Budget Trip to Chicago: 8 Tips for a Money-Saving Vacation

The idea that traveling to a big city will eat a hole in your wallet is entirely false.

Between the airfare and the cost of a hotel room, people believe that a vacation in the city will cost an ungodly amount. Traveling to a city such as Chicago doesn’t have to eat away at your savings account. You can enjoy the beautiful city of Chicago and save money if you plan accordingly.

Use these tips to help plan your vacation to Chicago on a budget.

Purchase a Chicago CityPASS

Have you heard of the Chicago CityPASS? This pass provides travelers with admission to the city’s top attractions for one low price and is a must-need when you’re on a budget trip to Chicago.

When you purchase your Chicago CityPASS, you’ll have direct access to these popular  attractions:

The pass is valid for 9 consecutive days, so you can spread out the fun or have a jam-packed vacation in Chicago – it’s completely up to you. For travelers planning a trip to Chicago on a budget, this pass is exactly what you need. Without this pass, you’ll pay full admission at each popular attraction. Talk about destroying a vacation budget in a matter of minutes!

Father and child viewing the city at 360 Chicago during sunset - Chicago, Illinois, USA
photo credit: 360 CHICAGO via Facebook

Take Advantage of FREE Activities and Attractions

Little do people know, cities such as Chicago are filled with free activities, attractions, and events. From street festivals to concerts, museums to parks, Chicago has a whole world of free entertainment for travelers. To save money and maximize your time, check out these free opportunities for those traveling to Chicago on a budget:

Millennium Park

Defy the notion that enjoying a weekend also means deep pockets. You can surely enjoy a weekend in Chicago on a budget when you visit Millennium Park. Filled with popular art installations such as Cloud Gate, this beautiful park is home to free events and plenty of fun.

Bring a blanket, purchase a snack from one of the many food trucks, and enjoy your time in this downtown Chicago attraction for absolutely free.

Chicago Riverwalk

Stroll along the award-winning Chicago Riverwalk, a 1.25-mile masterpiece on the south bank of the Chicago River. Unravel the pedestrian-friendly charm and scenic wonder that connect Lake Michigan to Lake Street.

chicago river with buildings and skylineNavy Pier

No Chicago vacation is complete without visiting Navy Pier. Witness the beauty and excitement that define Chicago at Navy Pier, a destination that gracefully tops the list of things to do in the city. While it’s free to roam the pier and take in all of the sights, it does cost money to enjoy the attractions. However, a ride on the enormous Ferris Wheel is absolutely worth the small fee! 

Lincoln Park Zoo

Who knew that you could visit the zoo for free? At the renowned Lincoln Park Zoo, guests visit for free and learn all about the zoo’s conservation efforts while seeing their favorite animals. So unlock the secrets to a budget-friendly family trip to Chicago on a budget by including Lincoln Park Zoo in your itinerary.

Close up of baby gorilla and his mom at the Lincoln Park Zoo in Chicago, Illinois, USA
photo credit: Lincoln Park Zoo via Facebook

Magnificent Mile

While shopping at the stores along the Magnificent Mile will cost a pretty penny, it’s still worth the experience to walk through the area.

Chicago Cultural Center

Experience the cultural heartbeat of Chicago at the iconic Chicago Cultural Center, where hundreds of thousands of visitors are drawn each year.

Related Post: Big Bus Tours Chicago Coupons, Reviews, and Tips

Explore the architectural marvel featuring two breathtaking stained-glass domes and indulge in a rich tapestry of free cultural offerings, including music, dance, theater events, films, lectures, and more.

Garfield Park Conservatory

Discover the botanical masterpiece that is Garfield Park Conservatory in Chicago, a true gem referred to as ‘landscape art under glass.’ Wander through one of the nation’s largest and most stunning conservatories, home to thousands of plant species from every corner of the globe.

inside of the garfield park conservatory in Chicago, Illinois, USA
photo credit: Garfield Park Conservatory via Facebook

Free Festivals and Events

Discover the budget-friendly side of the Windy City with cheap Chicago vacations. The city is home to numerous free concerts, events, and festivals throughout the year. If you plan to enjoy on a budget, try planning your trip around one of the many free events, such as:

