America’s third largest city is overstuffed with sightseeing options. Rich in architectural history, full of foodie favorites, and always ready for a good time, the capital of the Third Coast will not disappoint. Here’s the local’s list of our nine favorite places to visit in Chicago.
Chicago Botanic Garden
The Chicago Botanic Garden is an absolute slice of serenity. Featuring 28 gardens and four natural areas across 385 acres, it’s a spot you can lose yourself in for a whole afternoon.
Our favorite gardens are the English Walled Garden and the Japanese Garden, which includes three small islands of perfectly manicured pine trees, flowers, and bonsai trees.
The Art Institute of Chicago
The Art Institute of Chicago is one of the largest and best regarded art museums in the world.
If you like Impressionists, this is the place for you. They’ve got works by Monet, Van Gogh, Seurat, Renoir…the list goes on. Throw in such masterpieces as Grant Wood’s American Gothic and Edward Hopper’s Nighthawks and you’ve got a can’t-miss destination for any art lover to visit in Chicago.
Green Mill Cocktail Lounge
Any jazz club that can trace its roots back to Louis Armstrong and Bill Holiday is worth your time. Not only is the Green Mill in Uptown the oldest jazz club in the U.S., it just happens to be the best of them all.
The music is pure poetry and the general vibes are just off the charts. During many performances cell phones and talking aren’t allowed. So you’re left with the ever rarer modern opportunity to just sit and listen. Bliss.
Restaurant Row
It’s no surprise to locals that Chicago has been named the food and drink capital of the world by TimeOut and pretty much every other major foodie publication the last few years. It’s a city of culinary innovation through and through. No area better exemplifies Chicago’s dining bona fides better than Restaurant Row, a West Loop street jam-packed with James Beard winners and Michelin stars.
But where can you get a reservation?
You can’t go wrong with any one of Chef Stephanie Izard’s goat-inspired establishments (Girl & the Goat, Cabra, Duck Duck Goat, Sugargoat), but be sure to get a reservation first. Some of our other favorites are heavy metal burger bar Kuma’s Corner, current hot ticket Croatian spot Rose Mary, and Texas BBQ joint Green Street Smoked Meats.
Speakeasy
Since the days of Al Capone, Chicago has been known for its speakeasies. Even though the liquor laws changed a hundred years ago, these secret establishments have been thriving uninterrupted ever since. The key with any speakeasy: finding it is half the fun.
A couple of our favorites are Blind Barber in the West Loop and The Violet Hour (1520 N Damen Ave) in Wicker Park. With Blind Barber, it’s not just a clever name. They’ve got a cute cocktail bar hidden behind a full service barbershop. Stop in for a cut before you grab a drink!
The Violet Hour on the other hand, is hidden in plain sight. Behind an ever-changing mural on a busy Wicker Park street, lies a cocktail bar straight out of Alice in Wonderland. If the lantern out front is lit, it means they’re open for business. But chances are the long line outside will be an even more obvious clue.
Robie House
Venture down to Hyde Park to visit the home Frank Lloyd Wright described as “a cornerstone of modern architecture.” The Robie House is one of the finest examples of Wright’s Prairie School architecture, the first uniquely American style of architecture which emphasized integration with the local landscape.
Some consider Wright’s creations to be pure genius. Other people just find his designs pretty weird. But they are inarguably very interesting and absolutely worth a visit.
Chicago History Museum
Have you ever wanted to dive into a Chicago-style hot dog? Well, there’s only one place you can make that dream come true: the Chicago History Museum.
While smaller than many of the other museums around town, it’s the only one that focuses on the full story of Chicago, from founding to Fire to rebirth and modern day. The museum strikes a good balance between hardcore history and engaging interactivity. Or maybe we just love the hot dog thing.
Maggie Daley Park
Maggie Daley Park is the perfect spot to spend a few hours when you’re in that awkward afternoon lull between morning and evening activities downtown. It’s a playful stretch of green space designed to help your kids blow off steam, and to help you work off some of that deep-dish you just had.
With climbing walls, mini golf, tennis courts, art installations, a fieldhouse, and a gigantic playground with age-designated attractions, you won’t run out of things to explore any time soon.
Lou Malnati’s
If you’re going to eat deep-dish pizza while in Chicago, you might as well do it right. Gino’s East is good. Pequod’s is great. Lou Malnati’s is the best.
Not only do they treat pizza like the pie it is, pulling the dough up the side of the pan before they cook it, but they put the cheese down in layers so not a single centimeter of the pie goes unloved. Squeezing fresh tomatoes over top is the chef’s kiss of sweet finales. We get hungry just thinking about a slice.
