The Full Chicago: A Wrigley Field Weekend Guide
This is a summary post for my four-part Chicago series. If you want the full stories first start with the first post — Start Somewhere That Means Something.
Where to Stay
Hotel Zachary — 3630 N Clark St, Wrigleyville
The first thing worth knowing about Hotel Zachary is that Wrigleyville is its own neighborhood, about a 20-minute Uber from River North, the Magnificent Mile, and the Museum Campus. Everything we did on Days One and Two meant a ride each way. We considered booking the Zachary only for the nights around the game and staying somewhere more central — and more affordable — for the rest of the trip. But in the end we didn’t want to deal with moving bags and checking in and out twice, so we stayed all four nights at the Zachary and Ubered everywhere. It worked out fine, but it’s worth going in with clear expectations about the geography.
What you’re really paying for is the immersion. The hotel sits directly across the street from Wrigley Field and is named after the stadium’s original architect, Zachary Taylor Davis. The second-floor terrace bar has a direct view of the field, and on game days the energy starts at the hotel and rolls from there. It’s a Marriott property, so points apply. Book as early as you can for game weekends — it sells out.
Arrival Night
Alma at Hotel Zachary — second floor, reservations recommended on game days
Our arrival day was a comedy of weather delays and a dinner reservation that didn’t survive the chaos, and we ended up at Alma by default. We ordered the Zachary Old Fashioned — made with Koval’s Hotel Zachary private barrel bourbon and smoked sugar — and somewhere in the middle of that drink we stopped mourning the original plan entirely. Sometimes the detour really is the destination, and this was one of those times.
Day One: The River, the Mile, and 550 Bottles of Whiskey
Chicago Architecture Center River Cruise — departs from the Riverwalk at Michigan Ave and Wacker Drive
Pre-book this one. The 90-minute docent-led tour covers more than 50 buildings and tells the story of how the Great Fire handed a generation of visionary architects a blank canvas and what they built on it. It’s one of the best possible introductions to Chicago — the kind of thing that makes everything you see for the rest of the trip land differently. The open-air upper deck is the best spot, but dress for whatever the weather is doing, because it will do it directly at you. It sells out, so don’t wait.
The Magnificent Mile — Michigan Avenue
No booking needed, just walk it. We’re not big shoppers so this was less about buying anything and more about being in the middle of it, which is its own kind of fun. If you find yourself in Water Tower Place, look for the Chicago Sports Museum on the seventh floor inside Harry Caray’s restaurant — the Bartman ball, Sosa’s corked bat, Kris Bryant’s cleats from the 2016 World Series. We stumbled in without knowing it was there and stayed much longer than we planned.
Dinner: Untitled Supper Club — 111 W Kinzie St, River North
Pre-book this, and check the entertainment calendar before you go. From the sidewalk you would walk right past it — a black kiosk, gold script, nothing announcing what’s waiting downstairs. What’s waiting downstairs is an 18,000 square foot underground space sitting on the largest collection of American whiskey in the world, multiple rooms each with their own wall of bottles, the whole place Prohibition-era in spirit and impeccably done. It’s also a seven-time Michelin Bib Gourmand restaurant, so the food is taken just as seriously as the whiskey. We were in the Cabaret Room — worth asking for if you want to watch the band. Every Thursday they host Unbridled, a full burlesque show. If your visit falls on a Thursday, that’s your answer.
Day Two: Dinosaurs, Gangsters, and Garlic
The Field Museum — 1400 S Lake Shore Dr, open daily 9am-5pm
Give this at least half a day. The SUE the T. rex exhibit has its own dedicated 5,100 square foot gallery with interactive stations, animations, and a station that apparently lets you smell T. rex breath. I skipped that one and have no regrets. The T.REX 3D film requires a separate ticket and is worth adding. Buy your entry tickets online in advance to skip the line.
Untouchable Tours — Chicago Gangster Bus Tour — departs Clark St between Ohio and Ontario
Pre-book this. About two hours, fully in character the entire time, covering Capone’s Chicago, the St. Valentine’s Day Massacre site, the Biograph Theatre, and more. A few practical notes: arrive a few minutes early, there are no bathroom stops once you’re rolling, and there is no escape from the bus. Fitting, really, for a mob tour.
Dinner: D’Agostino’s (Dag’s) — 1351 W Addison St, Wrigleyville
Deep dish. The moment you sit down, order it — it takes 30 to 40 minutes and that is not a suggestion, that is the reality of deep dish. The garlic situation is not subtle. We were still thinking about it two days later. Worth every bit of it.
Day Three: Game Day
Gallagher Way — just west of Wrigley Field
The plaza outside the park opens before games and has its own energy before the first pitch even gets close. People are tossing balls around, the neighborhood is fully awake, and Jeni’s is right there for ice cream. Find a table and sit for a while.
Wrigley Field — 1060 W Addison St
Pre-book well in advance. On seats: the Catalina Club (sections 315-318, behind home plate) is the splurge option — all-inclusive food, beer, and wine, padded seats, private restrooms, and the only club at Wrigley with actual sightlines out to the field. The bleachers are the other kind of splurge — old wooden benches, full sun, among the real diehards, the experience people mean when they talk about “authentic Wrigley.” Either way, get there early. The park has history in every corner and it genuinely rewards time spent in it.
While you’re in the neighborhood, walk past the Wrigley Rooftops on Sheffield and Waveland — the buildings directly across from the outfield where home run balls occasionally land in the street. Obvious Shirts near the park has genuinely good Cubs gear, and I’d budget a few extra minutes for anyone in your group who takes cap selection seriously. The Billy Goat Tavern, home of the Curse of the Billy Goat and inspiration for the SNL sketch, is worth a stop if only to say cheezborger out loud in the actual place.
📋 Before You Go
Hotel Zachary books out fast for game weekends — lock it in early. If budget is a factor, consider staying there only for the game nights and somewhere more central for the rest of the trip. Plan on Ubering between Wrigleyville and everywhere else — about 20 minutes each way, totally manageable.
Pre-book: the river cruise, Untitled Supper Club, Untouchable Tours, and game tickets. All of them.
Check Untitled’s entertainment calendar before you go. If it’s a Thursday, go for Unbridled. Ask for the Cabaret Room regardless.
Catalina Club if you’re splurging on seats at Wrigley.
Order the deep dish the second you sit down at Dag’s. This is not optional.
Get the Zachary Old Fashioned at Alma. Possibly more than once. We did.
