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Ultimate 2016 Chicago Bachelor Party Planning Guide

A bachelor party enjoying a beer tour!

Ultimate Chicago Bachelor Party Planning Guide: Top 16 Ideas for Bachelor Parties in Chicago in 2016

We’ve been there. Your best friend announces he’s getting hitched. After congratulating him, even more news drops: he wants you to be his best man. And with great power, comes great responsibility, which includes planning an awesome bachelor party.

If you are planning a bachelor party in Chicago, you’re in luck. We’ve toured with numerous bachelor parties on our beer tours (which we’ve included as a great option below) over the past six years and have gleaned insight into the best Chicago has to offer. Here are our favorite 16 ideas for bachelor parties in Chicago in 2016.

1) Steak Dinner

Steak Dinner

Chicago once supplied the nation with over 80% of its meat via the Chicago stockyards. Paying homage to that magnificently meaty past, we have some of the best steakhouses in the world. These are perfect spots to indulge with all the lads. Here are some of our favorites:

  • Gibson’s. Once regularly frequented by Michael Jordan during the Bulls dynasty years, you simply can’t go wrong with modern Chicago classic.
  • Bavette’s Bar and Boeuf. For new, modern take on food with a speakeasy vibe, head here for an ultimate meal, including their incredible dry-aged steaks.
  • Ditka’s. Who makes great steaks? Da coach. The food holds up to the restaurant’s namesake. They have locations near downtown (in the River North neighborhood), Arlington Heights, and Oakbrook Terrace.
  • Gene & Goergetti. For the ultimate throwback experience, head here. Outside of the steaks, there is better food elsewhere, but the atmosphere is classic and the steaks stand up on their own.
  • RPM Steak. Another newer steakhouse that has become a city darling. Clean and sleek.
  • Tango Sur. Looking for something on the budget side without sacrificing quality? A local favorite, this Argentinean-style steakhouse located in Lakeview about 4 miles north of downtown. But you’ll likely more than make up for cab fare with the BYO option. Yes, that’s right, you can bring your own booze. This place is always packed, so definitely make reservations.
  • Las Tablas. Another budget option in Lakeview (the Lincoln Ave. location is closer to downtown), this steakhouse is not BYO, but it does have great Colombian-style steaks and great mixed cocktails, including one of the best mojitos in the city.

 

Tips: Expect to pay high prices downtown; steaks are often $60+ a la cart. Reservations are recommended.

2) Chicago Beer Experience Beer Tour

A bachelor party enjoying a beer tour!

We are admittedly biased, but our highly rated beer tours provide an awesome way to experience the city during bachelor party festivities. They take place in the early-to-mid afternoon to early evening, so they are great “gap filling” activities before you are ready to throw down at night. And what better way to cure a hangover than via beer tastings from some of the Midwest’s best breweries? You’ll even learn something about Chicago history and beer during your tours to take any day drinking guilt away.

You can take our tours in three different areas of the city: Lakeview & Lincoln Park, Bucktown & Wicker Park, or downtown in the Loop & South Loop. Cost is $59.90 per person, or $33.90 without beer tastings. For more information and how to book, check out our website here.

Tips: Consider a private tour for groups of 6 or more for your own private tour guide on your own schedule. Always book ahead.

3) Sporting Event

Wrigley Field Bleachers

The Wrigley bleachers are a fun way to fire it up; photo courtesy of Brian Holsclaw

Cubs, Bulls, and Bears, Oh My! Chicago has world-class sports teams, and even the Cubs are favored to win the World Series this year, which would be the first time since 1908. Below are the team ticket pages. In addition to team ticket pages, we included a ticket reseller aggregate website link, SeatGeek, in case tickets are sold out. We do collect a referral fee if purchased with that link at no additional cost to you, but feel free to use other ticket reseller sites, too.

 

Tips: Tickets are generally hard to come by for Bears games, can be for Bulls games, and the Blackhawks have become a hot ticket during their recent success. Baseball tickets are usually the easiest to obtain, although they can be tough if they are doing well or in popular series during the summer months. The Chicago Fire is our soccer team and are fun games to attend, but the stadium is annoyingly far from downtown with no easy mass transit options; try and find a bar with a party bus option for cheap, easy transport.

