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🇺🇸 Chicago — your itinerary

5 days · 14h of activities · $129 per person in tickets & dining

Map of Chicago

Day-by-day plan

Day 1 — Arrival

2026-08-05

1h · $0

Light afternoon after travel — ease into the city.

14:30
→ 15:30
Afternoon
🏛️Cloud Gate (The Bean) & Millennium Park
Chicago's iconic 110-ton polished steel sculpture in free Millennium Park — stunning at any time of day.
1h · Free · must-see

Day 2

2026-08-06

5h 30m · $80

09:30
→ 11:00
Morning
🎭Chicago Architecture River Cruise
Chicago Architecture Center's boat tour reveals 50+ landmark buildings and the story of the world's most influential skyline.
1h 30m · $48 · must-see
14:00
→ 18:00
Afternoon
🎭Art Institute of Chicago
One of the world's greatest art museums — home to Seurat's Sunday on La Grande Jatte and Grant Wood's American Gothic.
4h · $32 · must-see

Day 3

2026-08-07

4h · $34

09:30
→ 12:00
Morning
🏛️Navy Pier
Chicago's most visited attraction — Ferris wheel, IMAX, Chicago Children's Museum, and free lakefront access.
2h 30m · Free (rides extra) · recommended
14:00
→ 15:30
Afternoon
🏛️Willis Tower Skydeck & The Ledge
Step onto a glass balcony 103 floors above Chicago — spectacular on a clear day with 50-mile views.
1h 30m · $30–38 · recommended

Day 4

2026-08-08

3h 30m · $15

09:30
→ 12:00
Morning
🌿Lincoln Park Zoo & Conservatory
One of America's last free admission zoos — 200+ species in a beautiful lakefront setting.
2h 30m · Free · recommended
14:00
→ 15:00
Afternoon
🎯Chicago Blues & Jazz Clubs
Buddy Guy's Legends, Green Mill, and Kingston Mines — the living birthplace of electric blues.
1h · $10–20 cover · recommended

Day 5 — Departure

2026-08-09

0m · $0

Quick morning visit before heading to the airport.

Free time — explore on your own.

Budget breakdown

1 traveler · 5 days

Category	Per person	Per person
Attractions & activities Entry tickets and activity fees from your plan.	$129	$129
Restaurants (dinner each day) Midpoint of cost ranges; lunch usually $10-20 extra per day.	$0	$0
Lodging (estimate, mid-range) 4 nights × ~$140/night	$560	$560
Local transport (estimate) 5 days of metro / taxis / ride share.	$75	$75
Total trip estimate	$764	$764

Mid-range estimates. Travel hackers can cut 30-40%; luxury 2-3×. Lodging assumes mid-range hotel/Airbnb.

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