The Chicago RiverWalk
Tips for a summer getaway in the Windy City
BILL MALCOLM | Contributing Travel Writer
BillMalcolm@gmail.com
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. And the beaches along Lake Michigan are simply incredible.
WHAT TO DO
Osterman Beach is the LGBTQ beach, and it 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 a must and the fun starts early. Sidetrack — the mega video bar with a great rooftop terrace — features sing-a-long showtunes on Sundays, and the crowd goes crazy when they see a scene from Mommie 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, and you can dance the afternoon and evening away with a live DJ. You will find them at 3458 N. Halstead. Cell Block 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 North Halsted neighborhood (formerly known as Boystown, between Addison and Belmont on Halsted), although a few are found in Andersonville north of that area.
North Halstead Street
I walked with the Frontrunners. They meet at 6:30 p.m. on Tuesday at the Totem Pole on the Lakefront Trail at Addison and then have dinner afterwards. 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 near the shopping on Michigan Avenue.
Mark your calendar for Chicago Pride with a festival June 22-23 and a parade on June 30 as well as a Pride in the Park celebration in Grant Park on June 30. Also fun is Halsted Market Street days in August, another signature LGBTQ festival which runs for two days on Halsted.
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, and Stan’s Donuts is next door. You can walk to the bars in North Halstead, and Broadway Avenue is full of quaint local shops and restaurants including a Marianos, an 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. 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. 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 Andersonville. I avoid the Loop hotels like the plague. There is nothing to do there, and they cater to tourists.
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 eight miles.
O’Hare and Midway both offer flights with CTA subways into town. You can also take Amtrak. The CTA has an excellent bus and elevated transit system. Fares are just $2.50. Buy a VENTRA transit card to make boarding the bus or subway train hassle-free. The Versey is closest to the Diversey L Line Station on the Brown Line.
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 came in second 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.