Two-Day Ultimate Chicago Stag Do Adventure

Chicago: The Ultimate Stag Do Destination, with Perfect Pubs, Parties, and Pizza!

03 May 2023

A trip to Chicago for a stag do promises wild nights, stunning architecture, and delicious food. The groom-to-be and his friends can indulge in the city's famous deep-dish pizza, explore the vibrant nightlife, and visit iconic attractions like the Willis Tower and Navy Pier. With a bustling atmosphere and endless entertainment, Chicago is the perfect destination for an unforgettable stag do.

Travel plan

Getting latest place information
Day 1

Sights, Bites, and Booze

  • Hotel: The Wit, a stylish boutique hotel in the heart of downtown.
  • Start with a stroll along the Magnificent Mile, admiring the skyscrapers and high-end shops.
  • Lunch at The Purple Pig for Mediterranean-inspired small plates and sangria.
  • Take a riverboat architecture tour for stunning views of the city's iconic buildings.
  • Happy hour at The Signature Lounge on the 96th floor of the John Hancock Center.
  • Dinner at Lou Malnati's Pizzeria for Chicago-style deep dish pizza.
  • End the night with drinks at The Aviary, a trendy cocktail bar with inventive drinks.
Day 2

Culture and Sports

  • Breakfast at Wildberry Pancakes and Cafe for fluffy pancakes and eggs benedict.
  • Visit the Art Institute of Chicago for an impressive collection of art from around the world.
  • Lunch at Portillo's for Chicago-style hot dogs and Italian beef sandwiches.
  • Catch a Cubs game at Wrigley Field with cold beers and peanuts.
  • Dinner at Girl & the Goat for elevated comfort food and creative cocktails.
  • End the night at Kingston Mines, a legendary blues club with live music until the early hours.
  • With its diverse mix of food, culture, and entertainment, Chicago is the perfect destination for a memorable stag do. From sightseeing to sports, delicious cuisine to iconic attractions, there’s something for everyone to enjoy in the Windy City. So gather the guys, book your hotel, and get ready for an unforgettable weekend in one of America's great cities.

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

5-Day Adventure Guide to Chicago, USA

Chicago is a bustling metropolis on the shores of Lake Michigan, known for its architecture, food, and culture. Tourists can explore the city's many museums and parks, including the Art Institute of Chicago and Millennium Park. Be sure to sample the city's famous deep-dish pizza and catch a game at Wrigley Field or Soldier Field.

Windy City Wonders: A 4-Day Family Adventure in Chicago!

Experience the vibrant city of Chicago on a family friendly trip filled with unforgettable memories. Explore the iconic Millennium Park, where kids can splash in the Crown Fountain or marvel at the reflective Bean sculpture. Indulge in delicious deep-dish pizza, visit the Shedd Aquarium or catch a baseball game at Wrigley Field for an action-packed getaway in the Windy City.

The Ultimate 3-Day Chicago Adventure

Chicago boasts an impressive skyline and rich cultural diversity that attracts visitors from all over the world. Iconic landmarks such as the Willis Tower and Millennium Park provide excellent photo opportunities, while a stroll along the Magnificent Mile offers an extensive array of shopping, dining, and entertainment options. For a taste of Chicago's famous cuisine, deep-dish pizza and Chicago-style hot dogs are a must-try.

Chicago Adventures: 5 Days of Family Fun on a Budget

A family trip to Chicago offers a unique blend of culture, entertainment, and history. Start your adventure with a visit to famous attractions such as Millennium Park, where kids can explore the interactive Crown Fountain or take photos with the iconic Cloud Gate sculpture. Don't miss out on a fun-filled day at Navy Pier, where you can ride the Ferris wheel, enjoy live performances, and indulge in delicious food from various vendors.