Cindy’s Rooftop Bar offers this panoramic view.
For a quick bite — and great coffee — check out Cafecito, which is about nine blocks from Millennium Park and close to the Theater District. This Cuban café serves gourmet pressed sandwiches that were recently named “Best Cuban Sandwich in Chicago” by Time Out Chicago. The real star, though, is the coffee, which is a great way to kick off a day of exploring.
Of course, no Chicago trip would be complete without tasting one of the city’s famous hot dogs, and Chicago’s Dog House near the DePaul University campus serves some excellent samples. We had a classic Chicago-style dog with mustard, two kinds of pickles and celery salt, but the restaurant also serves a rotating lineup of game sausages (think alligator, kangaroo or buffalo) for adventurous eaters.
Further south in Lincoln Park is another great lunch spot, Franks ‘n’ Dawgs, which offers artisan sausages on a menu that changes monthly. We tried the bacon mac ‘n’ cheese dog and truffle sausage, but there were plenty of other options, including Chili Cheese Dawg and also the Fu, which is a favorite of vegetarians. If the weather is warm, there is also outdoor seating at the back.
Pictured: Bite Cafe serves twists on Eggs Benedict and other brunch items.
For an excellent brunch spot, try Bite Cafe in the up-and-coming West Town neighborhood. This local BYOB hangout offers a series of twists on classic brunch items, such as Pimento Cheese Eggs Benedict, as well as numerous vegetarian options. Another great brunch pick is HASH Chicago, near the border of Wicker Park, Ukrainian Village and Humboldt Park, which, as its name would imply, serves hashes of all varieties. We enjoyed the Tex-Mex-influenced Humboldt.
Chicago is also home to a lively bar scene. The Drifter is a speakeasy hidden inside the Green Door Tavern in the River North neighborhood. Travelers can find it by passing through a hidden door. There is usually a waiting list, but guests are free to drink upstairs until a text announces that their seat is ready. Inside, the speakeasy offers a range of cocktails from a menu composed of tarot cards, although the bar staff (the friendliest we encountered on this trip) are happy to whip up a custom concoction for you. While we were there, the speakeasy was also hosting a variety of Gilded Age-themed live entertainment programs, from juggling to burlesque shows.
Also busy is Scofflaw in Logan Square, which specializes in gin-focused cocktails, plus an extensive gin list.
For a more intimate option, The Violet Hour in Wicker Park (look for the door in the large street mural under the yellow light) serves artisanal cocktails in a quiet space. There are no cell phones allowed, and a combination of high-backed chairs and tables are set unusually far apart from each other, making this a good spot for conversation.
Finally, the new Cindy’s Rooftop Bar atop the Chicago Athletic Association Hotel is already well known (and quite crowded), but worth mentioning for its unbeatable views of Millennium Park and “The Bean” below. In addition to a wide range of cocktails, the bar serves shareable appetizers and entrées designed for three to four guests. Our Tip: We arrived at around 3:30 p.m. and asked the hostess to place us on the waiting list for a table at 4 p.m., when the kitchen reopens for dinner, and were able to grab a spot by one of the outdoor fire pits. After that, it was a short wait for our late lunch / early dinner.