Chicago may not be known as a premier bachelor party city on par with more famous destinations like Vegas or New Orleans, but the best rewards come to those who put in a little extra effort. Offering a friendly Midwestern vibe packed inside more bars and restaurants than any one group can possibly handle, the Second City is second to none when it comes to celebrating special occasions (like your bachelor party).
We’re going to be as honest as the Lake Effect is bitter cold—schedule this one for the warmer weather months. Trust us, you’ll be able to have so much more fun and no one will experience hypothermia. Also, we highly suggest starting this party on a Thursday to make the most out of the Saturday-only 5 a.m. bar closings. So roll up your sleeves and dive into our expertly curated 72 Hour Guide for the very best Chicago bachelor party—because you and your crew have got a lot of work to do.
—Jay Gentile
Day 1
3 p.m. Check Into the ACME Hotel
Welcome to Chicago. Time to check into your crash pad for the weekend. ACME Hotel is a cool, downtown spot, complete with its own high-class mixology den (Berkshire Room) and ridiculously over-the-top apres ski party bar (Bunny Slope) that you can rent out for you and your crew. Yes, there is a hot tub. No, there isn’t a stripper pole (but don’t let that stop you from inviting over some new “friends”). If that’s not enough, they’ve also got in-suite guitars, in-room beer vending machines, free Apple watches to check out during your stay, and hangover kits as part of their “Hair of the Dog” package…which you might want to seriously look into.
5 p.m. Drinks Near the Hotel
Chicago is a notoriously thirsty city, so no matter where you are, you’re never far from a stiff drink. The neighborhood around the hotel is centrally located but a bit touristy, although worthwhile haunts can be found at spots like tiki paradise 3 Dots and a Dash (where you can order a smoking treasure chest of booze packed with a bottle of Dom Perignon). Or if you’d rather not blow all your cash before you’ve visited the gentlemen’s club, post up on a stool at a nearby dive like Rossi’s—one of Chicago’s iconic “slashies” (part bar/part liquor store)—and commiserate with a glorious amalgamation of grizzled old timers, blue collar workers, and buttoned-up young professionals.
7 p.m. Steaks at Gene & Georgetti
It’s your first night in town, so you might as well be somewhat classy while you still can. And while a trip to a steakhouse may not seem like the most exciting idea in the world, a trip to the “so old-school it hurts” Gene & Georgetti is well worth your while. Chicago’s oldest (and still one of its finest) steakhouses offers everything you need to prepare you for your first night on the town from expertly cooked chops to decadent pasta dishes, not to mention cocktails as stiff as the breeze off Lake Michigan.
9 p.m. Listen to Live Local Music
Now that you’ve seen a bit of downtown, it’s time to get out into the neighborhoods, where the real action in Chicago takes places. Each neighborhood has its own unique style and vibe, from the frat bars of Wrigleyville to the hipster oasis that is Logan Square. The Wicker Park/Ukrainian Village area is a good middle ground between the two, and also happens to be blessed with an assortment of fine music venues like the Empty Bottle and (not far from here) The Hideout, a tiny out-of-the-way dive that will instantly become your new favorite bar. Stumble into either of these glorious establishments on any given night to see everything from up-and-coming indie rock bands to live comedy and unclassifiable weirdness.
12 a.m. Bar Hopping in Logan Square
Despite the occasional hipster overkill, Logan Square’s Milwaukee Avenue corridor is a booming scene that should not be overlooked when it comes to bachelor party tomfoolery. Grab drinks at one of Chicago’s leading craft breweries, Revolution Brew Pub, before wandering down the street to check out joints like the delightfully grungy dive Cole’s and nearby party hang East Room, which is hidden down an alley side street and always has something interesting going down. End your night at the one and only Slippery Slope playing Skee-Ball and dancing like a sweaty imbecile until 2 am. Luckily, Red Hot Ranch is serving Chicago-style hot dogs until 4 am.
