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Chicago on a Dime: Tips for Exploring the Windy City on a Budget

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beautiful Chicago River with amazing modern architecture

Chicago is a popular travel destination for many people all over the world, and it’s understandable why given the city’s abundance of five-star hotels, fine dining, and cultural attractions. Although it’s a beautiful city, prices there are infamously high. But do not worry! A sizable bank account is not necessary to enjoy Chicago’s cool culture. To help you make the most of your visit to Chicago, we’ve compiled a massive list of cheap things to do as well as suggestions for how to save money while exploring this incredible city. Here is a short guide on how to visit Chicago on a shoestring budget.

Consider Traveling Off-Season

summer and winter collage

Since the summer is Chicago’s busiest travel season, expect rates to be at their highest and hotel openings to be scarce. In the off-season, the city’s hotel rooms are typically about half empty, which results in significant savings! The opposite is true during the summer, when there are many people and higher prices. However, keep in mind that you’ll experience Chicago’s most bitterly cold weather during the winter. If you can tolerate the cold, this is when you’ll find some of the best prices.

Book Your Flight in Advance

Booking your flight at the right time can help you get the best availability and the lowest price, regardless of whether you are paying with cash or points and miles.

Book A Cheap Flight Tickets

Bookings for flights begin about a year in advance, and prices will frequently change before departure. As a general rule, you should book your airline tickets well in advance because prices tend to increase significantly in the days before departure, preying on any last-minute travelers who are forced to pay a premium. The destination and time of year are just two of the many factors that affect the dynamic pricing patterns of airline tickets.

Some reservations can be made a few weeks in advance, while others are better made months in advance, such as for a trip during a popular travel season when demand is high. To keep an eye on price changes, start tracking flight costs as soon as possible. To be notified when the price of your tracked flights changes, use Hopper or Google Flights.

Determine Which Chicago Airport Offers the Most Affordable Flights

O’Hare and Midway are the two airports in Chicago. Budget airlines serve both, and transportation costs to the city center are comparable; however, due to its closer location, Midway is slightly less expensive. Spirit and JetBlue, two low-cost carriers, typically fly to O’Hare; Southwest and Allegiant, two low-cost carriers, and Frontier typically fly to both. United and American airlines both have hubs at O’Hare, and they frequently offer inexpensive flights to the city.

Chicago O'Hare International Airport (ORD)

No matter how you intend to get to the city from the airport, Midway is more advantageous due to less traffic, shorter drives, less expensive Ubers, and even shorter train rides. Of course, if you’re going to downtown Chicago, that is. Different math may be used by visitors to the suburbs or other Chicago neighborhoods.

From The Airport, Take the L Train

Trains leave from both stations approximately every ten minutes; O’Hare has a Blue Line station, and Midway has an Orange Line station. Given Chicago’s congested traffic, this option is significantly less expensive than taxis, Ubers, or Lyfts, which cost 10 times as much and take almost as long.

Chicago O'Hare International Airport (ORD)

The L train costs significantly less than almost any other mode of transportation and travels to both O’Hare and Midway Airports. Both airports have quick access to downtown via public transportation, specifically the L train, which departs from O’Hare for $5 and takes 40 minutes, and departs from Midway for $3 and takes 30 minutes.

Use Public Transit System to Get Around

There is no need to rent a car when visiting Chicago unless you are driving there. This is a waste of money because Chicago has an excellent public transportation system that makes getting around the city much cheaper and occasionally faster than by car.

City transport

Due to the traffic and expensive parking, driving in the downtown area can be time-consuming and expensive. Use Chicago’s public transportation to completely avoid these exorbitant costs. Here, it makes sense to use public transportation and to walk when you can. Using public transportation can help you save money and avoid the hassle of parking if you’re looking to take a cheap vacation in Chicago.

Stay at a Hostel

Hostel

You’ll have to put off booking a fancy hotel room for the time being if you’re trying to explore Chicago on a tight budget. There is no denying that staying in a hostel is one of the best ways to save money when traveling for those on a tight budget. You can save a lot of money by looking for a cheap hotel room in Chicago and making reservations well in advance. Chicago is home to many high-quality ones. Try Hostelling International, which has a 4.5/5 TripAdvisor rating and is situated in the center of downtown Chicago.

Eat Cheap

When it comes to restaurant options, Chicago has one of the broadest selections you can imagine. If you’re looking to eat well here on a budget, there are lots of options. Eat where the locals eat instead of paying high tourist prices.

restaurants-dining out

A substantial breakfast is the best way to start the day. By skipping lunch, you can save money. Alternatively, you can get a quick snack in the afternoon to get you through until dinner. If you want a cheap dinner option, consider splitting a deep-dish pizza at one of Chicago’s best pizzerias.

