Congratulations, you’ve been handed the keys to the bachelor party kingdom. And by "kingdom," I mean Chicago—a city that delivers knockout blows in sports, bars, food, and everything else. Whether you’re here to cheer for the good guys, eat your weight in Italian beef, or finish the impossible bar crawl, this guide has you covered.
Location
People who "like" snowboarding know Shaun White. People who love snowboarding know Scott Stevens, Travis Rice, and Frank April. Similarly, casual punk fans know Fall Out Boy, but real punks listen to NOFX, Misfits, and Rise Against. A lot of times the most popular thing is a pretty good thing, but people who really love and really know a lot about a topic opt for lesser known, albeit better, alternatives. This is how you should think about Chicago.
The other guys will tell you to stay in The Loop or River North. That’s busch league, man. The Loop is just Corporate HQs, and River North is for fresh college grads figuring out how many vodka sodas they can charge to their dad’s AmEx. The real beauty of the city is in the neighborhoods. Specifically, you want to stay anywhere off the Brown Line between Sedgwick and Paulina. This area is highlighted in the thumbnail pic and also includes some big neighborhoods like Lincoln Park, Lakeview, and Old Town. But, Why Here? Because you don't mess with perfection. It's going to have the best bars, the best beaches, a good chunk of the restaurants, the friggin Chicago Cubs, and you'll be around your peers.
The Hook: Sports & the Lake
Chicago is the mecca of cool sports teams that can’t win. The good news? They might be playing your team. I have nothing but love for the Bulls, Bears, Blackhawks, and White Sox, but if you can only pick one game, make it the Cubs. Wrigley Field is historic and the bleachers are the best experience in baseball—just know it’s first come, first served for seating, and every Friday 1:20 PM game will be sold out. The rooftops are cool too, but it’s a different vibe—more about the all-you-can-eat-and-drink setup than actually following the game. But hey, a bachelor party is about the experience.
Wrigley also has a lot going on that isnt baseball. Big 10 football, concerts, festivals, and the list goes on, so check the schedule.
Leaving Wrigleyville after the game is over would be a mistake. The DraftKings Sportsbook is built into Wrigley and features the biggest TV screen you’ve ever seen. Sluggers is so fun it might ruin every other bar for you. Indoor batting cages, dueling pianos, and a sea of drunk twenty-somethings make this THE bar in Wrigleyville. Murphy’s Bleachers is a sneaky massive bar and an absolute classic. Its specialty is pregaming the bleachers, but don't buy food there because a glizzy is more than $10. Rizzo’s is a cool tailgate vibe especially if it's rainy. I saw Bob Stoops there once, but never Anthony Rizzo—devastating, honestly. Last, Country Club is a country sports bar with good deals on buckets when the rest of the strip has lines.
If you are not a sports person, I'd recommend renting a boat. You can find lake boat rentals that are all time, but they are pricey and would probably be the big thing for your bachelor party.
The Time Wasters: Summertime Chi
Not to be dramatic, but Summertime Chi is magic. If the sun’s shining, the lakefront is always an elite move—and it’s completely free. A smart planner will carve out some time to hit the closest beach because nothing says “peak summer” like a lake. Nevermind Lake Michigan, God of Lakes. For the full Chicago beach experience, North Avenue Beach is the spot. It’s massive, offers an iconic skyline view, and gives you options—sandy shoreline to the north, concrete waterfront to the south. Pick your poison. If you’re looking for something a little closer, some part of the Fullerton Beach lakefront is accessible for nearly the entire recommended area. Thanks to all the greenspace, it’s more mellow, and the full concrete waterfront makes it surprisingly clutch and my personal favorite. I know, a concrete beach sounds lame, but hear me out—it’s better. You can stop in for a couple of hours and bounce to the next thing without needing to shower off sand. Hell, most people who know they're not getting in the lake dont even wear a swimsuit.
Every weekend in the summer, somewhere on the North Side, there’s a free street fest happening—and it’s always a good time. The neighborhood alderman shuts down a few blocks, throws up some tents, and suddenly you’ve got live music, cold drinks, and a crowd that’s ready to party. Each one has a theme—could be music, could be art, could be some niche like “Mac & Cheese Fest” (yes, that’s real). Check Instagram for a wannabe influencer that aggregated all the dates into a schedule to go micro viral.
Chicago’s food culture is really good, and thanks to The Bear, it’s only getting better. I could try to list everything, but let’s be honest—that's impossible. Instead, I'm going to link you my Beli and two pretty solid lists I made when I was hungover.
