So, if you stay near Navy Pier (big tourist attraction) you’ll probably be in Streeterville. There are a lot of hotels in that area and it’s very close to “the Magnificent Mile” which is what Chicago’s upscale shopping area is called. If you like shopping and eating out, it’s a good place to stay, but it’s pretty touristy. If you plan to see Hamilton or a production at the Goodman Theater, and/or you’re more into culture and want a feel of the city that people work in, the Blackstone is probably a better choice.
In addition to the Museum Campus (with the Field Museum, Shedd Aquarium, etc.) the Blackstone is right across the street from Grant Park, near Buckingham Fountain, and just a few blocks south of the Art Institute and Millenium Park.
Millennium Park is pretty much my favorite / don’t miss thing in the city - the landscaping is gorgeous, the Crown Fountains and the Bean are really cool, the bike path and lake front are amazing, and the Pritzger Pavilion (outdoor concert hall) is amazing architecturally and has a ton of great, free concerts (lunchtime as well as evening, plus you can watch rehearsals), ranging from classical music to jazz to world music, etc. The concerts are world class, so if you like music, go!
https://www.cityofchicago.org/city/en/depts/dca/supp_info/millennium_park.html
http://www.grantparkmusicfestival.com/
You can buy wine/beer and sandwiches in the park during concerts, but it’s okay to bring stuff in (lots of people do) - go to Pastoral on Lake Street to pick up cheese, wine, etc.
The Art Institute is right next to Millenium Park and it is huge and amazing. They have a great French Impressionist collection and a new modern wing. Random famous stuff there: Seurat’s La Grande Jatte (inspiration for Sunday in the Park with George), American Gothic, Picasso Blue Guitarist, plus Monet, Gaugin, etc If you’re into art, it’s really a must. The in-house restaurant, Terzo Piano, is pricey but good.
Right across the street from Millenium Park is the Gage - more or less a French bistro, a bit pricey, but good food / wine.
http://chicago.seriouseats.com/2013...nnium-park-chicago-slideshow.html#show-321929
Suburbs: If you’re really, really into music and gorgeous scenery, Ravinia Park is also amazing. It’s the summer home of the Chicago Symphony but also has a chamber music series, does at least one opera, and has all kinds of concerts - blues, jazz, rock, etc. It’s located about 25 miles north of the city in Highland Park (where Jason Brown is from) but you can take a train from downtown (Ogilvy Transportation Center) right to the park, and the trains are timed so you can get to and leave from the concerts. You can buy a lawn pass (bring a blanket) or seats in the Pavilion (more expensive). You can buy food and wine there or bring it in. It’s really gorgeous and again, the music is world class.
https://www.ravinia.org/?ath=
Oak Park is my hometown, so it always makes me laugh when people recommend it as a place to go, because growing up I thought it was incredibly boring - Ernest Hemingway, who was born there, used to call it the town of broad avenues and narrow minds.
But if you’re into architecture, there are tons of Frank Lloyd Wright homes there, plus his home / studio which you can tour.
The downtown is kind of cute (cobblestones and stuff) and there are a fair number of ever changing boutiques and restaurants. Maya Del Sol (Oak Park Avenue) is fun and has good, somewhat pricey Mexican (not as good as Frontera or Topolobambo though) - if you go, have margaritas and try to sit outside in the back. Across the street is a cheap but good Middle Eastern place called Grape Leaves (no booze). Cucina Paradiso (North Boulevard near Oak Park Ave) has a really nice wine list and good Italianish food. Coopers Hawk Winery (Lake Street) is an Illinois chain (not cheap) but it’s actually really good - wine + food pairings. If you want to make a night of it, Fitzgerald’s (Roosevelt Road) is a bar with great live music.
Re transportation: you can take the green line (elevated train) from downtown Chicago to Oak Park but I would not suggest taking it back into the city after about 6:00 pm. You can also take Metra (commuter train) there and back - it runs every half hour during rush hour but far less frequently in off hours and on weekends. You can also rent a car or use Uber. Most of the stuff I mentioned is within walking distance of the train but for Fitzgerald’s you will definitely need a car or Uber.
http://flwright.org/
http://www.fitzgeraldsnightclub.com/
Otherwise, Chicago has a lot of fun neighborhoods to visit, but it really depends on what you’re interested in - West Loop for restaurants, Logan Square and Lincoln Park for walking around, Roscoe Village for antiques. Time Out Chicago has a great neighborhood listing as well as event listings:
https://www.timeout.com/chicago
Enjoy your trip! I’m homesick for Chicago!
I have heard it is great. Is it safe though?? 
my picky ass husband for not wanting to go!
. Both on foot and from the water!
