5-Day Adventure Guide to Chicago, USA

Discover the Windy City and experience the bold flavors, iconic architecture, and vibrant culture of Chicago.

03 May 2023

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.

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Travel plan

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Day 1

Arrival and Exploration

  • Check into the trendy Ace Hotel Chicago in the West Loop neighborhood
  • Walk around Millennium Park and see the iconic "Bean" sculpture
  • Head to Navy Pier for stunning views of Lake Michigan and take a ride on the giant Ferris wheel
  • Visit the Art Institute of Chicago and see works by famous artists like Picasso and Monet
  • Grab a Chicago-style hot dog (with all the toppings!) at Portillo's for a classic Windy City experience
Day 2

Chicago History

  • Take a riverboat tour of the Chicago River to learn about the city's architecture and history
  • Visit the Chicago History Museum to see artifacts from the Great Chicago Fire, Al Capone's reign, and more
  • Wander around Lincoln Park and visit the Lincoln Park Zoo for free animal sightings
  • Have a deep dish pizza from Gino's East—a true Chicago staple
  • Catch a show at the historic Chicago Theatre on State Street
Day 3

Neighborhood Hopping

  • Spend the morning exploring the diverse and artsy neighborhood of Pilsen
  • Head to the trendy Wicker Park/Bucktown area for boutique shopping and eclectic dining
  • Take a stroll along the 606, an elevated park and walking trail on an old train track
  • Visit the Ukrainian Village for Eastern European cuisine and culture
  • Have a nightcap at one of the many speakeasies in the Logan Square area
Day 4

Museums and Parks

  • Start off at the Museum of Science and Industry for interactive exhibits and hands-on activities
  • Have lunch at the Chicago Botanic Gardens, featuring over 385 acres of gardens, lakes and woodlands
  • Head to the Field Museum of Natural History to see Sue, the most complete Tyrannosaurus rex skeleton ever found
  • Relax in Grant Park and take in the stunning skyline views
  • Dine at RPM Italian, owned by celebrity couple Bill and Giuliana Rancic
Day 5

Shopping and Departure

  • Head to the Magnificent Mile for high-end shopping and dining
  • Check out the Macy's on State Street, the largest department store in the world
  • Explore the gorgeous South Loop and visit the Adler Planetarium for astronomical wonders
  • Have a farewell dinner at Girl & the Goat, known for their creative small plates and trendy atmosphere.
  • End the trip at the Signature Room lounge for cocktails and a 360-degree panoramic view of the city.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

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.

Destination

Chicago

Welcome to the Windy City, where the people are friendly, the pizza is deep, and the weather is unpredictable enough to keep things interesting. Just make sure to hold onto your hats (and your deep dish) while you're here.

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

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