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HERE is my list of random go-tos. I will call out Flub-a-dub-Chub for Chicago dogs because it sits on my favorite street in the city: Broadway. That same stretch has my favorite pizza (Nancy’s), one of my favorite dives (Monsignor Murphy’s), a upscale pizza joint (DryHop), the best wings you will ever eat (Crisp), and is just a hop away from an Irish spot called Galway Bay. Weiner Circle is another Hotdog Hallmark and is by Gaslight, Tin Lizzie, and Fullerton Beach. If you go to Weiners Circle, the Best Man is obligated to bring $100 and order a chocolate milkshake - it will make a memory that'll never be forgotten or fully explained.
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HERE is steakhouses and work dinners. These spots are an opportunity to go into the concrete jungle for one dinner and pick up the groom's check. Go to Michael Jordans or Harry Caray's Steakhouse for some big name appeal. Try to get a notoriously hard-to-get reservation at Bavettes or Asador Bastian for a steak that'll impress foodies. Gibsons is also a big name and they used to film The League there. It's a step above what you can get back home with less hype than Bavettes. It, and another steak house called Maple & Ash, are in the Viagra Triangle, which is a block away from a staple in Chicago's bar scene, Butch McGuires.
Last, I think I read somewhere that Chicago is the drunkest big city in America—and honestly, I believe it. You should order shots of Malort at Burwood Tap, the best all around bar in Lincoln Park. It's part of a walkable bar trifecta with Hallagans and AliveOne that'll stun anyone once the sun goes down. I also recommend day drinking at Kirkwoods off the Wellington train stop. Check out the Goose Island or Revolution brewery tours. Off Color is also fun if you want a brewery without the tour. Kingston Mines is the call if you want a mellow-er spot to hide from the zombie hoards of drunk youths.
Speaking of drunk youths, you should visit Old Town if your groomsmen are young and rowdy. Bars like Fireplace Inn, LG’s, and Utopian Tailgate deliver the kind of energy that turns “just one drink” into an early morning rally. You can stop by Twin Anchors, where they shot The Dark Knight, for some time-tested ribs with spicy bbq sauce. Old Town is also home to Second City, the legendary improv club that launch careers for John Belushi, Keegan-Michael Key, Bill Murray, Tim Robinson, Tina Fey, Mike Myers, and Jason Sudeikis.
And for you finance bros, your Wolf of Wall Street moment awaits. Head to the Chicago Board of Trade and visit the infamous Ceres Café inside . This place is legendary, and there are some unwritten rules: 1) Order a simple liquor + mixer. No beers. No craft cocktails. If your drink order has an “and,” you’re doing it right. Think rum & Coke, gin & tonic, or tequila & soda. 2) Arive after the market closes—around 4 PM CST—for the power tie and finance vest crowd. 3) Act like you’ve been there before. Don’t be that table. 4) Be gone by 7 PM.
Tips for the Perfect Trip:
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Google Maps is your friend. Just look up everything and see if you want to walk, bus, or train. Speaking of transit,
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The three day all-you-can-ride CTA pass is too good of a deal for $15. Get it and forget it. But there are three follow ups:
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You’re going to be walking – a lot. Don't be surprised if you break 10,000 steps daily and earlier than you expect. So, prepare if you're used to driving everywhere by wearing comfy shoes, staying in a single neighborhood, or planning out your stops.
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Using the L to arrive and depart is the big downside of this trip. If you're flying midway, don't even mess with the train right away and uber to where you're staying. I have a hack if you are flying through O'Hare, though: Use the Blue train to travel towards the city. Get off at Logan Square and get an uber to go east for a 75% discount compared to airport prices.
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If you're driving rather than flying from out of town, just leave your car parked where you're crashing and forget it exists until it's time to head home. Traffic isn't as bad as you imagine, but hell hath no fury like northside parking.
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Be Aware: Last, you need to be Aware. Capital A. You catch my drift? That means sometimes Chicago things happen in Chicago. It's easy to spot someone who's lost or in the wrong place at the wrong time. Especially at night. Especially if you're sauced. Especially if you're alone. You can be less Aware in brown line neighborhoods, but always use the Buddy system, boys.
The Golf:
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Sydney Marovitz Municipal (~$50) - It's an unranked, jam packed, 9-hole, 3-hour round.
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Sim bars are a dime-a-dozen in Chicago, so just google it and see what pops up. I like the 5-iron in River North that is off the Grand stop. They have clubs there so that helps
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There's no close top Golf, but the Diversey driving range is cool if you brought your own clubs. They have a gimmick put-put course too and an outdoor bar right off the lakefront trail.
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