Look For the Food Trucks

food truck

Knowing all the top restaurants in Chicago is essential for making the most of your visit, especially given the city’s countless mouthwatering gourmet options. Contrary to popular belief, some of the best restaurants in Chicago don’t have physical locations; in fact, you can usually find them wandering the streets on a sunny day or driving through the city’s nightlife. For every hankering, there is a good truck out there.

Use the Chicago CityPASS to Save Money

It can be difficult to visit Chicago for the first time. There are many enjoyable things to do and see in the large city of Chicago. Making decisions about your itinerary and which attractions to pay for can be difficult. At Chicago’s top 5 attractions, Chicago CityPASS members can save 48% on premium admission tickets. Over the course of nine days, visit the attractions at your own pace and in any order. You can save time and money with a single, simple purchase and mobile ticket delivery.

find coupons and deals

The top consideration when planning a trip is getting the most value for your money, and TripAdvisor named the Chicago CityPASS the best tourism pass in the city. Expedia also endorses them, and CityPASS currently has a TrustScore rating on Trust Pilot of 4.8/5. For their trip to Chicago, many people have already used the Chicago CityPASS and left positive reviews.

Carry Some Essentials

small easy to carry bag

Everything in Chicago will undoubtedly cost more than it does elsewhere, as is the case in any major city. This covers food and other essentials for daily life.

  • If your phone dies, having a portable, rapid charger will save you a lot of trouble.
  • Since there aren’t many laundromats in Chicago’s city center, pack enough clothes for each day of your trip. And make sure to find out if your hotel provides a laundry service.
  • In Chicago, layering is a necessity and the best way to prepare for changing weather conditions. A small improvement can be made with a few extra warm layers.
  • Hand warmers could be a great addition to your luggage if you’re not used to cold weather.
  • Packing cubes, which come in a variety of shapes and sizes, will make the process simple and organized.
  • Considering that most stores in Chicago charge a small fee for bags, bringing your own is a simple way to save money. They are compact enough to fit anywhere and to throw in your purse.
  • Bring this reusable water bottle with you throughout the day to help you stay hydrated, especially in the summer. It has a leak-proof, carry-along lid, so you can keep it nearby or pack it in your day bag. Your water will stay cold for a long time because it is also insulated.
  • It’s a good idea to be prepared in case it rains while you’re traveling because Chicago experiences its fair share of rain in the summer. When traveling, it’s always a good idea to have an umbrella on hand. An umbrella for travel is small and easy to pack in your bag or daypack.
  • Although Chicago has many excellent lodging options, the city can be noisy at night. Bring some earplugs if you are not accustomed to this.
  • Just in case, carry some hand sanitizer with you. The formula of a traditional hand sanitizer is gentle and kills 99.99% of common germs.
  • It’s simple to forget to pack a laundry bag for Chicago, but it’s a useful item to have. This is a good way to keep your clean and dirty items separate since laundry might not always be available.

Go to Navy Pier

Navy Pier, which was finished in 1916, is unquestionably one of Chicago’s top tourist destinations. This year-round destination that extends into Lake Michigan comes to life in the summer with daily cruises departing, live music performances, fireworks displays, and theater. Even in the fall and winter, Navy Pier is bustling with unique events, sights, and things to do for people of all ages and interests.

Chicago Cityscape - Navy Pier

Free activities include exploring this lakefront destination by strolling along the 3,300-foot-long Navy Pier. Swim in the fountain at Polk Bros. Park or watch the summertime fireworks. Many fantastic activities at Navy Pier are free or inexpensive.

Check Out the Chicago Cultural Center

The Chicago Cultural Center, located in a building that is as wide as a city block and was built in 1897, offers residents and visitors alike a place to enjoy amazing art and stunning architecture without spending a dime. Any given day, you might come across people admiring the largest Tiffany stained glass dome in the world, attending a free classical concert, or visiting one of the building’s numerous galleries to view an art exhibit. Don’t worry about paying admission; almost all events held in this building are free and accessible to all.

Chicago city sight

Every Wednesday from 12:15 to 1 p.m., the Preston Bradley Hall offers free classical music performances by aspiring pianists, violinists, cellists, and other musicians. Preston Bradley Hall presents chamber music, including jazz and vocalists, on the first and fourth Mondays of each month from 12:15 to 1 p.m.

