Weekend Adventures in Chicago

We’d be kidding ourselves if we ever claimed that Chicago was “boring.” It would honestly just sound ridiculous coming out of our mouths. There’s endless fun to be had in this city and a neverending list of new places to discover and explore.


You always want to make sure your adventure matches your style though. That’s why we’ve put together a few suggestions for you.




Evening Excursions


Photo: Michael Brosilow via Steppenwolf Theatre


Steppenwolf Theatre: Steppenwolf’s original productions have attracted performers and directors from around the world. From comedy to drama—and everything in between—this multi-stage playhouse has all the theatrical bases covered.


Logan Theatre: Perhaps a movie sounds better? You can catch many of the current Hollywood hits at this Logan Square staple along with frequent screenings of classic throwback films. Don’t forget to grab a drink in its lounge-style lobby and bar before your movie starts.


Photo via IMR Chicago


Entente: Schwa graduate Chef Brian Fisher scored big on his first restaurant opening, bringing home a Michelin star. The food is beautiful, elegant and completely Instagram worthy. The great news is that it all tastes even better than it looks.


Remedy: What else do you have to do on the weekend except stay up late? That’s why we’re directing you towards one of the many superb 4 a.m. bar options throughout Chicago. Remedy doesn’t skew nearly as divey as many of the other late night spots. Its cocktails are solid and the jukebox has everything from Kid Cudi to David Bowie to Spoon.




Foodie Paradise


Uptown’s Vietnamese Bakeries: Start your day early with the freshest baked goods and bánh mì from one of Uptown’s Vietnamese bakeries. Take a stroll down Argyle Street—right off the red line stop—and step into Ba Le Sandwich Shop, Hong Xuong Bakery and whatever else peaks your interest.


The Chopping Block: We all love it when someone else cooks for us, but self-validation is pretty great, too. Take a cooking class at The Chopping Block’s Merchandise Mart or Lincoln Square locations. You’ll be impressing friends with steak, pasta, tapas or whatever else you want to master in no time.


Photo: Christian Seel via The Alinea Group


The Aviary: Could you fill an entire weekend with food in Chicago? Yes. Would it be doctor recommended? No. The Aviary cocktail bar puts as much care and experimentation into its drinks as many of Chicago’s most revered kitchens. Take a break from food and keep your drink game strong.


Food-Focused Street Fests: Take your snacking to the streets with street fests that put food first like Lincoln Park Greek Fest, WingOut Chicago, Ribfest, Pilsen Food Festival and Taste Of Randolph.




Stylish & Skillful


Photo via Spout Home


Sprout Home: Home decor means more when you created it—and a little extra green is always nice during Chicago’s cold months. Book a public or private terrarium-making class at Sprout Home in West Town.


Photo: Courtney Laper via Vintage Garage Chicago


Vintage Garage: Springtime means Vintage Garage Chicago is back in session. Every April through October, on the third Sunday of every month, an Uptown parking garage transforms into a vintage shoppers paradise with up to 100 vendors selling clothes, jewelry, furniture, home decor and more.


Local Fashion In Hyde Park: The Hyde Park neighborhood is attracting more and more local designers. Get a new look that’s truly Chicago by visiting Dearborn Denim (Chicago made jeans for men and women), Sir & Madame (husband and wife owned boutique), The Silver Room (community-fostering jewelry, clothing and home decor storefront), Modern Cooperative (beautiful vintage shop) and other outlets near Harpers Court.


Congruent Space: This off-the-beaten-path boutique is constantly bridging the gap between art, and fashion. Stop in and catch one of its frequent installations and pop-ups.







Game On


Photo: Amber Boutwell via IMR Chicago


Punch Bowl Social: West Loop’s newest gaming bar has everything—seriously, everything. Punch Bowl Social offers bowling, virtual reality, arcade games, karaoke and, of course, well-stocked bars.


Fireside Bowl: You won’t catch legendary punk shows here anymore, but it's still one of our favorite places to bowl in Chicago. Don’t ever change, Fireside.


Headquarters Beercade: The “barcade” concept exploded in Chicago in recent years, but Headquarters’ cocktail menu, game selection and central location always keep us coming back for another round. Oh, yeah, most of its games are free to play, too. We like that a lot.


SPiN: Ping pong is no longer a game for dive bars and your parents’ basement. SPiN has elevated the sport and created an entire haven for paddle kings and queens.




