Chicago is one of my favorite cities to visit, and as someone who lived there for nearly a decade, it's a city I'm proud to share with friends whenever they ask where to go. This is the city of big shoulders - a town where nobody's afraid to grab a beef sandwich dripping with juice, scream for their sports teams, and look at the world a little differently. Bring the guys and Chicago will keep all of you busy for a long weekend without ever feeling like a tourist trap.
What Do You Call Your "Guys Trips"?
Chicago rewards a group that picks one good neighborhood to base out of and works outward from there. Here's what to lock in first.
- Base in the Loop and you're walking distance to Millennium Park, the Riverwalk, and the Art Institute, while the Blue Line runs from O'Hare straight downtown 24/7 - leave the rental car at home.
- Chicago's signature foods aren't one thing. Gyros, Italian beef, deep dish, Chicago-mix popcorn, and the no-ketchup hot dog are five separate missions for the weekend.
- You can catch the Cubs, White Sox, Bulls, Blackhawks, and Bears without ever leaving the city, and Wrigley Field is worth a tour even on a no-game day.
- The architecture river cruise was voted the #1 boat tour in North America by USA Today readers - one of the few touristy things worth doing on its own.
- Summer turns the Lake Michigan shoreline into 26 miles of free public beaches, volleyball courts, and sailing - most first-timers don't expect to find waves on a lake.
- Don't Be Boring: Chicago Guys Trip Ideas
- Chicago is The Best Midwest Sports Town
- Fill Up on Iconic Chicago Foods
- Chicago Museums Are Among the Best In the World
- Architecture Tours
- Enjoy Chicago's Lakefront and Freshwater Beaches
- Chicago Blues and Jazz Clubs
- Chicago On Screen: Movie and TV Locations
- Beef, Sports, and Big Shoulders: Chicago Is Our Top Midwest Guys Trip
As one of the biggest cities in the United States, it can be a challenge knowing where to stay. Luckily, getting around is easy: the "L" train runs around the clock, the Blue Line drops you from O'Hare straight into the Loop, and rideshares are everywhere. Since the city is mostly flat, it's also great for biking and walking. The specific hotel address matters less here than in some other cities - just pick the neighborhood that fits your crew. The Loop keeps you central, River North puts you in the thick of the nightlife, and Wrigleyville is the move if this is a Cubs pilgrimage.
Don't Be Boring: Chicago Guys Trip Ideas
Sure, you can visit the city of big shoulders, stay at a posh hotel, and hit a couple pizza places like Lou Malnati's and Gino's East ... or ... you can build a whole theme around your Chicago guys weekend and turn it into a real adventure.
| Idea | Description | Activities | Key Locations |
|---|---|---|---|
| Sports Extravaganza | Catching a game from Chicago's major sports teams | Attend a Cubs or White Sox game, Bulls or Blackhawks game, tour Soldier Field | Wrigley Field, United Center, Soldier Field |
| Culinary Tour | Exploring Chicago's renowned food scene | Deep-dish pizza tasting, steakhouse dinners, food tours, craft brewery visits | Giordano's, Lou Malnati's, Bavette's Bar & Boeuf |
| Lakefront Adventure | Enjoying activities along Lake Michigan | Jet skiing, sailing, biking the Lakefront Trail, beach volleyball | Navy Pier, North Avenue Beach, Lakefront Trail |
| Nightlife Experience | Experiencing Chicago's nightlife | Bar hopping, live music venues, rooftop bars, craft cocktail lounges | River North, Wicker Park, Logan Square |
| Cultural Immersion | Diving into Chicago's history and culture | Museum visits, architectural boat tour, historic neighborhoods, blues clubs | The Art Institute of Chicago, Millennium Park, Magnificent Mile, Buddy Guy's Legends |
Those are just a few ways to frame a real guys trip to Chicago, mixing sports, food, adventure, nightlife, and culture. Let your imagination run and have some fun with it. Chicago has always been bigger than its nickname.
Chicago is at its best in summer, when you can bounce between air-conditioned museums and the open lakefront in the same afternoon - though a fall mancation built around a Bears Sunday or a crisp Wrigley day game works just as well.