Attend the Grant Park Music Festival

The Grant Park Music Festival, which has been Chicago’s summer musical sensation for more than 80 years, shows how classical music performed by a top-notch orchestra and chorus can have a profound effect on a community.

Concerts

Summertime trips to Chicago can be pricey, but this festival in famous Grant Park is a ton of fun for free! Free classical music concerts, radio broadcasts, community events, and more are all included over the course of ten weeks. Summer nights are perfect for classical music.

Discover the Lincoln Park Zoo

Lincoln Park Zoo is committed to being the hub of Chicago’s wildlife in a city where skyscrapers are constructed daily. Here, kids learn to love animals, adults rediscover what it’s like to wonder, and nature is prioritized rather than just an escape. Visit one of the last free zoos in the nation to see more than 200 species of animals, including apes, zebras, and giraffes. The 35-acre attraction introduces visitors to a variety of big and small animals from all over the world, including mammals, birds, and reptiles.

rhino zoo

Throughout the year, the zoo also hosts special events like kid-friendly sing-alongs, outdoor yoga classes, the Summer Wine Fest, and Craft Brews at the Zoo. For the most recent schedule of events taking place during your visit, visit the zoo’s website.

Check Out the Second City

show time festivals

The Second City has been entertaining audiences for more than 50 years and specializes in sketch comedy and improvisation. This is Chicago’s first improvisational theater company, and it’s in Old Town. Amazing standup, improv, and sketch comedy can be seen for only $10. As Stephen Colbert, Tina Fey, and Bill Murray all performed here early in their careers, it’s likely that you’ll see some future celebrities perform.

Visit the Garfield Park Conservatory

One of the biggest and most beautiful botanical conservatories in the country is the Garfield Park Conservatory in Chicago. The Conservatory, also known as “landscape art under glass,” features eight indoor display gardens that house thousands of plant species from all over the world.

The Garfield Park Conservatory

The enormous greenhouse, which is divided into spaces like the cactus-filled Desert House and the lush green Fern Room, is home to about 120,000 plants representing 600 species. Additionally, the conservatory provides free digital tours that lead visitors through its nine unique rooms and garden areas.

Experience Millennium Park

Park in Chicago

Without visiting Millennium Park, a trip to Chicago is not complete. More than just a tourist destination, Millennium Park captures the spirit of Chicago. The famous Cloud Gate statue (also known as “The Bean”), interactive fountains, serene gardens, free events, public art, skating rinks, rock climbing, and a lot of open space are all found on the lakefront campus, which is situated in the center of downtown Chicago.

Go to the Smart Museum of Art

Water lightbulb

The Smart is the University of Chicago’s fine arts museum and is home to exhibitions that provoke thought as well as an exquisite collection of more than 16,000 objects, including contemporary masterpieces, ancient Chinese artworks, rich examples of European painting, and controversial modern art. The galleries of this museum, which is on the campus of the University of Chicago, are always free to visit, and you might run into some academics browsing the collection. The organization collaborates with art academics to create exhibits and educational programs for the general public that promote appreciation of art in all of its forms.

Don’t Miss Out On the Magnificent Mile

One of the most well-known shopping districts in the world, The Magnificent Mile is home to a bewildering assortment of well-liked shops, eateries, attractions, and buildings all on one famous street.

The Magnificent Mile - Chicago

The Magnificent Mile is an excellent location to discover Chicago on a tight budget. This area of the city is the best for shopping and dining, with a variety of glitzy establishments. Enjoy admiring renowned Chicago landmarks like the Tribune Tower, the John Hancock Center, and the Chicago Water Tower even without spending any money. Enjoy the city’s busiest, most crowded shopping district.

Consider Including Harold Washington Library Center on Your List

It’s not always simple to stand out from the crowd and make a mark on Chicago’s famous skyline. But the Harold Washington Library hasn’t had any trouble accomplishing that. The Harold Washington Library also needs our focus for a useful reason. It wants to tell a story in a brazenly postmodern way. Numerous symbols that communicate the building’s purpose, celebrate its setting, and honor its forebears in architecture are amusingly displayed throughout the structure.

The Chicago Public Library’s main branch has nine floors filled with books, computer labs, meeting spaces, and other amenities. Visit the library’s exhibit space on the ninth floor to see art on display, take in the Winter Garden’s skylights, or explore the small Harold Washington Museum, which houses artifacts associated with the structure’s namesake.

