Guys Trip Ideas In Illinois

starved rock state park water fall hiking illinois

If you're planning a guys trip, you'll find that Illinois offers an impressive mix of urban excitement and outdoor adventure that's perfect for male bonding. From the bustling streets of Chicago to the serene wilderness of state parks, you can craft an itinerary that suits any group's interests and energy level. Whether you're drawn to the roar of motorcycle engines along Route 66, the thrill of a Bears game at Soldier Field, or the satisfaction of sampling craft spirits at local distilleries, the Prairie State holds countless opportunities for creating lasting memories with your friends. Let's investigate the best options for your next guys getaway.

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About Illinois And Why It Makes A Great Place For A Guys Trip

Illinois, situated in the heart of the American Midwest, is the sixth most populous state and serves as a dynamic destination for guy trips with its blend of urban excitement and outdoor adventures.

Bordered by Wisconsin to the north, Indiana to the east, and the Mississippi River to the west, Illinois offers over 55,5131.1 square miles of diverse landscape. The state's climate features four distinct seasons, with hot summers (ideal for water activities) and cold winters that transform the landscape into a winter sports haven.

Chicago, the state's largest city with nearly 2.7 million residents, anchors the state's northeastern region and provides world-class entertainment, sports venues, and the world-famous "Chicago-style" deep-dish pizza. A fascinating fact about Illinois is that it's home to the initial-ever McDonald's franchise, opened by Ray Kroc in Des Plaines in 1955.

The best times for guys trips typically fall between May and October when weather conditions are most favorable for outdoor activities. However, winter months offer unique opportunities for skiing and ice fishing.

The state's rich history, from Abraham Lincoln's legacy to the Prohibition-era gangsters, adds an intriguing backdrop to any group adventure.

Top Guys Trip Ideas In Illinois

Chicago Bears Gameday Experience at Soldier Field

Experience the electric atmosphere of an NFL Sunday at the iconic Soldier Field, home of the Chicago Bears since 1971. Before the game, join the massive tailgate party in the South Lot where die-hard fans set up elaborate spreads and welcome visitors to join their pre-game festivities.

Take in the stunning backdrop of Lake Michigan and Chicago's skyline while watching the Bears battle their rivals, especially during classic matchups against the Green Bay Packers. After the game, head to nearby Reggie's Rock Club in the South Loop for their famous post-game party featuring local craft beers and live music.

Route 66 Motorcycle Expedition

Cruise along the historic Mother Road starting from Chicago and heading southwest through Illinois's heartland. Stop at iconic Route 66 landmarks like the Gemini Giant in Wilmington, the restored Standard Oil Gas Station in Odell, and the famous Cozy Dog Drive-In in Springfield, birthplace of the original corn dog.

Experience authentic roadhouse culture at the Luna Cafe in Mitchell, known for its vintage neon signs and colorful history as a former speakeasy. Make sure to photograph the massive 19-foot-tall Paul Bunyan statue holding a hot dog in Atlanta, Illinois.

Starved Rock State Park Adventure Weekend

Explore 18 canyons carved into sandstone bluffs at this stunning state park just 90 minutes from Chicago. Hike to dramatic waterfalls like St. Louis Canyon and Wildcat Canyon, which freeze into massive ice formations during winter months.

Book a guided fishing trip on the Illinois River for walleye and smallmouth bass, or try your luck at seasonal ice fishing. End your days at the historic Starved Rock Lodge's Back Door Lounge, featuring local craft beers and impressive views of the Illinois River Valley.

Chicago Craft Beer and Deep Dish Pizza Tour

Start at Revolution Brewing in Logan Square, Chicago's largest independent craft brewery, before heading to Half Acre Beer Company for their famous Daisy Cutter Pale Ale.

Continue the excursion to Lou Malnati's in River North for their legendary deep-dish pizza with butter crust and Wisconsin cheese. Finish the night at Hopleaf in Andersonville, featuring 68 draft lines and anymore bottled craft beers as well as a dedicated Belgian beer menu that rivals any collection in North America.

Lake County Golf and Whiskey Weekend

Play a round at ThunderHawk Golf Club in Beach Park, designed by Robert Trent Jones Jr. and consistently rated as one of Illinois's top public courses.

Visit the award-winning North Shore Distillery in Green Oaks for their custom gin and vodka tasting experience. Schedule an afternoon tee time at Shepherd's Crook Golf Course in Zion, known for its links-style layout and challenging wind conditions.

Cap off the weekend at Buffalo Creek Brewing in Long Grove, housed in a Bavarian-themed building with outdoor beer garden and lawn games.

