Chicago, Capital of Architecture — 4 days

An iconic skyline and the Midwest's food scene. Day-by-day itinerary: Arrival & Millennium Park; Architecture & Willis Tower; Museums & Navy Pier; Departure.

Day-by-day itinerary

Day 1 — Arrival & Millennium Park

• 13:00 — Arrival at O'Hare airport
• 14:30 — CTA Blue Line to the Loop — O'Hare (ORD) → Loop
• 15:30 — Check in, the Loop
• 17:00 — Millennium Park & Cloud Gate ('The Bean')
• 20:00 — Deep-dish pizza dinner

Day 2 — Architecture & Willis Tower

• 10:00 — Architecture cruise on the Chicago River
• 13:40 — Walk to Willis Tower — Chicago River → Willis Tower
• 14:00 — Willis Tower Skydeck
• 20:00 — Steakhouse dinner

Day 3 — Museums & Navy Pier

• 10:00 — Art Institute of Chicago
• 14:30 — Bus to Navy Pier — Art Institute → Navy Pier
• 15:00 — Navy Pier & the Lake Michigan shore
• 19:15 — Bus/train to Wicker Park — Navy Pier → Wicker Park
• 20:00 — Dinner in Wicker Park

Day 4 — Departure

• 10:00 — Free morning on the Magnificent Mile (shopping)
• 13:00 — Airport transfer
• 16:00 — Return flight