Generally, the easiest tickets are generally from the teams doing the worst on the field. In addition to online resellers, you can always try to scalp onsite, but this is obviously more difficult for big groups. With a large enough group, you may want to call the teams directly to see if they have group packages available.

4) Bar Hopping

Chicago Bar Crowd

Chicago has a ton of bars and clubs; photo courtesy of Lance Neilson

One of the main goals of most bachelor parties is to fire it up and get after it with booze and nightlife. Lucky for you, Chicago is one of the best bar towns in the world. The Windy City is huge, but there are some great bar hopping areas where you can walk from one to the next. Here are our favorites by area:

River North; map

For the club scene, or the fancier bar scene, River North is where it’s at. Our favorite bars include Three Dots and a Dash (tiki bar; proceed down the alley), Theory (sports bar), Public House (sports bar), Rossi’s Liquors (dive bar), Untitled (speakeasy), Howl at the Moon (piano bar; super touristy, but lots of bachelorette parties), Vertigo Sky Lounge (fancy, expensive roof top), Rockit Bar & Grill (bar; check out upstairs), Sub 51 (bar/club, basement of Hub 51), Studio Paris (club), The Underground (club).

Tips: This is definitely one of the higher end and more popular parts of the city, but there still is a pretty diverse offering. Don’t be surprised by lines and cover charges, especially during the weekend.

Viagra Triangle/Rush & Division; map

One of Chicago’s original bar districts, this area has been dubbed the “Viagra Triangle” because the nice restaurants just to the south attract older wealthy men that are often accompanied with younger eye candy. But the bars are messy, drunk, and fun. Definitely not upscale, although there are some nicer, newer bars moving in. Our favorites include Hangge Upee (modern music dance floor on top, 80s and 90s in basement, must be drunk to enjoy, but a ton of fun if you are, open till 4 AM, 5 AM Saturdays), Butch McGuire’s (a Chicago classic standard bar, open till 4 AM, 5 AM Saturdays), Zebra Lounge (hidden gem piano bar; it is a smaller space), Hopsmith Tavern (new beer bar), The Lodge (another Chicago classic; dive bar), McFadden’s (if you are young and drunk).

Tips: By heading just about a mile and a half north of River North, the pretentiousness drops drastically, and this area offers a much more casual, party vibe. New offerings are starting to transition into the area – a much needed development. Lines are less frequent, although they will occur, especially on weekends. Cover charges are rare here.

Wicker Park; map

The original “hipster” neighborhood, the hipsters have largely moved on. Your best bet to bar hop is down Division Street, but don’t forget gems along Milwaukee and to the north and south. Our favorites include Bangers & Lace (great beer bar), Gold Star (dive bar), Happy Village (neighborhood ping pong bar), Fat Pour, Anthem, or The Boundary (all bro-y sports bars), and Easy Bar (chill).

If you are willing to venture a bit further up towards and into the Bucktown neighborhood, check out Emporium (arcade bar; locations in both Wicker Park and Logan Square), Lemmings and Lottie’s (neighborhood pubs), Map Room (one of the best beer bars in the city, chill vibe), Danny’s (still pretty hipster), and the Charleston (chill neighborhood cocktail bar).

Tips: This area used to be really hipster, but it has pretty much totally transitioned into a traditional yuppier area, with a few exceptions. Generally, don’t expect lines and covers here.

Logan Square; map

Some of the hipsters have moved here, and this is one of the hottest spots in the city outside of downtown, and generally far more casual and hipster than the more upscale downtown. Some of our favorites include The Owl (4AM hipster bar), the Whistler (music venue and bar), Boiler Room (chill, cheap pizza), Revolution (craft brewery), Billy Sunday (craft cocktails), and Lost Lake (tiki bar; closed due to fire but reopening, so check).

Tips: the hipster areas have fragmented across the city, and this is one of the largest. With rents rising, bring your skinny jeans, facial hair, and dark rim glasses while you can. Some of the bars will be much smaller and less accommodating to large groups, so you may need to do a little recon if you are rolling with a huge crew, and expect some nasty looks if you are too bro-ey. 

