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Architecture, deep dish, lakefront, and the most-rewarding American city most travelers skip.

Chicago is one of the most-underrated cities in America — world-class architecture, exceptional museums, serious music scene, and the most-photogenic skyline in the Midwest.

What's Inside

  • A 4-day Chicago route across the Loop, Wicker Park, and the lakefront
  • Where to stay: Loop, River North, or West Loop
  • Architecture boat tour: which company, why it's the best 90 minutes in the city
  • Museums: Art Institute, MSI, Field, plus the underrated ones
  • Food: deep dish reality, Italian beef, hot dogs, and the new restaurant scene
  • Day trips: Milwaukee, Lake Geneva, the Indiana Dunes

Ideal For

Architecture lovers and Midwest-curious travelers.

Trip Details

Best season: May-October
Recommended trip length: 3-5 days
Guide length: 36 pages

Delivered as a printable PDF immediately after purchase.

Chicago Destination Guide

SKU: HITW-DG-US-CHICAGO
$4.00Price
Quantity
    • A 4-day Chicago route across the Loop, Wicker Park, and the lakefront
    • Where to stay: Loop, River North, or West Loop
    • Architecture boat tour: which company, why it's the best 90 minutes in the city
    • Museums: Art Institute, MSI, Field, plus the underrated ones
    • Food: deep dish reality, Italian beef, hot dogs, and the new restaurant scene
    • Day trips: Milwaukee, Lake Geneva, the Indiana Dunes
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