Worldwide icon-chevron-right North America icon-chevron-right United States icon-chevron-right Illinois icon-chevron-right Chicago icon-chevron-right 11 Chicagoans reveal where they go to cheer themselves up

11 Chicagoans reveal where they go to cheer themselves up

Time Out Tastemakers told us about the places they go when they're feeling down

Photograph: Jaclyn Rivas
By Time Out Tastemakers |

After a long afternoon at work or a day when you're simply feeling down, escaping to the streets of Chicago may only add to your frustration. Urban life is filled with inconveniences and annoyances, meaning that your bad mood could quickly take a turn for the worse. Thankfully, Chicago is also filled with places and attractions that will brighten your mood—or at least make you temporarily forget why you're so blue. There are parks, restaurants and locales with the power to put a smile on your face—you just have to find the ones that work for you. We asked our Time Out Tastemakers to tell us about their go-to feel-good spots. The next time that your day is haunted by dark clouds, reference this list for a bit of inspiration.

“I love to go to the lakefront and just watch the water. It's really calming and relaxing after a bad or stressful day. I also like to go to Jeni's Splendid Ice Creams if I'm having a really rough day to treat myself.” —Marissa Auslander

“A walk through one of Chicago's many parks or a stop at a local pub usually cheers me up. Most recently, it's a bar stool at Half AcreOld Irving Brewing or Maplewood Brewery. You rarely see a sad face in any of those breweries.” Hilary Mikulich 

“If I'm coming off of a rough workday in the Loop, a Nutella crepe and white-chocolate martini at Crepe Bistro (ideally accompanied by the charming old man who plays an accordion) is usually just enough indulgence and sugar to pick me up.” —Jill Failla 

Garfield Park Conservatory is honestly the cure to any bad day. The surrounding nature and vegetation sends feelings of restoration, calmness and true breaths of fresh air within you. And if it happens to be cold outside, the warmer temperatures can make it feel like a mini vacation. Take a book, a sketch pad, journal or even your knitting and just hang out for a while.” —Erika DeVriendt 

“Kibbitznest on Clybourn is the perfect pick-me-up after a long day in front of a screen. This bar-library-bookstore of sorts touts the mantra ‘Where old-fashioned human communication is KING!’ and is a Wi-Fi-free zone so you can put those reports out of your mind surrounded by books, good friends and cheese boards. With near daily drink specials, book club meetings and events, this spot never loses its charm.” —Nicole Long 

“I treat myself to a decadent dessert to boost morale, like the glazed old fashioned from Doughnut Vault or coconut red velvet from Do-Rite Donuts. No one does speciality doughnuts like Chicago.” —Kanchan Garg

“When I’m down, I visit Belmont Harbor. It’s my happy place, the place where I feel more centered after I leave. I throw my shoes on, grab my headphones and watch the boats go by and the waves crash up against shore barricade.” —Mary McMahon 

“Whenever I’m feeling down I’ll head over to Mindy’s Hot Chocolate and get myself a cup of her award-winning hot chocolate. Mindy Segal honestly ruined me. I can’t drink any other hot chocolate since hers is so decadent.” —Jyoti Gill 

“Open Books Warehouse and Bookstore in Pilsen. The smell of books is a drug to me, and this is where I get my fix. Not only are they, as their name suggests, a warehouse-sized bookstore, but they also run literacy and writing programs for kids all over the city.” —Emma Meyer

“I go biking down the lake front path all the way south to Promontory Point. It is extremely relaxing with amazing city views and fantastic people watching.” —Ben Pisik 

“I live in Wicker/Bucktown so I’ll head to Ipsento Coffee 606 on Milwaukee Avenue after a trying day. It's a coffee shop but in the evening they offer a drink menu as well. The large windows open out to a Bloomingdale Trail entrance. This particular spot also has huge stones that people hang out on, making it a fun spot to people watch.” —Priyanka Das