chicago

Chicago is one of my favorite cities to visit and as someone who lived there for nearly a decade, it’s also a city I’m proud to share with friends when they ask for recommendations of fun places to visit. This is the city of big shoulders, a manly city where they aren’t afraid to grab a big beef sandwich dripping with juice, cheer on their favorite sports teams, and enjoy new and unique ways of looking at the world.

When you are planning your bachelor party, the first question always seems to be "Where should we go?" If you want a fun night out with friends and don't want to break the bank, then this list of 10 cities is for you. From Las Vegas to New York City, these top destinations will make your trip unforgettable!

We've talked in the past about how great of a city Chicago is to visit for a guys weekend getaway, but it is also a fantastic city for a romantic getaway too. From fantastic museums to some of the world's best and most creative food, Chicago is a great city to share with someone special. 

There's a joke that I used to hear from friends when I lived in Chicago, who said, "It's not a hot dog, it's a salad!". That sums up the Chicago-style hot dog pretty well. Unlike the classic American hot dog where many people simply put ketchup and mustard on top - Chicago folks go ALL IN! While there are a nearly infinite number of variations, the core ingredients for a "Chicago-Style" hot dog are pretty easy - an all-beef frank topped with tomatoes, sweet pickle relish, chopped onions, pickle spear, pickled sport peppers, and mustard ---- NEVER --- ketchup!

Often times, going to a NASCAR race is about the only thing on your agenda. Frankly, most tracks are so far out in the middle of nowhere that it's difficult to plan anything other than an awesome weekend of racing. Chicagoland Speedway is different though and there's a surprising amount of stuff to do at the race and beyond. With that in mind, we set out to the Camping World 400, Monster Energy NASCAR Cup Series race at Chicagoland Speedway followed by some time exploring the surrounding area of Joliet, Illinois. 

Summer is over and the kids are headed back to school, but don't worry - travel season never really ends! Fall offers a ton of great opportunities for a father and son to get out and spend time together too. This is your opportunity to share stories, pass down important life skills and bond while creating new memories that will last a lifetime. Just imagine the thrill you'll share as you fly down the side a mountain in Idaho while you regain the joy of being young again and he conquers his own fear and doubt.

Kimpton Hotels is a relatively new brand, but it is certainly a great choice if you are planning your guys weekend. After all, the point of a guys weekend is doing something special, so why stay at the average business hotel when you come to Chicago? Instead, why not try a super stylish boutique hotel like one of the ones that Kimpton runs - Hotel Monaco, Hotel Allegro, and Hotel Burnham.

I feel like everyone has memories of "The Riv", so it was a sad day when I heard last year that it was closing, but at 2 am on Tuesday morning they imploded the Monaco tower, signaling that Vegas has moved on. It's weird to think of being emotional about a place such as the Riviera but it's something special for me as it was the first Vegas hotel that I stayed in. Plus, over the past 20 years I visited it for other events ranging from conferences like Comdex and CES to pool tournaments and last year to see the amazing neon facade one last time.

One of the few nice things about traveling for business is being able to rack up some serious reward points that I can figure out how to spend on my own. While the idea of using them to head off on a guys weekend with the boys is appealing, it's important to also take care of the homefront and spend some time with the wife as well. 

From muscle cars and trucks to concept cars and some of the most extreme sports cars ever designed, there was something for everyone at the 2015 Chicago Auto Show and for 3 days, I had the run of the show to touch, smell, sit, stare and dream of having some of these in my garage!

We will be dripping out other content over the next few months from our experience here, but if you are attending the show between now and February 22, here are some of the stuff you will not want to miss!

While the Cubs are the perennial underdogs, having not won a World Series in over 100 years, their home in Chicago is one of the most iconic sports stadiums in the whole world. In previous years, the Cubs have played at Hohokam Stadium, shared with the Oakland A's but this year they opened up the season at their very own stadium "Cubs Park", affectionately referred to as "Wrigley Field South".

As someone who has enjoyed numerous games at Wrigley I can say that even though it is someone that should be on the bucket list for any sorts fan, the park is an absolute dump. From obstructed views to cramped bathrooms and nets installed to keep concrete from falling on people's heads it is one of those places that should probably just be shut down - if it wasn't for the antique charm and sense of history that radiates from every square inch of the facility.

The word "Oktoberfest" likely causes images of a raucous bar scene with giant steins of beer and busty waitresses dressed in dirndls. What if I told you that there was a family-friendly restaurant with authentic German food that was a perfect date location too? That's the quick synopsis of our experience at Edelweiss Dining - located in the Chicago suburb of Norridge.

For more than 30 years, this restaurant has served up some of the best authentic German food in all of the Chicagoland area.

In Chicago there is unfortunately a very small window of time that we can enjoy the full value of a convertible, so it had better be a great one to pique my interest and it needs to be as practical as it is fun to drive.

Does the Chrysler 200 match up? Let's find out...

The Abbey Resort in Lake Geneva has positioned itself as the gateway to all the great fun that the Lake Geneva area has to offer.

This is the direct antithesis of the other well known resort in Lake Geneva, the Grand Geneva Resort. Grand Geneva, (the former PlayBoy Club!) offers nearly everything a guest could possibly want, all in one resort. Instead of competing directly with this, The Abbey focuses on providing a fantastic core resort experience and then connecting guests with all the awesome guys weekend activities in the Lake Geneva Area.

Visiting Skydive Chicago was absolutely one of the best Mancations I have ever taken.

If you are looking for a high adrenaline trip skydiving with Skydive Chicago is the place to go. Skydive Chicago is located just west of the city in Ottawa, IL. Not only is this Chicago's Premier Dropzone but as far as I am concerned, they are also the BEST! With a 220 acre mega resort, top notch skydive instructors, and a vast amount of non-skydiving activites this is an ideal trip for guys looking for the ultimate adrenaline rush!

Remember when you were a kid?

Did your dad take you to the ballpark and you wondered what it would look like if you could explore the whole thing and see the areas only the players could see? Well, you don’t need to be a kid, you just need to visit Chicago’s Wrigley Field!