Wow yes! Any advice like this would be greatly appreciated. I have wrote these down and if you can think of anymore please feel free. Thanks
I combined my posts for you. There are several great local pizza spots but not close to the tourist areas. Lou Malnati’s is my personal favorite of the ones downtown. Local Deep Dish Pizza places are Pequods and D'agostinos (half a mile west of Wrigley Field).
Walking through Lincoln Park is a must do. Beautiful scenery with the Chicago Skyline just South of you. The North Pond restaurant in Lincoln Park is a great romantic spot for Dinner. Need reservations and be prepared to spend $200 at a minimum (its on the Northern end of Lincoln Park). Navy Pier, Millennium Park and Grant Park are downtown. ( The Bean, Buckingham Fountain, Crown Fountain, etc). Walking along the Waterfront is really fun.
Standing on the North Avenue Beach, Shedd Aquarium, and Adler Planetarium have amazing views of the city. 360 Degree Observation deck on the 94th floor of the John Hancock Building. Much better view than at the top of Sears( Willis) Tower. Also the Signature Lounge on the 96th floor at the John Hancock is a great spot for drinks.
Night Time Chicago River Cruise is a must. They start at Michigan Ave Bridge. Just walk down the steps ( also several bars on the water there). I love the Museum of Science and Industry. It’s the only thing worth going to the South Side for IMO... Field Museum is good too. Never been to the Art Institute of Chicago. Not an art museum fan.
Really cool area is at the North end of downtown. The very end of Rush Street connects to State Street. This area is called the Triangle. There is a Lou Malnati's there along with many other restaurants and bars. Another neat area is on Clark street by Wrigley Field with about 200 Bars side by side. Wrigley Field does tours you would just check their website for times.
Probably my favorite restaurant is the Girl and the Goat. Reservation is definitely needed. Very unique menu. Au Cheval might be the best Cheeseburger you will ever eat. (been voted best in America by the Food Network). Its very close to the Girl and the Goat. You have to go there not at your standard lunch or dinner time or the wait will be tremendously long.
Best Advice for the whole Trip. Keep your wife off the Magnificent Mile on Michigan Ave if you want to be able to pay your Credit Card Bill that month. LOL