Chicago is a great city to visit any time of year. Fabulous architecture, incredible museums and affordably-priced hotels (with no hidden resort fees), plus a great gayborhood (aka Boystown) mean there’s lots to do.
I took my favorite airline, Southwest, which serves close-in Midway Airport. From there you can hop on the Orange Line to your hotel. It’s a quicker ride than from O’Hare although American and United both have hubs there. To get around the city, you can ride the CTA. Get a Ventra card for easy of riding on both the “L” (aka the Elevated which is their Metro). They have a great elevated subway system (hence the name L), as well as a good bus system. Rental cars and Uber are not needed.
WHERE TO STAY
I always stay in the Lakeview East neighborhood. Bargain hunters will love The Inn at Lincoln Park (innlp.com or reservations at innlip.com) which has super low weekday rates and reasonable weekend rates. My other favorite is the Hotel Versey which is a music-themed hotel that is also reasonable and is a short walk to Boystown, the gay Village where everyone is welcome.
Both hotels are on Diversey Pky. (on the Brown Line at Diversey) with cute shops and neighborhood restaurants of every type within steps. There are even a handy Trader Joes at 667 West Diversey Pky. if you forget something, great pizza at Renaldi’s on Broadway and the Clark Street Dog for a quick bite after a night of partying. The Veggie Grill at 614 W. Diversey Pky. has healthy bowls and salads.
Most of the bars are on Halsted St., aka Boystown. Don’t let the name fool you. Everyone is welcome. Like most gayborhoods, it has been severely gentrified and struggles to keep its identity as rents rise and small businesses move out. It’s still a lot of fun though.
The original video bar, Sidetracks, is still going strong with sing-along show tunes on Sunday afternoons until 8 p.m. Watch out for flying napkins when they play Evita or Titanic. Members of the Windy City Chorus sing-along.
You will find dancers at the Lucky Horseshoe (3169 N. Halsted) as well as affordable libations from $5.
The leather crowd is up the street at the Cellblock, 3702 N. Halsted.
You can dance the night away at Hydrate or hang out with the locals at the NorthEnd Tavern (3169 N. Halsted). I also like the friendly crowd at Little Jims.
WHAT TO DO
Buy a CityPass and save 50 percent on all the museums and other top attractions. More information is available online. You also get VIP entry and are able to skip the ticket lines.
Don’t miss the Art Institute where the Warhol exhibit, “Andy Warhol-From A to B and Back Again” continues through Jan. 26. It explores the strange and wonderful career of this 1960s icon.
The Shedd Aquarium has a great live show, “Land and Water” with whales, dolphins, and even a red-tailed hawk (plus a walking seal). Don’t miss the 4-D “Shark” experience movie where the chairs rock and mist is sprayed in the area while you learn about the fascinating story of sharks. Don’t miss the “Amazon Rising” exhibit as well. The Adler Planetarium is also nearby and both look out onto Lake Michigan.
The Field Museum is another must and is also near the Shedd. Enjoy the Field Bistro at this natural history museum which features locally sourced cuisine, coffee, and craft beer. I liked the “Wildlife Photos of the Year” exhibit, the “Fantastic Bug Encounters” exhibit as well as the “Dinosaur Experience”.
A walk through Millenium Park is another must include their ice-skating rink. You will also find a winter wonderland out on Navy Pier.
Walking around Halsted St. and nearby Broadway is another must. Don’t miss Unabridged Books on Broadway. The Center on Halsted (3656 N. Halsted) is another stop and features a Whole Foods in the same building.
FOR MORE INFORMATION
Pick up a copy of GRAB Chicago Magazine for more bar and activity ideas. They also have a map of the attractions. You will find them in print and online.
The Windy City Times is also a great resource. The Chicago Reader is your weekly which also has great ideas of what to do and where to go. The Northalsted Business Alliance also publishes a Boystown guide. More information and ideas may be also found at choosechicago.com. You cannot beat a winter getaway to the Windy City. Yes, it’s cold, but the museums are warm. It’s the Paris of the Midwest. You might even run into their new Mayor, Lori Lightfoot.
Bill Malcolm writes this syndicated LGBTQ2A+ value travel column which focuses on seeing a city without breaking the bank. He focuses on affordable hotels, using public transit and other fun ideas to enjoy a city like a local. This is a hobby. Special thanks to Michelle Gonzalez of Choose Chicago for helpful ideas and a CityPass.