Look at a map of Chicago’s various neighborhoods, and you will find more neighborhoods than most states have cities. Chicago is such a diverse place, that as you go from one hood to the next you will often feel like you are time traveling, country hopping, or maybe just downright confused. One thing is for certain though, no matter what neighborhood you are in there will never be a shortage of drinking and dining to be found. And if you didn’t know, drinking before 5 is highly encouraged in Chicago. Below is just a spattering of choices to start with in your Chicago neighborhood tour.
Center: Armitage and Lincoln Avenue
Although it serves home to the famous Lincoln Park Zoo, this neighborhood is known for a lot more than Polar Bears and Swan shaped paddle boats. Lincoln Park is a trendy neighborhood a few miles North of the city, and there is plenty to do here if you like to eat and drink. Take a walk down the plush green streets, check out the beautiful (and quite pricey) old architecture of the houses, and enjoy your day just a few blocks West Lake Michigan. As you get closer the water, you will end up at the famous Lincoln Park, Chicago’s largest Public Park. Once you have worked up an appetite, check out one of the neighborhood favorites, Stanley’s Kitchen and Tap on Lincoln, which has been featured in a ton of magazines, including MAXIM.
Center: Milwaukee Avenue
Bumpin’ hipster dance clubs such as The Dark Room will give you some pretty sweet, and cheap, local bands and an array of whiskey choices. If shopping is your thing, Wicker Park is definitely one of the famous neighborhoods in Chicago to partake in this pleasure. Be sure to check out G Boutique for some risky fun. If you need a beer (or 4) during your girlfriends shopping expedition, check out The Map Room, one of the coolest small travelers pubs you’ll ever set foot into, with over 200 beers to choose from - 26 of them on tap. If all of that shopping and drinking has you famished, for dinner try out Big Star for crazy taco combinations, such as the famous tacos de pescado. And who couldn’t use some more beer? Big Star has yummy rare beers on draft, and tasty Margaritas that will knock you on your butt! Wicker Park may be the definition of hipsterville, but hipsterville at its finest.
Center: Intersection of Halsted/Belmont/Clark Streets
Boystown was the first recognized “Gay Village” in the United States (sorry San Francisco). Style and funky fashion play a key element in meeting your fellow neighbors in these parts. The nightlife is eclectic here, and an array of bars are open until 3am weekdays and 5am weekends. Amazing restaurants are plentiful, as well as cool shops with everything from Vintage Clothes to old Record Stores. One of the big things Boystown is known for is the Chicago Annual Pride Parade. It is the last Sunday of June every year, and had over 450,000 attending this past Summer.
Center: Clark and Addison Streets
Bordering Boystown, but pretty much its exact opposite, you will find the all to well known Wrigleyville. Surrounding the famous Wrigleyfield, home to the Chicago Cubs, this neighborhood is a Mecca of bars for the post fraternity broha’s who live nearby. Bars here are jam packed with people in baseball jerseys, and you will find plenty of TV‘s to “watch the game, bro”. Be warned, usually by 10pm on weekends, or nights of sporting events, you aren’t getting a beer anywhere without waiting in a line outdoors to even step foot into the bar. (Yes, you can walk right next door to the another bar, but you will find the same exact line.) Make sure to hit up the famous Chicago Cubby Bear for some cool bands and memorabilia. For more on Wrigleyville visit MyWrigleyVille.com
Center: Wrightwood and Sheffield Avenue
Lakeview is known to be the best neighborhood in Chicago for drinking and dining in many 20-somethings beer-goggled eyes. Streets and streets of options never leave the thirsty or famished at a loss for a spot to quench their cravings. When you do make it to Lakeview, check out the Vic Theatre for their Brew & View, definitely one of the coolest events in the city. The Vic Theatre is a classic old theatre hosting some awesome bands, but on nights they aren’t booked they convert themselves into an old school Movie House. Treat yourself to the “Dinner & a Movie” Special, or if your just looking for some cocktails check out the website for their daily drink specials. To work up your thirst, enjoy the many small boutiques, coffee shops, and dog parks that Lakeview has to offer. Parking can be difficult in the Lakeview neighborhood, so avoid the headache and take the El train.
Center: Halsted and West Randolph Street
The West Loop won a spot on our compilation, because it’s one of Chicago’s coolest up and coming neighborhoods. Bordered by the Loop, think Urban mellow. Envision warehouse lofts, trendy boutiques, awesome nightlife, chic wine bars, and an array of restaurants for the food lover in you- including the new popular Girl and the Goat. To quench your thirst check out the quaint wine bars around the area, such as the classy Tasting Room or the more mellow Juicy Wine Company. Both have a fun young crowd and an astounding choice of wines by the glass or bottle to experiment with. For late night fun, check out Funky Buddha Lounge for some dancing and innovative cocktails, all made with organic hand squeezed juices and spiked with the finest spirits.
Center: West Foster Avenue and North Clark Street
A bit more North of The Loop is where you will find Edgewater. And don’t pass by Andersonville, which is the warm beating heart right in the center of Edgewater. You’ll find cool old brick houses right on the beach, and trendy locally owned stores, restaurants and bars. Definitely a unique little neighborhood in the bustle of such a big city. To experience Edgewater, do it up right. Hit up The Coffee Studio to get your morning buzz on, a cool little independent local coffee house (voted one of the 10 best in America recently by Bon Appetit Magazine). And because drinking before 5 is encouraged in Chicago, get your afternoon buzz on at Hopleaf Bar, which offers so many beers your head will spin (in good way). Once you’ve worked up an appetite, try out one of the quaint locally owned foodstops, such as The Edgewater Lounge. End your evening with foot tappin’ Jazz at the famous Green Mill Jazz Club - watch out for the ghost of Al Capone to make an appearance.