Chicago

I have 2 I can recommend. I love the Silversmith with its high ceilings and boutique hotel feel. I also frequently use the Hampton Inn & Suites Majestic. It is a floor up from a theater that used to be called the Majestic Theater. Are you taking a river cruise? I love that. I also always walk down to the park along the lake shore. The Art Institute is fabulous. You will have a great time. Just be aware of your surroundings and you'll be fine. I never feel less safe here than any large city.

How much money a night do you want to spend on lodging?

I think the most interesting thing about Chicago is the number of ethnic neighborhoods, with their restaurants and shops. Lots of cool neighborhoods. Check schedules for neighborhood fairs and festivals. But you have to consider your transportation options.

Most people would go to the Chicago Museum of Art for sure.

You should take an architectural tour. There are both walking ones and ones by boat. I have done both and enjoyed them both.

Thank You so much for the suggestions.

Can you please suggest restaurants ( we like it all).
We do love visiting different neighborhoods. Can we get help with which ones not to miss?

Thank You
Maria

I like the Lincoln Square neighborhood, northwest of downtown. Eat at Gene's Sausage and Deli there.

If you're staying downtown on the Magnificent Mile (Michigan Ave north of the river) where the big hotels are, and you're old enough to remember the Saturday Night Live Cheezborger, Cheezborger, Cheezborger skits, you should visit the Billy Goat Tavern (cheezborger which is UNDER the street ( a sight in itself).

As you can see I'm not a 4-star restaurant person, so look for Italian Beef sandwiches as well as the Hot Dog places all over. Ravenna, Skokie, Evanston areas for Jewish delis.

Take a cruise on the lake.

Born and raised until I graduated college in Chicago. While the news has a lot about Chicago crime, if you follow the advice of visiting other big cities you will be fine.

I would stay downtown in the Loop or the Magnificent Mile. Not sure about hotel costs now but try looking at booking.com or last minute. There are always people downtown at night and unless you are partying until all hours, either an Uber/Cab or the CTA will be fine. Apart from NYC, Chicago has some of the best ethnic restaurants which are usually in the neighborhoods not downtown.Look on Yelp/Tripadvisor for some good ones.

Things to do-

Walk along the Lakefront for a while or just relax at Millennial Park, though The Bean is under repair.
Boat Tour
The Art Institute has the finest Impressionist collection in the US.
Museum of Science and Industry to see the captured German U-Boat.

Not sure when you are going and whether your Mom likes baseball, but a Cubs game at the Friendly Confines of Wrigley Field is always a treat.

We used to live in Chicago and it’s one of my favorite cities. Stay north of the Chicago River in Streeterville or River North. Or even along busier Michigan Avenue.
The Art Institute is wonderful; don’t miss it! Chicago is known for its architecture so I recommend that you take the Art Institute’s architectural river cruise on their boat up the Chicago River.
There is so much good dining there. Wells Street has lots of restaurants including Topo Gigio, Orso’s, Lou Malnati.