The Ultimate 3-Day Chicago Adventure
Experience the Windy City - Chicago, where history meets modernity.
03 May 2023
Sophie Watts
US Travel Writer
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.
Travel plan
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- Hotel: The Palmer House Hilton
- Start the day off with a hearty breakfast at Lou Mitchell's, a classic diner with a vintage vibe.
- Visit the Willis Tower (formerly the Sears Tower) and take in the incredible views from the Skydeck on the 103rd floor.
- Walk along the Magnificent Mile, Chicago's famous shopping district, and stop at Navy Pier for some carnival fun.
- Take a river architecture tour to learn about Chicago's stunning skyline and its history.
- End the day with a deep-dish pizza at Pizzeria Uno, birthplace of the famous dish.
- Start the day at the Art Institute of Chicago, where you can see famous works like "American Gothic" and "Nighthawks."
- Walk through Millennium Park and get a selfie with the iconic Cloud Gate (a.k.a. "The Bean").
- Head to Wrigleyville and tour the legendary Wrigley Field, home of the Chicago Cubs.
- Check out the quirky Museum of Contemporary Art for some modern art inspiration.
- End the day at Second City, the legendary comedy club where stars like Tina Fey and Amy Poehler got their start.
- Start the day with brunch at Yolk, a popular spot with a creative menu.
- Take a stroll through the trendy Logan Square neighborhood and check out the street art.
- Visit the Lincoln Park Zoo and Conservatory for some animal encounters and beautiful botanical gardens.
- Explore the historic Pilsen neighborhood, known for its colorful murals and delicious Mexican food.
- End the day in Hyde Park, home of the University of Chicago and the gorgeous campus of the Museum of Science and Industry.
- Chicago is a city full of character and charm, with endless things to do and see. Whether you're a foodie, an art lover, or just looking for a good time, this itinerary will give you a taste of what the Windy City has to offer.
Length of stay
Type of trip
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.