best places to visit in the USA for 40th birthday

22 Best Things In Downtown Chicago With Teens (2024)

Last Updated on March 1, 2024 by Nicole

I have had the pleasure of visiting Chicago countless times over the last 20 years. My husband was born and raised there and with 8 brothers and sisters, and hundreds of nephews, nieces, and cousins still living in the Chicago area, it is a destination that we visit often and know well. I have spent many nights in downtown Chicago at fantastic restaurants and bars, staying in gorgeous hotels, and of course, enjoying everything that Chicago has to offer. With 4 kids currently between the ages of 17 -25 years old, we have also experienced some spectacular family activities and attractions in Chicago. So, when people ask me what are the best things to do in downtown Chicago with teens, I have a few recommendations up my sleeve!

And so do a lot of other top travel bloggers! In this article, I share not only what I think are the best things to do in downtown Chicago with teenagers, but also what other travel bloggers recommend.

This post may contain affiliate links. That means that I may earn a small commission, at no extra cost to you, if you buy something through my site. This helps me run my website and produce the articles that I hope you find helpful.

Other Fantastic Cities In The United States To Visit With Teens

Chicago is often compared to New York City. It is the third largest city in the USA, behind New York and Los Angeles. Like them, Chicago offers phenomenal restaurants, museums, theatres, outdoor spaces, and professional sports.

As you will see from this article, there are lots of amazing, interesting and fun things to do in downtown Chicago (not to mention amazing weekend getaways from Chicago as well). However, if interested, I have been to almost all major American cities, several of them with my kids. I haven’t written about most of my experiences (a lot of them I visited before I started this blog), but here are some itineraries that you might find helpful:

Best Things To Do In Downtown Chicago With Teens

Here are the 22 best things to do in downtown Chicago with teens. They range from amazing outdoor experiences to world renowned museums with cool interactive exhibits. Some are budget-friendly while others are splurge-worthy. Most are suitable for both younger and older teens, are in and around downtown, and easy to reach with public transportation. All have parking options, but in most cases, parking is expensive in downtown Chicago so try and leave your car behind.

After reviewing this article, if you are interested in the Shedd Aquarium and Skydeck Chicago, plus the Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour, then consider purchasing the City Pass. You can save up to 48% when compared to purchasing each of these individually.

best things to do in chicago
Navy Pier on Lake Michigan in downtown Chicago

By Jennifer from Family Trip Guides

Navy Pier is a “can’t miss” experience in the “Windy City”. Don’t mistake this destination as “just” a shopping centre on a pier on Lake Michigan. It is actually over 3/4 of a mile and filled with over 70 small shops, restaurants, gardens and attractions. There is so much to fun things do at Navy Pier that you could spend several days enjoying it.

The best way to navigate your time is to check out the list of attractions on their website ahead of time. If you are interested in family fun, consider the Chicago Children’s Museum, the Chicago Funhouse Maze, Remote Control Boats, Pepsi Wave Swinger or the most iconic, the Ferris Wheel. You can even catch a live performance at the Yard at Chicago Shakespeare Theater, an enormous live performance stage offering a variety of shows for all ages all year round.

The beauty of Lake Michigan and its shores are not the only nature to enjoy from the Pier. You can also enjoy Crystal Gardens which is a one acre botanical garden on the pier with a six story glass atrium. 

There are also excursions that you can do from Navy Pier on Lake Michigan. My kids loved the high speed thrill ride on Sea Dog cruises. This jet-propelled ride includes 360° spins and lots of splashes.

There are dozens of great restaurants and casual food stalls. They have traditional amusement park food like hot dogs and Dippin’ Dots as well as sit down restaurants. If you haven’t eaten at the famed Billy Goat Tavern yet in Chicago, check it out for great burgers and hot sandwiches. You can also try the famous “Cheezborger!” 

