Chicago in October is an absolute delight. As the summer heat fades and the fall foliage sets in, the city comes alive with a mix of seasonal events, cultural experiences, and iconic sights. Whether you're drawn by Halloween festivities, art and film festivals, or the vibrant colors of autumn, Chicago offers an incredible variety of activities that will leave you enchanted.
If you’re planning a trip to the Windy City this October, there's no better place to stay than The Chicago Hotel Collection. With boutique locations in the heart of the city’s top neighborhoods— Magnificent Mile, River North, and Wrigleyville—you’ll be perfectly situated to enjoy all the best attractions. When you Book Direct and Save, you not only receive exclusive perks but also ensure you're close to everything that makes Chicago special.
Here’s a list of the top 10 things to do in Chicago this October, so you can plan your perfect fall getaway.
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1. Chicago Architecture Boat Tour
Chicago's skyline is a marvel of modern architecture, and the Chicago Architecture Boat Tour offers a unique way to experience it. As you cruise down the Chicago River, knowledgeable guides will share the stories behind some of the city’s most iconic buildings, including the Willis Tower, the Wrigley Building, and the Tribune Tower. The crisp fall weather makes October an ideal time for this tour, as you’ll see the city’s architecture framed by stunning autumn foliage.
Why Stay at The Chicago Hotel Collection?
Staying in River North means you're just steps away from the departure points for these boat tours. After a day of sightseeing, you can easily return to the comfort of your hotel, with plenty of dining and nightlife options nearby.
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2. Lincoln Park Zoo Fall Fest
For family-friendly fun, the Lincoln Park Zoo Fall Fest is a must-visit. This free zoo transforms into a festive wonderland on weekends in October, featuring pumpkin patches, corn mazes, hayrides, and live music. It’s a wonderful way to enjoy the fall season with kids (or just to feel like a kid again yourself).
Why Stay at The Chicago Hotel Collection?
Located close to Wrigleyville, The Chicago Hotel Collection provides easy access to Lincoln Park and other nearby attractions. Staying here gives you the flexibility to enjoy a peaceful zoo visit by day and catch a Cubs game or explore Wrigleyville’s vibrant nightlife by night.
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3. Art Institute of Chicago
October is a perfect time to explore the cultural heart of the city at the Art Institute of Chicago. Whether you're a lover of Impressionist art or fascinated by modern pieces, the Art Institute's world-class collections will inspire you. In addition to its permanent exhibits, the museum often launches special exhibitions in the fall, offering something fresh for repeat visitors.
Why Stay at The Chicago Hotel Collection?
A stay at the Magnificent Mile location places you just a short walk from the Art Institute. You can spend a full day at the museum and then return to the luxury and convenience of your boutique hotel, ideally situated near shopping and fine dining.
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4. Chicago International Film Festival (October 16–27, 2024)
Film buffs will not want to miss the Chicago International Film Festival, which takes place in October and showcases hundreds of films from around the world. From documentaries to high-profile premieres, this is the perfect event for anyone who loves the art of cinema.
Why Stay at The Chicago Hotel Collection?
The River North location is close to some of the main theaters that host festival screenings. After an evening of watching films, you can relax in style at the hotel, surrounded by some of the city's best bars and restaurants.
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5. Halloween Events
Chicago takes Halloween to a whole new level. Events like the Arts in the Dark Parade, haunted houses such as 13th Floor Chicago, and spooky experiences like the Chicago Ghost Tours will give you plenty of thrills. Whether you're looking for family-friendly fun or something to give you chills, there’s no shortage of ways to celebrate Halloween in Chicago.
Why Stay at The Chicago Hotel Collection?
With locations in Wrigleyville, River North, and Magnificent Mile, you’ll have easy access to Halloween events in different parts of the city. Staying in the heart of these neighborhoods allows you to enjoy the festivities and return to your hotel without a long commute.
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6. Navy Pier’s Pumpkin Lights
Navy Pier is always a bustling destination, but in October it becomes even more magical with Pumpkin Lights. Thousands of glowing pumpkins, artistic installations, and interactive light displays make this a must-visit spot for both kids and adults. There are also plenty of seasonal food offerings to keep you warm as you stroll along the lakefront.
Why Stay at The Chicago Hotel Collection?
The Magnificent Mile hotel is a short distance from Navy Pier, making it convenient to enjoy this enchanting display and then retreat to the luxury of your downtown accommodations.
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7. Open House Chicago (October 19–20, 2024)
Open House Chicago is a two-day event where more than 150 architecturally significant sites across the city open their doors to the public, many of which are usually closed. This is a rare opportunity to explore Chicago's hidden gems and learn more about its architectural history.
Why Stay at The Chicago Hotel Collection?
Staying at any of The Chicago Hotel Collection's locations will put you in proximity to many of these sites, making it easy to hop from one fascinating building to the next.
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8. Millennium Park
A visit to Chicago wouldn’t be complete without a trip to Millennium Park. In October, the park’s beauty is enhanced by the fall foliage, making it a picturesque setting for photos with iconic landmarks like Cloud Gate (The Bean) and the Crown Fountain. Plus, you might catch an outdoor concert or public art installation while you're there.
Why Stay at The Chicago Hotel Collection?
The Magnificent Mile location is a short walk from Millennium Park, allowing you to soak in the beauty of the park without having to travel far from your hotel.
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9. Chicago Marathon (October 13, 2024)
Whether you’re running or cheering from the sidelines, the Chicago Marathon is one of the city’s biggest events. Watch thousands of athletes race through the streets of Chicago, passing iconic landmarks and bustling neighborhoods.
Why Stay at The Chicago Hotel Collection?
With locations in River North and Magnificent Mile, you’ll be perfectly positioned to watch the race and then relax in comfort. Plus, you can explore the neighborhoods the marathon runners pass through after the event.
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10. Chicago’s Fall Foliage
Chicago's parks and lakefront trails come alive with color in the fall. Whether you're taking a walk through Lincoln Park, biking along the Lakefront Trail, or venturing out to the Morton Arboretum, the city's fall foliage is a breathtaking sight.
Why Stay at The Chicago Hotel Collection?
Staying in Wrigleyville or River North gives you quick access to some of the best parks and outdoor spaces where you can fully appreciate Chicago's fall beauty.
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Book Direct and Save with The Chicago Hotel Collection
When planning your October adventure in Chicago, remember to Book Direct and Save with The Chicago Hotel Collection. Not only will you enjoy boutique accommodations in prime locations, but you'll also receive exclusive benefits that enhance your stay. Whether you're exploring the architectural marvels, enjoying fall festivals, or celebrating Halloween, The Chicago Hotel Collection ensures you're in the heart of the action.
Don't miss out on everything Chicago has to offer this October—book your stay today!
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