By Bill Malcolm*

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) means there’s lots to do.


From Midway Airport, 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 ease of riding on the “L” (aka the Elevated, which is their Metro). Chicago also has a good bus system. Rental car and Uber not needed.  

Chicago - Your Windy City Weekend Getaway


I always stay in the Lakeview East neighborhood. Bargain hunters will love The Inn at Lincoln Park, 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 Parkway (on the Brown Line at Diversey) with cute shops and neighborhood restaurants of every type within steps. There is even a handy Trader Joe’s at 667 West Diversey Parkway; 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 Parkway has healthy bowls and salads.


Most of the bars are on Halsted Street, 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 showtunes 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 US$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.

Chicago Skyline - Your Windy City Weekend Getaway


Buy a CityPass and save 50% on all the museums and other top attractions. More information at You also get VIP entry and are able to skip the ticket lines.

Don’t miss the Art Institute or the Shedd Aquarium, which has the 4-D “Shark” experience movie where the chairs rock and mist is sprayed in the area while you learn the fascinating story of sharks. Don’t miss the “Amazon Rising” exhibit as well. The Adler Planetarium is also nearby and, like the aquarium, looks 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.

A walk through Millenium Park is another must, including their ice-skating rink. You will also find a winter wonderland out on Navy Pier. 

Walking around Halsted Street 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.

Biking Chicago - Your Windy City Weekend Getaway


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 at

The Windy City Times is also a great resource. The Chicago Reader also has great ideas of what to do and where to go. The Northalsted Business Alliance publishes a Boystown guide,  More information and ideas may be also found at  You cannot beat a winter getaway to the Windy City. Yes its 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.

Featured image: @nathan_arizona via Instagram. Additional images courtesy of Choose Chicago.