Wrigleyville; map

Generally the youngest and sloppiest of the barhopping areas, this area has its moments, especially if you are in the 21-25-age range. Definitely changing as the Wrigleyville renovations are starting to impact the area. Our favorites include Sheffield’s (one of the best beer bars in the city), Darkhorse (chill), Murphy’s Bleachers (classic), Irish Oak (chill), Merkle’s (drunk), Deuce’s and Diamonds (clubby, not our favorite, but it’s Wrigley).

Tips: you bar hop in Wrigley at your own risk. Don’t expect the best service or nicest people. Do expect a lot of sloppy drinking. Not necessarily recommended for older groups; this area trends young outside of Cubs games.

Other notable bars:

Some of our other favorites for big fun groups that aren’t necessarily bar hopping but still somewhat close to downtown include Mahoney’s (big and fun bar with a dance floor) and the River West neighborhood corridor containing Richard’s (old school, some say you can still smoke inside, but you didn’t hear it from us), Emmit’s (fireman bar featured in the movie Backdraft, which you should watch if you haven’t), and the Dawson (nice new cocktail bar).

5) Whirlyball

Whirly-ball

Whirlyball courtesy of Chase N.

Make bumper cars into a game for adults? Yes please. Whirlyball is a fun sporting activity that really doesn’t demand that much physical effort – perfect for nursing a hangover, and a great bachelor party idea. You simply pill into bumper cars, grab a lacrosse like looking stick, then try to score a ball in a hoop. Easy peasy. There is a Chicago location that is very close to downtown, as well as locations in the suburbs of Lombard and Vernon Hills; check it out here.

6) Lakefront trail, including beaches

Lakefront trail

Chicago Lakefront Trail by Oak Street Beach; courtesy of David Wilson

Who do Chicagoans put up with such terrible winters? The beautiful 18-mile lakefront trail. You can bike, run, walk, and meander down and up the city’s Lakefront path that stretches from 5800 N. Sheridan all the way to 71st Street.

Even better, there are even great beaches connected by the path, and some have bars. The biggest and best one for bachelors would be North Avenue Beach complete with the Castaways Bar, where you can order booze and food while debating what volleyball game to join. You can then beach-bar hop to Oak Street Beach, too, and have the skyscrapers tower over you for an impressive view.

Tips: Fully utilizing our path and beaches depends on the time of year. Beach season extends from June-September, but it can be dicey on the margins; watch out for north winds that can make the lakefront much cooler than the rest of the city. People use the path all year round, even in the snow. 

7) Blues Clubs

Buddy Guy

See blues musicians such as the legendary Buddy Guy perform; courtesy of Aaron Warren

To paraphrase Chicago legend Buddy Guy, you play the blues because you have the blues, but when you play ‘em, you lose ‘em. And the same thing is true for listening! So if you are a little bummed that your best mate is moving on with a special someone, or you are just looking to listen to incredible music, check out one of Chicago’s great blues clubs. Our favorites include Kingston Mines on the north side and Buddy Guy’s Legends in the South Loop; there is also Blue Chicago in River North and B.L.U.E.S. right by Kingston Mines in Lincoln Park.

Tips: Expect to pay a cover charge for blues clubs, which are good things to support. There may be lines, especially at Kingston Mines, which is also open until 4 AM (5 AM on Saturdays).

8) Trolley

Chicago Trolley

Chicago party trolley well underway; courtesy of Tyler Bedgood

You know what’s better than drinking? Drinking in a moving vehicle! There are several trolley options in Chicago that you can rent where you can BYO and really fire it up as you move throughout the city. The barhopping can become even more geographically epic with one, too. Some well reviewed companies include LimoTainment, Chicago Trolley & Double Decker Co., and Premier Trolley and Limo.

Tips: You’ll want to book this in advance. Plan ahead so you can BYO, and make sure to double check with the company on the current rules for boozin’ and cruisin’. 

