Date Ideas that are not just Eating & Drinking
Ready to shake up date night? Whether you’re planning a first date or spending time with your longtime love, Lakeview East is full of fun ways to make it memorable. Sure, dinner and drinks are great- but why stop there? Discover our favorite date ideas for you and your better half.
However, if you are looking for dinner and drinks, browse our Lakeview East Dining Guide! It highlights every single bar, restaurant, and cafe in the neighborhood.
Live Shows
The Newport Theater | Fringe, Drag, Burlesque, and More
Nestled above the streets of Wrigleyville, The Newport Theater is one of Chicago’s hidden gems and a premier destination for fringe theater.
This intimate 100-seat venue showcases an innovative lineup of artist-produced burlesque, drag, comedy, and variety performances, creating unforgettable entertainment in a unique setting. Guests can enjoy a full bar offering craft beers, domestic favorites, wine, soft drinks, and mixed drinks, with no food or drink minimum required. Originally home to Links Hall before evolving into an improv and comedy theater, The Newport Theater has long been a stage for bold, creative voices. Today, it continues that legacy by celebrating a diverse range of performers, perspectives, and artistic expression while delivering exceptional live entertainment.
Newport Theater Calendar
The Laugh Factory | Comedy
The Laugh Factory is a legendary Chicago live comedy joint. Located right at the intersection of Broadway and Belmont, you can come by for some laughs seven days a week. The club hosts a variety of events, ranging from traditional standup and “Fresh Faces” showcases for up-and-coming comics to special engagements and private theater rentals.
Keep in mind, the Laugh Factory does require a 2 drink minimum (can be non-alcoholic or alcoholic). You must be 18+ to enter!
Click here for tickets
The Annoyance Theater | Comedy, Drag, & Improv
For over 35 years, The Annoyance Theatre has created some of Chicago’s finest comedy. Home of such iconic shows as, Co-ed Prison Sluts, That Darned Antichrist, and Splatter Theater, The Annoyance uses improvisation to create new and original plays, musicals, sketch-comedy, and more in a vibrant, creative atmosphere. With shows 7 days a week, The Annoyance has something for everyone!
Check All Shows Here
Blind Wolf Comedy | Wednesdays at 8 pm
Whether you’re a comedy fan or simply looking for a fun mid-week night out, Blind Wolf Comedy is the place to be every Wednesday night. Tucked away inside the Blind Wolf Speakeasy, inside The Den Hotel, this FREE professional comedy showcase kicks off at 8:00 p.m. and features a fresh lineup of local favorites and touring comedians each week, all curated and hosted by Chicago comedian Devin Glass. It is free to RSVP!
Creative & Crafty
Pansies Pottery | Pottery Classes
New in 2026, Pansies Pottery is a boutique pottery studio! They provide quality wheel throwing instruction to small groups in a charming storefront. The Friday Night Date Night Class is $125. They keep it personal with just six wheels, ensuring you and your partner get plenty of attention, navigating the basics of wheel throwing while sipping your favorite beverage. You will be guided through the steps and learn how to transform a lump of clay into a unique, personalized bud vase. Get centered, connect, and make beautiful things! Price includes two wheels, aprons, premium clay and all tools.
There’s a variety of class choices to choose from, the 90 minute Clay for a Day Beginner Wheel Throwing Workshop is where you can learn basic wheel throwing techniques in this getting to know us mini 90 minute workshop. Together , you will center, lift and shape a vessel to be fired and ready to display in your home. The workshops are inclusive and limited to just 7 participants, giving each attendee plenty of one-on-one assistance. Price includes all materials and firing one vessel! BYOB, and is $60. Held on Saturdays 2PM.
View All Class Options Here
Shine Bright in Life | Community Arts Center
Shine Bright in Life is a art space designed for all! They offer tons of different creative art classes, from sewing to painting. They offer creative, soulful experiences designed to nurture your intuition, support your wellness, and help you shine from within. This is a playful, pressure-free space where there are no mistakes, only learnings; helping you explore, create, and shine brighter! Come create art, without worrying about the mess, or buying the materials necessary.
Saturday Night Paint Parties: Paint Party is a playful, no-pressure night to unwind, explore, and have fun with paint. Each session features a monthly theme and gentle guidance to help you experiment with the elements of design: line, shape, pattern, color, texture, movement, and dimension. All experience levels are welcome—truly. As adults, we often lose that fearless, curious spirit—but Paint Party helps you reconnect with it. This class gives you permission to play, take risks, and create the way you once did as a child: freely, joyfully, and without judgment. Paint parties happen one Saturday a month, from 7 to 9 pm.
Let’s Dance!
Fred Astaire Dance Studio | Dance Lessons
Fred Astaire is a dance studio, ran by professional dancers who are patient, kind, and fun to work with! Learn to dance is a judgement free environment, and unleash your inner dancer. They specialize in teaching brand new students, giving them confidence, a sense of rhythm and a LOVE for dance!
Register For a Class Here
Dance on Broadway | Dance Lessons
Dance On Broadway is a brand new state of the art dance studio located in the heart of Lakeview East. They offer classes for adults in Ballet, Pointe, Jazz, Hip-Hop, Contemporary, Modern, Tap, Latin and more! This summer, they have an Adult Open Latin class every Wednesday from 7:30-8:30 PM. This would be fun for dancers to step into Latin Basics and enjoy a night of dancing.
