Chicago: weekend visit advice needed

Lincoln Park for the neighborhood to stay in and stroll in.

I am a ride or die Chicagoan. There is so much to do. Chicago is very walkable and there are amazing restaurants everywhere. I would try more off the beaten path places personally, e.g., avoid Lincoln Park, but that's just me. Try Logan Square. https://chicago.eater.com/maps/best-logan-square-restaurants-bars-chicago

If you can get into Kasama you should definitely try. There is honestly just too much to do but you can't go wrong. 

https://www.theinfatuation.com/chicago/guides/chicago-special-occasion-restaurants

Have a drink for me! 

Lincoln Park or Gold Coast to stay and shop and dine. I don't know where to stay, it's been a while... 

I agree that Lincoln Park is lovely!  In addition to the park/zoo that the neighborhood is named for, you can walk along Lake Michigan, visit a lot of restaurants/shops, and walk to adjacent neighborhoods (e.g., Lakeview for a Cubs game, Old Town for Second City.  Some of the fanciest restaurants are probably already booked but the New York Times just released its updated Chicago best restaurant list!  https://www.nytimes.com/article/best-restaurants-chicago.html

If she’s bougie I’d stay in the west loop/ Randolph street and Fulton market are known as restaurant row and has all the famous restaurants and swanky bars. 

It’s gotten over the top ridiculous in the past 5 years but it’s fun.

The hoxton is a really nice hotel and there’s a soho house. 

Let her do the planning! 

I second Lincoln Park for the neighborhood to stay and to stroll in. I visited Chicago with my young adult daughter last summer. We rented a lovely AirBnB on the southwest corner of Lincoln Park. The neighborhood is safe, quaint, and walkable to many restaurants, shops, the zoo, and comedy clubs. It's also a long walk or a short ride share to the Art Institute of Chicago, the Bean, Miracle Mile, etc.

West Loop is super bougie and hip. Lots of top restaurants (all of Stephanie Izard's - Girl & the Goat, Duck Duck Goat, Little Goat Diner), Rick Bayles restaurants (Lena Brava), The Publican. Bonci pizza for lunch, Publican Quality Meats or Ramen-San. Dessert is Bombobar. There's a food hall. Great hotels - anything along Randolph Street (Nobu Hotel, Hoxton). Very easy to spend a weekend there and take a train to downtown Millenium Park/Grant Park, walk along the river and the lake. Absolutely try and do the architecture boat tour - it's the #1 touristy activity I recommend in Chicago!

Hello there. I recently returned to the Bay Area but I lived in Chicago for more than 20 years. I would stay downtown and take the L to a couple neighborhoods. (Riding the L is a fun experience in itself!) Chicago is so famous for architecture, I would definitely stay in a hotel in a noteworthy building. The ones that come to mind are the Chicago Athletic Association, the Langham, and the Hotel Intercontinental. Definitely do the architecture cruise or a walking tour. I would not stay in the West Loop -- it is way too commercial and soulless. Downtown you can go to the Art Institute, Millennium Park, and walk the Riverwalk. Do the architecture tour. Have lunch at the Gage or at Revival Food Hall. Avec or Publican would be fun spots for the birthday dinner or look at that NYT roundup that another poster mentioned. Chicago is famous for theater so you could see what is showing at the famous ones such as Goodman and Steppenwolf. Also fun to go to the symphony or see what is at the Auditorium Theater or if there's something happening at the pavilion in Mil. Park. I'd take the L to Southport Corridor (stroll Southport, see a movie at the Music Box, walk around Graceland Cemetery) and go to a game at Wrigley), Andersonville (stroll Clark Street, starting at Foster), or Lincoln Square (stroll Lincoln Ave south of Lawrence). You could also go to Hyde Park and see the new Obama Center and all the things around the University of Chicago. So hard to choose! Don't forget to walk the lakeshore path or rent bikes. You'll have a great time.