All Time Favorites
Chitown! I've been to Chicago now 3 times over the last decade or so- and it is just such a great city to spend time in and explore over a long weekend. Every single time I have gone has been over Labor Day weekend in September, which I believe provides the perfect weather. However, one of my great missions is to eventually swim in Lake Michigan, and it just has not been hot enough over that weekend for me to finally take the dive in. Another reason to go back! What do I love about Chicago and what are my favorite things to do, here we go:
- The views! I love the skyline view from the water. This was the first city I had traveled to where skyscrapers lined the waterfront, and I just think it is the coolest scene. Also get some aerials from the John Hancock or Willis Towers (be prepared to wait, but it's worth it. I opt for John Hancock because they have a bar with views at the top)
- Beaches in the city? Yes please! There is a huge beach party scene complete with volleyball action, bars and restaurants, laying out, boat parties, swimming in the Lake, all right in the city limits! And this beach is huge!
- The running and biking scene is amazing here. The Lakefront trail is the shit!!! You get miles and miles of path right along the water that goes forever, and is super flat. I've taken advantage of this path every time and I love it - the restaurant scene here is really good so I'm always trying to work all that food off for sure
- The parks/touristy things, there are many and they are worth checking out. The Bean, Millennium park, Cloud gate, Navy pier, Grant park, Buckingham fountain, the Riverwalk- do them all they are all in downtown and easy to get to and are totally worth doing.
- The shopping: the Magnificent mile has all the stores and restaurants you could ever want.
- Stay by the Magnificent mile in the downtown area- that will put you right in the middle of everything (halfway to both beaches/river and parks/attractions)
- The Food and Drinks! So many good restaurants! A few of my faves - Alinea, Girl and the Goat, The Purple Pig, The Publican - and I usually end up at Giordano's for pizza because you need to show someone who's never had Chicago style pizza in Chicago what it's all about. Another place you are going to wait forever, but it's worth it (the stomachache also too- worth it!) Last time I went with Joe in 2016 we went to a pop-up bar "Saved by the Maxx", which was set up exactly as The Maxx diner from Saved by the Bell the TV show. It was awesome- probably not still there but if they ever bring it back and you watched that show growing up you must go!
That all should keep you busy for a 3 day weekend. Eat everything, drink everything, then go for a long bike ride and end up relaxing at the beach. Sounds perfect to me!