Stroll along the Chicago river and stop for a drink on one of the many patios.
Laugh the night away with world-class improv and sketches at the renowned Second City theater. Where our very own Andrew Coates performed (well in Toronto). Andrew took Sarah to her first show in March 2025.
Take in Chicago's legendary skyline on a world-famous architecture river cruise.
Experience Chicago's lively lakefront at the iconic Navy Pier, home to dining, attractions, and stunning views.
Explore lush gardens and a diverse collection of animals at one of the country's oldest free-admission zoos.
Step into a Victorian glasshouse and explore stunning botanical collections at the Lincoln Park Conservatory.
Immerse yourself in centuries of artistic masterpieces at the world-renowned Art Institute of Chicago.
Coffee: Sawada Brunch: Land & Lake, Beatrix Miru, Small Cheval, The Smith, Barrio, Sushi San, La Scarola, Dawson
Bisous, Lone Wolf, Bar Estereo, Three Dots and a Dash, London House (rooftop), Luxbar, The Smith, Cindy's Rooftop
Portillo's, Gibson's Bar & Steakhouse, RPM Italian, RPM Steak
Deep Dish: Lou Malnati's, Giordano's, Pequod's Thin Crust: Ranalli's, Robert's, Pizzeria Portofino