Things to Do

Got some extra time to wander around the city? Why not turn this into a mini weekend adventure! Let us be your virtual tour guides and point you to (in our opinion) some of Chicago’s must-see spots and/or our personal favorites.

But first, an Editor’s Note: We are writing this page exactly a year before we get married, so who knows what the future will be like. So… we’re going to be a bit lazy here! TimeOut Chicago has the definitive list of things to do in Chicago; it’s constantly updating and adapting to the season and weather. Check out their many excellent guides here (a highlight in particular is this evergreen guide) in case our picks don’t quite tickle your fancy.

The Classics

Us at the bean in 2017
  • The Bean. What can we say… it’s The Bean! Spend 10 seconds getting an awesome, iconic picture… then you’re good to leave. Just do not lick it.
  • Millennium Park. This is the park where The Bean is located, so if you are at The Bean, you are at this park! There’s an outdoor amphitheater with free concerts, beautiful public art and botanical gardens, and easy access to the Art Institute. It’s a nice place to hang out that offers a great view of downtown.
  • Magnificent Mile. A very long street with many shops, all culminating in a seven-story mall containing even more shops. It is fun if shopping’s your thing!
  • Sears Tower. If you have never been up high in a building before and want to go very high up in a building and look down at the city of Chicago and you are okay spending a good chunk of money to do this, go to the top of the Sears Tower! (Note: calling this “Willis Tower” is the easiest way to identify you are a tourist).

Outdoorsy

The first time we went on an architecture boat tour in 2019
  • Bike or walk the Lakefront Trail. Stretching along Lake Michigan is 18 miles of beautiful walking and biking paths. All across the city are public bike stations (Divvy’s) that you can rent and ride up and down the lake. It’s one of the most gorgeous features of the entire city, and something we cannot recommend enough. Once when Nate was unemployed, he spent a day walking the entire thing… in the snow. He says he would do it again in a heartbeat!
  • Go on a scenic architecture boat tour. You might think that slow boats along the river is boring, or that looking up for an hour and a half while people talking about architecture is boring, but you would be very wrong. You’ll learn so much about the history and city of Chicago while exploring the Chicago River. While you’ll find many companies offering tours, our favorite is Chicago’s First Lady, run by the Chicago Architecture Center.
  • Bike or walk the 606. This is the Lakefront Trail for our neighborhood. Basically exactly the Lakefront Trail, except ~1/5th the size, not at all near the lake, completely man-made, and above ground. Beautiful, fun, and practical, but… not the Lakefront Trail.
  • Take a stroll through one of our two bird sanctuaries. Sure, it’ll be too cold to swim in the lake, but that doesn’t mean there isn’t anything else to do there! If you love birds, right near the harbors of Lake Michigan are two bird sanctuaries that are shockingly peaceful and quiet for being right in the city. Our favorite, Montrose Park Bird Sanctuary, is worth a visit even if you do not enjoy looking at birds.

Indoorsy

Us seeing a midnight showing of Rocky Horror Picture Show at the MusicBox Theatre in 2023
  • Catch a showing at the Music Box Theatre or The Logan Theatre. Despite The Logan Theatre technically being our closest movie theater, we much prefer the hour-and-a-half walk to the Music Box Theatre (where we are annual members) where we have seen such classics as 2001: A Space Odyssey, Ferris Bueller’s Day Off, and of course, 80 minutes straight of cat videos (Catvideofest). Both theaters are charming centerpieces of their neighborhood, offering a mix of both the latest movies and some older classics. Grab a popcorn, a PBR, and watch a movie in a place (almost 100 years old) you’ve never been!
  • Adventure through one (or more) of our MANY museums. The Art Institute, Field Museum, Shedd Aquarium, Museum of Science and Industry, Adler Planetarium, Chicago History Museum… it’s honestly hard to name them all. Whether you want to just recreate that one scene from Ferris Bueller’s Day Off or see just how many museums you can hit in a single day (which is easy since almost all of them are in the same spot, conveniently known as “Museum Campus”), we cannot recommend Chicago’s museums enough!
  • See a comedy show! Sometimes, seeing improv shows are cringe, sometimes they are lackluster, sometimes they are second-hand embarrassing. However, at The Second City (where many famous SNL comedians have gotten their start) or I/O Theater, they are always hysterical! Tickets are decently-priced and there isn’t a single bad seat in the house!
  • Explore some neighborhoods. Technically this one isn’t exclusively indoors like the others, but the goal is that you’ll mostly be enjoying cute shops, restaurants, bars, etc. indoors that the brief period of walking to that destination outdoors is mostly negligable. We have a ton of cute neighborhoods in Chicago, all of which have their own personality. Of particular note:
    • Logan Square – this is where we live! Lots of bars and coffee shops, cute little local shops, and very hipster. If you were to wear sweatpants to our Farmers Market, you would be silently judged.
    • Wicker Park / Bucktown – tons of shops that include more name-brand selections that are still cool (Carhartt, Free People, etc.) but also some of our local favorites (Myopic Books is a must-do if you even remotely enjoy books).
    • Fulton Market – this is the quintessential place to get brunch. Very fancy, upscale area with very fancy, upscale shops and restaurants. The fanciest bar in the world (in our opinion), The Aviary, is located here and serves incredible drinks.
    • Boystown – the first officially recognized gay village in the United States. Rainbows everywhere, great thrift stores, fun nightlife, incredible drag shows, and a ton of enjoyment overall to explore.
    • Hyde Park – home to the University of Chicago, which makes Hyde Park one big college town. The campus itself is beautiful, but the surrounding area is pretty trendy, and so close to the lakefront that you can’t go wrong!
    • Wrigleyville – the Cubs won’t be playing in November, so it won’t be as jam-packed as it normally is, but it’s still a fun place to walk around if you want to see a store selling Cubs merchandise on literally every corner.