Chicago is The Best Midwest Sports Town
You can't go wrong with a visit to Wrigley Field. While the Southsiders may tell you that Rate Field is the place to catch a game, Wrigley is an icon and a national treasure that any sports fan will love - and an entire neighborhood, Wrigleyville, has grown up around the park since it opened in 1914. Catching a game here is the kind of day most baseball fans plan a whole trip around, but if the timing isn't right you can still do a Wrigley Field Ballpark Tour.
If you aren't a baseball fan, don't worry - you can catch a Bulls or Blackhawks game at the United Center, a Bears game at Soldier Field, or a Chicago Fire match at Soldier Field too. Worth knowing if you're planning around the Bears: they still play at Soldier Field for now, but as of this writing a move looks increasingly likely - Illinois lawmakers let the stadium-funding bill die as their spring 2026 session ended, nudging the team toward a proposed new stadium in Hammond, in northwest Indiana. A bachelor party crew can build the whole weekend around a single marquee game and figure out the rest around it.
Fill Up on Iconic Chicago Foods
Chicago's most iconic foods aren't for anyone on a diet or afraid to get messy. This is an industrial city at heart, and while it has some of the best high-end restaurants in the world, you need to try the local icons too. Unlike cities with one or two signature dishes, Chicago has several: gyros, Italian beef sandwiches, deep dish pizza, Chicago-mix popcorn, and of course the Chicago-style hot dog are all must-try items.
Here's our pick for where to get the best ...
Gyro - Gyros are a worldwide favorite today, but the sandwich was popularized in the 1970s by Chicago food distributors. For anyone who's never had one, it's a Greek-style sandwich with thin slices of a beef-and-lamb mixture wrapped in pita with tzatziki, tomato, onion, and a side of fries.
Best Places to Get a Gyro in Chicago: Virtually every hot dog stand in Chicago serves gyros, and most use the same meat provider (Kronos Foods). For generations The Parthenon was the spot, but that iconic Greektown restaurant closed back in 2016. In its absence, we think Nick's Drive-In is the place to go - one of the few stands in town still making its own meat, and the flavor shows. Other solid options include Central Gyros and Hub's.
Italian Beef Sandwich - not to be confused with a cheesesteak or a French dip, this Chicago original features thin slices of seasoned roast beef simmered in au jus on an Italian roll. A proper beef is dunked in the au jus before being wrapped in paper and served. Variations include a "combo" (Italian sausage piled in with the beef), a "garlic cheesy beef" (served on a garlic bread roll), or my favorite ... a Garlic Cheesy Beef Combo.
Best Places to Get an Italian Beef Sandwich in Chicago: Al's Italian Beef claims to be the originator (opened in 1938) and it's still one of the best in town. Despite being chains, both Buona Beef and Portillo's do a very good beef too. Just get it dipped and dripping - and assume the proper Italian stance so you don't wear the gravy on your shirt.
Deep Dish Pizza - this style has spread across the country, but Chicago still does it best.
Best Places to Get Deep Dish Pizza in Chicago: Hands down, my pick for Chicago-style deep dish is Lou Malnati's - keep it simple with sausage and cheese on the butter crust. Other popular choices include Gino's East, Giordano's, and Pequod's Pizza, whose caramelized cheese crust has a cult following of its own.
If you can't decide, or just want to sample a bunch of the best in one go, you can also book the Pizza City USA Pizza Bus Tour.
Chicago-mix Popcorn - Chicago is famous for its popcorn. There are two main flavors, caramel and cheese, but mix the two together and that's when the magic happens.
Best Places to Get Chicago-mix Popcorn: I go back and forth depending on my mood, but my go-to is Nuts On Clark, closely followed by Garrett Popcorn Shops when I want a sweeter, more burnt-caramel flavor. Both have locations at O'Hare, so I can get my fix running between flights.
Chicago-style Hot Dog - some say it's healthier to eat a hot dog in Chicago because they put a salad on top. My doctor disagrees. A Chicago-style dog starts with an all-beef frank on a poppy seed bun, then gets yellow mustard (NO KETCHUP), chopped white onions, bright green relish, a dill pickle spear, tomato slices, sport peppers, and a dash of celery salt.
