If the weather is nice, this is one of the top things to do in Chicago. Amazing architectural history of the best city for architecture in the United States. Book with Chicago's First Lady (run by the Chicago Architecture Center).
Walk along the river between River North and the Loop to realize what the coastal folks have been missing out on.
When Dave first moved to Chicago, he didn't have many people he knew, so he spent many weekends in the Art Institute to put that History of Impressionism class he took to good use. Come for the Isle of the Grand Jatte, stay for the Modern Art.
You've heard of The Bean. Or at least, most people have. Come see it with your own eyes and be more impressed than you're anticipating.
Wicker Park is the namesake of our neighborhood, and it's home to an excellent farmer's market on Sunday mornings and a pleasant little dog park for Chickpea. It also hosts the best trees for setting up a hammock within a reasonable walk of our apartment.
Well, the Cubs found a way to squander what looked like a sure playoff berth and ended up collapsing this September, tearing our hearts out in the process. That said, you might as well walk in the neighborhood and admire this great American ballpark from the outside even if you can't catch a game. Plenty of good options for drinks and bites in the surrounding blocks, too. We like Big Star Taco.
Ipsento offers great coffee in a post-industrial space and is usually playing great music. Take a stroll on the 606 elevated trail (where Dave did much of his marathon training) while you're there.
If you like donuts, it's not going to get much better than Do-Rite in West Loop.
Strong cocktails in a chic setting and not far from the hotels.
You wouldn't know by the name, but this is some of the best Chinese food around.
Koval is a Jewish-owned distillery and produces some of the finest bourbon and whiskey to come out of the Windy City.
Off Color Brewing is where Dave asked Rachel whether she'd like to be involved in a ring-buying process, if he was planning on buying a ring. So, it was kind of like a soft-launch proposal? Anyways, she said yes, and the beer is good.
The Robey has a rooftop bar with awesome views of the Chicago skyline. It's also where the last scene in the Netflix series Easy was filmed, if that means anything to you.
The tiki bar theme is a bit corny if you think about it too hard, but if you go, you'll get the opportunity to drink some very elaborate (and tasty) drinks.
Aside from making great cocktails, this happens to be the setting of one of Rachel and Dave's first dates in Chicago! Technically a speakeasy because of its unmarked entrance, but everyone knows about it. They don't like when people wear baseball caps inside.
High quality Peruvian food for a delicious brunch option. We talked to the sous chef while we were there once, and you'd be in good hands to have him as the person cooking your food.
Rachel won a contest on Instagram for a free meal. We liked it so much, we went back the next night (and because the original restaurant we were going to was on fire, so we had to pivot).
A classic spot to take guests for dinner when they're in town. Plant-based food, but carnivores will still have a great culinary experience.
This Italian restaurant was featured on a travel show we enjoy, so we decided to try it out for Rachel's birthday this year, and it definitely lived up to the hype.
High quality New American fare. If it's good enough for Bubby's birthday, it's good enough for you.