🌆 Chicago Day & Night Adventure
From sky-high glass ledges to lakeside strolls, here’s how to hit Chicago’s Top 5 Landmarks — either in one epic day trip or as a glowing night tour.
1
Willis Tower Skydeck
South LoopStep onto the glass “Ledge” 103 floors above the city. Clear views into four states and unmatched photo ops.
- Hours: Daily, usually 9am–10pm (Sat from 8:30am).
- Tip: Best at sunset or early morning to skip the crowds.
💡 Book timed tickets online and arrive 15–20 min early.
Buy Tickets
2
360 CHICAGO
Magnificent MileFormer Hancock Observatory — skyline vistas, CloudBar cocktails, and the wild TILT ride that leans you over Michigan Avenue.
- Hours: Daily ~9am–11pm (last entry ~1 hr before close).
- Tip: Do 360 at night if you Skydeck at sunset.
3
Millennium Park
LoopSnap “The Bean” (Cloud Gate), splash at Crown Fountain, and chill under the Jay Pritzker Pavilion’s steel ribbons.
- Hours: Daily 6am–11pm.
- Tip: Early morning = best Bean reflections with no crowds.
4
The Art Institute of Chicago
Grant ParkHome to Monet’s Water Lilies, Seurat’s Sunday on La Grande Jatte, and the famous lions out front.
- Hours: Mon/Wed/Fri–Sun 11am–5pm; Thu until 8pm; closed Tue.
- Tip: Use the Modern Wing entrance on Monroe St to skip lines.
☀️ Day Itinerary (10am–8pm)
- 11:00am — Start at the Art Institute (highlights pass).
- 1:00pm — Walk through Millennium Park (Bean + Crown Fountain).
- 2:30pm — Head up to 360 CHICAGO for afternoon skyline views.
- 4:30pm — Early dinner around Mag Mile.
- 6:30pm — End with Skydeck at golden hour → sunset.
- Optional: stroll Navy Pier if open.
🌙 Night Itinerary (3pm–11pm)
- 3:00pm — Begin at Millennium Park (daylight Bean).
- 4:00pm — Visit the Art Institute (Thu best, open late).
- 5:45pm — Dinner + ride at Navy Pier Centennial Wheel at twilight.
- 7:30pm — 360 CHICAGO for night skyline.
- 9:15pm — Skydeck finale: city lights from 103 floors up.