By Bill Malcolm (he/him)*
Chicago is worth a visit in the winter. The museums are great. The hotel prices are more reasonable. And there is so much to do.
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WHAT TO DO
The Art Institute of Chicago is an absolute must. Great displays of Van Gogh, Warhol, Picasso, and more. Lots of impressionist painters as well. You can spend two full days there. Try the salmon salad in The Café. Get there when they open (at 11 a.m.) to avoid the crowds. You will find them near the Monroe Red Line CTA Station. Other great museums include the Museum of Science and Industry and the Shedd Aquarium.
The Peggy Notebaert Nature Museum and the Lincoln Park Zoo are both nearby the Hotel Versey and are great options for a winter day.
Enjoy the stunning Chicago architecture. Take a walk along the Riverwalk or even an architectural tour. My favorite is the Wrigley Building along Michigan Avenue.
Explore the shops on Broadway, including Cram at 3331 N. Broadway (cramfashion.com).
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WHERE TO STAY
I always stay at the Hotel Versey, now part of the Hilton Tapestry Collection. Located at 644 West Diversey Parkway, just south of the gayborhood, it is full of nearby shops and restaurants. The rates are lower during the week (and during the winter). You get free use of the LA Fitness next door (with indoor pool). Parking is available. Trader Joe’s and Barnes and Noble are across the street, and the Fresh Market is steps away.
Image Credit: Choose Chicago
NIGHTLIFE
Just up the street from the Hotel Versey is the gayborhood formerly known as Boystown (now known as Northalsted).
Make your first stop at the iconic video mega bar, Sidetrack. They have something every night. I like the show tunes which run multiple days including 4 p.m. on Sunday.
You will find go-gos and dancing at Hydrate, 3458 N. Halsted. Sunday Funday features US$4 wells. Also fun is the KitKat Club.
The leather bar on Halstead, CellBlock, is very cruisy.
The Lucky Horseshoe has dancers.
The Center on Halsted is the community center. A Whole Foods and senior housing is in the complex.
For bar ads and maps, pick up a copy or read online, GRABChicago.com. GRAB Chicago Magazine is Chicago ‘s monthly LGBTQ+ publication and is full of local happenings.
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WHERE AND WHAT TO EAT
The new Lucky Cat coffee bar is just around the corner from the Hotel Versey and has better coffee than both Starbucks and Stan’s Donuts (which are also nearby).
I like the shrimp salad at Trader Joe’s. You will find them at 667 West Diversey.
Stan’s Donuts at the corner of Clark and Diversey has great donuts, breakfast burritos, and more.
Rosatti’s just east of the Diversey CTA station has great mega slices of pizza for just US$6. You will find them at 953 W. Diversey Parkway.
The Fresh Market has great hot food and a nice croissant breakfast sandwich. They even sell wine. You will find them at 2730 N. Halsted at the corner of Diversey and Halsted.
The Tuk Thai-isan Street Food (2852 North Clark) next to Century Plaza features great curry dishes and Thai original dishes. They bring a jug of water to go with their spicy red curry dish. It is my current favorite.
Image Credit: Choose Chicago
GETTING THERE
I took the Amtrak from Milwaukee. It has six round trips a day and goes 90 mph making only three stops. From Detroit, Dallas, St. Louis, D.C. and even Seattle and SF, you can also take Amtrak to Chicago.
I flew United back to Indy out of O’Hare. A great airline. New equipment. Great entertainment. Professional staff. And a beautiful terminal. Take the Blue Line CTA to O’Hare via the Diversey Bus to Logan Square CTA. You can go anywhere in the world from O’Hare.
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FOR MORE INFORMATION
GRAB Chicago Magazine (online and print) has a great map of the bar scene areas. You can pick up a copy at Sidetrack and other locations. they run my column!
Winter is a perfect time to visit Chicago. The crowds are gone. The hotel rates are reasonable. And you can see how the locals enjoy this top rate American city.
*Bill Malcolm is North America’s only LGBTQ travel columnist. He focuses on value and going local. He pays his own way. And he boycotts hotels with resort fees/destination fees/amenity fees and other junk charges. He pays his own way and received no compensation of any kind for this column.
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