Free, Cheap and Fun Things to Do in Chicago

When it comes to free, cheap and fun things to do, the Windy City is our kind of town, offering up all kinds of unique attractions, sights and eating experiences.

4 Awesome, Affordable Chicago Hotels

Carlton Inn Midway Chicago, TripAdvisor Award of Excellence Winner.

La Quinta Inn Suites Chicago Downtown, TripAdvisor Award of Excellence Winner.

Fairfield Inn Suites Chicago Downtown River/North, TripAdvisor Award of Excellence Winner.

Best Western River North Hotel, Rated 4 out of 5 on TripAdvisor.

Save on Admission with a Go Chicago Pass

As with most major cities you can visit these days, a great way to save on the cost of tickets to some of the most in-demand attractions and activities is by purchasing a pass.

The Go Chicago Pass is an option worth checking out.

Depending on the type of pass you purchase you can save between 25% to 55% on admissions and tickets.

Some of the major attractions and activities you can use a Go Chicago Pass for include the Big Bus Hop-on Hop-off Tour, Shedd Aquarium, Skydeck, Field Museum,  Adler Planetarium, The Art Institute of Chicago, 360 Chicago Observation Deck, Navy Pier and Architectural River Cruises.

Choose your pass based on how many days, how many attractions or you can even build your own pass.

At many of the attractions your Go Chicago Pass will give you skip-the-line privileges—a great perk when it’s raining or the sun is beating down.

Get Started By Taking A Hop-on, Hop-off Bus Tour

To kickoff your visit to Chicago, we highly recommend going on a hop-on hop-off bus tour. They are a great way to get a sense of the layout of the city, see where the major sites are located and gain interesting and helpful insights and tips.

When it comes to hop-on hop-off tours there are a few different companies to choose from: Big Bus Tours Chicago, Chicago Trolley & Double Decker Co. and City Sightseeing. If you purchase your ticket online you can usually save 10%.

Architectural River Tour

Chicago is known for it’s eclectic architecture.

To understand why, you have to go back to 1871 and “The Great Fire”. The Great Fire raged for three days and destroyed more than 17,000 of the city’s buildings. Out of this devastation rose opportunity, an opportunity for Chicago’s architectural community to create a modern American city.

Wooden structures were banned from being part of the plan, which ushered in steel-framed construction and eventually the world’s first skyscrapers.

Within a couple of years the entire city was rebuilt and a downtown core boasting many architectural styles was the result.

The best way to explore and learn about Chicago’s architectural heritage is by taking an architecture river tour.

These guided tours gently cruise down the Chicago river providing you with a beautiful perspective and point out the unique characteristics and tell the colourful stories behind some of the city’s most notable buildings.

A couple of options to choose from are: 75-Minute Chicago Architectural River Cruise and 90-Minute Chicago Architectural River Cruise.

Go on a Gangster Tour

One of the things that is part of the folklore of Chicago is Al Capone and the gangsters that ruled the city back in the 1920s and 30s.

1920 to 1933 was the Prohibition era, which was when the sale of alcohol was illegal. As a result bootlegging became big business for the North Side Gang (the Irish) and the Chicago Outfit (the Italians) gangs of the city.

Competition was fierce. Eventually a truce was negotiated giving the North Side Gang control of the north side of the city and the Chicago Outfit control of the south side.

Things were civil until the truce fell apart. Once this happened bloodshed ruled the day.

Gang leaders were murdered or severely wounded. Al Capone took over the Chicago Outfit with retribution in his eyes. His bloody reign culminated with the infamous St. Valentine’s Day Massacre.

Tired of the bloodshed in the city, efforts to put Capone and his like behind bars, escalated. Eventually authorities had their man—Al Capone was convicted of tax evasion in 1931 and sentenced to 11 years in prison.

To this day tourists from all over the world are still intrigued by this period in Chicago’s history and the cast of characters that ruled the streets.

One way to explore it further is to go the Lincoln Park & Gangster Tour hosted by Free Tours By Foot. On this tour you will walk in the footsteps of Chicago’s notorious gangsters, stopping at many of the scenes of their crimes and demise—including the site of the St. Valentine’s Massacre–and learn how prohibition affected Chicago.

This tour is totally free although at the end of the tour tipping your guide is appreciated.

If you prefer you’re touring on a comfortable bus with occasional off-and-on points, then the Chicago Crime Tours gangster tour is right for you.

