Unwind in Style: Your Ultimate Holiday Staycation at The Robey


Discover the perfect holiday escape right in the heart of Chicago with a staycation at The Robey, where history and modern luxury meet in the Windy City. Nestled in the vibrant neighborhoods of Wicker Park and Bucktown, The Robey invites you to experience the magic of a holiday staycation like no other.

The Robey: Your Chic Chicago Staycation Destination

As a distinguished member of the Design Hotels portfolio, The Robey is more than just a hotel; it’s an architectural masterpiece. Located at the iconic intersection of Damen, Milwaukee, and North Avenue, this historic 1929 Art Deco flat iron building welcomes you to a world of timeless elegance and contemporary sophistication.

Why Choose The Robey for Your Holiday Staycation

This holiday season, The Robey beckons with a warm and cozy ambiance that sets the perfect backdrop for your festive celebrations. Whether you’re planning a family reunion, a joyful gathering with friends, or a romantic holiday retreat, our guest rooms offer the ideal sanctuary.

Imagine waking up to panoramic views of the Chicago skyline while cocooned in the luxury of plush bedding and modern amenities. Each room is thoughtfully designed, blending stylish furnishings with inviting decor to ensure your stay is not only memorable but also relaxing.

A drone tour of The Robey

Exclusive Holiday Offers

To make your holiday stay even more delightful, The Robey presents exclusive promotions for your Chicago staycation. Stay for three nights or more and enjoy a generous 15% discount—an ideal opportunity for an extended holiday retreat. For those with flexible plans, we offer a 10% discount for bookings made up to one day prior to your stay.

If you’re ready to lock in your plans, our prepaid and non-refundable rate comes with an enticing 18% discount. It’s an excellent way to save while experiencing The Robey’s renowned warmth and hospitality.

This holiday season, immerse yourself in the charm of Chicago with a staycation at The Robey. Book your urban retreat today, and let The Robey be your home away from home as you create cherished memories in the heart of the city. 

Explore the allure of Wicker Park and Bucktown from a fresh perspective, at The Robey, your ultimate Chicago holiday staycation destination. Book your room now on their website!

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