Vintage hunting and drinking are two beloved pastime activities, so why not combine them? You’re going to start the evening at this establishment that smartly pairs selling dead people’s hoards (the website’s words, not ours) with casual cocktails.
Just off Milwaukee and Diversey avenues, you’ll know you have arrived at Consignment Lounge when you come across a neon sign of a cleverly woven C and L underneath the colorfully printed words “Color TV.” Note: If you ever happen to drive by when the bar is closed, the window gates depict a Kevin Heisner mural titled “Shlumper.”
Inside, the energy is high but relaxed. Consignment Lounge is a neighborhood bar; it’s not the place to go for intricate, Michelin-star-worthy concoctions, according to Mark Pallman, a photographer and videographer who owns the business with his wife, Katie Piepel, who works in real estate.
At Consignment Lounge, all orders go through the bar. After you decide on your first beverage of the evening, grab a seat — options include high tops overlooking Diversey Avenue, chairs at a few tables scattered about, and couches occupying a back room.
While you hang out, you’ll likely find your eyes catching on the various knick-knacks, glassware and artwork dotting the walls and shelves. Have you ever been at a bar and wished you could have taken home an object you lusted over? Well, this watering hole allows you to do just that: about 95 percent of everything on display (save for the cups used to serve customers, for example) is for sale.
The business is Pallman’s “hair-brained idea” that allows him to channel his love of shopping at estate sales into a community gathering place. That means merchandise is regularly rotating, so Consignment Lounge is never quite the same spot twice.
With a name like Mr. E’s Late Nite, it comes as no surprise this is a go-to spot for midnight bites, especially on a night of booze indulgence.
After however many drinks you land on at Consignment Lounge, walk the 8 minutes east on Diversey and south on Milwaukee to arrive at this hot dog joint. The small, all-window storefront is decorated with red-and-blue neon signs advertising Vienna Beef and your usual suspects of beer.
Open until midnight most nights and 1:30 a.m. Friday and Saturday, Mr. E’s Late Nite is all about no-fuss classics, including burgers, hot dogs and Italian beef sandwiches — all beef, no bull, like one sign inside the restaurant proudly pronounces.
You’ll order your meal at the counter. If you’re lucky, one of the diner-like stools along the window will be open, giving you the ideal opportunity to watch people and cars go by as you enjoy a Chicago dog.
“It’s an affordable approach,” owner Esam Hani told Block Club Chicago. “People just want a burger sometimes or a beef. It fits the economic times we’re in.”
You’ll close out the night at Whirlaway Lounge, half a mile directly south of Mr. E’s via Sawyer Avenue. In theme with the prior establishments, Whirlaway Lounge is a cherished neighborhood spot and has been for more than 40 years; it’s “where you’re a stranger only once.”
From the outside, the bar is unassuming: it occupies the ground floor of a small, two-story apartment building, only a burgundy awning denoting the business. Inside, you might feel as though you’ve entered an old friend’s house. Sports ephemera line the walls adorned with string lights, while board games for every interest stuff shelves on one wall. 
It’s Maria Jaimes, the bar’s owner beloved around the community, who receives the most credit for the establishment’s energy being the way it is. She can often be spotted at the bar, both in person and immortalized in various photos decorating the walls.
Before Jaimes and her husband, Sergio, took over the bar in 1980, it was operated by its original owner who, legend has it, named the spot Whirlaway after an eponymous 1941 Triple Crown-winning racehorse with the same name.
In a bar as classic as Whirlaway, it’s only right you order a fitting drink. Make it a Chicago handshake, a shot of Malört paired with an Old Style beer, and enjoy it at the bar or a table along the opposite wall.