🎃 After Dark: Halloween Adventures with The Chicago Hotel Collection

When October arrives, Chicago transforms. Crisp air rolls off Lake Michigan, golden leaves blanket the streets, and the city’s skyline glows beneath a harvest moon. Halloween isn’t just a day here — it’s a month-long celebration of costumes, creativity, and classic Chicago charm. Whether you’re planning a spooky weekend getaway, a night of haunted fun, or simply want to experience the city’s fall magic in comfort and style, The Chicago Hotel Collection puts you right in the heart of it all.

From the Gold Coast to Wrigleyville, our hotels connect you to the best of Chicago’s Halloween spirit — local parades, ghost tours, themed pop-ups, and costume parties galore. Here’s how to make the most of October in the Windy City.

👻 Haunted History Meets Boutique Luxury

Chicago’s streets are filled with stories, and October is when those tales come alive. Step outside any of our four unique locations — Ambassador Gold Coast, Mag Mile, River North, and Wrigleyville — and you’re just minutes from haunted landmarks and legendary city tours.

• Stay at The Chicago Hotel Collection Ambassador Gold Coast and stroll to the iconic Historic Gold Coast Mansions, rumored to host their own ghosts from Chicago’s gilded age. The neighborhood’s tree-lined streets and 1920s architecture create an atmospheric backdrop for evening walks and Halloween photoshoots.

• Near our River North location, you’ll find the Richard’s Bar Halloween Costume Crawl, a local favorite where downtown Chicago nightlife meets fall fun.

• Guests at Mag Mile can wander to Navy Pier’s Haunted Maze or take a spine-tingling Ghosts and Gangsters Tour, exploring Chicago’s Prohibition-era secrets.

• Up north in Wrigleyville, our hotel is steps away from rooftop parties, Halloween bar crawls, and the famous Nightmare on Clark Street, where the neighborhood transforms into a costume-filled festival.

Wherever you stay, you’ll be surrounded by history — and just the right amount of haunt.

🏙️ Fall in Love with Chicago’s Autumn Vibe

Halloween might steal the spotlight, but October in Chicago offers beauty that lasts all day long. Start your morning with a pumpkin-spiced latte from a local café, or take a crisp walk along the lakefront trail. From Lincoln Park’s changing colors to Oak Street Beach sunsets, Chicago’s fall scenery is as breathtaking as its skyline.

Each Chicago Hotel Collection property was designed to complement that local character:

• Ambassador Gold Coast blends vintage elegance with modern comfort — think skyline terraces, historic charm, and cocktail lounges perfect for cozying up after a day of exploring.

• Mag Mile places you right in the middle of downtown excitement, surrounded by high-end shopping, iconic restaurants, and lively Halloween events.

• River North embodies the city’s creative pulse, with its vibrant art scene, galleries, and nightlife that truly come alive in October.

• Wrigleyville is your go-to for a laid-back neighborhood feel, complete with sports bars, rooftop views, and Halloween celebrations that last all weekend.

🍸 Sip, Savor, and Celebrate

Each of our locations offers on-site dining and cocktail experiences that bring the spirit of the season to life.

At The Ambassador Gold Coast, enjoy craft cocktails by candlelight in The Library Bar, or gather your group for dinner in The Ambassador Room, where locally inspired dishes meet warm autumn flavors. Guests at our Mag Mile or River North properties can take advantage of nearby culinary favorites — from rooftop lounges with skyline views to neighborhood gastropubs offering Halloween-themed menus.

And since every stay includes our Guest Benefits Package, you’ll enjoy daily breakfast for two, nightly drink tickets, and exclusive local discounts. That means more pumpkin cocktails, caramel-apple martinis, and fall comfort food — for less.

🎭 Events You Can’t Miss This Halloween

Chicago’s event calendar is packed from early October through Halloween night, and our hotels give you front-row access. A few must-experience highlights include:

• Arts in the Dark Parade (Oct. 19) – A magical nighttime parade down State Street filled with puppets, performers, and glowing floats.

• The Haunted Halsted Halloween Parade (Oct. 31) – Chicago’s most iconic costume parade in the heart of Northalsted, with prizes, music, and a full-city celebration.

• Navy Pier’s Fireworks & Frights – Family-friendly fun with fireworks lighting up the skyline over Lake Michigan.

• Wrigleyville Halloween Crawl (Oct. 26) – More than 20 bars, costume contests, and endless themed cocktails — all steps from our Wrigley property.

Whether you’re traveling with friends, family, or your special someone, you’ll find Halloween events for every kind of traveler — from spooky sophistication to all-out party energy.

🕯️ Stay in Style — and Save

There’s something unforgettable about experiencing Halloween in a city as alive as Chicago — and there’s no better way to do it than with The Chicago Hotel Collection. Each property offers spacious accommodations, boutique style, and personalized service designed to make your stay effortless.

When you book direct, you’ll unlock exclusive savings and special perks available only through our website — including lower rates, flexible policies, and immediate access to your Guest Benefits Package, featuring:

• Daily breakfast for two 🍳

• Three drink tickets per night 🍸

• Ongoing discounts on attractions and travel after checkout 🌆

Skip the third-party fees and go straight to the source — it’s the easiest way to save while enjoying a truly local Chicago experience.

🧡 Your Chicago Halloween Awaits

This October, make your getaway more than just a weekend trip — make it a story you’ll remember. From haunted tours and skyline views to cozy hotel lounges and citywide festivities, The Chicago Hotel Collection delivers everything you love about fall in Chicago.

Book direct today at www.thechicagohotelcollection.com to secure your Halloween stay — and experience the city’s most stylish side of spooky.