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Ultimate Chicago Bachelor Party Planning Guide: Top 18 Ideas for Bachelor Parties in Chicago in 2020

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 over the past nine years and have gleaned insight into the best Chicago has to offer. Here are our favorite 18 ideas for bachelor parties in Chicago in 2020.

1) Comedy Club

a man standing in front of a brick building

Chicago has been a comedy destination for decades. Most famous of the bunch is Second City, which has fed many comics to Saturday Night Live and stardom. There are also other clubs, such as iO TheaterZanies, and The Laugh Factory.

2) Chicago Beer Experience Beer Tour

a group of people posing for the camera

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 warm-up activities before you 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 three different tours: Bacon & Brews in Lakeview & Lincoln Park, Pioneers & Pints in Bucktown & Wicker Park, or Sin & Suds in the Loop & South Loop. The cost is $67 per person or $36 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) Bar Hopping

a group of people standing in front of a 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 some key neighborhoods to target:

  • West Loop / Fulton Market. This area has become the hottest area for new restaurants in the city over the past 10 years, and the bar scene is catching up, too.
  • River North. Prior to the rise of the West Loop, this was the most happening area close to downtown. It still offers plenty of bars and clubs.
  • Logan Square / Avondale: Rapidly gentrifying, this area still captures the hipster essence. You’ll find more locals here compared to downtown areas.
  • Wrigleyville. This area is changing since the Ricketts have poured money into it and redeveloped it, but it still is probably the rowdiest and centers on a younger demographic (early-mid 20s), particularly during non-Cubs game days.
  • Rush & Division / Viagra Triangle. Old-timers will remember this area as the spot in the 1960s and 70s, but it still has some old school charm and new places to balance it out. Butch McGuire’s is a Chicago classic and the Hangge Upee can’t be missed for a wild time.

4) Steak Dinner

a plate of food

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.
  • Chicago Cut. This steakhouse has become a favorite of local celebrities and sports stars. A scene on the Chicago River with delicious food to boot.
  • 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.
  • Swift and Sons. A newer steakhouse, this West Loop establishment has quickly established itself as one of the city’s best. The beef wellington is deadly and a perfect thing to share with your best mate.
  • RPM Steak. Another newer steakhouse that has become a city darling. Clean and sleek.
  • 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.
  • 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 makeup 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 carte. Reservations are recommended.

5) Blues Clubs

a man holding a guitar

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).

6) Axe Throwing

a close up of a bench

There’s not much more manly than throwing axes! Take your turns at throwing axes at a target in different styles and make a competition out of it. Probably a good idea to do this BEFORE any serious drinking begins. Bad Axe throwing has a couple of locations in the city, and Ragnarok Axe Throwing has a South Loop location.

7) Lakefront trail, including beaches

a city street

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

Who do Chicagoans put up with such terrible winters? One reason: 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.

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.

8) Whirlyball

a group of people in a room

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.

9) Sky-Dive

a man flying through the air while riding a snowboard

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

a man jumping in the air

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) Sporting Event

a group of people standing in front of a large crowd watching

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 drinking beers in the stands with the boys can really set things up nicely for a fun weekend. Here are the major area teams:

Tips: 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.

12) Festivals

a group of people walking down the street

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. Guides and dates can be found easily online. Our favorites include Wells Street Art FairRibfest, 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.

13) Speed Boat Tour

a small boat in a body of water

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 WendellaShoreline, or the Chicago Articture Foundation.

Tips: You can usually buy tickets for 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. 

14) Trolley

a group of people sitting at a train station

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 LimoTainmentChicago 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’. Chicago recently passed a law that may require a security guard for larger groups.

15) Arlington Race Track

a person riding a horse on a track

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.

16) Golf

a group of baseball players standing on top of a grass covered field

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 HillGlen ClubCantignyRavisloeOrchard Valley, and Pine Meadow (if you are truly up for a challenge). Note that these are all located in various suburbs, so plan accordingly.

17) Casino

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 HorseshoeAmeriStar, or Blue Chip in Indiana.

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

18) Gentleman’s Club

a close up of a logo

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: ScoresAtlantisClub 390 and Blackjacks.

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. 


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


Bruce, Founder of Chicago Beer Experience Beer Tours

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