I am the trip planner for a multigenerational trip to Chicago over five days that include Memorial Day weekend. In our group are the grandparents (this writer and her husband) that visited Chicago 3 or 4 times a year, son #1 with his wife (limited time in Chicago previously), their 3 year old son/our grandson, and son#2 with his long time girlfriend (late 20s) that are Chicago "rookies".
Here is our tentative itinerary. We welcome suggestions, comments, etc.:
Friday - Grandparents, son#1 with his wife and grandson arrive via car and check into hotel (Residence Inn on Dearborn). Walk around area for brief orientation, etc. and then a quick dinner at Rock Bottom. Grandma and wife of son#1 attend "Motown" at Oriental while grandpa and dad watch grandson.
Saturday - Grandparents, son#1, wife, and grandson take bus #10 to Museum of Science and Industry. Either have lunch there or close to Museum (Potbelly near Museum). Son#1 and wife head to Robie House tour and grandparents bring grandson back to hotel.
Son #2 and girlfriend arrive at O'Hare at noon, metro to downtown, and check into hotel.
2:30 - Son #2 and girlfriend take "Must See Chicago" tour with Chicago Architecture Foundation.
Late afternoon - all gather at Eataly to peruse OR walk through Millennium Park (weather dependent)
Grandparents take grandson to dinner (pizza) and spend time at hotel pool while others spend dinner/evening together.
Sunday - Son #1 and "Grandpa" take History Tour with Urban Kayakers - Chicago River 10-noon
Son #2 and girlfriend - take 11:00 Tastebuds Food Tour (3 hours)
Wife of son#1, Grandma, and grandson attend performance of "The Very Hungry Caterpillar" at The Ruth Page Center for the Arts on North Dearborn - Show is at 11 - one hour long
2:00 - Five of the group travel to and tour Wrigley Field
7:00 - Reservation at Maggianos - Everyone likes Italian and this is a family friendly place
After dinner - those interested go to Willis Tower
Girlfriend has early flight back to DC
1:00 - Grandpa and sons attend Indians/White Sox game
2:00 - Grandma, wife of son#1 and grandson go on Bobby's Bikes "Tike Hike" bike tour - 2 hours
Dinner and evening plans open for all
Son#1, wife, and grandson to Shedd - arrive at opening - back to hotel by early afternoon at latest
This day is "open" for son #2 and grandparents all day (Architecture boat tour?) - joined by the others for late lunch and afternoon
3:30/4:00 - All depart
So, any suggestions? Particularly for dinner on Monday Memorial Day - and Tuesday for lunch? Considering Beatrix for lunch on Tuesday???
Any other suggestions for places to see/visit?
Also - any "favorites" for jazz or blues for those who like a late night session?
Thanks for any/all comments, suggestions, help.