How Headout makes choosing experiences effortless
We curate the best ways to experience
We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.
We partner with the best
Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.
All the best options, in one place
Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.
Book with complete peace of mind
Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.
Slide 1 of 41/4
Frequently asked questions about Chicago attraction tickets
Top draws include the 360 Chicago Observation Deck, and the iconic Willis Tower Skydeck — all perfect for first-time visitors.
You can grab tickets online in advance for Big Bus tours, 360 Chicago, and the Skydeck.
Explore Millennium Park with “The Bean,” relax on the Navy Pier waterfront, or view street art in Wicker Park. You can also enjoy free audio-guide walking portions included in some Big Bus ticket tiers.
The “L” train, buses, and bike-share are great options — and the Big Bus Hop‑on‑Hop‑off pass offers a flexible way to get between major sights with live commentary.
Besides the Big Bus, try architecture river cruises and food‑and‑culture walking tours for an in-depth local experience.
The Loop and River North neighborhoods put you within walking distance of the Big Bus route beginning, plus quick access to 360 Chicago and Skydeck.
- 360 Chicago—located on the 94th floor of the John Hancock Center, with stunning 360° and tilt-your-heart-butter-over-the-edge views.
- Willis Tower Skydeck—America’s tallest observation deck, 1,353 ft up, complete with the famous glass “Ledge.”
A solid 2–3 days gives you time for a hop-on, hop-off tour, a visit to both observation decks, museums, and lakefront strolls.
Museums like the Art Institute, Field Museum, and Shedd Aquarium are all easily accessible via the Big Bus routes.
