Level Old Town.