DEAR TRAVELPOLOGY: WHAT SHOULD I DO IN CHICAGO WITH MY MOM?

Chicago

Dear Travelpology,

My mom and I will be in Chicago next week (Mon-Thurs) and I’m looking for suggestions of what to do. My mom is very cool and fun, if I do say so myself. 😉 Of course, we’ll do the art museums, Navy Pier, and shopping on Michigan Ave, but do you have anything else up your sleeve that might be fun?

Sincerely,
I’ve only been to Chicago for work

Thanks for writing I’ve-only-been-Chicago-for-work! Here are some of my favorite stops in Chicago that should be fun for both you and your mom:

SHOWS
I recently went to a Second City improv show which was pretty fun. There was definitely a lot of swearing and it was a bit raunchy, but nothing too terrible for a cool mom to handle. Tickets are hard to come by so we booked a matinee show.

I love musicals and Chicago always has at least a few great shows in town. The Lion King and Billy Elliott are playing right now.

Have you ever heard of the Moth podcast? Short stories by real people with no scripts. It’s amazing! They do live StorySlams around the country and they do perform in Chicago once a month.

MUSEUMS
The new modern wing at the Art Institute is really beautiful so definitely go there. I would skip the Shedd Aquarium (it’s expensive and not nearly as amazing as the aquarium in Atlanta). I was also a little disappointed by the Museum of Science and Industry the last couple times I was there — I think the Field Museum is your best bet.

FOOD
Here’s the low-down on cheaper Chicago food: Lou Milnati’s (or Giordano’s) for deep dish pizza. Portillo’s (or Al’s) for Italian beef. Hot Doug’s for hot dogs (there is usually a huge line but if you are going during the week, you may be in luck!)

If you’re both into food and want to walk around a ridiculously beautiful grocery store go to Fox & Obel near Navy Pier. You can also enjoy some over-priced breakfast in the café or pick up prepared dishes to bring back to the hotel,

Coco Pazzo Cafe is a yummy Italian place on St. Clair. Perfect for a classy but not-too-stuffy dinner.

DRINKS
I always make a stop at the Signature Lounge (above the Signature Room) at the John Hancock. Take the free elevator up to the 96th floor and enjoy a drink and the beautiful view. It’s really awesome day or night (or sunset). Make sure you go to the women’s bathroom for a good view!

The Trump Tower is now open! It’s a combination hotel and condo development, but they have a restaurant called Sixteen (on the 16th floor) that’s supposed to be ridiculous! If you feel like dressing up and grabbing an overpriced drink or dessert, I’d go there for sure.

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