The easiest parking is at the Pier’s garage but you do pay a premium. If you want a more affordable spot, check out Spothero. In addition, free shuttles link the Magnificent Mile if you want to start or end your day with more shopping, or you are staying nearby. The Magnificent Mile is less than a mile away.

best things to do in downtown chicago with teens
View of Downtown Chicago, including Magnificent Mile (Photo courtesy of Pixabay)

The Magnificent Mile In Downtown Chicago

By Lisa of Planning Away

The Magnificent Mile on North Michigan Avenue in downtown Chicago is Chicago’s premier commercial district where you will find amazing restaurants, incredible shopping, and elegant hotels.

Shopping on the Magnificent Mile is a must on any trip to Chicago. There are over 450 retail stores including major department stores such as Macy’s and Nordstroms, as well as speciality boutiques. There are high-end designer fashions available as well as discounted outlet shopping.

Some of the most well known landmarks in the area include the Chicago Water Tower and John Hancock Center (now referred to 875 North Michigan Avenue) which has a rooftop observation deck and fine dining available. There are also countless well known skyscrapers and historic buildings. It is easy to walk around and admire them while shopping or enjoying a meal. The Magnificent Mile is a great place to visit no matter what time of year, but especially during summer vacation.

Some of the best hotels in the city are located on or around the Magnificent Mile. If you want to easily access most of the best attractions in Chicago, this is where to stay. Millennium Park, the beaches of Lake Michigan, Navy Pier, the Chicago Art Institute, among other things, are only a short walk away. You can explore together or let your teens roam around on their own.

Best Hotels in Downtown Chicago

Over the years, I have stayed at some great hotels in Chicago. However, my two favourites are the Omni Chicago Hotel and the Sofitel Chicago Magnificent Mile.

Omni Chicago Hotel

For years, especially when our children were young, this was our hotel of choice. This is an “all-suite” hotel so rooms are very large and every suite not only has a bedroom with one king or two double beds, but also a separate living room area with a sleeper couch. Accordingly, we were able to fit our family of 6 into one suite with everyone having a little bit of their own space and have easy access to everything that downtown Chicago offers.

Sofitel Chicago Magnificent Mile

The Sofitel has a luxurious contemporary feel. We often stayed there when our kids were older or my husband and I were travelling alone. The rooms are still large, but normally are only one room with a bathroom. The hotel is located closer to the designer shops and Lake Michigan. If you are looking for more of an adult experience, or prefer contemporary style, then I’d recommend booking your stay here.

For stays at either hotels, or other options nearby, explore this interactive map and find great prices.
best things to do in Chicago
Cloud Gate or the “Bean” in Millennium Park (photo courtesy of Trisha and Modi from Try Wandering More)

Millennium Park

By Trisha and Modi from Try Wandering More

Located in the heart of Chicago’s downtown, Millennium Park is the largest public space (25 acres) within Chicago’s Grant Park (319 acres). 

Millennium Park is one of the best places to visit in Chicago with its beautiful architecture, landscape and art. The Park can be visited and enjoyed by people of all ages and guess what? It’s free. You’ll love that you don’t have to worry about money, lining-up, planning ahead, etc. Just go, walk around and have a great time.

There is lots to do in Millennium Park. Take photos with ‘The Bean’ or ‘Cloud Gate’ installation that looks like a huge drop of liquid mercury. Admire Jay Pritzker Pavilion, another architectural wonder, with an 11,000 person seating area and an artistic steel canopy. Free concerts are regularly given, especially in summer!

If you’re looking for tranquil spots filled with greenery head to these three spots:

  1. Lurie Garden, a 5-acre botanical garden;
  2. Millennium Park Monument dedicated to the founders; and
  3. Boeing Galleries, with its outdoor modern sculptures.

If you’re with kids, go splash around in the Crown Fountain or take the fascinating 935-feet BP Bridge with beautifully designed stainless steel railings to Maggie Daley ParkHere kids have lots of choices from the skating ribbon, 40-feet rock climbing wall, play garden, mega slide, play boats and Enchanted Forest. See below for more information about popular attractions at Maggie Daley Park.

If you are hungry, head to the Plaza at Park Grill for a delicious meal with a view.