Day 2
12 p.m. Eat Italian Beef at Al’s
What the hell? How you been in Chicago almost 24 hours and you’ve yet to tangle with an Italian beef sandwich? Correct such an egregious oversight by making the pilgrimage to Little Italy and worship at the temple of Al’s #1 Italian Beef (the original location on Taylor Street), where Chicago’s most iconic sloppy sandwich was invented. There are ways to order, so best know what you’re doing: order yours with “sweet and hot” (meaning peppers and giardiniera), “dipped” (meaning the sandwich is dipped but not over-soaked in the juice), and add an Italian sausage as part of a “combo” if you’re feeling adventurous. Then stand back (there are no seats here) and bite into it, because things are about to get wonderfully messy.
2 p.m. Booze Cruise (or “Brew & View”)
If you’re here in summer, a trip aboard one of the Vince-Vaughn-from-The-Break-Up style tourist boats is a no-brainer. The river is beautiful, the buildings are so close you feel like you can touch them, and yes, you can drink on the boat. Heavily. Companies like Wendella offer a variety of cruises to choose from, including special bachelor party-approved events like beer & BBQ cruises. If (stupidly) you’re here during a time of year when the boats aren’t running, a fun indoor alternative is catching a flick at Chicago’s infamous Brew & View, where they’re screening classic flicks like Star Wars and Slap Shot in a boozed-up concert hall.
4 p.m. Nine Holes of Golf (or Video Games at Emporium)
If you’re feeling nice and tipsy after the cruise and still looking to get in some action before dinner, a trip to the beautiful (and public) Sydney Marovitz Golf Course located right on the shores of Lake Michigan is never a bad bachelor party idea (depending on how long you’ve been drinking, of course.) If the weather isn’t cooperating, head indoors and keep the booze flowing at one of Chicago’s many “barcades” (bars/arcades) like Emporium, where you can dominate your boys in foosball and Donkey Kong while sampling the latest craft offerings from up-and-coming local brewers like Metropolitan and Off Color.
7 p.m. Dinner at Longman & Eagle
If you like your restaurants with 400+ whiskeys and an upstairs boutique crash pad in case you can’t make it back to the hotel, you’ll love Longman & Eagle. The Slagel burger with Widmer’s cheddar (these are both Midwestern companies) and beef fat fries is tough to pass up, but they also take it a step further with slightly fancier (but not too fancy) dishes like Cornish hen pot pie and wild boar Sloppy Joes. If the weather’s good, you can also down canned beer and do shots of Malort (it’s a Chicago thing) in their adjacent garage-style Off Site Bar.
9 p.m. Second City/Comedy
Chicago is the home of improv comedy and while it may be touristy, Second City never disappoints. The always-on cast of comics (Second City vets include Bill Murray, Tina Fey, Stephen Colbert, and way too many others to mention) are primed and ready to deliver a devilishly professional set that skewers politics and everyday life in a style you won’t soon forget. For a more under-the-radar (and cheaper) comedic experience, check out indie fringe theatres like The Cornservatory and The Lincoln Lodge. If you do make it to Second City, a trip to the legendary Old Town Ale House (Anthony Bourdain fave with nudie pics of politicians painted by the owner from his studio below the bar) is an absolute must.
12 AM Club/The Mid
If you’ve had your fill of dive bars and want to get a better look at the fairer sex, it might be time to try your hand at one of Chicago’s nightclubs. This is of course a dicey proposition, as the ratio of d-bags to nightclubs is alarmingly high in any city (and Chicago is no exception.) However, a decent time among the untz-untz crowd can be found at places like The Mid and Smart Bar, two of the city’s premier clubs where the music won’t make you want to cover your ears and hide in the corner. Instead, you’ll be spilling vodka tonics all over the dance floor and thinking you look totally cool in the process.
Day 3
1 p.m. Cubs Game (or Eat Deep Dish Pizza)
By this point in the article, you know you should visit Chicago in summer. You would be a fool not to. And the main reason is this: You would miss out on a trip to Wrigley Field. Whether or not the Cubs are in the thick of another World Series chase this year (spoiler alert: they will be), there is simply no better way to spend a sunny day in the city than at one of America’s premier ballparks. (Just ask Ferris Bueller.) If you’re here off season or when the Cubbies are away, drown your sorrows in deep dish pizza with a trip to one of the city’s more iconic (and less touristy) pizza makers like Pequod’s.
