Chicago's Most Unique First Date Ideas
1. PILSEN ART WALK
The Chicago Arts District hosts 2nd Fridays Gallery Night, the monthly opening receptions at the galleries and artists' studios centered around South Halsted and 18th Streets in Chicago. The event begins at 6:00pm and runs till 10:00pm. Visit the 30+ creative spaces as they showcase an exciting display of art and artists from Chicago and beyond. This unique art community opens its doors, free of charge, and lets you get up close and personal with the art and artists. Pick up a map at the information center at 1821 S. Halsted and explore the city's most vibrant art community, the Chicago Arts District, where people meet ART!
Address: 1945 S Halsted St, Chicago, IL 60608
2. VICTORY GARDENS BIOGRAPH THEATER
This indie theater, located in the heart of Lincoln Park, is a gem. Maybe it's just me, but there's something magical about going to a theater, any kind of theater, whether it's for an opera, play, musical, or even a comedy show. Liquor & Latkes was playing the night I visited the Victory Gardens Biograph Theater and featured Jewish rappers, singers, comedians, graffiti writers, and Rabbis. Check their calendar for a list of current plays.
Address: 2433 N Lincoln Ave
3. ALIVE ONE
Located in Chicago’s Lincoln Park area, aliveOne combines the very best of music and spirits. Separated into two different rooms, the front offers a fully stocked bar with 16 different beers on tap, including some of Chicago's best microbrews, and an “allLive” jukebox containing live recordings of Rock and Roll’s best bands from the past and present.
Address: 2683 N Halsted St
4. WALK THROUGH OLD TOWN
Old Town is a historic neighborhood, home to many of Chicago's older, Victorian-era buildings. It offers a plethora of restaurants for those wanting to do the traditional dinner date. However, if you're shooting for a more casual first-date experience, there's laid-back options such as coffee and dessert shops, neighborhood bars (like the Benchmark), and comedy clubs like Zanies and Second City.
5. BAR PASTORAL
Bar Pastoral boasts an intimate, comfortable atmosphere to enjoy artisan cheese, bread and wine with your date. You can craft your own cheese plate from 24 options across four categories and pick the wine for pairing from the rotating menu, currently featuring 34 bottles. All the choices will give you and your new friend lots to discuss!
Address: 2947 North Broadway Street
6. HAPPY VILLAGE
Happy Village is the perfect down-to-earth neighborhood pub to grab a beer and play ping pong. One single Chicagoan loves it "because hanging out in the beer garden is like hanging out at your cousin's backyard graduation party: plastic furniture, a party tent and the steady hum of a sizable crowd sipping on cans of beer. It's perfect for that get-to-know-you conversation on a late summer afternoon. Oh, and you can have pizza delivered!"
Address: 1059 North Wolcott Avenue
7. BOTTLE & BOTTEGA
Bottle & Bottega is the perfect first date for those seeking a creative outlet with the help of flowing libations. With multiple locations throughout Chicago, all you have to do is show up ready to paint and drink your favorite bottle of wine. Locations include Lakeview, South Loop, Evanston, Glen Ellyn, and La Grange.
Address: Different locations - Check website.
8. MILLENNIUM PARK SUMMER CONCERT SERIES
The architecturally-stunning Millennium Park plays host to the free Millennium Park Summer Music Series (formerly known as Downtown Sound and Made In Chicago). Grab a seat at the Jay Pritzker Pavilion or spread out on the Great Lawn for outdoor concert performances from local, national and international acts every Monday and Thursday evening June – August at 6:30pm. Get more details on all the performers as well as the latest updates to the concert schedule at cityofchicago.org.
Address: Jay Pritzker Pavilion, Millennium Park (201 E. Randolph St.)