By Bill Malcolm* (he/him)


Chicago is a great city to visit any time of year, but it is even better in the summer: the Lakefront Trail, the beaches, bicycling, festivals, and more. And it’s one of the most LGBTQ+ friendly cities in the world. Not to mention the beaches along Lake Michigan are simply incredible. 




Osterman Beach is the LGBTQ+ beach and also has an outdoor restaurant. It’s a wonderful way to spend the day enjoying the refreshing Lake Michigan waters. (CTA Stop Thornton on the Red Line, then walk east and south to the beach.) Many of Chicago’s great beaches feature magnificent views of the stunning downtown skyscrapers. 

Sunday Funday at the bars on Halsted Street is necessary. Sidetrack (the mega video bar with a great rooftop terrace) features showtunes on Sundays where the crowd sings along to all of the classics. There is something fun going on there every night. Drink prices are reasonable (US$9 for Chandon champagne). 

Gogos (men and women) are featured at Hydrate as you can dance the afternoon away with a live DJ. You will find them at 3458 N. Halsted Street.

Cell Block up the street has a frisky leather crowd.

Find a complete list of bars and a map in GRAB Magazine ( Most of the bars are in Northalsted (formerly known as Boystown, between Addison and Belmont on Halsted) although a few are found north of that area in Andersonville. 

I walked with the Frontrunners. They meet at 6:30pm on Tuesdays at the Totem Pole at the Lakefront Trail (at Addison) and have dinner afterwards. Lots of runners and walkers.

Walk the new River Walk along the Chicago River downtown. It now offers restaurants and bars as well as architecture boat tours. They also have a new winery, City Wintery.  You can find boat rentals, water taxis, kayaking, and more here. It’s a new attraction right of the shopping on Michigan Avenue. 

Enjoy the incredible skyscraper architecture. Take a boat tour run by the Chicago Architecture Foundation or visit the Chicago Architecture Center. Like all downtowns, Chicago is struggling in the post Covid world of teleworkers that make the need for offices less urgent.

Mark your calendar for Chicago Pride (in June with a festival 22-23 June and a Parade on 30 June) as well as a Pride in the Park celebration in Grant Park on 30 June. The Halsted Market Street days (in August), is another signature LGBTQ+ festival. 



Chicago - Your Windy City Weekend Getaway

I always stay at the Hotel Versey by Wyndham in the very walkable Lakeview neighborhood. Trader Joe’s is across the street if you need anything. Stan’s Donuts is right next door. You can walk to the bars in Northalsted, and Broadway Avenue is full of quaint local shops and restaurants including a Marianos (upscale grocery store featuring fresh juices, a salad bar, a hot food bar, and a wine bar. Hotel rates vary by demand so avoid Cubs weekends and other festivals. Weekday rates tend to be lower.  




Chicago is known for its pizza and hot dogs. But a new Pho restaurant on Clark near the Century Plaza looks good. Sample all Chicago foods at the Taste of Chicago Festival 6-8 September (2024).



Biking Chicago - Your Windy City Weekend Getaway

I drove from Indianapolis, Indiana which is fine until you get near Chicago which features horrendous traffic. 

O’Hare and Midway both offer flights with CTA subways into town. You can also take Amtrak. 

But once you are here you will not need a car. The CTA has an excellent bus and subway (L) system. Fares are just US$2.50. Buy a VENTRA transit card to make boarding a bus or L (subway) train hassle-free. 




GRAB Chicago Magazine comes out monthly (and carries my column). It includes a map at the back of where to find LGBTQ+ businesses in the 2-3 areas of the city that especially cater to the community. It is the only print and online publication in the city. Windy City Times is another publication in the city and is only available online.

Chicago has a lot of annoying taxes and fees. My least favorite is the excise tax which tacks on 15% or more for a bottle of wine. They even have a tax on soft drinks. Their sales tax is already quite high as are the hotel taxes. On the plus side, the hotels in Chicago don’t charge resort fees like are now found in many cities. 

O’Hare Airport (ORD) has lots of delays and cancellations due to its mega size. In the week I was there, it was closed twice due to thunderstorms. Closer in, Midway is a better option as is Amtrak or driving. 

The Reader (the weekly) is in print again and online and features lots of musical events and arts coverage.

The Sun Times is now owned by WBEZ public radio and is US$2 daily. The Chicago Tribune charges US$4 daily. WGN (Chicago’s very own) is the local independent channel. I also like WFLD Fox Chicago for its news and events coverage). is the visitor website. I thank them for their helpful travel updates. 

You will continually be amazed by this friendly city of neighborhoods, the Paris of the Midwest. 


*Bill Malcolm is North America’s only syndicated LGBTQ+ travel columnist. He received no compensation of any kind from any business for his commentary on what to do in Chicago, a rarity among travel columnists who often only cover things provided to them at no charge which obviously colors their objectivity. He also boycotts hotels with resort fees (aka amenity fees or destination charges) as well as airlines which have non-transparent charges (booking fees, carry-on baggage fees, etc.). 


All Image Credits: Choose Chicago