Ultimate Chicago Stag Do: 3-Day Adventure

Get ready for a wild ride in the Windy City with your squad.

22 April 2023

Chicago is a perfect destination for a fun and exciting stag do. From visiting iconic attractions like the Willis Tower and Navy Pier to exploring the city's famous nightclubs and bars, there are plenty of things to do for a memorable stag weekend. The windy city also has an excellent culinary scene and offers a variety of delicious local foods to try during the trip.

Travel plan

Getting latest place information
Day 1

Arrival and Exploration

  • Check in at Freehand Chicago, a trendy boutique hotel in River North, which offers a comfortable and budget-friendly stay
  • Grab a hot dog at Portillo's, an iconic fast-food joint known for its mouth-watering Chicago-style hot dogs
  • Take a stroll through Millennium Park and snap a picture in front of the famed Cloud Gate sculpture (aka 'the Bean')
  • Indulge in authentic deep-dish pizza at Giordano's or Lou Malnati's
  • Catch a Cubs game at Wrigley Field or tour its legendary stadium
Day 2

Beer, Art and Music

  • Begin the day with a hearty brunch at Yolk, a must-visit breakfast spot that serves inventive pancakes
  • Sip on local craft beers at Revolution Brewing, a popular brewery in Logan Square
  • Head to the Art Institute of Chicago and explore its impressive collection of modern and contemporary art
  • Check out a live music show at the historic Metro, which has hosted famous acts like Nirvana and R.E.M.
  • End the night with a nightcap at The Violet Hour, a trendy speakeasy with inventive cocktails
Day 3

Lakefront and Architecture

  • Start the day with a scenic run or bike ride along the lakefront trail
  • Take an architecture boat tour and learn about the city's iconic buildings like Willis Tower and the Tribune Tower
  • Visit Navy Pier and experience its fun-filled activities like the Ferris wheel and the Centennial Wheel
  • Stop by Pizano's Pizza for a quick lunch and try their thin crust pizza
  • End the night with a cocktail and a view at The Signature Lounge, located on the 96th floor of the John Hancock Center.
  • Chicago offers a perfect blend of city life and natural beauty, making it a perfect destination for any stag do. With renowned foods, impressive architecture, miles of bike paths and beautiful parks, your group’s stay in this city will be unforgettable.

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

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 Fun Frenzy: Explore, Indulge, and Immerse!

A trip to Chicago offers a plethora of family-friendly activities and attractions. Explore the iconic Navy Pier where you can enjoy rides, games, and spectacular views of Lake Michigan. Immerse yourselves in the vibrant culture of the city by visiting Millennium Park, home to famous landmarks like "The Bean" and a host of interactive public art installations. Finally, don't forget to indulge in Chicago's deep-dish pizza and explore the numerous museums and zoos that cater to children's interests.

Two-Day Windy City Romance Guide

Chicago offers a perfect backdrop for a romantic trip with its picturesque skyline and waterfront views. The city’s rich history, lively culture, and delicious food make it an ideal destination for couples who want to experience the ultimate romantic getaway. Take a stroll on the stunning Lakefront Trail, grab some deep-dish pizza, and catch a show at one of its renowned theaters for an unforgettable romantic trip.

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.