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

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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: The 5-Day Adventure

Exploring Chicago on a limited budget is possible with the city's many free attractions including Millennium Park, Navy Pier, and the Lincoln Park Zoo. Budget-friendly accommodations can be found in the city's hostels and Airbnb's located in the trendy neighborhoods of Wicker Park and Logan Square. Delicious local cuisine at affordable prices can also be found in the city's diverse dining scene ranging from deep-dish pizza to ethnic street food.

Discovering Chicago's Windy Wonders on a Budget

Visiting Chicago on a limited budget is possible and rewarding. Explore iconic attractions like Millennium Park and the Magnificent Mile, while also taking advantage of free events hosted throughout the city. Save money on accommodations by booking a hostel or budget-friendly hotel, and take advantage of the city's excellent public transportation system to get around easily.

Chicago in 4 days: Romance, Art, and Adventure

A romantic trip to Chicago begins with a stroll along the picturesque Riverwalk, taking in the stunning views of the city’s skyline. Embark on a journey to the top of the Willis Tower to marvel at the spectacular panorama or catch a show at the iconic Chicago Theatre. Relax with a glass of wine or craft cocktail in one of the city’s rooftop bars, or indulge in a romantic dinner at one of its many acclaimed restaurants.

2-day Chicago Adventure: Art, Food, and Culture!

A trip to Chicago as a tourist would include exploring famous landmarks such as the Willis Tower and Navy Pier. One would enjoy visiting cultural attractions like the Art Institute of Chicago and the Museum of Science and Industry. Lastly, experiencing the city’s unique food scene, including deep-dish pizza and Chicago-style hot dogs, would be a must.