Chicago makes for a perfect winter weekend visit. I always stay in the Lakeview East neighborhood just south of the gayborhood formerly known as Boystown (newly re-christened as “Northalsted” to promote inclusion). You will find most of the bars and gay businesses on Halsted Street itself although like with many cities, gentrification has taken its toll (as has COVID). Still, the ‘hood is a lot of fun.


I always stay at the music-themed Hotel Versey (644 W. Diversey Parkway near the Diversey Brown Line Station). The rooms are also musically themed and it is steps to fun shopping and restaurants (and just a short walk to the hood.) Weekday winter rates are a steal and the weekend rates are also better than anything you will find downtown. Book your room at or on the Wyndham website.  They let you use the LA Fitness for free next door in the Century Plaza Shopping Center which also features a Landmark Theater if you want to catch a show. Parking for 72 hours in their parking garage is just $20.

Just steps away from the hotel is all the shopping and restaurants you will need. My favorite pizza is a nearby Renaldis (2827 N. Broadway). Farther up Broadway you will find Unabridged Books (3521 N. Broadway), one of the last remaining independent bookstores which features a wide array of LGBTQ titles. They have been around since 1980 and are still going strong. Broadway features loads of independent shops and restaurants and is a fun way to spend the day.

Bring you appetite for the new nearby Dom’s Kitchen and Market (2730 N. Halstead Street) where every kind of food is available freshly prepared. Created by 2 former landmark Chicago grocers, the owners came out of retirement to open this trendy food hall. There is also a Trader Joe’s across the street (677 W. Diversey Parkway) if you want to eat in your room. If you need anything, you will find the Walmart Neighborhood Market at 2844 N. Broadway. Other hotel options in the neighborhood include the Best Western Hawthorn Terrace and The Willows. All are just steps to the Lakeshore Path which runs along nearby Lake Michigan.


Hop on the L or the CTA bus for a trip to the Loop to experience the incredible Chicago architecture. My favorite is the Wrigley Building on Michigan Avenue near the Chicago River. Even the new buildings are stunning. Chicago does have the best architecture of any city in the U.S.

Millennium Park in the loop features ice skating in the winter and other attractions. The Shedd Aquarium and Art Institute are also musts and perfect for a winter visit. Navy Pier has a great flower show every spring and is also worth a visit.

Shop at the Japanese clothier Uniqlo for value stylish clothes. There are 2 locations-one on Michigan Avenue and one downtown in the Loop. And Michigan Avenue is a must for people watching and shopping.


Make your first stop to Sidetracks. The famous Sunday afternoon Showtunes now happen on Mondays as well. Tuesday is Trivia night. You can’t beat this mega video bar institution. Many other LGBTQ bars are nearby.


Chicago is a major hub for all transportation types with both O’Hare and Midway Airports as options. Try the Amtrak train if you have the time. They have great service from around the country and Chicago’s Union Station (and historic Great Hall) are worth a visit even if you are not taking the train.   Just north of there at the Ogilvie Metra Station you will find the French Market which features a great food hall. Try the crab grilled cheese sandwich.


If you are driving, look out for the new red-light cameras at intersections. Short yellow lights make it very likely you could easily get a ticket by mail from the City if you enter an intersection while the light is no longer green. I have never encountered such short yellow light times. Clearly designed to raise revenues.

The CTA public transportation is a great way to get around. Buy a VENTRA pass so you don’t have to look for change. The Metro or subway service is known as the “L”.

I love the Mayor, Lori E. Lightfoot, who like the Mayors of Madison (WI) and Seattle, is a lesbian.

Like many U.S. cities, an increase in crime is an issue but I felt safe walking around the areas I visited.

Effective January 3, you much show proof of vaccination to go to the gym or a restaurant (as well as many other facilities). Many places like Sidetracks already required that. Bring you vaccination card if you plan to visit.

Speaking of name changes, remember Lake Shore Drive? It also has a new name, Jean-Baptiste Pointe DuSable Lake Shore Drive, in honor of the City’s Black founder.


For more information, visit (or pick up a copy). GRAB Magazine is Chicago’s only remaining in print LGBTQ magazine (since Windy City Times went all digital).

About the Author

Bill Malcolm is the nation’s only LGBTQ+ syndicated value travel columnist. Residing in Indianapolis, he travels with a focus on the local and value orientation.