Parking And Public Transportation Recommendations

If you are staying on or near the Magnificent Mile, consider walking and admiring some of the best architecture in North America along the way, not to mention the superb shopping opportunities. It is only a 20-25 minutes walk from either the Omni or Sofitel hotels. However, if you don’t want to walk, there are other options.

To get there by public transport – take the Brown, Green, Orange, Pink, and Purple Lines to Washington/Wabash; Red Line to Lake; and bus to Michigan Avenue. If you’re driving, park at the nearby Millennium Park Garage, Millennium Lakeside, Grant Park North, and Grant Park South. Pre-purchase parking online to save some money but like many places in Chicago, parking will be expensive.

best things to do in downtown chicago with teenagers
Maggie Daley Park (Photo courtesy of Pixabay)

Maggie Daley Park

By Nicole from Go Far Grow Close

Maggie Daley Park is a kid’s dream destination no matter the age and one of the best things to do in downtown Chicago with teens. It offers mini golf, bungee jumping, roller blading and a climbing wall in summer, as well as ice skating in the winter. You can rent equipment or bring your own.

In addition, it offers free use of outdoor tennis and pickle ball courts but you have to bring your own equipment. They are on a first come first use basis unless you purchase a permit for advanced reservation. There are lights for evening play until closing time.

shedd aquarium in downtown chicago
Shedd Aquarium (Photo courtesy of Unsplash)

Shedd Aquarium In Downtown Chicago

By Karen at Outdoor Adventure Sampler

Shedd Aquarium is one of the largest indoor aquariums in the world and the first to include saltwater as well as freshwater exhibits. It’s located on the shore of Lake Michigan, only 30 minutes walk from Crown Fountain in Millennium Park, with excellent views of the lake.

Shedd Aquarium is a research facility that focuses on conservation and animal rescue as well as entertaining the public with incredible displays of life in all water environments.

Aquarium members, Illinois residents, educators, police, firefighters, and military personal can all get free admission. The budget-friendly City Pass for popular Chicago attractions includes admission to the Shedd Aquarium.

Public transportation is the best way to get to Shedd, as parking nearby is limited and expensive. The Aquarium tickets can sell out for the day so reserve ahead so you are not disappointed.

Make sure you see the snow-white Beluga whales. You can hear the clicking and squeals of these “canaries of the sea”. At the Polar Play area, you can touch sea creatures while the whole family will enjoy the antics of sea otters and penguins. You can also see dolphins cavorting in floor-to-ceiling tanks. No matter what your age, it is amazing to see these animals.

Aquatic presentations take place in Abbott Oceanarium throughout the day and are included in your admission. Watch as marine mammals such as California sea lions, Pacific white-sided dolphins, and Belugas respond to their trainers and give an exciting show. If you can, pay a little bit more and have a “once in a lifetime” experience by going behind the scenes to become a trainer for a day.

best things to do in Chicago
A painting in the Art Institute of Chicago (photo courtesy of James from Travel Collecting)

Art Institute of Chicago

James Ian from Travel Collecting

The Art Institute of Chicago is the second largest art museum in the United States (after the Met in New York City). It is home to some of the most iconic pieces of art in the world. 

The museum is centrally located in Grant Park, with its main entrance on Michigan Avenue (a short walk from the Magnificent Mile and adjacent to Millennium Park). A second huge modern wing, designed by the famous architect Renzo Piano, opened in 2009. Together, the two wings house almost 300,000 works of art. 

Some of the most famous American pieces are American Gothic by Grant Wood (possibly the most famous American painting in existence); Nighthawks by Edward Hooper and an Andy Warhol print of Marilyn Monroe. The collection isn’t limited to American art. There are famous pieces by Picasso, Monet and the iconic A Sunday on La Grande Jatte by Georges Seurat.

If you are into architecture, take a peak inside the Stock Exchange Trading Room on the lower level.  Designed by architects Sullivan and Adler in 1894, it was moved to the Art Institute in 1977 when the original Chicago Stock Exchange was demolished.