This tour delves a little deeper into the gangster world, and because you’re travelling by bus you get to stop and see a few more of the infamous sites including a secret room, complete with vault, that was discovered in the basement during the construction of Harry Caray’s pub in 1988.

For more Chicago gangster tour options including a nighttime tour check out Viator.

Looking for a free tour?

You’re in luck. The Chicago Greeter Program gives you the chance to hang with a real, authentic Chicagoan as they take you on a tour of their favourite neighbourhoods and local spots. The tour is free but afterwards, if you enjoyed what you saw and heard, your guide will be very appreciative of a tip.

Tour Wrigley Field

Even if you’re not a baseball fan, one of the fun, cheap things you must do when you visit Chicago is to take a guided tour of Wrigley Field  where the Chicago Cubs baseball team plays.

Built in 1914, Wrigley Field is the second oldest stadium in the major leagues.

This tour was excellent. Even one of our reporters, who is definitely not a baseball fan, said the tour was fantastic.

What makes it so great?

The colourful stories, the unique aspects and features your learn about like the ivy on the outfield wall, what happens if a ball gets lost in the ivy, the bleacher bums, the score board, the announcer’s booth and more.

Purchase your tickets online and make sure you schedule your visit on a non-game day.


Because when the Cubs are out of town the tour includes going into the Cubs dugout and the visitors’ dressing room–the same dressing room where the greatest names in baseball history would have suited up; players like Babe Ruth, Hank Aaron, Willie Mays and more.

Note: if you would like your picture in front of the outfield ivy, your tour will cost a few bucks more.

Go to a Chicago Cubs Baseball Game

Once you’ve done the tour of Wrigley Field you just have to go to a game there.

Even if you decide not to do the guided tour of Wrigley, you should still buy yourself a ticket to a Chicago Cubs game. It truly is one of the fun things you can do when visiting Chicago.

The Cubs are one of the most beloved sports teams in the world.

Even though the team hadn’t won the World Series for over 108 years, their fans stood by them (they finally won in 2016). Yes, Cubs fans are passionate about their team and when you attend a Cubs game you can attest to this fact yourself.

The atmosphere at a Cubs game is awesome.

Unlike so many stadiums, the fans here don’t have to be prodded into making noise. Whenever there was a potential turning point in the game, the fans began to cheer and kept cheering. Many times they stood on their feet.

The fans. The green field. The ivy-covered outfield wall. The blue sky. The city in the background. A  Chicago style hot dog in one hand, a beer in the other. There’s nothing like a Cubs game at Wrigley Field.

Get last minute tickets to a concert or game

You never know who might be in Chicago playing a concert or show, or what sporting event could be going on.

A great, reliable source for last minute tickets is Stubhub.

Pause in Grant Park

Grant Park is a large urban park (over 300 acres) located at the foot of the city’s business area. There are a variety of things to check out.

Within the park you’ll find  Millennium Park. Here you’ll find the mesmerizing Crown Fountain with its 50-foot, glass video screen towers at either end featuring the faces of real Chicagoans, and the The Cloud Gate sculpture, affectionately known as The Bean–just try an resist checking out your reflection in this gleaming centre of attention.

Millennium Park also boasts an outdoor concert venue. Many times during the day you can take in a rehearsal. Live performances are usually at night. During the summer, you can even watch a movie there.

Another spectacular thing to see in Grant Park is the Buckingham Fountain.

One of the largest fountains in the world, since 1927 it has wowed the crowds as 134 jets put on a 20-minute dancing water display. For a real show, check it out at night when it’s accompanied by music and lights.

Grant Park is also home to The Art Institute of Chicago, Adler Planetarium, The Field Museum of Natural History and the Shedd Aquarium, but more about these popular spots later.

Head Down to the Navy Pier

Navy Pier is a 3,000-foot-long playground that stretches almost a mile out into Lake Michigan. Here you’ll find theatres, museums, restaurants, shops, special events, people watching, boat watching and shoreline views.

Up for a little excitement? An exhilarating thing to do is to go on a jet boat ride.

Prefer classic transportation? Why not book your spot for a tall ship sailboat cruise past the skyline.

And if you visit Navy Pier in the evening on a Wednesday or Saturday night between Memorial Day and Labour Day you are in for a treat–there are free fireworks on these nights.

Visiting during the summer and looking for a cheap ride?

The Navy Pier free trolley runs from Memorial Day through Labour Day. Pick it up along its route if you want to head down to Navy Pier, or hop on at Navy Pier and use it as a free way to get to some of Chicago’s other popular attractions including The Art Institute, Millennium Park, Maggie Daley Park and Grant Park.

