Crisp air, golden leaves, and a shimmering skyline—fall in Chicago is a season of surprises. With stunning architecture, walkable neighborhoods, independent shops and restaurants, and a vibrant nightlife, the Windy City offers endless opportunities for exploration. Fall (September-November in North America) is the perfect time to visit: the summer crowds have dispersed, the weather is pleasant, and hotel rates are more affordable.
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Getting There
Getting to Chicago is easy and convenient. I flew United Airlines to O’Hare and took the Blue Line CTA into the city. United even accommodated an earlier flight at no extra cost, complete with free internet for MileagePlus members. The return flight was on a legacy United aircraft—not a regional jet. Once in the city, I relied on the CTA and walking to get around. Chicago’s public transit system, including buses and subways, makes navigating without a car a breeze. Amtrak also offers excellent service. For shopping trips to Michigan Avenue, consider the #143 Lakeshore Express or #151 bus.
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Where To Stay
My favorite place to stay is the Hotel Versey by Hilton, near the Brown Line Diversey CTA station. Located in North Lincoln Park, the neighborhood is filled with charming shops and restaurants along Broadway, Clark, and Diversey. Guests enjoy complimentary access to the adjacent LA Fitness, which includes an indoor pool. Parking is available next door for US$30 per day. While breakfast isn’t included, Stan’s Donuts—a Chicago icon—is right next door. Try their breakfast burrito! Trader Joe’s is across the street, and the nearby Fresh Market offers delicious fast-casual options like salmon. Café Deko (Halsted and Diversey) is perfect for coffee, and Tuk Tuk Thai-isan Street Food on Clark is excellent. Barnes & Noble across the street is great for book lovers. Other great neighborhood hotels include the Willows Hotel, City Suites, and Best Western Hawthorne Terrace—all free of surprise resort fees. Budget travelers might enjoy the Heart O’ Chicago Motel, which includes free parking.
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What To Do
Explore the new RiverWalk Trail downtown, featuring restaurants, bars, and breathtaking architecture. Take an architecture cruise, hop on a water taxi, or rent a kayak to enjoy the Chicago River, lined with high-rises from every architectural genre. Shoreline Sightseeing offers many options, but the best tours are run by the Chicago Architecture Center aboard the First Lady boats. Shop along Michigan Avenue, also known as the Magnificent Mile. Visit the Art Institute of Chicago, currently showcasing an impressionist exhibit. For outdoor enthusiasts, walk or bike along the lakefront path starting at Diversey Avenue.
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Nightlife
Chicago’s nightlife is vibrant and diverse. Sidetrack (3349 N. Halsted), the original video bar, is a must-visit. Tuesdays feature storytelling nights, while Sundays and Mondays are dedicated to showtunes. The North Halsted area (formerly Boystown) is packed with LGBTQ+ bars and venues. For a comprehensive guide to nightlife and events, check out GRAB Magazine.
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Where To Eat
I enjoyed lunch at the new Washington Food Hall at 25 West Washington near City Hall in the Loop. Their lunch pizza special is a great deal and tastes fantastic. The Hampton Social (multiple locations) serves excellent salmon and calamari. For a classic Chicago experience, grab a Chicago-style hot dog (no ketchup!) and fries at Clark Street Dog at Clark and Halsted.
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For More Information
For more tips on local happenings, pick up a copy of GRAB Magazine or read it online. It’s Chicago’s monthly LGBTQ+ publication and features my travel column.
Whether you're a first-time visitor or a seasoned traveler, fall in Chicago offers something for everyone. Pack your scarf and sense of adventure—this city never disappoints.
*Bill Malcolm is North America’s only syndicated LGBTQ+ value travel columnist. He received no compensation for any endorsements mentioned.
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