Hotels We Love: The Hotel Zachary In Chicago Turns A Trip To Wrigley Field Into A Full-On Event

I don’t care much about baseball. In fact, I don’t think I can name a single player in the MLB right now. But I love going to baseball games. While basketball probably has a better claim to being “America’s Pastime” in 2022, baseball games are still more fun (and better at competing with the ever-improving at-home TV watching experience). And even as a person who doesn’t follow the sport, there are certain places you yearn to see someone hit a dinger or chase down a fly ball at least once — AT&T Park (Giants Stadium in SF), Fenway in Boston, Yankee Stadium, and, foremost among these, Chicago’s Wrigley Field.

Like a day at the county fair, seeing a game at Wrigley satisfies a very specific Americana itch. You’re sitting smack dab in the heart of the country, at the kickoff point of Route 66, taunting batters like Cam in Ferris Bueller’s Day Off — it transcends sport and crosses into that much cooler space of a “community-based hang session” where knowing not to have ketchup on your hot dog is as culturally significant as knowing who’s pitching. And with the opening of the Hotel Zachary right across from the stadium in 2019, that singular experience now feels very worthy of a full Chi weekend.

I stayed at the Hotel Zachary in the fall of ’21 (full disclosure, the Cubs were playing at Louisville during my trip) and fell in love with the property. Not just for its proximity to Wrigley, but for the amenities, the scene in surrounding Wrigleyville, and the dining and bar options. Here’s my rundown of this new(ish), exceedingly stylish “hotel we love.”


Hotel Wrigley Field
Hotel Zachary

Well, first let’s talk about that proximity. I stayed in a 4th-floor suite and the famous Wrigley sign was literally a stone’s throw away. I yelled “it’s right there!” probably 40 times (and I was staying alone!). But a hotel that leaned into baseball in a corny way would annoy the hell out of me because sports fandom never really feels very stylish and it often feels anti-sexy (I’m very down to wear a jersey with a smear of nacho cheese across the front, but that’s not the energy I want from a hotel).

Instead of overdoing the baseball, Hotel Zachary emphasizes the stadium’s architect, Zachary Taylor Davis, and presents schematics and renderings from 1914 as part of the design. The rest of the interior keeps that “big city in the industrial revolution” vibe — with lots of iron, a wall covered with drawers for holding blueprints, and street lamp-style fixtures. The rooms feel similarly sturdy, solid, and built to last. My suite featured a massive velvet couch that I spent hours sprawled on, a nice library full of big, heavy volumes about Chicago’s early days, and a living space and balcony big enough to host a little pre or postgame cocktail hour.

So what makes it cool? That aforementioned proximity to Wrigley combined with the 1920s style of Chicago’s downtown hotels. Plus so many good eating and drinking options that it’s truly ridiculous (that’s what happens when you have 40K people descend on the neighborhood a few times per week).


orichette pasta

Mordecai — based on the bottom floor of the hotel, with a street entrance and a distinct (though similar) personality — comes from Michelin-starred chef Jared Wentworth. The food and cocktails are the thoughtful, inspired, and refined sorts of comfort foods that often get labeled “New American.” The point there is that we’re talking about flavors you’re sure to recognize with style and refinement that will push the boundaries of the ballgame crowd a little. The orichette and braised short rib I ordered definitely felt like they could be found on other menus around town, but they were also unctuous, more buttoned-up than the menu gives credit for, and deeply satisfying.

The cocktail menu was just as elevated and a few clicks more inspired. The Mordecai Toddy made with brandy and rum milk punch is an absolute standout.

If going down to Mordecai is a little too far (it’s literally downstairs), The Bar at Hotel Zachary is based right in the expansive, second-floor lobby. The food is very solid, the charcuterie is strong, and the drinks are mixed at a wide-open bar by a very cheery (and solidly-knowledgeable) staff. Often hotel bar drinks get overly sugary to please the sweet-craving American drinking public. That’s not an issue here — the options are well-balanced and the menu takes some clever twists while referencing plenty of classics.

Everyone on the team can make a solid old fashioned, which should be a bar pre-requisite across the country.


  • Free WiFi
  • Pets allowed
  • 24-hour gym & fitness center
  • Public work spaces
  • Room service
  • Free Coffee/Tea
  • Dry Cleaning Service
  • Wake up Calls
  • Service by request


room the zachary
The Hotel Zachary
  • Queen
  • King (w & w/o field view)
  • Double Queen (w & w/o field view)
  • Ballpark Junior Suite
  • Ballpark Loft Suite
  • Marquee Suite

It drives me f*cking crazy when the artisanal decor of a room is repeated incessantly across the hotel. Even if you don’t see other rooms, you feel that generic-ness. The Hotel Zachary avoids all this, impressive for a hotel owned by a massive parent company (Marriott). The decor is original and unique to each room (I toured five, total). The shape of the larger rooms also gives off this vibe, as the rooms are fit to accommodate the space vs. having a static floorplan.