Two Foods You Have to Try

You can’t get very far into your visit to Chicago without a local asking whether you’ve tried one of the foods the city is famous for—deep dish pizza.

Deep dish pizza is baked in a round, high-sided pan similar to a cake or pie pan.

To make sure the crust is baked through, a deep dish pizza is baked longer than a flat crust pizza (approximately 30 minutes). This longer cooking time means you won’t find cheese on the top of a deep dish pizza as it would burn due to the longer baking time. So, instead, the ingredients of a deep dish pizza are in the reverse order of a typical pizza i.e. the cheese goes in first, then the “toppings” and then the sauce.

When we asked Chicagoan’s for their deep dish recommendations the names we heard the most were: Uno Pizzeria & Grill, Girodano’s, Lou Malnati’s Pizzeria, Gino’s East and Pizzano’s.

The other local delicacy you’ll be asked if you’ve tried is a Chicago style hot dog.

What is this exactly?

It’s a steamed, all-beef hot dog topped with yellow mustard, bright “neon” green relish, onions, tomato wedges, a pickle spear, sport peppers and a dash of celery salt served on a steamed, poppy seed bun.

Aficionados will point out that the adding of the toppings must strictly follow this order in order to taste each ingredient with every bite.

You may have noticed one popular condiment is not included–ketchup.

Mention the word “ketchup” and staunch defenders of the Chicago style hot dog are likely to make the sign of the cross.

A true Chicago-style hot dog will never feature ketchup. Why? Because locals insist that ketchup overpowers and destroys the taste of a Chicago style hot dog rather than compliments it.

A couple great places to get an authentic Chicago style hot dog include: Portillo’s and Downtown Dogs.

Take in the Distinctive Sound of the Chicago Blues

During the 1940s African American workers from Mississippi, Alabama and Louisiana headed north to Chicago for industrial jobs and a better life. Many were musicians and who brought with them the Delta blues.

After they settled in Chicago these musicians modified their sound by switching from acoustic guitars to electric ones, they amplified their harmonicas, and added bass, drums and sometimes saxophone.

With that, the distinctive style of Chicago blues was born, a style of music that is synonymous with Chicago still today and continues to be a major influence on other genres including soul, rhythm & blues and rock.

With the blues being such an integral part of the fabric of Chicago, no trip would be complete without spending a couple of hours at one of the city’s blues bars.

One of the oldest blues bars in the city is Kingston Mines. Established in 1968, it’s been home to the blues for over 50 years. Open seven days a week, it features two stages that don’t shut down till 4:00 and 5:00 am. Hungry? Dig in to their full barbecue menu.

Voted best blues club on Chicago’s north side, it features a friendly, intimate atmosphere and some of the city’s hottest players. Another cool thing is B.L.U.E.S. and Kingston Mines offer a dual cover charge, so if you go to one club you don’t have to pay a second cover charge to get into the other one.

Another intimate spot for the blues is Blue Chicago. Get there early as seating is very limited in this narrow space.

At the other end of the spectrum is House of Blues. Located a little further south, it features one of the largest stages in the city.

Buddy Guy is one of the most famous blues musicians from Chicago. He even has a blues club, appropriately called Buddy Guy’s Legends. Every January, Buddy himself performs at the club. Not a night owl? No problem. At Buddy Guy’s Legends they have lunchtime sets at 12:00 pm, Wednesday through Sunday and dinnertime sets, seven nights a week, between 5:00 and 6:00 pm.

The Original Second City Comedy Club

If you love to laugh you’re in the right city. Some would say Chicago is the centre of the comedy universe. First of all it’s home to the original Second City comedy club.

Established in 1959 this improv comedy mecca has produced a who’s who of comedy stars over its six decades of existence, including comedians such as Bill Murray, John Candy, Gilda Radner, Chris Farley, Steve Carrell and Tina Fey.

Any night of the week you can find a venue in Chicago to take in stand-up, sketch or improv comedy. Comedy clubs can found throughout the city. If you’re staying north of the Chicago river a great spot to check out is The Comedy Bar, located above Gino’s East restaurant.

On Tuesday nights The Comedy Bar is particularly  fun because it’s Tomato Throw Show night. As you enter the club you’re handed fake tomatoes, then throughout the night whenever a comedian performs a joke that bombs, you toss a tomato at them. At the end of the night, the comedian who has had the least amount of tomatoes tossed their way, is the winner.

For more options for a night of laughs check out this list of the top comedy clubs in Chicago.