Sporty

Us at Comiskey Park in 2016

Chicago has many sports teams, fields, and arenas. Of particular interest during our wedding time include two teams:

  • Bears (Soldier Field). Da’ Bears. DAH BEAHS! Fun team name to say, but a sad place to walk out of when they inevitably lose.
  • Blackhawks (United Center). Of all the sports in all the times of the year, this is our favorite of the bunch. Even when they lose (which again, they often do), the crowd is ELECTRIC. Tickets are cheap, the crowd is a blast, and the beer pours are large. What more could you ask for?!

Food

Us getting Lou’s in 2021

Let’s be honest… this is the most important section on this entire page. We have food from every cuisine, but I know what you’re thinking: what are the classics. The must-dos. The most “Chicago” food of them all. And, without further ado, here’s that list:

  • Best Pizza: Piece Brewery and Pizzeria. It’s technically cheating since this is not Chicago style at all, but New Haven style. But good pizza is good pizza, and Piece is the best pizza in the city.
  • Best Deep Dish Pizza: Lou Malnati’s. It’s a chain, sure, and you might have watched The Bear and thought that the correct answer is Pequod’s Pizza, but it’s just… not even close. We’re sorry, but you can’t compete with Mama Lou’s butter crust. Just remember, the cheese is under the sauce!
  • Best Chicago Tavern Style Pizza: Pat’s Pizza and Ristorante. Yes, this is the third category on this list devoted to pizza, but we have to! To locals, deep dish is something you only do when people from out of town come visit. Tavern style is the main pizza style here that Chicagoan’s would consider “Chicago.” There are many poor attempts, but Pat’s is the best! Cracker thin crust, wonderfully flavorful tomato sauce, and a perfect amount of cheese. After one square, you’ll need another stat! Note: there is an impostor “Pat’s Pizza” on the South Side that is not the same as the one linked above, but that is what they want you to think – do not fall for this trap!
  • Best Italian Beef (or in our case, Eggplant Parmesan): Ricobene’s. Technically we have never had this since we’re both vegetarian, but we know it’s a Chicago staple so we have to say it. Everyone we’ve brought here loves it, and it’s a place we went to constantly during our days on the South Side. It’s an authentic Chicago experience from its iconic decor to its tucked away location. They also have pizza here, but it’s meh.
  • Best Hot Dog (or in our case, Veggie Hot Dog): Portillo’s. Is it actually the best? Who cares – it’s Portillo’s. The quintessential Chicago spot. Get a “Chicago style” hot dog (which Nate thinks is the most perfect assortment of toppings ever) and do not ask for ketchup on it at all costs (a Chicago sin). And, while you’re there, get a Cake Shake for dessert!
  • Best One-Stop-Shop Restaurant: Time Out Market Chicago. Literally if there is one place we could recommend visiting above all else, it is this. A beautiful and spacious two-story food hall with samplings from restaurants all around Chicago. It’s a great place to go and snack around the city all within a single space. It’s also located in Fulton Market, which is a super cute and trendy neighborhood to walk around!
  • Best Beer: Revolution Brewing. Don’t worry, you’ll get to try plenty of this (for free) at our wedding!

And now, just a rapid fire list of places (mostly centered around our neighborhood) that we love to bits:

Believe it or not, this is just a subset of the places we love to eat around the city. If you’re looking for something very specific, don’t hesitate to reach out to us for recommendations. We love talking about food!