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

Getting latest place information
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

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.

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.

Chicago in Four Days: A Budget Adventure.

Chicago is a vibrant and culturally-rich city located on the shores of Lake Michigan. For a budget-friendly trip, be sure to take advantage of free attractions such as the Lincoln Park Zoo and Millennium Park. Chicago is also known for its world-class cuisine, so be sure to sample the iconic deep-dish pizza and other cheap eats.

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.