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

Experience the Windy City like never before - Chicago awaits you!

03 May 2023

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.

Travel plan

Getting latest place information
Day 1

An Introduction to the Windy City

  • Hotel: The Gwen a luxury hotel with an art deco feel in the heart of downtown. Expect stunning city views and a chic rooftop terrace.
  • Start your day with a nutrient-packed breakfast at Kanela Breakfast Club
  • Take a stroll down the Magnificent Mile and check out some high-end stores
  • Devour an authentic deep-dish pizza at Lou Malnati's
  • Make a stop at the Art Institute of Chicago and admire some of the world's most famous masterpieces
  • Walk off your lunch with a stroll through Millennium Park, where you can pose next to the iconic "Bean"
  • End the day by sipping a classic Chicago-style cocktail at The Aviary, with its creative and unique concoctions
Day 2

Exploring the Cultural Scene

  • Grab a delicious pastry and coffee at Beatrix Bakery before starting your day
  • Learn about Chicago's musical history at the Blues Heaven Foundation
  • Head to the Chicago Cultural Center, which hosts exhibitions, performances, and events throughout the year
  • Refuel with lunch at Au Cheval, known for its delicious burgers and fries
  • Take a river cruise down the Chicago River, and learn about the city's architecture
  • End the day by indulging your sweet tooth at the famous Molly's Cupcakes, with its unique cupcake flavors and fun, nostalgic decor.
  • With so much to see and do, 2 days in Chicago may not seem like enough time, but you can pack in plenty of diverse activities to make it a trip you won't forget!

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.

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 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.

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!