One of my favorite cities. Like a mix between LA+Seattle with seasons though and city pride everywhere you look.
Pride for Sports Teams there are unrivaled, and they have reason to be that way. Bulls, Blackhawks, Cubs, White Sox and Bears all reside in chi-town and you’ll see remnants of it everywhere as well as the 4-star city flag. I’ve never seen a city rep their flag like they do there. In fact, I didn’t even know cities had flags, which led me to look up Los Angeles and laugh for a good while.
Anyways, to start, flying into O’Hare makes things really easy and it’s a nice airport with transport from the burbs to the city (Blue Line).
Begin by getting a city Viator pass, it gets you use to both the the trains and the buses, which can get you basically anywhere in the city and beyond. (I got an unlimited 3 day pass)
The rest is up to you but here are my recos:
Must Do: Millenium Park/The Bean. Whatever sporting event is happening during that season (United Center/Wrigley), Take a walk down Milkwaukee/Damen and hang with the locals, lots of great stores and food/coffee spots.
Food: DEEP DISH PIZZA: It’s known for it so get it. My favorites are Giordanos and Gino’s East, but the original Uno’s is also there!
Italian Beef Sandwiches: Al’s is awesome, but I could not stop thinking about Johnnie’s Beef in Elmwood Park. It’s a little bit far out there (takes about an hour on the bus from downtown) but it’s $5 for an amazing sandwich. Beware it’s cash only though!
Chicago Dogs: I only really ever go to Portillo’s but I’m sure there are plenty of bomb places.
Wildberry Pancakes & Cafe: Best breakfast! Right across the street from the bean, so go here first then walk off the food in the park. Beware long waits though, this place is very busy on the weekends. The french toast is amazing.
Piece Pizza: Awesome NORMAL pizza and award winning beer. They even have a Girl & the Goat collaboration pizza (A $$$ restaurant, so I have never been there).
Drink: Emporium – 2 locations, it’s basically a barcade with lots of beer and tons of games for a quarter. Similar to “barcade” in NYC but better and bigger.
Goose Island Brewpub: One of my favorite places.
Coffee: Walking down Milkwaukee, I found a number of cool looking coffee shops, but none better than the one called “The Wormhole”. Really chill vibe and kind of nerdy at the same time. There is a car in there as decor. Rad.
Farther down Milkwaukee/Damen, you can find Mindy’s Hot Chocolate. Another cool spot for food and drinks!
Skyviews: I’ve been to both the John Hancock Observatory (360 Chicago) and the Sears Tower/Willis Tower (Skydeck) and they’re both pretty cool. I think you have to go to the Skydeck though, it’s higher and the glass over the edge is pretty legit. Beware of major tourists and waiting in lines for pictures, otherwise hope for a clear day for these beautiful views.
Not Recommended: Wicker Park, just because there is a movie, doesn’t mean it’s worth going to.