Collected by Meredith Blackburn , AFAR Local Expert
Places I loved when Chicago was my home.
7705 N Eastlake Terrace, Chicago, IL 60626, USA
Pick up your morning coffee at one of the many local coffee shops, and walk to Rogers Beach (known by locals as Lighthouse Beach). The sunrise over Lake Michigan is stunning! Locals fish off the lighthouse pier in the early morning semi-darkness....
McCormick Blvd, Skokie, IL 60076, USA
Located a bit north of downtown Chicago is the Skokie Northshore Sculpture Park. This two-mile stretch of McCormick Boulevard runs north/south between Touhy Avenue and Dempster Street and features over 60 incredible sculptures. The one featured...
Lincoln Park, Chicago, IL, USA
Chicago is one of my favorite cities in the USA. It's bursting at the seams with fantastic restaurants, hole-in-the-wall pubs and bars, world-class stadiums, art galleries, and everything else you'd expect in an Alpha World City, though it retains...
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...
1230 W Greenleaf Ave, Chicago, IL 60626, USA
For the most relaxing beach experience, travel a short distance north on Lakeshore Drive and you will find idyllic beaches that you can have almost all to yourself. Here you'll feel free to play, exercise or take a romantic stroll away from the...
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...
5236 N Clark St, Chicago, IL 60640, USA
Up in Andersonville Svea has served genuine Swedish sausages, meatballs and pancakes in giant portions for decades surrounded by exactly the same blue and gold decor. They don't have a website, they're cash only and you'll definitely have to wait...
746 W Webster Ave, Chicago, IL 60614, USA
I last visited Toast on a Tuesday with an old friend I hadn’t seen in ages. Unlike the weekends which are crowded and busy with long waits, on Tuesday we walked right in and were immediately seated in a window booth. We ordered the omelette...
1501 N Kingsbury St, Chicago, IL 60642, USA
Chicago has a lot of improvised comedy shows with 195 listings on Yelp, the most famous of which is Second City and some of the funniest of which are hosted by the iO theatre. Where else but the iO theatre can you see improv done in iambic...
805 S State St, Chicago, IL 60605, USA
As you can imagine, there’s a lot of discussion over who has the best pizza in Chicago; so, here’s what I know for sure: Lou Malnati’s serves a great stuffed pizza, they’re one of the oldest pizza names in town and they have yet to franchise...
736 W Fullerton Ave, Chicago, IL 60614, USA
If you want a quiet chill place for a cup of tea, a sandwich and a book, Bourgeois Pig is your place. Big wood tables, jazz music playing and the largest loose leaf tea selection in Chicago makes this the ideal afternoon destination. The Bourgeois...
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...
1400 S Lake Shore Dr, Chicago, IL 60605, USA
Dinosaurs, pyramids, cave paintings, sharks—if you don't like the Field Museum then you must never have been a kid. Home to an extensive assortment of magical displays highlighting all facets of natural history from around the world, the...
1035 N Western Ave, Chicago, IL 60622, USA
The Empty Bottle in Ukrainian Village offers great music in a small venue with an angled stage so the views are pretty good from anywhere in the house. The drinks are reasonably priced with friendly bartenders and the location is a bit divey but...
2051 N California Ave, Chicago, IL 60647, USA
Bang Bang is pie heaven! Everyday they have a fruit, a cream, and a chocolate selection, and they change up their menu daily based on what's in season and newly developed recipes. It's first-come-first-served, so go early before they run out! They...
4802 N Broadway, Chicago, IL 60640, USA
Open and thriving since 1907, the Green Mill Cocktail Lounge survived both prohibition and ownership by Al Capone in the 20’s. That alone should make you want to visit. Additionally, the plush restored interior hearkens back to its speakeasy roots...
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