Best Places to Get a Chicago-style Hot Dog: This one's tough, but the key is starting with a great sausage. While many stands run the ever-popular Vienna Beef, my favorite, Superdawg, makes its own.
Chicago Museums Are Among the Best In the World
Chicago has museums that guys will actually want to spend a day in: the Griffin Museum of Science and Industry (the longtime Museum of Science and Industry, renamed in 2024), the Adler Planetarium (the first planetarium built in the Western Hemisphere), the Field Museum of Natural History, and the Chicago History Museum. The Art Institute of Chicago also runs exhibitions that guys gravitate toward, like its collection of Medieval and Renaissance arms and armor. And anyone who loves giant ferocious animals needs to stop by the Field Museum and say hi to SUE - the largest and most complete T. rex ever discovered, now posed in her own dedicated gallery upstairs in the Evolving Planet wing and updated to reflect what scientists have learned about these dinosaurs since she first arrived in the 1990s.
Architecture Tours
Chicago has a long history of innovation in building. The city hosts some of the tallest buildings in North America and some of the most ornate masonry designs too. The best way to take it in is an architecture river cruise with a guide who can point out the details and walk you through how the city rebuilt itself after the Great Fire. Our recommendation is one run by the Chicago Architecture Center - their docents are excellent, and their First Lady cruise has been voted the #1 boat tour in North America by USA Today readers, so it's the rare guided tour that isn't a tourist trap.
Enjoy Chicago's Lakefront and Freshwater Beaches
Whether you want a bike ride along the Lakefront Trail, a beach volleyball game, or an afternoon sailing, Chicago packs a surprising amount onto its shoreline. The city has 26 miles of lakefront and more than two dozen public beaches, and locals and visitors flock to the sand and fresh water all summer. Some first-timers are even surprised to see waves - but they don't call Lake Michigan a Great Lake for nothing.
Chicago Blues and Jazz Clubs
Like many Midwestern industrial cities, Chicago saw a huge number of African American families relocate here during the Great Migration in the first half of the 20th century to find factory work. They brought southern food with them - and southern music. Today Chicago has some of the best blues and jazz clubs outside the South, including iconic rooms like Kingston Mines, Rosa's Lounge, and of course Buddy Guy's Legends, where Buddy Guy himself still plays a run of shows every January. It's a natural late-night move for a guys weekend after the game lets out. If the crew wants a louder night instead, River North and Wicker Park stack bars and cocktail lounges close enough to walk between rounds.
Chicago On Screen: Movie and TV Locations
Chicago is one of the most popular destinations in America for film and TV production. So it shouldn't be a surprise that film tours - walking or a bus, bike or even segway is a top choice to spend a half-day with the guys. Ferris Bueller talked his way through the Art Institute, Willis Tower, and Daley Plaza; the Dark Knight tore down Lower Wacker Drive; the Blues Brothers wrecked Daley Center; and FX's The Bear shoots its exteriors at the real Mr. Beef on Orleans.
Guided tours hit the highlights without you having to map it yourself - a good catch-all is this downtown TV and movie sites walking tour, while film buffs can go deeper on a Ferris Bueller tour at the Art Institute or an action-movie locations day tour. We'll have a full Chicago movie-locations guide coming soon for crews who want to build a whole day around it.
Beef, Sports, and Big Shoulders: Chicago Is Our Top Midwest Guys Trip
If I had to send a crew to one Midwest city for a long weekend, it's Chicago every time. Base in the Loop, ride the L instead of fighting for parking, and you can stack a Wrigley day game, a beef-and-deep-dish food crawl, an architecture cruise, and a late night at Kingston Mines into three days without ever feeling rushed. Go in late spring or early fall and you dodge both the brutal winters and the peak-summer crowds. And if the group still wants more, Milwaukee is only 90 minutes up the road for a Brewers game or a brewery afternoon, which turns a Chicago weekend into a bigger Illinois-and-beyond guys trip. Grab the guys, book O'Hare, base yourself in the Loop, and give it three days - that's all it takes to see why the city of big shoulders outgrew its nickname a long time ago.
