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Although May can sometimes be cool in Chicago, we had spectacular weather on the recent visit to the Windy City. Since I lived in and around Chicago for nearly 15 years, I know the town well and have friends and family to catch up with as well. Greg came with me so I wanted the trip to be a combination of showing him some of my favorite neighborhoods and restaurants, meeting up with my friends, and also enjoying some of the world class culture that is home to Chicago.

Museums

We selected two major museums to visit: the Natural History aka the Field Museum, and the Art Institute of Chicago which is a large gallery museum and not a university as the title would suggest. The field museum has 20 exhibits but most impressive is the display of architectural bones of dinosaurs and other prehistoric creatures. The Art Institute has a large selection of classic and modern art as well as a unique collection of miniature rooms and battle armor for both warriors and horses.

Wrigleyville

Two of my favorite neighborhoods in Chicago are Wrigleyville/ Boystown and Wicker Park. At the time I lived there, the Wrigleyville neighborhood was a combination of sports fans hanging around Wrigley Field, goth kids hanging around The Alley, gays and curious types along Halsted Street, and general yuppies who enjoyed the diverse restaurants, shops, music venues, plus accessibility to the beach and red line train. Although they were closed this trip, I wanted to visit the Cabaret Metro (i.e. Metro) and The Vic Theater, as I have seen some phenomenal rock shows here. Instead we met up with my sister Deb who lives north of Chicago and bounced around Halsted Street.

First stop is Beatnix which has everything from wigs to costumes to high heels in size 14 to blingy trinkets. Second stop is The Chicago Diner, “Meat Free since ’83” a great vegetarian restaurant. We then stumbled upon the Wake & Bakery on Broadway. After walking around a while we drove west to the Chicago Music Exchange – dreamland for any guitarist and I regret we didn’t have more time before they closed. They even have individual quiet booths where guests can try out guitars.

Tip: If the forecast says rain, I like to bring a light weight, quality raincoat. I love my single breasted London Fog mid-thigh jacket; it rolls up small to fit in a day-bag, takes little space in the suitcase, it’s machine washable, you can wear it over sweaters or jackets or alone, and looks really sharp. Of course an umbrella is good too but in a windy city, sometimes  you’ll do better with a good rain coat, boots and hat.

Live Music

Although rock shows were evasive, we had excellent luck with both Blues and Jazz.  We found the Kingston Mines to be showing acts but the online booking was a bit confusing so we just showed up at about 7:45 on Saturday night. The agent offered us a seat at the bar for the 8PM showing and with COVID spacing we had both excellent view and all the space we needed. Although Andys is a hot jazz spot near our hotel, I have fond memories of the Green Mill so on Thursday we took the red line train up, and after a sketchy but short walk to the venue we once again got lucky and were seated in the front of the bar facing the band. Sadly the photos didn’t turn out well because it was dark in the room but the band was hopping and there were couples dancing right in front of us.

Tip: Not every town has live music like Chicago, so when you’re here you have to check out the real deal!  My favorites are Green Mill and Andy’s for jazz; Blues etc. and Kingston Mines for blues; Cabaret Metro, Subterranean, or the Vic for rock. But there are many many choices- check out the Chicago Reader for the latest show listings.

Restaurants

I’m both proud and embarrassed to admit that I gained 10 pounds in as many days eating and drinking our way around Chicago. We had some absolutely delicious meals and we didn’t even scratch the surface of what’s available. I guess I will be hitting the treadmill when I get home…