This is on our list of top 5 Chicago deep dish spots. Because we love you and take Chicago pizza very seriously, we want to ensure you don't go to a place that starts with a G. There's lots of options but this one won't disappoint. Make a reservation well in advance--it's always full in there!
Connie's Pizza is a Southsider Chicago classic--not traditional deep dish but nevertheless a pan crust for the ages. For guests staying in or near the downtown (loop), this is a great Chicago pizza option. Crispin's family originally resided in the Southside neighborhoods The Italian Village (now University Village) and Little Village (La Villita)--Connie's was family pizza night staple growing up. Kaaren admits that Connie's is the pizza that opened her heart to the beauty of Chicago's thick stylings. It is the official pizza of The Chicago White Sox and The Chicago Sky; Make sure to leave those Cubs hats at home. :) Great for big groups and little ones.
We love winter and being active in the cold. If you're up for a cold day activity, you can't beat the views from the skating ribbon located in the heart of downtown. Registration required--make sure to check the website for closures and more info.
This is our favorite bookstore in Chicago! It is a queer feminist bookstore is a staple in The Andersonville neighborhood. We used to live in Andersonville and Edgewater and there's a ton of fun antique shops, gay bars, and restaurants to check out.
Simon's is famous for its jazz and rockabilly nights--best paired with Glogg, a cup of traditional Swedish mulled wine. We love Simon's for its classic Chicago bar vibes and its spooky haunted history. Make sure to hit the ATM before as its always and forever cash only.
If you're on the Northside, The Hopleaf is a beer lover's dream! A perfect place to warm up in front of the fire with some delish Belgian treats like steamed mussels and frites. No worries, there's also plenty of great veggie options, organic wines and spirits too.
This is a non-negotiable for first time Chicago visitors. This museum is located in the neighborhood of Pilsen where Crispin's family has many historical community roots. This is a great indoor activity should we get a particularly cold and/or snowy week.