Chicago's Stag-tastic Day Trip

Experience the ultimate boys' weekend in the Windy City of Chicago.

22 April 2023

A trip to Chicago for a stag do promises an unforgettable experience. With a lively nightlife scene, Chicago offers an array of bars and nightclubs perfect for a bachelor party. From catching a game at Wrigley Field to exploring the city's famous architecture, Chicago's vibrant culture and diverse attractions make it an ideal destination for a celebration with the lads.

Day trip plan

Getting latest place information
Day

Chicago's Classics with a Twist

  • Start the day off with some caffeine at Intelligentsia Coffee, a local favorite.
  • Take a stroll through Millennium Park and snap a selfie with "The Bean."
  • Head to Lou Malnati's for a slice of Chicago-style deep dish pizza.
  • Tour the Art Institute of Chicago to see works from Van Gogh and Picasso.
  • Grab a craft beer flight at The Berghoff, a historic German restaurant.
  • End the night at The Green Mill, a jazz club that once hosted Al Capone.
  • Note: While this itinerary is suitable for a stag do, please note that some venues may have age restrictions or require a dress code.

How to get there

Plane

The best way to get to Chicago by plane is to fly into O'Hare International Airport or Midway International Airport, both of which are served by major airlines from most major cities in the world. You can check prices and schedules on websites like Expedia or Kayak.

Car

The best way to get to Chicago by car is to take one of the major highways, such as I-90 or I-94, which both run through the city. However, be aware of traffic congestion during peak travel times.

Train

The best way to get to Chicago by train is to take an Amtrak train, which connects the city to other major cities in the United States, such as New York, Washington D.C., and Los Angeles. The main train station in Chicago is Union Station.

Boat

The best way to get to Chicago by boat is to take a ferry from Navy Pier to locations such as Michigan City or St. Joseph. However, this mode of transportation is not as common as the others and may have limited availability depending on the season.

Bus

The best way to get to Chicago by bus is to take a Greyhound bus, which connects the city to most major cities in the United States. The main bus station in Chicago is the Greyhound Station.

More travel plans

Chicago on a Budget: Three Days of Fun!

A family friendly trip to Chicago, United States offers an exciting blend of entertainment and education for all ages. Explore the iconic Navy Pier with thrilling rides, beautiful gardens, and stunning lake views. Immerse yourself in the city's rich history by visiting unique museums like the Shedd Aquarium, Field Museum, and the interactive Chicago Children's Museum.

Chicago on a Budget: 3-Day Adventure Guide

Chicago is a vibrant and exciting city that can be enjoyed on a limited budget. Visitors can take in panoramic views from the top of Willis Tower, explore the diverse neighborhoods of Lakeview and Wicker Park, and visit the free-admission museums such as the Art Institute of Chicago. To save on accommodation costs, travelers can opt for budget-friendly hostels or seek out affordable Airbnb rentals.

Discover Chicago: A Family-Friendly Adventure on a Budget

A family-friendly trip to Chicago offers a perfect blend of fun and educational activities. Explore the interactive exhibits at the renowned Field Museum, embark on a scenic boat tour along the Chicago River, and get a stunning, panoramic view of the city from the Skydeck Chicago. Don't forget to indulge in some deep-dish pizza and visit the beloved Lincoln Park Zoo during your visit!

Chicago in a Day: Romance and Adventure

A romantic trip to Chicago, United States offers a perfect blend of scenic beauty and metropolitan charm. Take a romantic stroll by the lakefront or catch breathtaking views from the Willis Tower. Experience culinary delights at the famous eateries, and don't miss out on the city's vibrant arts and culture scene.