A Guide to Some of Our Favorite Spots in the City

Chicago Athletic Association Hotel

In her family’s frequent childhood trips to Chicago, Amelia always favored this place’s Venetian Gothic facade. Imagine her delight when the shuttered private club reopened as a hotel in 2015. Even if you aren’t a guest, everyone’s welcome to pop in for a round of bocce or shuffleboard in the Game Room, elbow their way to a lovely view of Lake Michigan and Millennium Park at Cindy’s Rooftop, or curl up with a book near a fireplace in the Drawing Room.

Pro tip for folks in need of late-night carbs: Shake Shack is on the first floor.

Pro tip for cocktail hounds: Treat yourself to a reservation at Milk Room, if your travel timing allows. This tiny (and we mean TINY!) appointment-only bar will serve you drinks made from rare and flat-out rad alcohols, like Campari from the ’70s and bourbons from the day humankind invented the wheel, or whatever. A special occasion on top of a special occasion, if you will. But when in Rome!

Miller’s Pub

Food and drink options in the Loop can be a little hit or miss. Miller’s Pub is a definite hit for drinks (and decor—stained glass! Weird oil paintings! Rich mahogany!). Skip the food, unless your martini requires the grounding presence of an order of fries, and be sure to sit at the bar itself (or in the window seats next to the bar) for the best experience. If you’re lucky, Amelia’s favorite bartender, the wild-haired Beaker, will serve you.

Fun fact: While seated at the west end of the bar in 2017, Geoff and Amelia officially decided to move in together.

Chicago Architecture Center River Cruise

If a) you have time and b) the weather isn’t crummy, you must—simply must!—take an architecture tour of Chicago by boat. While several companies offer these tours, the Chicago Architecture Foundation’s is far and away the most comprehensive. And as a couple that’s devoted to nerd stuff, well ... we say “Most Knowledgeable Docent” is the only criteria that matters. Sit on the open top deck for the best views of landmarks such as “the location of Amelia’s first office job” (303 E. Wacker, by Mies Van Der Rohe), “the landmark building Geoff once considered living in” (River City), and “the towers from that one Wilco album cover” (Marina Towers).

Art Institute of Chicago

We’ll blink twice if we’re required to plug the Art Institute in order to get married at the School of the Art Institute ... 👀. Truly, though, this museum has a top rating for a reason (and it’s even better as its employees’ unionization progresses!). Some of our favorite sights include the Thorne Miniature Rooms; Paris Street, Rainy Day, by Gustave Caillebotte; The Child’s Bath, by Mary Cassatt; Woman at Her Toilette, by Berthe Morisot; Still Life with Dead Game, Fruits, and Vegetables in a Market, by Frans Snyders; and Nighthawks, by Edward Hopper.

Chicago Cultural Center

A scant 0.3 miles north of our wedding venue, the Chicago Cultural Center is a gorgeous (and free!) place to visit. Killing time before the wedding? Need a cute backdrop for adding your outfit to the ’gram? This is a slam dunk, folks. Be sure to check out the Tiffany dome, as well as whichever art installations are currently displayed on the floors below.

American Writers Museum

Opened only since 2017, this museum is a great place to appreciate the long history of American letters and better understand its evolution. But, it’s also intimate enough that you can still get through most of it within an hour or two.

Momotaro

Formal dining upstairs, more casual dining/bar downstairs. The menus overlap somewhat between each level, and if you see a chilled silken tofu appetizer among them, please trust us and order it. (Everything else is wonderful, too.)

The Publican/Publican Quality Meats

These next-door sister restaurants offer lovely sit-down dinners and hearty takeout deli sandwiches, respectively, all featuring—you guessed it—excellent meats.

The Aviary

Again, here’s one for the cocktail hounds. If you have an extra night in Chicago and can snag a reservation, why wouldn’t you want to drink in the bar that supposedly inspired the bachelor party scene in Parks and Recreation? (“They have a vodka that’s served in the form of a flash of light!”) In reality, the drinks deserve the hype, none of them are light-based, and the atmosphere is sleek but cozy.

Pro tip: ask your server if the cocktail that requires a slingshot is on offer that day. Not a joke.

Garfield Park Conservatory

A true jewel of a building, first opened in 1908, the conservatory is home to exotic plants from around the world, separated into rooms representing different climates. Come for the architecture, stay for the palms, cacti, ferns, flowers, and other flora.

Long Room

Geoff’s go-to bar in his bachelor days. The bar where Amelia, flustered, accidentally told Geoff she loved him much too soon in the relationship. (Luckily it all worked out in the end.) Also the site of some of our engagement photos (see above).

Simon’s Tavern

The site of our first date! It’s a Swedish bar in a historically Swedish neighborhood. Excellent jukebox, lovely (if crumbling) murals on the walls, reportedly haunted (we believe it).

The Green Mill

Site of our first kiss! The Green Mill is practically mythical in status. Birthplace of beat poetry, with some Al Capone lore if you like that sort of thing, plus low lights, strong drinks, cozy booths, swing dancing on select evenings, and unbeatable jazz the rest of the time. And—shoutout to everybody from Davenport, IA!—you’ll likely see “Bix Lives” scrawled in lipstick on the wall of the ladies’ room.

The Hideout

THE HIDEOUT FOREVER. The former cottage became a bar and music venue in 1934, and it has since hosted the likes of Mavis Staples, Andrew Bird, Sarah Sherman (2021 SNL cast addition), and just, like ... so many artists we love. (The Bangers, our wedding band, have also had the good luck to play there—it’s an important venue for us all!)

Pro tip: heed the sign behind the bar that suggests the Wooden Leg cocktail. Not drinking? No problem. The Hideout is what turned The Bangers (and all our friends) on to Lagunitas Hoppy Refresher, a delightful flavored seltzer.

Music Box Theatre

Honestly, we’d get married at the Music Box if we could. The meticulously maintained movie palace, built in 1929, shows independent/small-release films (as well as our sacred annual Christmastime double feature of White Christmas and It’s a Wonderful Life). Select screenings are preceded by tunes from a live organist. Also the site of some of our engagement photos (see above).

Pilsen Community Books

One of our favorite independent bookstores in the city! Now fully employee-owned and operated, so you know your money’s going in the right pockets. Hit them up if you need a new read to page through, and if you’re lucky, you just might be blessed by the presence of Polo the shop dog.

Pullman National Monument

We love old stuff, and we love the National Park Service. If you do, too, then kill two birds with one stone and visit Chicago’s first national monument, the preserved Pullman Historic District, a planned community built in the 1800s by the Pullman Company for the workers who built its train cars. The site was added to the National Park System in 2015 and only opened its new visitor center last year, so much of its grand architecture is freshly restored.

Heart of Italy District

Once home to a significant population of Tuscans, this block still features a number of classic Italian eateries that have been open for decades. Our favorite is Bruna’s, "the third-oldest Italian restaurant in Chicago," which has been in business since 1933 and is generous with the wine.

Skylark

Are you even at a Chicago bar if you can’t order pierogies with your beer? Bring cash (it’s cash-only), with a focus on extra $1 bills for the vintage photo booth.