Chicago: The must-do list
Collected by Meghan Callaghan
Chicago, the city I call home, is a gorgeous spot to take in culture, beautiful architecture and eat some of the best food around. There's plenty to see and do, eat and drink, and great places to stay. Here's my list of what not to miss.
2657 N Kedzie Ave, Chicago, IL 60647, USA
In 2011, one of Chicago’s most popular restaurants, Longman & Eagle, expanded into an inn with the creation of six rooms. The owners, two of whom run the music venue Empty Bottle, built and outfitted the whole place. Each of the rooms is...
Chicago, IL 60601, USA
Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel...
1616 N Wells St, Chicago, IL 60614, USA
The Second City has come a long way since the small cabaret theater that launched in 1959. As a sketch comedy and improvisational performance theater, the venue has been keeping people laughing for over 50 years. Situated in the historic Old Town...
6836 N Sheridan Rd, Chicago, IL 60626, USA
Ask any local where to try your first real deep-dish pizza and they'll say "Giordanos." It's obviously the best in town. Chicago-style pizza is unique and totally different than what you'll find in Italy. More like a pie, the crust is tall and...
337 E Randolph St, Chicago, IL 60601, USA
I know, I know, Lollapalooza may be a little overpriced and overrated. But the truth is, it is still one of the best music festivals in the country. Amazing live performances by well-known artists and new talents, worldwide travellers, a quirky...
Streeterville, Chicago, IL 60611, USA
The architectural boat tour of downtown Chicago is the single best way to see this city in a whole new way. From first-timers to lifers, it doesn't matter how long you've been in town, this perspective is going to be new to all. There are many...
Illinois Medical District, Chicago, IL, USA
Chicago is the king of comedy, hot dogs, and extreme Midwest weather. But since the Great Chicago Fire of 1871, the city has been reinventing itself. Today, clever design projects (such as “Color Jam,” shown) top the list of reasons...
51 W Kinzie St, Chicago, IL 60654, USA
On the website for Siena Tavern there is a button called 'From Scratch.' Click it. The name of the link pretty much says it all for this downtown Chicago eatery. Homemade and handmade pasta, sauces, dressings, and more are abound at this River...
435 N Clark St, Chicago, IL 60654, USA
From the folks of Lettuce Entertain You Enterprises in Chicago comes their newest venture: voodoo magic. No, they are not selling dolls of those you disdain. However, you CAN buy incredibly well-crafted drinks that are served in skull-like glasses...
4750 N Lincoln Ave, Chicago, IL 60625, USA
Founded in 1927 by two brothers from Poland, this market is a true throwback. When John and Gene started their sausage shop in the city of Chicago, it was still the era of Prohibition. Fast forward a few years, moves, and expansions, and the...
116 W Hubbard St, Chicago, IL 60654, USA
No, they do not serve turtle soup at this establishment; in fact, no turtles will be harmed in the making of your meal. Slurping Turtle is a fun, casual, won't-break-the-bank-but-still-is-gourmet place to mosey into for a fun dinner out with...
2001 N Clark St, Chicago, IL 60614, USA
It's enormous, it's full of animals, it's open all year round, and, best of all, it's (gasp!) free. The Lincoln Park Zoo is one of the single greatest things to do in Chicago. Visit the monkeys in their house of hilarity, or swing past the penguin...
1060 W Addison St, Chicago, IL 60613, USA
Steeped in history, loved my many, loathed by some, and sorely in need of a championship, Wrigley Field is a true cornerstone of the always controversial sporting world. No trip to Chicago is complete without a visit to this monument to to...
301 S Columbus Dr, Chicago, IL 60605, USA
Officially open to the public way back in 1927, even after all these years, Buckingham Fountain remains one of THE must-see sights in Chicago. Sitting on the edge of Lake Michigan, and intermittently erupting with spires of water, Buckingham...
201 E Randolph St, Chicago, IL 60602, USA
The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife's favorite quote, and a local sight in Chicago. Sometimes people feel they...
401 N Franklin St, Chicago, IL 60654, USA
I have two pieces of advice for you regarding the Doughnut Vault: 1. Go early. They open at 8am Tuesday-Friday and 9:30am on Saturdays and if you want a breath of a hope of a chance of getting a doughnut before they sell out, you want to be there...
Lower, 430 N Michigan Ave, Chicago, IL 60611, USA
Billy Goat Tavern achieved international fame in the 1970’s with a Saturday Night Live skit that mocked the order process and the lack of options. No Pepsi… Coke! No Fries… Chips! The tavern’s been open since 1934 on the lower level of Michigan...
