Start your bachelor party adventure off in Wrigleyville, home of the iconic Wrigley Field. Catch a Cubs game, or take a tour of the stadium. Afterward, enjoy a cold brew at one of the many bars and pubs lining the streets. Stop by the Irish Oak for pub grub and drinks, or head over to Big Star for tacos and margaritas.
Head over to River North for a day of luxury and indulgence. Start at the Langham Spa, where you can unwind with a massage or facial. Grab lunch at The Purple Pig, a cozy, communal eatery offering a selection of Mediterranean-inspired small plates. In the evening, hit up the Underground for top-notch cocktails and dancing.
The West Loop is a foodie's paradise, with some of the city's best restaurants and bars. Start at Publican Quality Meats for a hearty breakfast sandwich, then hit up the many breweries and distilleries in the area. For dinner, head over to Girl & the Goat for inventive, flavor-packed dishes. End the night at the Aviary, a speakeasy-style bar with creative cocktails.
End your bachelor party adventure in Lakeview, with its eclectic mix of shops, bars, and restaurants. Start at the Vic Theatre for a concert, then hit up Schubas for more live music or Kingston Mines for blues. Refuel at DMK Burger Bar or Crisp, both offering delicious burgers and Korean fried chicken. Finish the night on a high note at Smart Bar, one of Chicago's premier dance clubs.
Consider renting a car or using ride-hailing services like Uber or Lyft to get around the city. The estimated cost for a rental car is $40-$60 per day, but parking can be expensive in popular areas. Ride-hailing costs vary depending on distance and demand.
If you have more time, consider visiting the Navy Pier, Magnificent Mile, or Millennium Park. For a day trip, take a ferry to explore the charming town of St. Joseph, Michigan. If you have less time, cut out a neighborhood or two and focus on the must-see attractions in those areas.
Chicago O'Hare International Airport (ORD) is the largest airport in the area, located 18 miles northwest of downtown Chicago. Chicago Midway International Airport (MDW) is 10 miles southwest of downtown. Both airports offer a variety of transportation options to get into the city center.