Register For a Class Here
Salsa Sundays at The Cubby Bear | Salsa Dancing & Lessons
Every Sunday night is Salsa Night at the Cubby Bear in Wrigleyville! Dance Salsa, bachata, cumbia, and the cha-cha. Doors open at 7 pm, and dance lessons kick off at 8 pm. Be sure to check the Cubby Bear event calendar before attending
Upcoming Events at Cubby Bear
Game On
Bonus Round Game Cafe | Board Game Cafe
Bonus Round is a welcoming board game café located in Lakeview, just a short walk from the Belmont Red Line. Designed as a place to gather over fun games, delicious food, and great company, the café offers a full-service menu featuring shareable snacks, sandwiches, espresso drinks, tea, craft sodas, mocktails, beer, wine, and cocktails.
Home to a curated library of more than 500 board games, Bonus Round invites guests to discover everything from the latest releases to timeless favorites. Visitors can browse the collection on their own or receive personalized recommendations from the café’s knowledgeable Game Guides, who are always happy to help players find their next favorite game.
At its core, Bonus Round is committed to creating a welcoming, inclusive, and judgment-free environment where everyone—regardless of experience level—can feel comfortable, have fun, and connect with your date.
Book Your Table
Replay Lincoln Park | Arcade Bar
Replay Lincoln Park is home to hundreds of vintage arcade games, that you can play for FREE! They also have pop-a-shot, skee-ball, and air hockey, for some flirty friendly competition. But wait, there’s MORE. Replay Lincoln Park transforms into a rotating decked out pop-up throughout the year. They’ve transformed to Paddy’s Pub from It’s Always Sunny in Philadelphia, Game of Thrones, Shrek’s Swamp, Stranger Things, and more! Come get your game on, entry is free!
The Quandary Escape Room | Escape Room
An escape room is the perfect way to mix adventure, teamwork, and plenty of laughs. You’ll work together to solve puzzles, uncover clues, and race against the clock, making it a fun way to test your communication skills and celebrate each victory along the way.
Book Your Adventure Here
Couples Massage
Stillness Holistic Spa
Stillness Holistic Spa, is an elevated yet comfortable concept Spa where you be able to decompress and re-energize with Holistic techniques that will bring a full sense of well being. They offer all the following for duos: Therapeutic Massage for Two, Quietude for Two, Tranquility Massage for Two, Serenity Massage for Two, and Stillness Massage for two!
Book Online
The Now
The NOW Massage Lakeview offers 3 signature massage styles and custom enhancements such as Deep Tissue, Gliding Cupping, and Crystal Hot Stones! When booking your appointment, you can choose if it’s just for you- or for you and a guest. The NOW is open 7 days a week, from 9 am to 8 pm (and 10 am to 9 pm on Sundays).
For the Love of Animals
Cuddle Bunny
This place is as adorable as it sounds. Cuddle Bunny is a place where you can go and hangout with adorable snuggly bunnies! Cuddle Bunny is dedicated to providing a welcoming, comfortable space where guests can enjoy the companionship of domesticated rabbits, whether during a relaxing daytime visit or a unique weekend evening experience. Its mission is to offer an escape from the stresses of everyday life, creating an environment where visitors can unwind while enjoying the mood-boosting benefits of spending time with friendly bunnies.
In addition to bunny social hours, Cuddle Bunny offers fitness and holistic wellness experiences designed to nurture the body, mind, and spirit. Weekend evening activities, typically held from 6:00–8:00 p.m., include bunny yoga and meditation, sketching, knitting and crocheting, book clubs, poetry and creative writing, crafting, tie-dyeing, neon blacklight painting, and other rotating events.
Book Your Visit Online!
The Catcade
Cats + An Arcade = The Catcade. Located on Belmont, the Catcade is a non-profit, arcade-themed cat rescue, lounge, and our version of a cat café. Their lounge simulates a home environment. Cats are not kept in cages, instead they get to live in a 950 sq. ft. lounge where guests can pay $20 to visit the lounge and spend time playing, cuddling, and socializing the rescue cats! All of the cats are adoptable, with the exception of the adorable resident cat, Leo. Bring your date for an hour of kitty playtime, and your date will be unforgettable!
CuddlePups
Get ready for an hour of serotonin. CuddlePups offers a one-of-a-kind experience where guests can spend an hour surrounded by a room full of gentle, affectionate Italian Greyhounds—the sleek, lovable “supermodels” of the lap-dog world. Designed to promote relaxation, connection, and plenty of laughter, every visit provides a proven mood boost through the simple joy of cuddling, playing, and interacting with friendly pups. At CuddlePups, every session benefits both guests and the dogs, who thrive on the gentle affection, socialization, and positive attention they receive. Between visits, the pups enjoy ample time to rest, nap, and engage in enrichment activities, ensuring their health and wellbeing always come first—a commitment reflected in the business’s hundreds of five-star reviews.
Beyond creating memorable experiences, CuddlePups is committed to giving back to the community. One dollar from every ticket supports local dog rescue organizations and community nonprofits, while the space is regularly donated for rescue events and complimentary visits are provided to organizations focused on mental health and animal welfare. Whether visiting for a unique date night, celebrating a special occasion, gathering with friends, or simply looking to unwind, guests will find CuddlePups to be a heartwarming experience that leaves everyone feeling happier—and makes a meaningful impact both inside and outside its walls.
