When you live in Chicago and love football, you face a brutal reality: Bears tickets are expensive, Bears football is often painful, and those home games at Soldier Field require a level of commitment that isn't always worth the return on investment. I know this from experience - years of watching a franchise bounce between mediocre and historically bad while charging premium prices for the privilege.
What Do You Call Your "Guys Trips"?
- Detroit is just over four hours on I-94 with affordable hotels, a revitalized downtown food scene, and ticket prices that make Soldier Field look absurd - even with the Lions playing competitive football now.
- Green Bay delivers the ultimate bucket list experience at Lambeau Field, where the tailgate culture and stadium mystique justify the 3.5-hour drive regardless of either team's record.
- Indianapolis offers the shortest drive at under three hours, putting one of the NFL's best modern stadiums in easy weekend territory with a walkable downtown.
- Cleveland's lakefront stadium and legendary Dawg Pound intensity sits about 5.5 hours out, with Canton's Pro Football Hall of Fame just an hour south for a full football pilgrimage.
- The reality of Midwest NFL volatility means you can never count on your team being good - so invest in stadiums and experiences that deliver regardless of the scoreboard.
The Midwest has produced some of the NFL's most frustrating franchises. The Browns, Lions, and Bears have all been NFL teams that went from champs to chumps overnight at various points, taking turns breaking their fans' hearts for decades. But here's what those franchises also share: passionate fan bases, historic stadiums, and cities that know how to make game day an event. When Illinois guys trips are built around football, these destinations deliver whether your team wins or not.
Detroit: The Road Trip That Changed Everything
Ford Field in downtown Detroit became my go-to Bears road trip precisely because everything about it felt easier than fighting for Soldier Field tickets. The 4.5-hour drive on I-94 is straightforward, hotel prices downtown run half what you'd pay in Chicago on game weekends, and tickets - even with the Lions playing competitive football now - still feel reasonable.
The Eastern Market tailgate scene sets this experience apart. Instead of cramped stadium lots, thousands of Lions fans gather in a historic farmers market district about ten minutes from Ford Field. The energy builds for hours before kickoff, and the walk across the pedestrian bridge to the stadium with a sea of Honolulu Blue creates exactly the kind of atmosphere you're chasing on a guys weekend.
Downtown Detroit's restaurant revival means postgame options extend well beyond chain spots. The Slippery Noodle, Greek Town, and the bars around the stadium corridor offer a legitimate night out. Hotels like the Hilton Cleveland Downtown sit within walking distance, eliminating the need for designated drivers or expensive rideshares.
Green Bay: The Bucket List Trip
Lambeau Field needs no sales pitch. The NFL's oldest continuously operating stadium sits in a town of about 100,000 people that essentially shuts down on game days. The 3.5-hour drive from Chicago through Milwaukee makes this an easy weekend trip, though finding hotel rooms requires booking months in advance.
What makes Green Bay worth the pilgrimage regardless of the Packers' record is the tailgate culture. Nearly every house within a half-mile of Lambeau becomes its own party, with homeowners renting driveways and offering access to grills and coolers. The Titletown District across from the stadium adds restaurants, bars, and green space that extend the pregame experience.
Stadium tours run on non-game days through the Packers Hall of Fame, letting you walk the tunnel and stand on the Frozen Tundra. For Wisconsin guys trips, timing a visit around a home game transforms a football weekend into something you'll reference for years.
Indianapolis: The Underrated Option
Lucas Oil Stadium doesn't get the attention it deserves among Midwest football fans, which works in your favor. The drive from Chicago takes under three hours on I-65, putting Indianapolis in easy day-trip territory - though the downtown scene justifies an overnight stay.
The stadium itself ranks among the NFL's best - a retractable roof, excellent sightlines, and a brick exterior that blends with the surrounding downtown. Georgia Street between the stadium and the convention center fills with pregame energy, and hotels sit within walking distance in every direction.
Indianapolis offers something the other cities on this list don't: affordable parking. Street parking downtown is free on Sundays, and surface lots within walking distance run significantly cheaper than Chicago equivalents. The Slippery Noodle - the oldest bar in Indiana - sits across from the stadium and anchors postgame plans.
Cleveland and Canton: The Full Pilgrimage
Cleveland's Huntington Bank Field requires more commitment at 5.5 hours from Chicago, but the city earns its spot on this list for two reasons: the Dawg Pound atmosphere and proximity to Canton. The legendary end zone section sets a standard for fan intensity that makes neutral observers uncomfortable, and the lakefront stadium offers views of Lake Erie from the upper deck.
The Muni Lot tailgate rivals anything in the NFL - a massive public parking area where die-hards arrive hours early with elaborate setups. Browns fans have perfected the art of turning losing seasons into communal experiences, and visiting fans willing to engage respectfully often find themselves welcomed into the festivities.
The real opportunity here involves extending the trip to Canton, about an hour south on I-77. The Pro Football Hall of Fame sits in the city where the NFL was founded in 1920, and the 118,000 square feet of exhibits, the bust gallery, and the Super Bowl theater justify a half-day visit. Time your trip around the Hall of Fame Game in early August for the full football experience.
Making These Trips Work
The logistics favor group travel. Split gas, hotels, and parking four ways and these trips become remarkably affordable compared to Chicago home games. Book hotels two to three months out for Detroit and Indianapolis, further in advance for Green Bay.
Travel on Saturdays when possible - arriving the night before means exploring the city, hitting the tailgate scene properly, and avoiding the rush. For Midwest guys trips built around football, the pregame matters as much as the game itself.
Why the Drive Beats the Home Game
Maybe college football is so big here because the NFL teams are often extremely disappointing. The Big Ten offers Michigan, Ohio State, Notre Dame, and Wisconsin - all within striking distance of Chicago, all with stadium atmospheres that rival the pros. But the NFL road trip offers something different: cities worth visiting, stadiums worth experiencing, and fan cultures that welcome outsiders.
The Bears will be good again someday, probably. The Lions were terrible for decades before their recent run. The Browns have tested their fans' patience beyond reasonable limits. None of that changes the fact that these cities deliver football weekends worth taking - and the game is only part of what makes them worth the drive.
