Discovering Chicago's Windy Wonders on a Budget

Experience the Windy City without blowing your budget!

21 June 2023

Visiting Chicago on a limited budget is possible and rewarding. Explore iconic attractions like Millennium Park and the Magnificent Mile, while also taking advantage of free events hosted throughout the city. Save money on accommodations by booking a hostel or budget-friendly hotel, and take advantage of the city's excellent public transportation system to get around easily.

Travel plan

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Day 1

Windy City Wonders

  • Hotel: Freehand Chicago
  • Start the day with a classic American breakfast at Wildberry Pancakes and Cafe
  • Step into the modern art world at The Art Institute of Chicago
  • Stroll down to Millennium Park for some Instagram-worthy photos of The Bean
  • Cross the Chicago River on the DuSable Bridge to explore the Magnificent Mile
  • Fill up on deep-dish pizza at Giordano's before ending the day with a cocktail at The Signature Lounge on the 96th floor of the John Hancock Center
Day 2

Culture and Cuisine

  • Grab a coffee and pastry from Do-Rite Donuts before exploring Chicago's Pilsen neighborhood
  • Learn about Mexican art and culture at the National Museum of Mexican Art
  • Head to Navy Pier for carnival games and a ride on the iconic Ferris wheel
  • Experience Chicago-style hot dogs at Portillo's
  • End the day with a comedy show at The Second City, launching pad for many SNL stars
  • Chicago's diverse neighborhoods and iconic attractions make for a memorable trip that won't break the bank, especially with Freehand Chicago's affordable rates. Chicago may be known as the Windy City, but it'll blow you away with its culture, cuisine and charm.

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

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 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.

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

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.

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.