Chicago makes for a perfect summer vacation. Beaches, festivals, biking along the lake, or just hanging out at the Kathy Osterman (Hollywood) Beach (the queer beach) in the Bryn Mawr neighborhood are all great options.  The gayborhood, Boystown has been re-christened as “Northalsted” to promote inclusion. You will find most of the bars and gay businesses on Halsted Street.

I always stay at the Hotel Versey (644 W. Diversey Parkway)  near the Diversey Brown Line (at the intersection of Clark/Broadway/Diversey) just south of the gayborhood. The rooms are also full of murals featuring local attractions and parking is just $20 for your entire stay at the garage next door (Century Shopping Center) which also features a LA Fitness which is free to use for hotel guests. Book direct at to save.  Weekday rates are reasonable and the weekend rates are also better than anything you will find downtown. Plus, you can walk to the bars or just enjoy the many nearby shops and restaurants. There is even a Trader Joe’s across the street and just west of there is the new Dom’s Kitchen and Market (2730 N. Halstead Street).

Just steps away from the hotel is my favorite Italian restaurant which also will sell you a slice of their amazing pizza. Called Renaldi’s Pizza (2827 N. Broadway) it is a local favorite. Try the Spingione Sausage Pizza.

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. Don’t miss Cram Fashion at 3331 N. Broadway. Grab a salad or enjoy a glass of wine at Mariano’s.

Bring your appetite for the new nearby Dom’s Kitchen and Market (2730 N. Halsted Street) where every

kind of food is available freshly prepared. If you need anything, you will find the Walmart

Neighborhood Market at 2844 N. Broadway. Next door to the Hotel Versey you will find Stan’s Donuts, a local favorite which also has grilled cheese and cookies.

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.

Bargain hunters will also love the Heart of Chicago Motel which is near the Andersonville neighborhood further north and features free parking.


Head to the LGBTQ beach, the Osterman (Hollywood) Beach. Enjoy the asada skirt steak tacos at the restaurant on the beach, Lakebreeze. And have a margarita.

Hop on the L or the CTA bus for a trip to the Loop to experience the incredible Chicago architecture.

Walk along the new Riverwalk  and then head up Michigan Avenue which features the best shopping in the Midwest.

Enjoy the buildings. My favorite is the Wrigley Building on Michigan Avenue near the Chicago River. Even the new buildings are stunning such as the Trump Tower. Chicago does have the best architecture of any city on the planet.

Millennium Park in the loop is a must. The Shedd Aquarium is also recommended.  Navy Pier has a Ferris wheel.

Rent a Divvy Bike and explore the city.

Catch the Cezanne exhibit at the Art Institute.

The Lincoln Park Zoo is another fun idea.

Don’t miss Northasted Market Days, a summer street festival now in its 40th year, which will be held August 6 and 7. Lots of eye candy.


Make your first stop to Sidetracks (3349 N. Halsted), America’s biggest and oldest video bar.

The famous Sunday afternoon Showtunes now happen on Mondays and Fridays as well. Don’t miss the roof top bar. There is something going on every night. You can’t beat this mega video bar institution.

Many other LGBTQ bars are nearby. The North End at 3733 N. Halsted is a sports bar. The Lucky Horsehoe features adult entertainment.  Charlie’s is a western themed bar. Just north of Andersonville, you will find Touche and Jackhammer on North Clark which are popular with the leather crowd.


Chicago is a major hub for all transportation types with both O’Hare and Midway Airports as options. Try

the Amtrak.  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.

Southwest has a huge hub at closer in Midway Airport where you can also take Porter from Toronto. Hop on the Orange Line for a quick ride in.


If you are driving, look out for the many red-light cameras at intersections which are eager to give you a ticket for going just a few miles over the speed limit. Short yellow lights also make it very likely you could easily get a ticket if you enter an intersection while the light is no longer green. It’s a revenue raiser pure and simple for the City and a total scam. So drive slow and do not try to go through an intersection if there are only seconds left to cross. Better yet, walk, take the CTA, or rent a B Cycle to get around. You don’t need a car in the City.

The CTA public transportation is a great way to get around. Buy a VENTRA pass so you don’t have to look for change.

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

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 founder.


Visit (or pick up a copy). GRAB Magazine is Chicago’s only remaining in print LGBTQ magazine. Check the maps at the back of the magazine on where to find the bars, restaurants, and other LGBTQ businesses. The Chicago Reader is the biweekly alternative publication.

You will be amazed at everything Chicago has to offer. It is the Paris of the Midwest, and is arguably one of the most LGBTQ+ friendly cities in the world. Just ask Mayor Lori E. Lightfoot or the First Lady.

Chicago will surprise –especially the great beaches along Lake Michigan, the miles of bike paths, the great parks along the lake, and the interesting neighborhoods. You cannot beat Chicago for a vacation.

More info can be found on the official tourism website.

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.