View Chicago from Above to Get a Full Perspective

A must-see destination, Skydeck Chicago offers Instagram-worthy moments from the ground to the sky. Skydeck Chicago, a well-liked observation deck, is situated on the 103rd floor of Willis Tower, formerly known as Sears Tower. Step outside the third-tallest structure in the Western Hemisphere, which is in addition to being Chicago’s tallest building. Enjoy breathtaking panoramas of not only Chicago but also the landscapes of four other states. A glass balcony called The Ledge extends four feet beyond the deck. Every day of the week, year-round, the Skydeck is accessible.

chicago-city-view

Start on the lower level to explore the interactive museum that highlights the distinct character, history, and neighborhoods of Chicago. The tallest building in the Western Hemisphere, the 103-story Willis Tower, offers breathtaking views that, on a clear day, extend 50 miles and across four states. If you’re feeling particularly brave, venture out onto The Ledge, a glass-floor balcony that protrudes 1,353 feet from the building’s side and offers unrivaled views.

Enjoy Chicago’s Public Beaches

chicago beach

If you visit during the summer, as opposed to the off-season or the winter, spending time on Chicago’s public beaches is one of the best ways to enjoy the city on a budget. The beaches along Lake Michigan, which stretch from north to south, provide a variety of recreational opportunities. The 26 miles of picturesque lakefront in Chicago are home to a number of public parks and gardens, an 18-mile lakefront trail, and more than two dozen free beaches that are accessible to the public during the summer.

Head to Humboldt Park

There are so many reasons to love Humboldt Park, including its vibrant cultural corridor, historic namesake park, and deep Puerto Rican roots. With a historic boat house, lagoons, and a recreation of Wrigley Field to the west, Humboldt Park is a well-liked summer destination for families. Puerto Ricans make up a large portion of the neighborhood. The National Museum of Puerto Rican Arts and Culture, the only museum in the country entirely devoted to the topic, is located inside the park.

Humboldt Park

When you pass beneath one of the enormous Puerto Rican flags that serve as the neighborhood’s entrances, you’ll know you’re in Humboldt Park. The Paseo Boricua, which has evolved over several generations into the center of the Puerto Rican community in Chicago, is delineated by these flags.

Numerous family-run eateries serving regional specialties, vibrant murals painted by regional artists, and an endless stream of exciting cultural events draw countless tourists each year. The Humboldt Park neighborhood holds numerous annual events to celebrate its history. Each year, more than a million people attend the Puerto Rican Parade in June, making it one of the most popular Latino events in the nation. Or attend Fiesta Boricua, a yearly block party that celebrates the community’s culture, in August.

Take the Chicago Riverwalk

The Chicago Riverwalk offers a lot more activities than just leisurely riverside strolls. The Riverwalk is a way of life that is distinctively Chicagoan and offers something for everyone. Stunning outdoor bars and restaurants, museums, pier fishing, boat trips, kayaking, public art, bird watching, and a harmonious fusion of sublime nature and shiny city are just a few of the things you can eat, drink, do, and explore.

Chicago Riverwalk

As the sun sets, the Riverwalk is the picture of romance. Take a boat tour under the stars, enjoy live music, and dreamily observe the sparkling lights that illuminate the still river waters.

Visit Maggie Daley Park

Chicago

Maggie Daley is a brand-new 20-acre park in the Loop neighborhood that has taken over the site of the previous Daley Bicentennial Plaza. The BP Pedestrian Bridge connects Maggie Daley Park to Millennium Park. A children’s playground, a climbing wall, mini golf, picnic areas, a skating rink, tennis courts, and a formal garden are all available at Maggie Daley today. Programs offered by the Chicago Park District, such as the well-liked Summer Day Camp, are held at the Maggie Daley Fieldhouse. Renting skates and skating around the ribbon is enjoyable in the winter, but you must purchase a ticket in advance.

View the Murals on 16th Street

Instagram pictures

The 16th Street Murals are a great place to see street art come to life and take some awesome Instagram pictures. Bold murals can be seen pretty much everywhere along 16th Street, including on the fronts of houses, along railroad overpasses, and wrapped around train platforms. It’s not graffiti, though. World-renowned street artists use these surfaces as their canvases. When you see how these gifted artists transformed a crowded downtown area into an artistic haven, your mouth will drop. Take a stroll down 16th Street to see famous local artists like JC Rivera and Hebru Brantley’s murals, as well as Belgian street artist ROA’s infamous painting of a severed possum.

One of the top tourist destinations in America is Chicago, a city rich in history, culture, and architecture. The tips we’ve provided will be very helpful if you want to explore this special city without breaking the bank.

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