9) Sky-Dive

Skydiving

Looking for something a little more adrenaline seeking? How about jumping out of a plane? If you are looking for something a little less dangerous and close to downtown, check out the iFLY Lincoln Park facility where you can try it indoors. Looking for the real thing? Check out SkyDiveChicago (yours truly even survived from this operator, which I recommend!) or Skydive Midwest, but you’ll need to venture out of the city.

10) Cocktail Class

Bartender slicing a banana.

You probably won’t be able to learn how to slice a banana with a samurai sword, but isn’t this one hell of a stock image?

Just like our beer tours, why not learn a little while you imbibe? Friend of the tours BarredinDC took a cocktail class from Hollow Leg during a bachelor party this year and is still raving about it; they even have an awesome venue space pretty close to downtown. Check them out here!

11) Festivals

Wicker Park Fest

Wicker Park Fest; courtesy of yenna

Chicago is always jammed packed with festivals in the summertime, each taking place on different weekends in different areas in the city. Here’s the best guide we’ve found from our friends at Metromix. Our favorites include Wells Street Art Fair, Ribfest, and Wicker Park Fest.

Tips: Although event organizers will typically ask for a donation when entering street festivals, it is not required on city streets, although it’s nice to pay to support the community. Expect big crowds, bands, and lots of food and beer tents. Not a bad way to spend an afternoon. 

12) Speed Boat Tour

Seadog Boat Cruise

An exhilarating way to see the city; courtesy of Chad Kainz

Chicago has one of the best skylines in the world. Why not enjoy while zooming around on a huge speedboat? Check out our friends at Seadog Cruises for a unique, cool bachelor party idea. And if you want something more chill, then you can tone it down with other architecture boat tours through Wendella, Shoreline, or the Chicago Articture Foundation.

Tips: You can usually buy tickets of these day-of, so you can play it by ear based on the weather. But they can sell quickly during nice summer days. Seadog is located at Navy Pier; some of the other companies are located on the Chicago River by Michigan Avenue. 

13) Arlington Race Track

Horse Race

If you have time to spare to venture into the burbs, or are already out in the burbs, consider the Arlington Race Track. You and the boys can drink some beers while betting a few bucks on the ponies, where Al Capone used to lose $50,000 a week in the 1920s. Who knows, maybe you’ll even get lucky. Check out track info here.

14) Golf

Golf

The Chicagoland area has some good public golf courses if you want to hit the links. For the closest courses to downtown, check out Harborside International. Prices vary in price depending on tee time from $45 to $68+ per person.

Others include Cog Hill, Glen Club, Cantigny, Ravisloe, Orchard Valley, and Pine Meadow (if you are truly up for a challenge). Note that these are all located in various suburbs, so plan accordingly.

15) Casino

Stock Image Gamblers

These stock image gamblers sure are cooler than we are.

Need a gambling fix outside the horses at the track? We don’t have any casinos downtown (yet), and this isn’t Vegas, but you can definitely still lose some money here. Check out Rivers Casino by the O’Hare airport, or the Horseshoe, AmeriStar, or Blue Chip in Indiana.

Tips: the Horseshoe runs a free shuttle to and from the city of Chicago. 

16) Gentleman’s Club

Stripper

At one point, Chicago was considered the “Paris of the United States” and had the “Wickedest Place On the Continent” for its lascivious activities, but no more. The strip club scene is not considered the country’s best, but there still are some spots you can check out should you desire to some exotic activities.

Check out: Pink Monkey (BYO, topless), VIPs (booze, not nude), The Admiral (no booze or BYO, nude); Polekatz (booze; nude).

In the suburbs: Scores, Atlantis, and Club 390.

Tips: Honestly, Chicago is not known for strip clubs, and for good reason. Check out the Yelp reviews…yikes. Also, keep in mind that regulations also often limit what clubs can offer (e.g. booze but limited skin, or visa versa). Expect to pay too much for too little. But we know that it’s often a necessary part of a bachelor party, so we included the list. 

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We hope this helps! Regardless, be safe and have a blast on your bachelor party. We’re sure you’ll plan a great one.

Cheers,

Bruce, Founder of Chicago Beer Experience Beer Tours

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