5-Day Chicago Highlights and Culinary Delights Itinerary

Begin with a hearty breakfast at Lou Malnati's Pizzeria, a Chicago classic known for its deep-dish pizza. Afterward, take a stroll through the lush greenery of Grant Park and visit the majestic Buckingham Fountain.

Enjoy a diverse culinary experience at Eataly Chicago, where you can explore various food counters and enjoy a wide range of Italian delicacies. Post-lunch, immerse yourself in art at the renowned Art Institute of Chicago with a fast-pass ticket, featuring a vast collection of masterpieces.

Indulge in a memorable dining experience at Girl & the Goat, known for its innovative dishes and vibrant atmosphere. After dinner, take a leisurely walk along The Magnificent Mile, enjoying the upscale shops and city lights.

Start with breakfast at Little Goat Diner, a diner-style eatery with a creative menu. Then, join the Chicago Gangsters and Ghosts Guided Walking Tour to explore the city's darker history and hear chilling tales of the past.

For lunch, savor the flavors of authentic Mexican cuisine at Big Star, known for its tacos and whiskey selection. Afterward, visit the historic Wrigley Building and take a walk on the Chicago Riverwalk to enjoy the architectural beauty and the river breeze.

Dine at Gibsons Bar & Steakhouse, a classic Chicago steakhouse offering prime cuts and a lively atmosphere. Cap off the night with the Chicago Prohibition Speakeasies Bus Tour or Walking Tour, delving into the city's clandestine past and enjoying some hidden libations.

Enjoy a breakfast at Portillo's Hot Dogs, a Chicago institution known for its classic hot dogs and Italian beef sandwiches. Afterward, spend the morning at the serene Lincoln Park & Zoo, exploring the zoo and the nearby park.

Have a leisurely lunch at Pequod's Pizza, famous for its caramelized crust pizzas. Post-lunch, visit the vibrant Navy Pier and take a spin on the iconic Ferris wheel, enjoying the views of Lake Michigan and the city skyline.

Dine at Longman & Eagle, a Michelin-starred gastropub known for its creative menu and extensive whiskey selection. After dinner, experience the lively atmosphere and live performances at the historic The Chicago Theatre.

Start your last day with breakfast at Kuma's Corner, a rock music-themed eatery famous for its gourmet burgers. Afterward, take a guided walking tour of the Chicago Underground Pedway & Downtown Secrets, uncovering hidden gems and architectural wonders.

Enjoy a diverse culinary journey at Chicago Favorite Foods Guided Walking Tour, sampling the city's signature dishes and learning about its food culture. After the tour, visit the 360 Chicago Observation Deck Sip and View to relax with a drink and enjoy the final panoramic views of Chicago.

Conclude your trip with a memorable dinner at Xoco, offering a modern take on Mexican street food. Reflect on your Chicago experience as you enjoy the flavors, and perhaps plan a return visit.