Take in the View

Tall buildings equal great views.

Stretching 1,482 feet into the sky, the Willis Tower (known for years as the Sears Tower) is the second tallest building in the Western hemisphere.

On the 103rd floor (1,353 feet) you can take in the incredible view from the Skydeck which includes the Ledge, a glass box that extends 4.3 feet out from the side of the building.

Another great spot to get a sky-high view of the city is the John Hancock Center’s 360 Chicago Observation Deck.

Located on the 94th floor, this observation area isn’t quite as high as the Willis Tower (103rd floor) but it’s still equally spectacular.  If you’re looking to save a few bucks on the admission fee another option at the John Hancock Center is to head up to the Signature Lounge, two floors higher (96th floor), where admission to this viewing area is the cost of a drink.

The Willis Tower and the John Hancock Center are the first places that come to mind when people think Chicago and great views but they are not the only options. For some more unique options, check out the article: Chicago Rooftops: Panoramic Views of Downtown on a Budget.

Different Museums

Chicago’s architecture has a long and storied past. Learn more about this stuff at the Archicenter, which is a free thing to do all week from 9 A.M. to 5 P.M.

Top up your knowledge of energy-efficient technology at the Peggy Notebaert Nature Museum which is made up of 17,000 square feet of rooftop gardens.

For something a little different, take advantage of free admission Tuesdays and make an appointment to visit the International Museum of Surgical Science where various exhibits portray the breakthroughs and failures that shaped modern surgical science.

Stupendous Strolls

Looking for free things to do and a way to enjoy a little nature?

Head to the Chicago Botanic Garden, a living plant museum spread over nine islands and covering over 385-acres–it’s home to all kinds of stuff including beautiful bird varieties, sculptures and plants from around the world.

Feel like talking to the animals? The Lincoln Park Zoo is one of the most revered in the country and free to visit 365 days a year. Birds, bears,primates, apes, lions, sea lions—they’re all here and more.

A few blocks away you’ll find Oz Park. Named in honour of in honor of Lyman Frank Baum, the author of The Wonderful Wizard of Oz, who lived near by, the park includes statues of the Tin Man, Scarecrow, Cowardly Lion, and Dorothy & Toto.

A trip to Chicago wouldn’t be complete without hitting the Lakefront Trail, the 18-mile paved pathway that runs along Lake Michigan. There are lots of spots to stop along the way including parks, beaches, gardens and concession stands.

A short jaunt north of the City is the unique Skokie Northshore Sculpture Park. Pack a picnic and spend the afternoon winding through the woodlands and past over 60 large-scale contemporary sculptures.

Consider staying at this Hotel

When your Thrifty Tourist reporters visited Chicago, we stayed at the Best Western River North Hotel. This was not complimentary accommodations. We sleuthed it out and paid for it all on our own.

Would we recommend it?

A resounding, Yes.

It was affordable, clean and comfortable. Our room was spacious and had a great shower. It was also located within a couple blocks or less of the Big Bus Hop-on Hop-off tour, the free trolley that goes to Navy Pier, Blues Chicago blues club, The Comedy Bar comedy club, a Portillo’s Chicago style hot dog place, the restaurants of Clark Street, the L train (subway), a grocery store, Walgreens and a McDonald’s for that cheap breakfast.

The daily parking rate was only $25 too–every other hotel we checked out was $40 a day. Lastly, the staff at the front desk were very friendly and helpful.

Don’t forget to Check Groupon for Chicago Deals

ad for Groupon, another way to save on cheap things to do in torontoOne great way to save on local fun things to do in Chicago is to peruse Groupon, the money-saving website that features local discounts in 150 cities. Visit the Chicago “Things to Do” Groupon page or Chicago “Food & Drink” Groupon page and you’ll find savings of anywhere from 40-90% on attractions, tours, boat cruises, theatre tickets, dinner spots and accommodations. The Groupon Chicago pages are a smart place to start when you’re first planning your trip and even when you’re in the middle of your Chicago visit because new deals get added weekly and even daily many times.

Be thrifty and practical! This information was accurate when published, but can change without notice. We recommend you confirm all details with the provider in question before planning your excursion.

Photo Credits: nan palmero, Laertes, MT_Image, Wildcat Dunny, Lori Hebert Photography, sonofabike, auntjojo, Steven Vance, Señor Codo, Girodano’s, Portillo’s, Viator, Big Bus Chicago, Buddy Guy’s Legends, TripAdvisor, Willis Tower.