Chicago’s Hidden Gems

The view from the new Cindy's Rooftop bar atop the Chicago Athletic Association Hotel.
The view from the new Cindy's Rooftop bar atop the Chicago Athletic Association Hotel. // All photos by Adam Leposa

Travel Agent just got back from a weekend in Chicago, and we picked some of our favorite spots to send your Millennial clients. 

Where to Eat

For a quick bite — and great coffee — check out Cafecito. About nine blocks from Millennium Park and close to the Theater District, this Cuban sandwich shop serves gourmet pressed sandwiches that were recently named “Best Cuban Sandwich in Chicago” by Time Out Chicago. The real star, though, is the coffee - a cafecito, cortadito or a café con leche is a great way to kick off a day of exploring. 

Classic Chicago-style hot dog at Chicago's Dog House.
Classic Chicago-style hot dog at Chicago's Dog House. 

Of course no Chicago trip would be complete without sampling one of the city’s famous hot dogs, and Chicago’s Dog House near the DePaul University campus serves some excellent examples. 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. 

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A bit further south in Lincoln Park, Franks ’n Dawgs is another great lunch spot. Accessed through a passage between two buildings, Franks ’n Dawgs serves artisan sausages on a menu that changes monthly. We tried the bacon mac ’n cheese and truffle sausage, but options ranged from a Chili Cheese Dawg (andouille sausage, house ground chili, cheddar cheese whiz and scallion curls) to, for vegetarians, Fu (marinated tofu, fried brussels sprouts, shallots, scallion puree, pickled vegetables, feta cheese and white balsamic). If the weather is warm, there is also outdoor seating in the back. 

For an excellent brunch spot, try Bite Cafe in the up-and-coming West Town neighborhood. This BYOB neighborhood hangout offers a series of twists on classic brunch items, like Pimento Cheese Eggs Benedict, as well as numerous vegetarian options. Another great brunch pick is HASH Chicago near the border of Wicker Park, Ukranian Village and Humboldt Park, which, as its name would imply, serves hashes of all varieties. We enjoyed the Tex-Mex influenced Humboldt (black beans, hominy, tomatoes, chihuahua and choice of chorizo or soyrizo served with salsa verde). 

The Drifter's cocktail menu is presented on tarot cards.
The Drifter's cocktail menu is presented on tarot cards. 

Where to Grab a Drink

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 door hidden by shelves downstairs from the bar, next to the restrooms. There is usually a wait 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, from juggling to burlesque shows. 

Also busy is Scofflaw in Logan Square, which specializes in gin-focused cocktails, plus an extensive gin list. Other spirits are also on the menu, like in the Six Demon Bag, which incorporates rye, rum, Lucky Falernum, lemon and demerara.  

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 set unusually far apart from each other makes 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 well worth mentioning here for its unbeatable views of Millennium Park and “The Bean” below. In addition to a wide range of cocktails, many of which incorporate kombucha and other healthy ingredients, the bar serves shareable appetizers and entrees designed for three to four guests, although half portions for couples are also available. Our tip: We arrived at around 3:30 pm and asked the hostess to place us on the waitlist for a table at 4 pm, when the kitchen reopens for dinner, and were able to grab a spot by one of the outdoor fire pits without too much trouble. After that it was only a short wait for our late lunch / early dinner. 

The Garfield Park Conservatory is one of the largest conservatories in the country.
The Garfield Park Conservatory is one of the largest conservatories in the country. 

What to See

The Art Institute of Chicago is deservedly famous for its collection of Impressionist artwork, with Seurat’s A Sunday on La Grande Jatte - 1884 and Monet’s Stacks of Wheat among the most famous highlights, but there are a few lesser-known exhibits that are well worth checking out. The Thorne Miniature Rooms, for instance, are a collection of 68 meticulously detailed interiors representing European styles from the late 13th century to the 1930s and American furnishings from the 17th century to the 1930s. These miniatures will be of particular interest to film buffs, as they are said to have inspired the rigidly symmetrical, diorama-like style of filmmaker Wes Anderson. Another unusual spot is a reconstruction of the Trading Room in the original Chicago Stock Exchange, which was built from 1893 to 1894. This spot can be booked for private events, with a capacity of 300 guests reception-style or for a seated dinner, or 650 with viewing from the upper gallery. 

If it’s a sunny day, don’t miss the Chicago Lakefront Trail, which stretches 18 miles along the shore of Lake Michigan, running by the Art Institute, Millennium Park (with a common photo op at “The Bean”) and the Shedd Aquarium. Close to Millennium Park is also the Chicago Cultural Center, home to the world’s largest Tiffany glass dome and host to a number of events throughout the year. 

Finally, just off the Green Line near Garfield Park is the Garfield Park Conservatory. One of the largest conservatories in the nation, this suggested-donation attraction houses a vast collection of palms, ferns and tropical plants in a network of greenhouses, along with a variety of Illinois native plants outside. The Conservatory isn’t all about plants, though — the displays are interspersed with works by various artists, with exhibits we saw ranging from mannequins clad in vaguely post-apocalyptic fashion to a glass roof by Chihuly

Keep visiting for the latest tips, trends and research on Millennial travelers. 

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