5 p.m. Hit the Beach (or Explore the 606)
Another glorious part of Chicago summer is spending time on the beach, where the buildings are seemingly sprouting right from the sand downtown and you’re never far from a cold one in the hot sun. Chicago is blessed with a hefty arsenal of beach bars from the raucous party hangout Castaway’s at North Avenue Beach to the calmer Caffe Oliva at the more under-the-radar Ohio Street Beach. If it’s too cold for beach weather but still decent enough out that you aren’t cursing the cold with every step, you can get a unique vantage point of the city while exploring the neighborhoods on the newly opened 606 elevated trail, modeled after NYC’s High Line.
7 p.m. Tacos at Big Star
Alright, enough nature. It’s time to get back to business. For the final dinner of the trip, a visit to Wicker Park’s Big Star makes a solid choice as you can either tear through tacos al pastor on the buzzing front patio in summer or post up at a table inside while working your way through pitchers of margaritas and mezcal cocktails. Speaking of cocktails, after dinner walk across the street to the mural along Damen Avenue and find the doorknob, which opens to a secret cocktail emporium known as Violet Hour that’s been pouring some of the finest drinks in the city (and the country, for that matter) for years. Just don’t act like a total jackass. Yet.
9 p.m. Drinks on a Rooftop Bar
No matter what season you’re in town, there’s a rooftop bar in Chicago to suit any mood. On hot summer nights, head over to happening locales like the J. Parker and Cindy’s to sip cocktails with a well-dressed and (mostly) well-behaved crew while taking in massive views of the lake. Or get more down and dirty on the roof of a local neighborhood hang at quintessential establishments like biker bar Twisted Spoke and the “Trainwreck Rooftop Deck” at iconic punk venue Reggie’s. No worries if it’s cold, as many of Chicago’s hotel rooftops are open year-round including the gleaming mixology temple Apogee and the bumping party scene at ROOF on the Wit.
12 a.m. Pink Monkey
Finally, the big moment has arrived: a trip to the gentlemen’s club. Yet for a city as large as Chicago, the in-city strip club options are surprisingly lacking, with options ranging from clubs offering either full nudity and no liquor (The Admiral) to clubs with liquor but also pasties covering the strippers’ moneymakers (VIPs.) Splitting the difference nicely is the Pink Monkey, where the topshelf is freely on display and you can bring your own booze from a nearby liquor store. The dancers are hot, the vibe is fun, and the groom should find plenty here to keep himself entertained for hours. Just make sure he made his requisite phone calls to the bride a few hours prior and that the phone is now shut off.
5 a.m. Close Down a 5 AM Bar
While Chicago is famous for things like deep dish pizza and corrupt politicians, perhaps more integral to the fabric of the local scene is the glorious concept of the 5 am bar. Saturday night is the only night you can rage till 5 (you can rock until 4 at a few select bars with late-night liquor licenses the rest of the week), so you might as well take advantage of it on your last night in town. While many of your late-night options are terrible (whatever you do, stay away from The Beaumont), good times can still be had at classic 5 am haunts like Exit, The Owl, and Underbar. Just remember to drink a goddamn glass of water every now and then and you’ll be fine.
Zero Hour
That’s it, folks. Chicago bachelor party in the books. Get the hell out of town while you still can. However, if you’ve got time/room/willpower for an emergency brunch before heading to O’Hare International Airport, round up the crew one last time and head to the South Side to hit a brunch spot like The Duck Inn, where you’ll be straightened up and feeling slightly human again after a life-saving injection of Bloody Marys and chilaquiles. If you’re looking for a calm place to sip coffee and nurse your hangover before your flight, head over to Bridgeport Coffee and take in the neighborhood ambiance while questioning all of last night’s decisions.