Refreshing Escapes


White Sox or Cubs Game: Whatever pinstripes you wear on your heart, North Siders and South Siders can both agree an early season baseball game can be the perfect escape from the daily routine.


Walk In The Park: What’s your favorite Chicago park? Why don’t you go spend some time there?! Our favorites include Humboldt Park, Indian Boundary Park in Rogers Park and, of course, Millennium Park downtown.


Image via Chicago Trolley & Double Decker Co.


Architecture Tour: Learning more about the skyline that surrounds us can be an excellent excuse to get outside. Book a bus or boat tour of Chicago’s architectural highlights. Our favorites include Chicago Trolley & Double Decker Co. for its topside bus seats and Seadog Cruises for the thrills its speedboat tours provide.


Chicago Botanic Garden: Where else can you watch the flowers bloom in such abundance as the Chicago Botanic Garden’s 27+ gardens?




You, Rediscovered 


Chicago School of Shoemaking: You know that phrase, “Try taking a walk in someone else’s shoes”? Well, try making someone else’s shoes! The Chicago School of Shoemaking offers classes in shoemaking and other leatherworks. It’s a skill you never knew you wanted to learn and a sense of accomplishment you won’t be able to shake.


Chicago Music Exchange: Seasoned musicians and new students of rock alike can enjoy the boundless selection of vintage and new instruments at Chicago Music Exchange. Hone or discover your sound with a new guitar, bass, drum kit, amplifier or other equipment here.


Photo via Brooklyn Boulders Chicago


Brooklyn Boulders Chicago: Unless you count our skyscrapers, Chicago doesn’t offer a lot of elevation. Scratch your rock climbing itch at Brooklyn Boulders Chicago, one of the city’s most popular indoor climbing gyms.


It’s Your Park Day: Celebrate and sustain the parks that keep Chicago green and beautiful amidst an urban setting. This city-wide volunteer day is organized by the Chicago Parks Foundation to aid with park clean-up, improvements and other projects. Get more info and join in on June 16th.




Relax & Restore


Goat Yoga at Garfield Park Conservatory: When weather permits, the Garfield Park Conservatory hosts a herd of goats on its ground to keep its weed population under control—and to provide visitors with some super cute entertainment. You can take part in a free yoga class with these little guys on the third weekend of the month throughout spring and summer!


Image via IMR Chicago/spa at dana


spa at dana: Happy hour like you never have before! The spa at the dana hotel has a new after work deal: two 25-minute mini-treatments (choose from a head, neck and shoulders massage; facial; body polish or leg and foot treatment) plus a glass of Prosecco to drown out the day's stresses. There's always time for a little relaxation, even while you're on the go. Call ahead to make reservations.


Photo via Lincoln Park Conservancy 


Alfred Caldwell Lily Pond: A visit to Lincoln Park Zoo is always a great way to get away and back in touch with nature, but don’t miss an equally (if not more) peaceful attraction that’s adjacent to the zoo. The Alfred Caldwell Lily Pond is exactly what it sounds like: a shady lily pond that attracts picnickers, book readers and the occasional goose.


Image via AIRE Ancient Baths


AIRE Ancient Baths: You’ll feel like you’ve stepped back into ancient Roman or Greek times with this experience. AIRE’s baths are found inside of a restored factory originally built in 1902. Enjoy a calming soak or book a massage, too, for ultimate relaxation.




Dare To Explore


Bottle & Bottega: Discover what you can create when you combine a blank canvas and a full bottle of wine. Bottle & Bottega’s BYOB paint and sip parties are perfect for dates, girls nights out or solo adventures.


Cook County Forest Preserve: We’re willing to bet you didn’t know the Cook County Forest Preserve is the resting place of the first nuclear reactor. Yep. You’ll have to do a little bit of hiking to get find several “tombstones” marking where it’s buried through the preserve. No digging, please!


Photo via Weird Chicago


Weird Chicago Tours: These bus tours—most of which take place after the sun sets—provide insight into some of Chicago’s more grizzly historical moments including haunted history, true crime, and speakeasies. There’s even an entire tour dedicated to The Devil In The White City and Chicago’s first serial killer.


Photo via Shedd Aquarium 


Shedd Aquarium: Plan an “extraordinary experience” at the Shedd. You can watch a behind-the-scenes shark feeding, snap a picture with a penguin or get up close and personal with a beluga whale!




NO MATTER WHICH ADVENTURE YOU SEEK, LINE39 WINES ARE THE PERFECT COMPANION...NOW GET OUT THERE & FIND YOUR ADVENTURE!