Planning a summer escape to Chicago? July is the perfect time to explore this vibrant city — think swanky rooftops, boutique hotels, beachside brunches, Afrobeats nightlife, and scenic architecture tours. Whether you're heading on a solo trip, girls getaway, or baecation, this 3-day itinerary will give you all the vibes, views, and hidden gems to experience the best of Chicago in style.

Let’s dive into my curated guide on how to spend the perfect weekend in Chicago ✨

📍 Day 1: Boutique Vibes, Dinner & Afrobeats Nights

Where to Stay:
The Emily Hotel
Located in the trendy Fulton Market district, this boutique hotel is aesthetic goals. Think modern interiors, cozy rooms, rooftop access, and a vibe that makes you want to stay in and go out all at once.

Dinner Plans:
Fora Chicago
Start your trip with dinner at Fora — an elevated yet cozy spot perfect for easing into the city’s food scene. Their menu is fresh, stylish, and full of flavor.

Wind-Down Moment:
Parkside Park Chi
After dinner, take a stroll through this peaceful green space. It’s the perfect golden hour location for a chill moment or mini photo session.

Nightlife Pick:
Masada Chicago
Ready to dance? Masada’s Afrobeats and hip-hop sets bring the energy. Grab your girls and head here for an unforgettable night out — trust me, you’ll leave with sore feet and great memories.

📍 Day 2: Movement, Brunch & Rooftop Energy

Morning Workout:
The Emily Hotel Gym
Start the day with a light gym session to reset and refresh. It's a great way to stay on track during your trip while giving yourself an energy boost for a full day ahead.

Brunch/Lunch:
Shore Club Chicago – North Avenue Beach
Imagine sipping mimosas and enjoying avocado toast right on the beach. Shore Club is located by Lake Michigan and gives you the ultimate beachfront brunch experience.

Sunset Drinks:
The Wit Hotel Rooftop (Hilton)
As the sun sets, head to this swanky rooftop to wrap up your day. Great cocktails, city views, and an upscale vibe that perfectly closes out a Saturday in the city.

📍 Day 3: Markets, Brunch & A Scenic Send-Off

Morning Exploration:
Fulton Market District
This neighborhood is full of charm, creativity, and hidden gems. Walk around and explore boutiques, coffee shops, murals, and more.

Brunch Stop:
The Vig
Trendy, lively, and full of good eats — The Vig is the ideal brunch spot before heading to your final activity. Think chill vibes, delicious food, and cute corners for content.

Final Stroll + Architecture Tour:
Riverside Walk ➝ Wendella Boat Tour
Take the train down to Riverside Walk for a calming stroll along the river, then hop on The Wendella Architecture Boat Tour to end your trip. It’s the perfect mix of education and relaxation, with breathtaking views of Chicago’s skyline.

🧳 Chicago Travel Tips:

Pack Smart: Day-to-night outfits and comfy (but cute) walking shoes are a must. You’ll be exploring both urban areas and beach spots.

Reserve Ahead: Rooftops and brunch spots can book up in July — be sure to grab your reservations early.

Travel-Friendly Content Tip: Want to create content while traveling? Opt for golden hour moments and rooftop angles. Chicago’s skyline does not disappoint.