Staypineapple, An Iconic Hotel teamed up with AmazingCo to curate a range of Chicago experiences available exclusively to hotel guests. Discover the city in a whole new way through unique, self-guided tours that start inside the hotel. Be it food, adventure or photography, there is an experience for everyone.

Local Highlights The Loop

The perfect way to explore the stunning area around our hotel! Solve clues and riddles that uncover a path to local hidden gems and well-known attractions. Exclusive to hotel guests, this self-guided tour starts in the lobby and will have you acquainted with neighborhood hotspots before venturing out to must see destinations. Designed to orient you with your new surroundings, you’ll discover the best the area has to offer while enjoying your morning coffee, a picnic lunch, something sweet and a drink to finish. Allow 3 hours to complete the experience, or enjoy optional extras along the way to make it a full day experience.

• Self-guided experience

• Stunning picnic spread included

• Discover hidden Chicago gems

• Vegetarian, vegan & gluten free options

From $45 Per Person

Mystery Picnic
Lincoln Park

Brimming with charming eateries and interesting boutiques, Lincoln Park is a perfect neighborhood to spend the day exploring! Soak in the natural beauty of the outdoors from the area’s namesake park to the lakefront trails and beaches. This peaceful, tree-lined neighborhood is the perfect escape from the everyday hustle and bustle.

Starting with a picnic basket, have fun solving personally curated clues and riddles that’ll take you on a journey to collect your special gourmet picnic food bit by bit. Each clue you solve will lead you closer to your next picnic food pickup and even closer to your final stunning secret picnic spot.

From $45 Per Person

Mystery Picnic North Utica

Savor the day in beautiful North Utica! Home to some of the state’s favorite parks, this slow-paced town still has plenty to see and do. Whether trekking through its natural beauty or perusing boutique shops in town, North Utica is the perfect destination for a memorable getaway.

Starting with a picnic basket, have fun solving personally curated clues and riddles that’ll take you on a journey to collect your special gourmet picnic food bit by bit. Each clue you solve will lead you closer to your next picnic food pickup and even closer to your final stunning secret picnic spot.

From $45 Per Person

Designed exclusively for Staypineapple travelers.

Experiences start from your hotel. Less time in transit, more time exploring.

All experiences are self-guided, meaning it’s private and at your own pace.