Chicago itinerary — 3 days
Day 1 — Chicago
4 stops · ≈ 6 h 27 minRenowned art museum holding nearly 300,000 works from all over the world, spanning many centuries.
Popular recreational area with winter ice skating, a climbing wall & playground equipment.
Riverside pedestrian path featuring city views & dining, plus bridges, fishing piers & boat docks.
Observatory on the 94th floor of the John Hancock Building with a tilting glass lookout 1000ft up.
Reserve
9If you have time left — worth it too.
Lions, tigers, dolphins & more frolic in natural indoor & outdoor settings at this wildlife park.
Chicago Water Tower — a historic water tower.
Chicago River Boat Architecture Tours — boat cruises along the river showcasing the city's architecture.
Public sculpture with 2 50-ft. LED towers & a reflecting pool, by Catalan artist Jaume Plensa.
Among the world’s largest, Grant Park’s 3-level rococo fountain (1927) offers light & water shows.
State-of-the-art indoor aquarium, famous for its variety of habitats & views of Lake Michigan.
57-acre grounds with the Adler Planetarium, Shedd Aquarium & Field Museum, plus dining & lake beach.
State-of-the-art museum of science & invention, with the world's largest Tyrannosaurus Rex.
Sprawling, hands-on museum full of informative, child-friendly scientific & industrial exhibits.
- Buy or tap a Ventra card for CTA trains and buses — it works on both the 'L' and city buses.
- Chicago weather changes fast: bring layers and a windbreaker, especially near the lake, even in summer.
- Downtown streets follow an easy grid system (State and Madison are the center point), so navigation is simple on foot.
- Book popular attractions like Skydeck at Willis Tower and 360 Chicago online in advance to skip long lines.
- Tipping is expected: 15–20% at restaurants, $1–2 per bag for porters, and a few dollars for taxi/rideshare drivers.