Chicago's Outdoor Delights and Local Gems Itinerary

Spend your morning at the expansive Grant Park. Take a walk, enjoy the greenery, and visit the famous Buckingham Fountain.

For a late lunch, head to Giordano's for their famous deep-dish pizza. Afterward, explore the beauty of Millennium Park and see the Cloud Gate sculpture, also known as "The Bean."

Enjoy a delightful dinner at The Publican, known for its rustic fare and communal dining experience.

Start your day with a visit to the Adler Planetarium to explore the wonders of the universe.

For a unique dining experience, have lunch at Alinea, a three-Michelin-star restaurant known for its innovative and avant-garde cuisine. Afterward, take a relaxing walk along the Chicago Lakefront Trail and enjoy the scenic views of Lake Michigan.

Conclude your day with a cocktail at the famous The Signature Room at the 95th, where you can enjoy panoramic views of the city.

Indulge in a hearty brunch at Au Cheval, known for its decadent burgers and a must-visit for food enthusiasts.

After lunch, explore the vibrant neighborhood of Wicker Park. Visit local shops, street art, and enjoy a coffee at a cozy cafe like Asado Coffee Co..

For dinner, experience the lively atmosphere and excellent tacos at Big Star. Afterward, enjoy the local craft beer scene at a nearby brewery like Piece Brewery and Pizzeria.

Start your day with a visit to the iconic Chicago Theatre. Take a guided tour to learn about its rich history and influence on the city's entertainment scene.

For lunch, enjoy a classic Chicago hot dog at Portillo's Hot Dogs. Afterward, explore the vibrant neighborhood of Pilsen, known for its street art, cultural diversity, and delicious Mexican cuisine.

Immerse yourself in the local music scene with a live performance at a historic venue like The Green Mill, known for its jazz music and speakeasy vibe.

Spend your morning exploring the diverse and eclectic stalls at the Maxwell Street Market. Sample local street food and hunt for unique souvenirs.

For a late lunch, enjoy the vibrant atmosphere and delicious tapas at Cafe Ba-Ba-Reeba!. Afterward, take a guided tour of the Garfield Park Conservatory and immerse yourself in the beauty of its plant collections.

Dine at Lula Cafe, a neighborhood favorite known for its farm-to-table cuisine and laid-back ambiance.

On your last day, take a relaxing morning cruise on the Chicago River. Enjoy the architectural boat tour and learn about the city's famous buildings.

For a farewell lunch, savor the flavors of Italy at Eataly Chicago. Afterward, take a final walk along the Chicago Riverwalk and soak in the vibrant atmosphere of the city.

Conclude your trip with a memorable dinner at Girl & the Goat, a renowned restaurant offering a creative and seasonal menu. Afterward, take a leisurely stroll along the River North neighborhood and enjoy the nightlife.