The Ultimate Guys Weekend In Chicago

by Ronnie Charrier


Are you planning a bachelor party in Chicago? An important birthday (like my recent 30th)? Or maybe you just need a weekend with the guys... I find that my enthusiasm for events like these can sometimes be derailed when too much time is spent coming to a consensus on where to go and what to do. So for our third installment in our Best Of Chicago series, we set out to find the very best of what Chicago has to offer to make planning your next weekend with the guys simple and unforgettable.

Chicago has it all. Theater, restaurants, comedy clubs, sports, and a bar on every corner. But sometimes, the discerning man-about-town craves something different than hitting a series of watering holes. After months of research, here is how to plan the ultimate guys weekend in Chicago:

Step 1: Location, Location, Location

Hotel Felix

The first thing you need to plan is where to stay, and location is key. No one wants to be catching cabs in and out of the city at 4 in the morning. And with some of the one-way streets and bridges, sometimes what seems like a short distance can actually turn into a mission, when all you want is to collapse into your big, comfy, hotel bed.

Luckily, the Hotel Felix is in the perfect spot. Situated in the River North district of downtown Chicago, this elegant establishment is walking distance to some of the best nightclubs in Chicago. We were a short cab ride from the lake shore, and we able to leisurely meander our way to everywhere else that took our fancy. Our room had a stunning view of the city, and the bar in the lobby was well stocked and welcoming, a perfect place to "pre-game".

Step 2: Start the weekend off with a drink.


You’re here to have a good time right? And hopefully you’ve grown out of your Busch Light frat days and can appreciate a man's drink (no offense James Bond, but a shaken martini is just watery vodka). Despite the fact that Men's Journal listed Delilah's as one of America’s 10 best bourbon bars, and even though she carries over 750 different types of whiskey, the owner, Mike, insists that Delilah’s is not a whiskey bar. “We never set out to be a 'whiskey bar'. It’s just what happens when you love and collect whiskey for 20 years.”

Not only was Mike's collection of different spirits impressive (they’ve also recently begun adding unique tequilas to their list, just in case you favor the clear poisons), but his warm, knowledgable banter made us feel right at home. Mike spent quite a bit of time answering questions about their many different spirits and explaining which whiskeys we should try. The atmosphere was cosy and inviting, and the upstairs has a nice lounge feel with pool tables and plenty of leg room. 

Step 3: Steak.

III Forks

I’m going to make this short and let the pictures do most of the talking, as it's hard to put into words how outstanding our experience at III Forks was. Put bluntly, it was the best steak I’ve ever had. Chef Billy not only created a masterpiece 6-course meal, but also came out and chatted with us about the culinary inspiration for each course. The flavors of the meat were enhanced by the impeccably paired wine list, and by the end of the experience, our palates were singing, and our stomachs were full.

The staff were amazing, and they must have immediately identified the kid in me, when they gave me the option to "choose my own weapon": one of the coolest things I've ever done at a restaurant. Before our steaks arrived, a wooden tray was brought to our table, filled with an array of specialty steak knives, from which we selected our favorites. Although (as I mentioned) this was a seriously cool flourish on an already impressive meal, the tenderness of the steaks would no doubt have surrendered to a butter knife, let alone the monster I was wielding when they took the tray away. 

If you get a chance (and have the foresight), make your reservations for their patio. Located on the second floor, this spacious, open air venue offers you a 360 degree view of downtown Chicago, and one of the best skylines you'll see outside of New York.

Step 4: The Nightlife.

Chicago has one big advantage over many other cities that you might be considering for your guys weekend: last call for some clubs is 5 AM. So, with that in mind, we recommend a two-part approach to the big night out.


Shay refers to itself as an upscale cocktail lounge, but the bottle service, private tables, DJ table, dance floor, and all the beautiful people walking around will make you feel like you're on someone's private yacht. From the moment you enter, you feel transported to a life not yet lived, but suddenly within your reach. Enjoy the heart-thumping music of the DJ, take in the electric atmosphere, enjoy the premium bottle service...but don't get too comfortable. Even though we could have happily stayed for the entire night (only in part due to the attractive wait staff), this was just the appetizer!


Shay is designed to be “luxurious, yet accessible", designed to satisfy a variety of palates; with the private booths off to the side, and the very public dance floor in the centre. Cuveé, on the other hand, is unapologetically, and inescapably, all luxury. This high end club emphasizes its exclusivity from the moment you are admitted through its mysterious side-alley entrance (that is, if they let you in). The first thing you notice when you walk in (and, have no doubt, this is by design), is the private VIP tables in the middle of the room, elevated, complete with personal security and servers. While the overall effect was overwhelming at first, we soon got comfortable with the extravagant, opulent experience that is Cuveé. Trust me, this is where you want to be, and be seen.

Once inside, order any champagne over $500 and get ready for fireworks (I'm not referring to the taste profile of a good bottle of bubbly: I mean actual fireworks). While Cuveé opens at 11, like in any respectable venue of the night, things really don't start "poppin' off" until after 2 AM, and after that, my friend, all bets are off. I'd recommend making reservations if you want the full VIP treatment, and don't even bother trying to get in if you aren't dressed in your Sunday best.


Step 5: Recover.

IVme Hydration Clinic

The worst part of any weekend like this is the hangover the next day (especially if, like me, you are celebrating the close of your third decade on this earth). A bad hangover can make you regret all the fun and games of the night before, until that is, you go to IVme. No matter what you do for your weekend, make sure you end it with an appointment here the following morning. We did. And one hour later we felt like new men - the kind who didn't stay out until 5 am drinking.

For just $149 (keep a lookout for their monthly specials), they will hook you up with fluids, medications, vitamins, and oxygen therapy to alleviate the effects of dehydration and any head and body aches you have, all while you sit comfortably in one of their many lounge rooms. Yes, it requires a needle, but let me assure you, a little sting was preferable to that champagne headache that I had coming to me. We all left IVme ready to do it all over again!


We hope you found our tips useful - please fee free to tell us about your own Chicago experiences, and if you think you have a great theme for our Chicago weekender series, let us know. Like, share and mention this article so that we can continue to bring you the scoop of what's best in Chicago, and beyond!

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