Collected by Meena Thiruvengadam , AFAR Local Expert
I've lived a lot of places in my life, but few have captured my heart like Chicago. It's got beaches to rival southern California's, amazing architecture and one of the most beautiful skylines I've ever seen. It's also brimming with stellar bars, restaurants and things to do. Chicago is my kind of town, and these are some of my favorite reasons why.
99 Chicago Riverwalk, Chicago, IL 60601, USA
Catch this unique experience twice a year - a couple of weeks in April and October when each of the 20+ movable bridges over the Chicago River open in succession to let the sail boats out to or in from their Lake Michigan marinas for the summer...
108 E Superior St, Chicago, IL 60611, USA
If you fancy an epic place to stay while visiting the Windy City, The Peninsula, located in the heart of downtown, can cater to your every desire. If it's fancy digs you require, any room that you request will be top notch. For unwinding and...
1 N Michigan Ave, Chicago, IL 60602, USA
If you're visiting Chicago in the winter, be sure to make your way to one of the city's many ice rinks. For outdoor skating with a view, head to the McCormick Tribune Ice Rink in Millenium Park. The ice skating rink is sandwiched between Cloud...
141 W Jackson Blvd, Chicago, IL 60604, USA
You could say unmixed drinks are the specialty at this bar on the ground floor of the Chicago Board of Trade Building. Order a rum and Diet Coke and you'll get just that: a glass of rum with a can of Diet Coke on the side. This is a Monday through...
111 N State St, Chicago, IL 60602, USA
Chicago is amazing during the summer, but winter visitors are in for some seasonal perks. City ice rinks open. Christmas trees go up along Michigan Avenue. And the Macy's on State Street decorates its windows for the holidays. This Macy's is one...
201 E Randolph St, Chicago, IL 60602, USA
After walking the entire city I easily decided Millennium Park is hands-down Chicago's best attribute. I imagine the weather's not always as perfect as it was on my visit, but in the summer that attraction is unbeatable. (Ok, Central Park has it...
6300 W Touhy Ave, Niles, IL 60714, USA
I know, you're asking yourself, 'When did they put a reflecting pool in front of the Leaning Tower of Pisa?' Weird question, with an even weirder answer. This tilted structure is located in Niles, IL and is a recreational park for employees of the...
2548 N Halsted St, Chicago, IL 60614, USA
I always look forward to visiting Chicago, especially when it's work related and I'm encouraged to take customers out for dinner. A highlight of my last visit in November was dinner at Trattoria no. 10 on Dearborn. Holy Baby Cow Batman, that was...
809 W Randolph St, Chicago, IL 60607, USA
With 24 hours in Chicago, my friend and I headed straight to Girl and the Goat for the food, the drinks and the scene. We didn't have a reservation but after an hour of waiting, people watching, and having fun at the bar the unthinkable happened...
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...
5148 N Clark St, Chicago, IL 60640, USA
In the center of Andersonville, a trendy neighborhood on Chicago's far north side, you'll find a bar with 18 different Belgian beers on tap. One of my favorite memories at The Hopleaf (and let me stress, these are blurry memories) involves teasing...
163 W North Ave, Chicago, IL 60610, USA
Chicago may be known for its deep dish, but it's just as easy to rustle up a jumbo slice — without having to pay extra for a soda. The slices at Bacci Pizzeria are as big as any you'll find in New York City. A slice and soda cost $5, except on...
2413 N Clark St, Chicago, IL 60614, USA
The world may be craving sushi right now, but Chicago's contemporary American brunch spot Orange has put its own spin on the sushi trend. Orange's frushi substitutes fresh fruit for fish and vegetables to a create a sweet, shareable appetizer...
1551 N Wells St, Chicago, IL 60610, USA
I've been to most of Chicago's well-known wine bars, but this one surpasses the rest. In the fashionable Old Town neighborhood just north of downtown, Flight 1551 pours more than 250 wines by the glass and by the flight. Burger flights, hummus...
3868 N Lincoln Ave, Chicago, IL 60613, USA
Sola is a Hawaiian-inspired brunch spot in Chicago's trendy Lakeview neighborhood, but I don't ever recall having food this good in Hawaii. Try the sour cream pancakes with blueberry, lemon zest and lemon ricotta (my personal favorite, pictured...
1354 W Wabansia Ave, Chicago, IL 60642, USA
Can't make it to Lollapalooza? Just wait for The Hideout Block Party. The Hideout Block Party is one of the best - and latest - summer music festivals in Chicago. The two-day festival is held outside of The Hideout, an intimate Chicago live music...
17 E Monroe St, Chicago, IL 60603, USA
One of my favorite discoveries in Chicago is the Empire Ballroom inside The Palmer House. It's just up the stairs from the hotel's magnificent lobby and has a rich history most anyone working at the hotel will be willing to tell you more about....
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