  • Chicago Blues Festival (June)
  • Grant Park Music Festival (June – August)
  • Chicago Gospel Music Festival (June)
  • Chicago Jazz Festival (August)
  • World Music Festival (September)
  • Free Days at Select Chicago Museums (Free Museum Days Year Round)
  • Taste of Chicago Food Festival (Summer)
  • Free Ice Skating in Millennium Park (Winter)

Batting Practice at Wrigley Field

All baseball fans should get to see the historic Wrigley Field, even if their travel budget doesn’t include a game. Head to Wrigley Field early enough before the game to check out the Chicago Cubs’ batting practice.

exterior view of wrigley field with crowd of people standing outside in Chicago, Illinois, USAGet a 360° View of Chicago

For a small admission fee, you can see the entire city of Chicago from the 94th floor of the John Hancock Center. 360 CHICAGO Observation Deck also offers guests the opportunity to tilt over the side of the building (safely, of course) for daring and breathtaking views otherwise not seen. Visiting Chicago on a budget shouldn’t mean having to sacrifice the views.

See Chicago from the Summit of the Willis Tower

Experience Chicago in a whole new light by riding 103 floors to the Skydeck of the Willis Tower. Challenge your senses as you step onto The Ledge – a glass enclosure that grants you awe-inspiring, adrenaline-inducing views of the city below.

While there’s a small admission fee, the cost is a small sacrifice compared to the extraordinary experiences and fantastic views that await you.

aerial view of chicago skyline during summer daytime

Set a Food Budget

When people think of Chicago, they think of the iconic food. From deep dish pizza to a Chicago-style hot dog, you’ll want to try it all. Don’t be afraid to set aside some of your vacation budget solely for sampling Chicago’s finest cuisine.

Related Post: Famous Restaurants in Chicago: A Foodie’s In-Depth Guide

If you want to dine in style, find a restaurant whose menu prices meet your predetermined food budget. It’s also in your best interest to make restaurant reservations ahead of time as tables at the most popular restaurants fill up fast. Trust me, you want to try the food in Chicago – it might be your favorite part of the trip.

Save on a Hotel with Tripster Chicago

As with most city vacations, a convenient hotel can cost quite a bit. You pay for premium amenities, a prime location, and other extraneous fees. However, if you’re looking to visit Chicago on a budget, book your hotel through Tripster. You’ll find the right hotel for your travels at a great discount, too.

Close up view of the pink neon sign that says "The Drake" in black letter font on top of The Drake Hotel in Chicago, Illinois, USA
photo credit: The Drake Hotel (140 E Walton Pl, Chicago) via Facebook

Travel in the Off Season

One of the best ways to travel to Chicago on a budget is by visiting in the off season. Traveling in the off season ensures that you pay the lowest airfare, hotel room rates, and avoid the crowds.

The summer and winter months tend to be the most crowded times of the year. Try traveling to Chicago from either late March to early June or late August to early November. Keep in mind that Chicago gets chilly (or freezing, depending on your tolerance to the cold) during the fall and winter months, so pack accordingly.

Rely on Public Transportation

Parking in a busy city is pure madness. From dealing with broken parking meters on the side of the road to finding a parking garage that doesn’t cost too much, it’s practically impossible to park in the city. And don’t get us started on the cost of hotel parking garages!

Related Post: Things to Do with Teens in Chicago: 11 Exciting Activities

To avoid these astronomical fees altogether, rely on Chicago’s public transportation. The city has a great train system (known as the L), reliable taxis, and ridesharing services such as Uber and Lyft available to visitors.

Utilizing public transportation allows you to skip out on parking and rental car fees, which can demolish a vacation budget in no time. If you’re planning to vacation in Chicago on a budget, relying on public transportation can help you save money and also avoid the headache of parking.

Chicago skyline aerial drone view from above, lake Michigan and city of Chicago downtown skyscrapers cityscape, Illinois, USAStart Planning Your Vacation to Chicago on a Budget

People may say that going to Chicago on a budget is impossible. Now you know otherwise! Check out Tripster Chicago’s discounted hotels, attraction tickets, and show reservations to stay within your vacation budget.

What Did We Miss?

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Written by Anne Joyce Raymundo

Anne is a Filipino writer who formerly managed and created marketing strategies and materials for numerous websites and eCommerce platforms. Now, her voice...


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