Fun places in wi or Il?

Chicago is the best. You can walk around and see everything.

A weekend getaway to either downtown Chicago or Milwaukee is always fun! There are usually hotels you can find for cheap on Groupon or Expedia, and plenty to do in both cities. I recommend the museums in Chicago (assuming they're open). Otherwise, both cities have great restaurants and such. If you're looking to avoid larger cities, I believe it is Galena, IL that has a few wineries, and is supposed to be a great place to visit.

If you like wineries, there is Aeries in Grafton. They also have ziplining & a cool sky tour, as well as on-site lodging

https://www.aeriesview.com/

Southern Il (Carbondale area) has a lot of wineries- Blue Sky and Alto Vinyards are two of my favorite. There is a lot of nature to enjoy and some cool cabins to stay in around there. Grafton has the Grafton winery and Aeries winery, but also the loading dock is a fun spot. You could always stay at the Pere Marquette lodge and have a chicken dinner on Sunday. If in Chicago, I would recommend doing the architecture cruise on the Chicago River, checking out Revolution or Lagunitas Brewing, and then grab a slice of deep dish pizza. Also, the new rooftop bar at Navy Pier is supposed to be fun but I haven't been there yet to say for sure.

Lake Geneva, Wisconsin area is nice. Lots of shops, restaurants and water recreation. I live in Chicago and while I’m sure I’d feel differently as a tourist, I don’t see the draw in coming here, especially when the violence is as bad as it is lately.

A weekend in the city, you can find a hotel that will fit your needs. There are awesome restaurants like the Signature room in the 95th floor of a skyscraper, another one I would highly recommenced is Smith & Wollensky its right on the river next to the House of Blues. House of Blues also has good food an music. Of course there are the museums I'm not certain if they are open, another thing to do it to take tours of the city on the tour buses (double decker), you can buy a weekend pass for the attractions in the city as well. Downtown is just a short ride from Chinatown there is a place with amazing dumplings, while there there is Ice Max a rolled ice cream place, Kung Fu tea is the best bubble tea there. An amazingly romantic restaurant is a fondue place where each couple gets their own booth its called Gejas. Best sushi/ japanese steakhouse is Roka Akor, amazing drinks too.

https://www.thrillist.com/entertainment/chicago/things-to-do-in-chicago

https://www.citypass.com/chicago

https://qxydumplings.com/

https://gejascafe.com/

https://www.rokaakor.com/chicago/