Hot Spot for Singles: Chicago

Chicagoans know how to have fun and entertain no matter how bad the elements are outside. We loved this city because the people are superfriendly, the bars are rocking with tons of live music, the food is comforting and flavorful, and the culture is incredible. Come back during the summer months for music festivals in the city’s parks, partying on the outside decks, and plenty of people-watching along the Lakefront beaches. Read on for our top picks of activities, hotels, restaurants, and bars in the vibrant Second City.

Things to See and Do in Chicago

A great way to start your visit is by taking in the city on an architectural boat tour. We recommend The Chicago Architecture Foundation’s 90-minute river cruise for a beautiful and informative trip through the city in a relaxing setting.

Experience a sketch comedy or improvisation (improv) show at The Second City, an improv theater that’s birthed some of the country’s best comedians over the past 50 years. Mingle at the bar before the performance and share laughs with strangers seated at your table during the show. Hang out at the small bars and restaurants in the vibrant Old Town neighborhood afterwards. Locals will have a blast and make new friends when they sign up for improv training classes at The Second City Training Center.

Make time to catch a show in the theater district. Visit ChicagoPlays.com before you go for the best ticket deals.

Take a subway ride to Wrigley Field to check out the historical ballpark and baseball purists. Even if you’re not a sports fan, Wrigleyville is a must-see neighborhood in the windy city.  The main street outside the Cubs’ home is jam-packed with bars and restaurants, many of them featuring live music. You’ll see Cubs’ fans decked out in their jerseys well into the night getting down to live musicians and great DJs. From sports bars, to beer gardens, to clubs, Clark Street has a venue everyone will love.

If you’re in town and there’s no snow on the ground, do sightseeing via Bike and Roll Chicago. You can rent a bike or join one of several guided tours throughout the city. This is a great way to cruise the lakefront beaches and check out the fit locals while squeezing in some exercise yourself.

Our other favorite sight-seeing destinations include: the Museum Campus area along Lake Shore Drive, Navy Pier, Millennium Park, the John Hancock Building Observatory, and Willis Tower (formerly Sears’ Tower). Visit Chicago’s tourism website for more attractions.


Where to Stay

The 140-year-old Palmer House Hilton Hotel is Chicago’s original luxury hotel, located in a great part of town, close to Millennium Park. We love that they’re pet-friendly, offer girl’s weekend packages with shopping and spa services, and even have guided history tours of the building the first Saturday of every month. Potter’s Lounge is a sophisticated bar often frequented by locals for a fun after-work cocktail with friends or a hot place to start off your night.

The contemporary Hotel Palomar Chicago is a boutique hotel located in Chicago River’s North neighborhood. Take time to drink and dine in the Sable Kitchen & Bar for specialty cocktails and New American cuisine in a sophisticated atmosphere.

We like the Westin Michigan Avenue Chicago for its close proximity to the shopping district. Arrange an in-room spa service after a long day of sightseeing and shopping to recharge before you hit the town that night.

The Trump International Hotel & Tower Chicago won the 2010 award for the best large city hotel in America from Travel + Leisure magazine. We picked it for it’s beautiful river views, 23,000 square foot spa, and downtown location. It’s also a dog-friendly hotel that provides Fido with his own bed, treats, and water bowl to make sure he’s comfy during your stay. Meet singles at Rebar while sipping fancy cocktails and dine on fine cuisine at Sixteen.

Where to Eat
Whether you’re craving a Chicago dog on the run or a top-ranked meal in an elegant environment, this city’s got your gastro needs covered.

Some of our top choices for a great dining experience include: Frontera Grill for Mexican, Alinea Restaurant for New American, Moto for New American with tasting menus, Spiaggia for fine Italian dining, and Del Toro for Spanish tapas.

Get deep-dish Chicago pizza at Gino’s East, Giordano’s, or Lou Malnati’s locations throughout the city. Be warned that you’re likely going to have a long wait ahead of you on a weekend night, so take advantage of that time to mix and mingle with fellow hungry pizza fans and pick their brains for the hot spot to visit later that night.

If you have time on the weekends, check out the Chicago Dine Around tour (chicagogodinearound.com), where you’ll get on a coach bus with other guests and sample different cuisine in various neighborhoods around the city. This is a fun way for locals to try new places in their city and for tourists to see several neighborhoods in a short period of time.


The Nightlife
For a one-stop nightlife experience, check out the Hubbard Street bars. Chicago visitors will have a blast at Howl at the Moon, a dueling piano bar with a band that plays the audience’s requests all night. You’ll be sure to catch a few bachelorette parties there on the weekends taking advantage of strong, sweet fishbowl drinks and plenty of Jell-O shots.

Rachel Wilmot, a bartender at the Red Ivy, recommends Hub51 if you’re looking for a trendy club, or visit the Blue Frog Bar & Grill for karaoke. She said that O’Callaghan’s is a top pick of hers to visit anytime after midnight. Fellow bartender at the Red Ivy, Matt Atkins recommends the Dark Horse Tap & Grill if you want mingle with friendly locals.

For late-night live music, check out a hidden gem, Lonnie Walker’s Underground Wonder Bar where blues/jazz musician Lonnie and her band entertain until the wee hours of the morning.

We picked the brain of Jessica Downey, a blogger who writes about what’s hot for single ladies in Chicago, for her favorite places. “I would say these are all fairly relaxed, non-pretentious kind of places where you can meet locals.”

The Fireplace Inn: It’s a great place for an after-work drink. It’s a sports bar and restaurant plus it always has great specials.

Faith & Whiskey: It’s pretty laid back but has an edgy, rock bar sort of feel. It’s really good for 20-somethings. And it almost always has a great special or two (or three or four).

The Fifty/50: Great food, great beer, and outdoor seating. It’s a decent sports bar but attracts a variety of city people at night. Plus it’s in a really great neighborhood.

Old Town Social: It’s more for the late-night sort of crowd, but always a lot of fun.

Benchmark: A huge, fairly new sports bar that has a good nightlife and rooftop deck.

English: Order the fries, they are tasty and served up in a cone. It’s fun for nights or weekends and has a variety of patrons.

The Kerryman Bar: Great for food and beer. It’s perfect for 20-somethings and older than 20-somethings. You can also catch a game or mix it up at night with “Club Kerryman.”

Theory Sports Bar & Grill: It’s a smaller bar but a relaxed atmosphere and good for after work.

Jenina Nunez, another dating blogger for Chicago Now, told Single Edition some of her reasons why this is a fun city for singles. “Chicago is a great place to find your fill of sports bars. It's part of the culture and in those types of relaxed settings, it makes it easier for you to meet guys.”  Her top-ranked sports bars are the Gaslight and The Fifty/50.

“I also love River North and places like Rockit Bar & Grill or Hub51 on a Friday night because they draw fun after-work crowds. And if you're in town [in the beginning of the month], First Fridays at the Museum of Contemporary Art draw a great social crowd. It's usually themed, there are light appetizers, and there's a great after-party at a trendy Chicago spot.”

There are plenty of fun ways for Chicago residents to expand their social circles and meet more singles in their hometown. In the warmer months, sign up for the Singles Softball Sunday league, or join the Chicago Sports and Social Club throughout the year. We also like Chicago Meetup Groups for meeting people who share your interests and hobbies.