Chicago Long Weekend: The Boys' Bachelor Party
Four days, five guys, one bachelor in Chicago — Cubs game at Wrigley, Friday-night steakhouse at Maple & Ash, Saturday brunch + 606 trail + Big Star, the architecture boat tour the bride-to-be didn't believe we'd actually book, late-night speakeasies in River North. Built collaboratively by the group, planned around the bachelor's actual food preferences.
Entry requirements
Check visa requirements and passport validity for Chicago before you travel. Requirements vary by nationality and may change.
Official government travel pagesMap
Itinerary
Airport Transfer
Five-man Uber XL from O'Hare into the West Loop, ~45 min in afternoon traffic. The bachelor sits up front to set the playlist.
Check-in
West Loop boutique with a rooftop bar — book the Cosy Roomy Suites + a King, three rooms split among five guys. Group rate booked through Chris's corporate account.
Lunch
The single-cheeseburger that every food magazine ranks #1 in America. Drop into Au Cheval at 3:30pm to dodge the 2-hour evening queue. Add a fried egg. Add the bacon. Order five.
Cocktails
Three Dots and a Dash's older sibling — clean, well-edited cocktail menu with a Chicago twist, fireplace at the back. Easy pre-game before the steakhouse.
Steakhouse
Gold Coast steakhouse, wood-fire grill, the "I Don't Give a F*@k" tasting menu. Book the 8pm slot for a five-top in the upstairs dining room. The dry-aged tomahawk, the loaded baked potato, a magnum of Caymus. This is the Friday-night anchor.
Speakeasy
Grant Achatz's cocktail lab in Fulton Market — frozen-in-time spheres, ice-encased Old Fashioneds, drinks that require the bartender to break open the glass. Book the lounge bar (faster than the kitchen counter).
Brunch
Pre-Wrigley brunch institution since 1923 — fresh donuts at the door while you wait, hand-cut hash browns, the omelette comes in a skillet. Get a corner booth for five.
Red Line
Skip the rideshare price-surge — the L is the Chicago way to a Cubs game. Take Red Line northbound from Clark/Lake to Addison station, two blocks from Wrigley.
Pre-Game Beer
Original Wrigleyville bleacher bar across from the centerfield gate — 11 taps, Old Style by the can, every Cubs fan in town before the gates open. The bachelor wears the jersey he definitely shouldn't.
Cubs Game
Bleacher seats in right field, sun on your face, ivy on the wall. Chicago dogs, Old Style, sing Take Me Out to the Ballgame in the 7th. If the Cubs win, the marquee lights up the W flag.
Hot Dog
Chicago's most-mythologised hot dog. Order the foie gras dog with truffle aioli, the Anthony Bourdain hot dog (saucisson de toulouse), the corn dog. Disposable plates, paper napkins, no apologies.
Bar Crawl
Sluggers for the batting cages downstairs (yes, after a baseball game, take more swings). Stretch for the dive-bar tequila shots. Old Crow for the actual whiskey list. The bachelor pays.
Late Night
Outdoor beer garden two blocks south, fire pits, mac-and-cheese late-night menu. The trip's de-escalation venue — you'll thank yourself in the morning.
Brunch
Vegetable-forward farm-to-table that does the best brunch in the city — the Farm Breakfast (eggs, grits, greens, biscuit), the duck confit hash. Walk in or wait the 30 min; doesn't take reservations for brunch.
Bike Ride
Bloomingdale-line abandoned freight track turned 2.7-mile elevated greenway. Rent Divvy bikes at California stop, ride west-to-east through Humboldt Park / Bucktown / Wicker. The Highline of Chicago.
Tacos
Mid-afternoon taco-and-mezcal pit stop at the corner of Damen and Damen. Carne asada, al pastor, queso fundido. Patio if the weather's right. Order the frozen margaritas to bridge to the boat.
Boat Tour
90 minutes on the river with a docent explaining 60 buildings — the underrated Chicago activity that even the bachelor will admit was worth it. Book the upper deck on a Sunday afternoon. Beer on board.
Dinner
Caramelised-crust deep-dish — the cheese melted right into the pan, blackened at the rim. Order a 14-inch pepperoni + sausage for five, debate whether it beats Lou Malnati's. (It does.)
Cocktails
Unmarked door on Damen — Chicago's original cocktail temple. Curtains, candle-lit booths, a quiet rule. Order the Juliet & Romeo (Hendrick's, mint, cucumber, rose) and let the bartender pace you.
Late Night
Live jazz, a great cocktail list, the kind of place a bachelor party ends up because it isn't the kind of place a bachelor party usually goes. Cab back to the Hoxton afterwards.
Brunch
Last-day rehab brunch — the Korean fried chicken sandwich, the avocado toast, the bottomless coffee. Forgiving of hangovers.
Walk
Walk the south bank of the Chicago River from Wabash to Michigan, then up Mag Mile past the Tribune Tower and the Wrigley Building. Daylight architecture instead of the boat's evening angle.
Italian Beef
The original Italian beef joint that inspired The Bear. Order it dipped, hot peppers, on the messy side. Pay cash. Eat over the counter standing up.
Last Drinks
Rooftop in River North with the canonical Chicago skyline shot — closeout cocktails for the group photo, then head back to the hotel for the bags.
Airport Transfer
Hoxton checkout, group rideshare back to O'Hare, terminal three. The bachelor's flight to wherever he's getting married is the last out.
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