Things To Do
Millennium Park
We spent lots of Fridays here. Photo shoots, frisbee, the bean, concerts in the park (The Audians, Decemberists, Caribou, Wilco, Chicago Children's Choir, among many others), ice skating, splashing around in the fountain, you get it.
AMC River East 21
If you count seeing Dodgeball together as our first date, then this is the place it happened. A theater we haunted every Friday night (and some Saturdays, too) with classmates and friends. It used to be kind of a desolate stretch of neighborhood halfway between Michigan Ave and Navy Pier with not much but a TGIFridays around the corner and a halfway decent food court in the mall with the Nordstrom, but it was a big part of our world for over four years.
Harold Washington Library
When it was built, it was the largest public library building in the world (might still be for all we know). And it's also the place where we decided it was time to admit we liked each other. Also, Maggie wrote a lot of research papers here.
Pequod's Pizza
Micah's favorite pizza. Deep dish, nearly burnt, extremely satisfying.
Pizano's Pizza & Pasta
Maggie's favorite pizza. Slightly less thick than deep dish. Still extremely satisfying.
James R. Thompson Center
Okay, this is a weird one. One most weekdays, we would leave school in a giant group and tumble into a blue line train that would take us to Clark/Lake. And instead of transferring to our respective trains to take us to homes all over the city, we just stuck around in the Thompson Center's food court, and rode the clear glass elevators until they told us to stop. If nothing else, it's a stunning lobby (though I hear the building is owned by Google now, so who knows if they'll let you in).
Hopleaf
A quintessential fixture of Chicago's craft beer scene. This is the place where we learned about beer, spent a lot of our first real job money, and discovered one of the best sandwiches on the planet: the CB&J.
Big Star
Go with a group, sit out on the patio, eat some tacos, order a pitcher of margaritas with the big wooden spoon, and if you're very lucky, they'll have a breakfast burrito on the specials board, get that.
Au Cheval
You honestly can't go wrong with any food around Fulton Market, but this might be the best burger in all of the country. They don't take reservations so try going in the off hours, or how we used to do it: breakfast burgers.
Life on Marz Community Club
Kind of a later addition to our list of Chicago favorites. We didn't know about this brewery until we were in grad school, and they didn't open this slightly more accessible location until just a few years ago, but their beers are topnotch if you're looking for more beer options in the city (and, fun fact: the bridgeport location was one of our main options for a wedding venue)
The Wiener's Circle
A classic hotdog experience. Definitely not a place to ask for ketchup because you're technically not allowed to do that within city limits. You know the drill.
Al's #1 Italian Beef
Another classic Chicago dining experience. And if you've seen and loved The Bear, you're probably going to have to step into that world at least once over the weekend, right? Bonus: this spot is about 3 blocks away from our first apartment out of college: 1055 W Grace Apt 3W.
The Aviary
An indescribable cocktail experience. Some drinks are ecosystems, others come encased in plastic, and there are days when the egg on the menu is a soup.
Kimski
It's no secret that Chicago has a long and storied history as a landing pad for Polish immigrants (Maggie included), and at Kimski that history comes to life in the form of Polish-Korean fusion. It might sound weird at first, but when you think about it both cultures have a documented interest in fermentation, cabbage, and strong flavors.
Field Museum
The premiere field trip destination for Chicago elementary school students. The dinosaur exhibit alone is worth a visit.
Reckless Records
Hours and hours of browsing here, and the next best thing if you're not going to have time for a show at any of the small venues around the city.
Dark Matter Coffee
Maggie's brother's favorite coffee in the city, and he really knows his stuff.
The 606
The 606 is Chicago's version of New York's High Line. It's an elevated park stretching east/west, or west/east along a disused rail corridor, if you're into that sort of thing—we definitely are.
Nicky's Hot Dogs
Back in elementary school and high school, there was nothing better for Maggie than a bike ride to Nicky's for a giant bag of salty french fries, a cup of cheese, and an RC. Impossibly tiny restaurant, counter seating only, huge on nostalgia. Head west a few blocks and you'll see Maggie's neighborhood library. Turn left on to Narragansett Ave and you'll soon pass her elementary school, park, and childhood home (57th & Mobile), three doors down from the intersection facing the park if you're going to get a little stalkery.