There are, of course, giant flat screens in every room. Some rooms have a bathtub, though my Junior Suite didn’t — a disappointment, tbh. Perhaps the top perk of the rooms is the furniture. As mentioned, my couch was absolutely stellar (and huge!) and made this property feel like a place that had thoroughly invested in in-room comfort.


This isn’t a discussion. If the Cubs are in town, go see a game. It’s fun and easy and affordable and leads to a whole lot of people spilling out into surrounding Wrigleyville. And it’s not a 15-minute walk, it’s literally 0.5 minutes. Cross a street and you’re there!

When the game is over (or, more realistically considering the crowds, any other segment of downtime), head back across the street to Swift & Sons (again, we’re talking a few steps from the hotel entrance). This oyster bar is an absolute standout — one of the best places to down a tray of oysters in all of Chicago, with a deeply knowledgeable staff and some excellent cocktails on offer. The “Know Thyself” is a very moody rum cocktail made with black tea that nails the “Chi-Town spin on a dark rum drink.”


Chicago Bean

This is tricky and really comes down to how often you visit Chicago. If you go often enough where spending a full weekend in Wrigleyville is feasible, do it — there’s certainly enough to entertain you. The dining options abound.

If you only go to Chicago on occasion, you’ll want to get downtown. The Bean. The lake. The food. All that jazz. (Also, the jazz. And blues.)

The parameters here are pretty forgiving because a 20-minute cab can get you a lot in Chicago. Have you been to Small Cheval? We named it the best burger in the country (Lena Waithe cosigned) — so… you should probably taste that.

Also, The Underground, Kit Kat Lounge, I|O Godfrey, and TAO — the club game in Chicago matches NYC and LA. If you like to go out, be sure to go out while you’re in the Windy City.


hotel bed
Hotel Zachary

This is a spot where The Hotel Zachary really thrives. The thread count is super high — there’s none of that starchy-often bleached-kinda-scratchy thing that you get with mid-level sheets. Better still, the pillows are soft without feeling thin and cushy without feeling inflatable (you know those pillows that always sort of feel like they’re trying to resist the weight of your head?).

These pillows have the “melting” effect of a good pillow and though I’m sure they’re not down (just not tenable for a high-traffic hotel), they are an excellent synthetic.

Rating: 9/10


Tricky one! Those couches are fire and the beds are prime. There are cool bars and restaurants all over the place. The lobby is spacious and fun.

That said, this isn’t such a scene that you’re gonna fully meet someone in the hotel bar (you might, but it’s less probable than, say, The Williamsburg). Also, any place that allows kids gets a slight downgrade on the sexiness scale, and I write that as a person who has kids. More bathtubs would also be a boost here, as would room service.

Still, those big velvet couches…

Rating: 7/10


Hotel Suite Field View
Hotel Zachary

I’m not trying to over-emphasize it, but come on. This is great for IRL and great IG fodder, if you’re into that sort of thing. And while the field view is amazing, what’s even better is leaning out on the balcony while the crowds disperse after a big win.

It’s both a floss and a chance for world-class people-watching.

Rating: 9/10


fall in chicago

“Summertime Chi” is great, as Kanye said, but early fall is even better. Go in September when the weather is on your side but the leaves are beginning to change. If the Cubs are still in the pennant race, the game will carry a whole different energy.


chicago theater

While 20 minutes will get you downtown just fine, that can be a pretty spendy Uber in peak hours and there’s not a super-direct train. Meaning it can be something of a mission — not crazy but def not something you’ll want to do twice in a day (morning activity and evening dinner and clubs) if you’re on tight time or a tight budget.

None of this is the hotel’s fault, of course, and I see a few ways to play this:

  • Get a hotel downtown over a weekend and then get to Wrigleyville for a Monday or Tuesday game and Sunday dinner. That’s an incredible four-day trip with two different hotels.
  • Stay in Wrigleyville your whole trip — it has its own bars, etc.
  • Budget a few hundy for Uber and don’t stress about it.


Weekend rates for a month out look to hover around $240 for a queen or king room to $1200 for the Marquee Suite. The Jr. Suite I stayed in is priced at a very reasonable $460/ night.

See Rates Here