More Illinois Guys Trip Ideas

University of Illinois Football Game - Experience the roar of Memorial Stadium in Champaign as the Fighting Illini take on Big Ten rivals in an electric college football atmosphere.
Illinois Railway Museum - Explore North America's largest railway museum in Union, featuring over 450 historic locomotives and train cars with seasonal ride opportunities.
Nightmare on Chicago Street - Join thousands for this immersive zombie apocalypse Halloween festival in downtown Elgin, complete with themed zones, live entertainment, and elaborate costumes.
TPC Deere Run Golf Course - Play a round at this prestigious PGA Tour venue in Silvis, known for hosting the John Deere Classic.
Mississippi River Fishing - Cast a line for catfish, bass, and walleye along the mighty Mississippi's numerous fishing spots and marinas.
Revolution Brewing Tour - Sample craft beers at Illinois' largest independent brewery while learning about the brewing process in Chicago's Logan Square.
Cahokia Mounds - Investigate America's largest prehistoric Native American city near Collinsville, featuring massive ancient earthwork mounds.
Illinois Bourbon Trail - Visit multiple craft distilleries across the state, including J.K. Williams Distilling and Blaum Bros. Distilling Co.
Starved Rock State Park Adventures - Hike through canyons, waterfalls, and stunning rock formations while engaging in activities like rock climbing and kayaking.
Abraham Lincoln Presidential Library and Museum - Immerse yourself in history with interactive exhibits and impressive artifacts in Springfield.
Lake Michigan Charter Fishing - Book a deep-water fishing charter out of Chicago or Waukegan to catch salmon and trout on Lake Michigan's waters.

Other Destinations That You Might Also Enjoy Visiting

Wisconsin - The Badger State offers similar Midwestern charm with additional draws like the Green Bay Packers games, numerous craft breweries in Milwaukee, and excellent fishing on Lake Michigan.
Nashville, Tennessee - This vibrant city combines live music venues, bourbon distilleries, hot chicken joints, and professional sports with the Tennessee Titans, making it perfect for groups of guys seeking entertainment.
Denver, Colorado - The Mile High City provides a mix of urban amenities and outdoor adventure with craft beer tours, Rockies baseball games, and easy access to mountain activities like hiking and skiing.
Austin, Texas - Known for its legendary BBQ joints, live music scene, outdoor activities on Lady Bird Lake, and the University of Texas football games, Austin delivers a perfect blend of food, sports, and entertainment.
Minneapolis, Minnesota - Similar to Illinois cities, Minneapolis offers major league sports, excellent craft breweries, world-class fishing lakes, and the iconic Mall of America for a diverse guys weekend experience.

Illinois Is The Perfect Place For Your Midwest Guys Getaway!

Illinois delivers endless possibilities for your next guys getaway. Whether you're cruising down Route 66, hiking through Starved Rock's rugged terrain, or catching a Bears game at Soldier Field, you'll find something that fits your crew's style. Don't forget to sample Chicago's legendary deep-dish pizza and craft beer scene. With its perfect mix of urban excitement and outdoor adventure, Illinois makes planning your next bros' weekend a breeze.

A Romantic Oktoberfest at Chicago's Edelweiss

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.
Chicago: More Than The "Second City" When It Comes To Being A Perfect Guys Trip Destination

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.
A Chicagoland Guys Weekend Getaway at Camping World 400

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.
Romantic Getaway Ideas In Chicago For Foodies In Love

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.
The 10 Best Cities in the United States for a Bachelor Party

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!
Wrigley Field South - Cubs Park Spring Training Baseball in Mesa AZ

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.
History Of The Chicago Style Hot Dog

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!
Awesome Fantasy Suites & Themed Adult Hotel Rooms

Traditionally, our wives and girlfriends sit and wait for us to pick a hotel that they want for Valentine's Day - but why can't we turn the tables and do things differently? We scoured the internet looking for epic hotel ideas that will inspire romance this Valentine's Day in a completely different manner than the typical 4-star resort with breakfast in bed!

Each of these motels caters to fantasies or have themed rooms that will make your Valentine's Day that much more fun compared to a leeway gooey, boring romantic night at a typical hotel with red roses and chocolates.
Best Places In America to See Bald Eagles

Eagle-spotting is a thrilling and educational experience, but knowing where to go can be a challenge. Did you know that bald eagles are found in every U.S. state except Hawaii? This guide offers an extensive list of the best places across America to see these iconic birds in their natural habitats.
Steam Engine Train Rides In The USA: Scenic Trips and Rail Museums To Visit

I love to travel, and steam train rides are one of my favorite things to do when I visit a new area. Unfortunately, I find that while there are lots of places to ride an authentic steam train, it's often an afterthought when folks suggest things to do in an area. Let's change that! These steam engines have a special place in my heart - as they do with millions of other guys and even some women too!

These locomotives are giant hulking marvels of engineering that represented the pinnacle of technology in their day but are still amazing to experience. In our age, where we covet silent, clean, smooth, and safe modes of transportation, these great mechanical beasts bring us back to a day when none of that was required - just getting the job done and opening up new opportunities to expand and profit. Additionally, I find that while many of these rail museums offer novelty rides such as "Thomas The Tank Engine" or "Polar Express" tours, simply riding the rails allows you to go places and see things that are otherwise inaccessible by car or foot.
How To Find The Perfect Themed Hotel Rooms For Couples

There are business hotels and then there are hotels with themed rooms designed for a romantic getaway. These are fun and exciting with a little bit of naughty thrown in for good measure. Especially in a time like this where you might desperately need an escape but aren't really wanting to go out and hang around with people, finding a themed hotel room near you might just be the perfect solution. The interesting thing is that while you might think this type of getaway would be only found in California, New York, or Las Vegas... the reality is that there are options all over the country, including states you might normally think of as being more conservative such as Illinois, Kentucky, Pennsylvania, Wisconsin, Ohio, and even Utah!