Discover the Windy City's Urban Majesty
Chicago, America's architectural crown jewel, offers a stunning blend of skyscrapers, lakefront beauty, and world-class culture. This 5-day immersive experience takes you from the soaring heights of Willis Tower to the underground beats of blues clubs. From your first deep-dish pizza to your final sunset cruise on Lake Michigan, you'll be captivated by Chicago's dynamic energy and Midwestern warmth.
Our carefully curated itinerary balances iconic landmarks with neighborhood gems. You'll explore Frank Lloyd Wright's masterpieces, taste your way through historic food halls, and discover why Chicago's art scene rivals New York's. Each day reveals new dimensions of this city, from Millennium Park's futuristic sculptures to the historic jazz joints of the South Side.
"Chicago is that rare American city that doesn't feel like it's trying to be something else—it's unapologetically, energetically itself."
Travel + Leisure
Cultural Immersion & Unique Experiences
This tour goes beyond sightseeing to offer genuine Chicago experiences. You'll join a local chef for a hands-on deep-dish pizza workshop, step onto the field at Wrigley Field (when available), and learn improv comedy from Second City alumni. Our small group size (maximum 12 travelers) ensures personalized attention and access to intimate experiences most visitors miss.
What Makes Our Chicago Tour Special
- Local Experts: Guides who call Chicago home share insider perspectives
- Food Focus: 15+ tastings across our dedicated food tours
- Exclusive Access: Behind-the-scenes at Chicago cultural institutions
- Architecture Focus: Private river cruise with AIA-certified guide
- Flexible Itinerary: Free time to explore personal interests
Tour Map
Key Locations on Your Journey:
- The Loop: Chicago's architectural heart and business district
- Millennium Park: Home to Cloud Gate ("The Bean") and outdoor concerts
- Magnificent Mile: World-class shopping and historic landmarks
- Wrigleyville: Vibrant neighborhood surrounding Wrigley Field
- Hyde Park: University of Chicago and Obama family history
