Chicago is a great city to visit any time of year, but it is even better in the spring and summer: the Lakefront trail, the beaches, bicycling, festivals, and more. And it’s one of the most LGBTQ-friendly cities in the world. And the beaches along Lake Michigan are simply incredible.
WHAT TO DO
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 features magnificent views of the stunning downtown skyscrapers.
Sunday Funday at the bars on Halsted Street is a must and the fun starts early. Sidetrack (the mega video bar with a great rooftop terrace) features sing a long showtunes on Sundays where the crowd goes crazy when they see a scene from Mommy Dearest or Evita. There is something fun going on there every night. Drink prices are reasonable ($9 for Chandon champagne). Up the street, dancers (men and women) are featured at Hydrate as you can dance the afternoon and evening away with a live DJ. You will find them at 3458 N. Halstead. Cell Block up the street has a frisky leather crowd and a great beer selection. Stop for dinner at the Whole Foods Market. Find a complete list of bars and a map in GRAB Magazine (GRABChicago.com). Most of the bars are in the North Halsted neighborhood (formerly known as Boystown, between Addison and Belmont on Halsted) although a few are found in Andersonville north of that area.
I walked with the Frontrunners. They meet at 6:30 p.m. on Tuesday at the Totem Pole at the Lakefront Trail (at Addison) and have dinner afterward. Lots of runners and walkers.
Walk the new RiverWalk along the Chicago River downtown. It’s new and now offers restaurants and bars as well as architecture boat tours. They even have a new winery, City Winery. There are boat rentals, water taxis, kayaking, and more. It’s a new attraction right off 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.
WHERE TO STAY
I always stay at the Hotel Versey, 644 West Diversey Parkway (at Clark and Broadway) in the very walkable Lakeview neighborhood. Trader Joe’s is across the street if you need anything. Stan’s Donuts in next door. You can walk to the bars in Northalstead 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 Versey guests enjoy free entry to the LA Fitness in the Century Plaza next door, which also has a Landmarks Art Theater if you want to catch a film. Parking is just $30 for three days (a deal). Watch out for the $6 charge for bottled water on your bill, though. Hotel rates vary by demand so avoid Cubs weekends and other festivals. Weekday rates tend to be lower. The property is under new owners. Other hotels in the Lakeview/North Halsted neighborhood including the Willows, Best Western Hawthorn Terrace, City Suites, and the Majestic. Another option is the Heart of Chicago Motel north of Andersonville offers free parking and is walkable to the north side leather bars and shops and restaurants in the once Swedish neighborhood, Andersonville. I avoid the Loop hotels like the plague. There is nothing to do there and it caters to tourists. Stay where the locals live and walk everywhere.
WHERE AND WHAT TO EAT
Chicago is known for its pizza and hot dogs. But a new Pho restaurant on Clark near the Century Plaza looks good.
GETTING THERE
I drove from Indy which is fine until you get near Chicago which features horrendous traffic. Make sure you have an I Pass for the Illinois Tollway and Skyway which now charges $7.20 to go 8 miles.
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 elevated transit (L) system. Fares are just $2.50. Buy a VENTRA transit card to make boarding the bus or L (subway) train hassle-free. The Versey is closest to the Diversey L Line Station on the Brown Line. It is also served by the #36 Broadway bus and #22 Clark Street bus. Or you can walk east to Sheridan and catch the 152, 134 Express, and 143 Express if you want to go to the Loop or shop on Michigan Avenue (or visit the North Street Beach).
FOR MORE INFORMATION/TRAVEL TIPS
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 in print and online publication in the city. The ads and columns highlight ideas for what to do. Windy City Times is another publication in the city and is only 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 (aka destination fees, amenity fees, etc.) like are now found in many cities (Palm Springs, Boston, Las Vegas). I boycott hotels that tack them on, especially when they try to make them see like a government tax or when they are not disclosed until the actual booking trying to make the property seem more competitive than it actually is. Kimpton and Hyatt are the worst offenders. Marriott allows you to compare hotels with all taxes and fees. Expedia does not reveal them until booking time. It’s a hot mess.
Be ready for airport delays. O’Hare Airport (ORD) has lots of delayed and cancellations due to its mega size. In the week I was there, it was closed twice for hours due to thunderstorms (aka ground stop). I try and avoid it unless going internationally. Closer to Midway is a better option, as is Amtrak or driving. O’Hare is also a mega hub for American and United making domestic fares pricey.
The Reader (the weekly) is in print weekly again and online and features lots of musical events and arts coverage.
The Sun Times is now owned by WBEZ public radio and is $2 daily. The Chicago Tribune has cut coverage and laid off staff and charges $4 daily. Circulation has plummeted (I wonder why). WGN (Chicago’s very own) is the local independent channel, although it is no longer locally owned. I also like WFLD Fox Chicago for its news and events coverage. They just hired Paris Schutz to do political reporting (formerly with WTTW’s Chicago Tonight).
ChooseChicago.com is the visitor website. I thank them for their helpful travel ideas.
You will continually be amazed by this friendly Midwestern city of walkable, interesting neighborhoods. Chicago is an under-rated city to visit. The beaches alone are worth a trip in the summer. Put Chicago on your radar. You won’t regret your visit to the true 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). He came in 2nd place for travel writing in the 2023 Florida Press Association Excellence in Journalism awards for his columns on Milan and Chicago run by Embrace Magazine of Ocala.