Magnificent Mile, Chicago, IL 60611, USA
Chicago’s Magnificent Mile runs along Michigan Avenue between the Gold Coast and the Loop. There are 460 retail stores, from high-end designers like Gucci, Cartier, and Louis Vuitton to local boutiques and trendsetting fashion stores. In between...
909 W Belmont Ave, Chicago, IL 60657, USA
111 S Michigan Ave, Chicago, IL 60603, USA
Just imagine having 264,000 square-feet of modern art at your disposal seven days a week. That is exactly what you have if you visit the Modern Wing of the Art Institute of Chicago. Above is but one example of the funky-cool exhibits that await...
954 W Belmont Ave, Chicago, IL 60657, USA
Back when I was an innocent college student I used to sneak into Berlin where the people watching was epic and I could dance all night. The Berlin clientele have always dressed in a style all their own, like the girl in the Emma Peel-like catsuit...
5700 S Lake Shore Dr, Chicago, IL 60637, USA
Anyone who's into model trains should visit the Museum of Science and Industry in Chicago. Originally opened in 1941, The Great Train Story was the largest model train of its day. After being briefly shuttered in 2002 for extensive additions, this...
2391 N Stockton Dr, Chicago, IL 60614, USA
Lincoln Park is a wonderful green area nearing Lake Michigan in Chicago. It has a Zoo free to the public as well as green lawns and flower beds. Near the North end is the multiple room conservator. Like the rest if the park it is open free to the...
809 W Randolph St, Chicago, IL 60607, USA
820 W Randolph St, Chicago, IL 60607, USA
Stephanie Izard puts together a great restaurant. The Girl and the Goat has been hard to get into since it opened and Little Goat had a 90 minute wait when we went last month. 90 minutes for diner food! That's impressive. Other things that were...
825 W Fulton Market, Chicago, IL 60607, USA
A primo sourcing grounds for picnic provisions or a casual cafe meal, Publican Quality Meats is the latest food enterprise by the never-miss restaurant team behind Avec, Publican, and Big Star. Billed as a contemporary American butcher shop, its...
955 W Fulton Market, Chicago, IL 60607, USA
At visionary chef Grant Achatz’s bar, vessels such as “the Porthole” (pictured) are as original as the drinks. The chef-trained bartenders use fresh herbs, small-batch spirits, and hand-carved ice in their cutting-edge libations....
840 W Randolph St, Chicago, IL 60607, USA
I'm sure anything you get at this swank bar in the heart of the West Randolph restaurant loop is worth it but this bone marrow did NOT disappoint! Smooth and just salty enough with a touch of sweetness from the jam and the heartiness of the toast,...
233 S Wacker Dr, Chicago, IL 60606, USA
Willis Tower—originally known as the Sears Tower—was the world's tallest building for 23 years until it was unseated in 1996 by the Petronas Twin Towers in Kuala Lumpur. The 110-story skyscraper is still mighty impressive. Its "bundled...
615 W Randolph St, Chicago, IL 60661, USA
Please get the bacon wrapped dates stuffed with chorizo. They are incredible and it's hard not to sop your bread up with that sauce. I was also impressed with the chicken thigh. A lot of the other small dishes were good but not amazing,...
619 W Randolph St, Chicago, IL 60661, USA
When it opened doors in 1998, this West Loop destination helped pave the way for Restaurant Row and all of the gastronomic glory that would follow. Ever since, Blackbird's been filling seats (intimate banquette seating, thank you) with diners...
953 W Fulton Market, Chicago, IL 60607, USA
Next is famous for its ever-changing theme menus. The most recent is "The World's 50 Best Restaurants," featuring dishes created by the world's best chefs and curated by the Next team. When I was there we ate the centerpiece, and the floating...
2548 N Halsted St, Chicago, IL 60614, USA
Playing live blues music until 4am every night of the week, featuring all of Chicago’s talented local musicians and now newly renovated to take up 3 storefronts on Halstead, Kingston Mines is one of Chicago’s best bars. Go for the 3...
531 N Wells St, Chicago, IL 60654, USA
GT Fish & Oyster is a standout on Chicago’s seafood scene. Run by Michelin-starred chef Giuseppe Tentori, the restaurant serves elevated versions of many classics, including clam chowder with housemade oyster crackers and beer-battered cod with...
1520 N Damen Ave, Chicago, IL 60622, USA
The first rule of the speakeasy is that it can’t be easy to find. The Violet Hour’s door is directly across the street from Big Star. Look for the handle on the wall and the light above it, because the door mural changes frequently and...
4530 N Lincoln Ave, Chicago, IL 60625, USA
This is how your table looks after a night at The Grafton with the mostly empty glasses and a water carafe that’s been filled and emptied at least four times. Not pictured are the hollows you left in the seats from sitting there for 6...
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