Whether you love art, food, drinks, comedy, or really anything else, there’s a lot for you to do in Chicago. The architecture is beautiful, there’s always a fun event going on, and then there’s the Chicago River. If you’re just there for a day, it can be hard to figure out the best way to spend your time. Here’s what I recommend.
My first stop in Chicago is always Ann Sather Restaurant. Depending on where you’re staying, it might be a little bit out of the way, but trust me, this little Swedish restaurant is definitely worth the trip. They serve up one of the best breakfasts I’ve had, so it’s the perfect place to begin your adventure. You can’t go wrong with anything on the menu. The one mistake you could make would be missing out on the cinnamon rolls. I consider myself a bit of a cinnamon roll connoisseur, and you honestly can’t find better ones. They’ve even been lauded on the Food Network. They’re that good.
Once you’re content from breakfast, it’s the perfect time for a tour of the city. If you can only do one, opt for the Chicago Architecture Center’s famous architecture river cruise. The tours start pretty early, so it’s easy to fit one into your schedule. As the boat takes you around the river, the guide tells you about 50+ of the surrounding buildings, their architects, and the variety of architectural styles around the city.
When you think great barbecue, Chicago is probably not the first place that comes to mind, but the Revival Food Hall Smoque BBQ just might change that. They’ve got brisket, ribs, pulled pork, and all the classic sides that make a barbecue joint: cornbread, mac and cheese, and coleslaw. Don’t miss this place.
After lunch, head to the public sculpture Cloud Gate (more popularly known as The Bean). Here, you can see a stunning reflection of the cityscape and get your own iconic picture to share on instagram.
A very short walk away is The Art Institute of Chicago, so this is the perfect time to check out some of the world’s best works of art while you’re in the city. They have thousands of pieces you can see—both iconic and lesser-known ones.
Next, I’d recommend an afternoon caffeine pick-me-up: Limitless Coffee & Tea at Fulton Market. It has a clean, modern aesthetic, plenty of natural light, and an outstanding drink selection. They’re known for their inventive drink options, including charcoal lattes and beet lattes. You can find classics, like cortados and cold brews, too.
For dinner, check out Cabra Cevicheria. It’s a Peruvian-inspired spot designed around shareable plates. The dishes have bold, bright flavors, and the restaurant is on a rooftop, so you get great views of Chicago as you dine.
Looking for an evening drink? Only a few blocks away is MONEYGUN. It’s an update on the neighborhood bar. They have a simple menu, but, in this case, that just means they’ve spent time perfecting each and every drink. And, the low lights and the bar’s creative design make this spot a great place to end your night.
That said, if you still want to get a bit more out of your Chicago trip—and don’t mind a 2.5-mile trek north—check out one of The Second City’s 11 PM improv shows (if you’re there on a Friday or Saturday night). This place is a Chicago staple, opening in 1959. Why not squeeze in some hearty laughs while you’re in town?
If you need a place to stay after a fun night out, consider The Publishing House Bed and Breakfast—it’s right in the West Loop. The building was originally built in 1909, but it’s been recently renovated into an 11-room B&B that provides the feel of a boutique hotel. And, now it’ll be easy to get a delicious breakfast once you wake up!