Chicago on a Budget: The 5-Day Adventure

Discover the Windy City without breaking the bank!

21 June 2023

Exploring Chicago on a limited budget is possible with the city's many free attractions including Millennium Park, Navy Pier, and the Lincoln Park Zoo. Budget-friendly accommodations can be found in the city's hostels and Airbnb's located in the trendy neighborhoods of Wicker Park and Logan Square. Delicious local cuisine at affordable prices can also be found in the city's diverse dining scene ranging from deep-dish pizza to ethnic street food.

Travel plan

Getting latest place information
Day 1

Exploring the Windy City

  • Start your day with breakfast at The Bongo Room
  • Take a walking tour of the Loop with Free Tours By Foot
  • Visit the Art Institute of Chicago
  • Stroll through Millennium Park and take a selfie with "The Bean"
  • Enjoy deep-dish pizza for dinner at Giordano's
  • Hotel recommendation: The James Chicago centrally located and affordable.
Day 2

Offbeat Sights and Tastes

  • Have brunch at The Publican
  • Visit the International Museum of Surgical Science (weird but fascinating)
  • Check out the street art at The 606 trail
  • Have dinner at The Purple Pig (tapas-style plates)
  • Catch a show at The Second City
Day 3

On the Waterfront

  • Grab breakfast at Lou Mitchell's
  • Take an architecture boat tour of the Chicago River
  • Visit Navy Pier for a ride on the Ferris wheel
  • Have lunch at Portillo's (classic Chicago hot dogs and Italian beef)
  • Walk along the Lakefront Trail
Day 4

North Side Charm

  • Start your day with breakfast at Ann Sather
  • Visit Wrigley Field and catch a Cubs game (if in season)
  • Explore the shops and restaurants in Wrigleyville
  • Have dinner at Lula Cafe in Logan Square
  • Check out the nightlife in Boystown
  • Hotel recommendation: HI Chicago Hostel located in the Loop and great for budget travelers.
Day 5

Farewell to the City

  • Have brunch at Yolk
  • Visit the Museum of Contemporary Art
  • Go shopping on the Magnificent Mile
  • Have a farewell dinner at Alinea (expensive but worth it)
  • Grab a drink at The Signature Room on the 96th floor of the John Hancock Center

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.

Discovering Chicago's Windy Wonders on a Budget

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.

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.