Spring in Chicago is a magical time when the city comes alive with blooming flowers, outdoor activities, and exciting events. Whether you’re a local or visiting for the weekend, here’s your ultimate guide to making the most of a spring weekend in the Windy City.

Friday: Arrival and Evening Fun

Check-In & Explore Downtown

Start your weekend by checking into a centrally located hotel like The Peninsula Chicago or the trendy Chicago Athletic Association. Drop off your bags and take a stroll down Michigan Avenue for some shopping and sightseeing.

Dinner with a View

Kick off the evening with dinner at Cindy’s Rooftop, where you can enjoy stunning views of Millennium Park and the city skyline. If you’re craving deep-dish pizza, head to Lou Malnati’s for a classic Chicago experience.

Evening Entertainment

End the night with a show at the Chicago Theatre or a jazz performance at the historic Green Mill Cocktail Lounge. If you’re in the mood for comedy, check out The Second City, where many famous comedians got their start.

Saturday: Exploring the City

Morning: Outdoor Adventures

Start your day with a scenic walk or bike ride along the Lakefront Trail. Stop by Grant Park and Buckingham Fountain, then make your way to the famous Cloud Gate ("The Bean") in Millennium Park for some iconic photos.

Midday: Museum & Lunch

Visit the Art Institute of Chicago to admire its world-class collection, including works by Van Gogh and Monet. For lunch, grab a bite at The Purple Pig, known for its delicious Mediterranean-inspired small plates.

Afternoon: Neighborhood Exploration

Explore a unique Chicago neighborhood in the afternoon:

• Lincoln Park: Walk through the free Lincoln Park Zoo and enjoy the spring blooms at the Lincoln Park Conservatory.
• Wicker Park: Shop at indie boutiques and grab a coffee at a cozy café like The Wormhole.
• Pilsen: Admire colorful street murals and stop by the National Museum of Mexican Art.

Evening: Riverwalk & Nightlife

As the sun sets, take a scenic stroll along the Chicago Riverwalk, where you’ll find bars, restaurants, and live music. For dinner, dine at RPM Seafood for fresh seafood with a riverfront view. If you’re up for nightlife, head to a rooftop bar like Offshore at Navy Pier or experience Chicago’s speakeasy scene at The Violet Hour.

Sunday: Brunch & Relaxation

Morning: Iconic Brunch Spots

Enjoy a leisurely brunch at a classic spot like Wildberry Pancakes & Café or beat the rush at Beatrix. For a more upscale experience, try brunch at The Langham’s Travelle restaurant.

Midday: Springtime Relaxation

Spend your final hours in the city soaking up nature:

• Chicago Botanic Garden (if you have time for a short trip outside the city)
• Garfield Park Conservatory for vibrant spring blooms
• Maggie Daley Park to enjoy mini-golf or a casual walk
  

Afternoon: Last-Minute Stops

Before heading out, grab a final bite at Eataly or explore Navy Pier for some last-minute souvenir shopping. If you have time, an architecture boat tour along the Chicago River is a great way to end your weekend on a high note.