Collected by Sylvia Sabes , AFAR Local Expert
51 W Jackson Blvd, Chicago, IL 60604, USA
Chicago’s beloved South Side hat shop, Optimo, recently opened a downtown location in the historic Monadnock building. A favorite of Johnny Depp and former Mayor Richard Daley, the new shop sells handmade felt fedoras and porkpies that appear to...
220 E Chicago Ave, Chicago, IL 60611, USA
Not only does the Museum of Contemporary Art have great exhibitions on local and renowned artists, but the interior architecture of the museum itself is also an attraction. They also provide unusual events and tours—curator-led tours, musicians on...
1655 W Cortland St, Chicago, IL 60622, USA
To find the Trap Door Theatre, you walk down a narrow walkway between two white brick walls. A steel door opens onto the kitchen of Jane's Restaurant. A second door leads to a small black box theater. There, for the last 15 plus years, the Trap...
5751 S Woodlawn Ave, Chicago, IL 60637, USA
Located in the basement of the Theological Seminary, the Seminary Co-op is the only bookstore I've encountered where you might actually get lost. It's a basement labyrinth of books where you must duck beneath pipes as you browse the endless, dense...
141 W Jackson Blvd, Chicago, IL 60604, USA
For their roving, event-based Volume Gallery, Claire Warner and Sam Vintz pluck contemporary American designers like Thaddeus Wolf and Rich Brilliant Willing and set up short-run installations at galleries all over Chicago. One of Chicago’s own,...
951 Chicago Ave, Oak Park, IL 60302, USA
Frank Lloyd Wright built 700+ houses all over this nation but he lived and worked in Oak Park, just a 45 minute train ride from the city center of Chicago. His house and studio are now a museum with guided tours that let you see the playroom he...
2391 N Stockton Dr, Chicago, IL 60614, USA
565 W Jackson Blvd, Chicago, IL 60661, USA
Lou Mitchell’s diner has been open in the same location since 1923; so long, in fact, that diner patrons witnessed the heyday of Route 66, which started right here next to Union Station. The Chicago city council renamed Jackson Street “Lou...
233 S Wacker Dr, Chicago, IL 60606, USA
100+ stories, on top of the world, at the skydeck of the Willis Tower in Chicago. The city is extremely beautiful, and especially awesome from up here. On a pretty clear day like this one was, you can see quite far in all directions. This is a...
Place du Casino, 98000 Monaco
The sight of tuxedo-clad James Bond ordering his martini in the Casino de Monte Carlo makes a girl's heart race, her imagination run wild. Have your martini at the Hôtel de Paris' American Bar before crossing legendary Place du Casino for your...
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