Summertime Chi: 4-Day Weekend in Chicago

Go to a Chicago Cubs game at Wrigley Field. Eat a Chicago dog, soak in the crowd’s energy, and feel the shared joy (or heartbreak) that defines Cubs fans. Win or lose, the atmosphere is unmatched.

Charter a boat on Lake Michigan and spend the day in the Playpen. With a captain at the helm, it’s the perfect way to relax with friends, swim, listen to music, and experience Chicago from the water.

Attend an outdoor yoga class in one of Chicago’s parks or along the lakefront. The city offers free and low-cost classes—often listed on Do312—and practicing with the skyline and lake as your backdrop feels uniquely grounding.

Rent a Divvy e-bike and ride the Lakefront Trail. Cruising for miles alongside the water is one of my favorite ways to experience the city, offering expansive views and a deep sense of freedom.

Pack a picnic and wander through Lincoln Park. Find a quiet patch of grass, enjoy good food, and savor being outdoors when the weather is warm and the city feels fully alive.

Visit the Garfield Park Conservatory. Surrounded by lush flora and fauna year-round, it’s especially magical in the winter, when the rest of the city feels dormant.

Stop by Gramaphone Records, the center of House music culture. It’s a powerful reminder of Chicago’s influence on global music and a must-visit for anyone who appreciates the city’s creative legacy.

Attend a concert at The Salt Shed. With its incredible sound system and massive yet intimate space, plus an outdoor area perfect for drinks and connection before a show, it’s one of the city’s best live-music venues.

Spend a day at the Art Institute of Chicago. Open almost daily from 10 am to 5 pm, it’s a place where you can easily lose an entire day and still feel like there’s more to see—perfectly paced with breaks for snacks and a glass of wine at the café to keep you energized.

Avec: A beloved Mediterranean restaurant and wine bar known for its inventive small and large plates in a lively, communal setting; ideal for sharing dishes like chorizo stuffed dates and wood-fired flatbread with friends over a robust wine list.

Crying Tiger (River North): A vibrant Southeast Asian destination blending bold regional flavors with stylish interiors and creative cocktails, where shareable dishes like lobster pad Thai and Wagyu khao soi make it great for groups or special evenings out.

Kanin: A casual Filipino-Hawaiian bodega and local favorite in Ravenswood serving crave-worthy musubi and hearty bento boxes; don’t miss the standout ube banana pudding dessert.

Dorian’s: A stylish speakeasy bar known for its welcoming atmosphere and well-crafted drinks—perfect for an evening social stop or a laid-back nightcap in a casual setting.

PIZZ’AMICI: A relaxed pizza spot offering classic Italian pies with a Chicago twist—a solid pick for a casual lunch or late night slice that’s NOT deep dish.

Beatnik on the River: Nestled along the Chicago River, this bohemian-inspired restaurant and bar blends globally influenced cuisine with tropical cocktails and exotic decor, making it a memorable stop for brunch and day drinking.

Aba: An elevated Mediterranean restaurant with a California influence, offering modern small plates and an impressive wine and spirits program—excellent for a romantic dinner or special occasion.