You can purchase single day tickets to the Art Institute of Chicago at the entrance. Alternatively, you can get a Fast Pass that allows you to skip the general admission lines and gives you quicker access to special exhibitions. You need to purchase these tickets online in advance.

The museum is easily accessible by most public transportation. If you drive, there are underground parking areas a block away. 

Adler planetarium one of the best things to do in downtown chicago with kids
Adler Planetarium (Photo courtesy of Pixabay)

Adler Planetarium

The Adler Planetarium was America’s first planetarium. It was built for the purpose of exploring and understanding the universe. Today, it still inspires millions of visitors and offers a unique experience to see the skies and beyond above Chicago. It offers many fun things for teenagers to do, such as watching incredible shows and playing around with interactive exhibits.

In many people’s opinions, the Adler Planetarium is one of the most engaging museums in the city. The museum has three full-size theaters, interactive games and learning opportunities, and lots of antique instruments on display. It’s also home to the Doane Observatory, where you can see planets, stars, and galaxies up close. It is still an active public research observatory, one of only a few in the United States. active.

With your teens, stop by the Planet Explorers exhibit, and they can launch a rocket. Visit one of the theaters, where 3D and other movies explain some of the most exciting issues in space in thrilling ways.

The building itself is pretty cool to see. It has 12 sides for each sign of the Zodiac. Outside, check out the giant sundial designed by sculptor Henry Moore, and the shiny bronze Copernicus statue in front. The museum was designated a National Historic Landmark in 1987. There are also beautiful views of the city skyline from the lawn, the perfect spot for a picnic lunch.

best things to do in Chicago
View from “360” Chicago on Chicago Observation Deck (photo courtesy of Kylie from Between England and Iowa)

Chicago Observation Deck – 360 Chicago

By Kylie from Between England and Iowa

One of the best things to do in downtown Chicago with teens is to visit one of the observation towers. Chicago has two main observation decks: Skydeck and 360 Chicago. 360 Chicago at 875 North Michigan Avenue (formerly the John Hancock Center and right in downtown Chicago) has some of the best views of the city and Lake Michigan. The observation deck is located on the 94th floor and the tower is home to one of the fastest elevators in the United States.

A unique experience at 360 Chicago is ‘Tilt’. This is a section of windows that are tilted 30 degrees out over the side of the building while visitors hold on to hand rails. As you hang perilously over the side, you get a shocking view of the street 1030 feet below. If you are not a thrill seeker, then head to Bar 94. You can enjoy a large selection of cocktails, beers, wine, hot and soft drinks while taking in the view.

360 Chicago has several different ticket packages. Check online for the most up to date specials. A great money saving tip with an EXTRA experience to share with your teenagers is to take part in the one hour 360 Sky Yoga class. Tickets for the class PLUS free general admission to the observation deck is usually a lot less than a general admission ticket to 360 Chicago. The yoga class is very relaxing and gives you plenty of time to fully appreciate the amazing views!

The nearest CTA train stop is ‘Chicago’ on the red line, approximately an 8 minute walk from 875 North Michigan Avenue.

best things to do in Chicago with your teen
The Ledge on Skydeck Chicago in Willis Tower

Willis Tower – Sky Deck

By Nicole from Go Far Grow Close

Willis Tower, formerly Sears Tower, is the tallest building in Chicago and the third tallest building in the Western Hemisphere. It is the 110 stories and rises 1,451 feet (442 m). It is located in downtown Chicago, in the Chicago Loop, and was completed in 1974. Willis Tower is also home of Skydeck, one of the best things to do in Chicago with teens.

For families looking for thrills and fantastic views of Chicago, the Skydeck Chicago experience is an excellent choice. At 1,353 feet in the air, you can step onto “The Ledge”, glass boxes that extend out 4.3 feet from the Skydeck, and be stunned by the sheer drop to the streets below. The Ledge is the highest observation deck in the United States. You can even take a photo with a view of four states from atop the Skydeck in the Willis Building.

For the most spectacular views, the best time to visit Skydeck Chicago is either just after opening or after sunset. If you’re planning on catching the sunset or taking in the nightscape of Chicago, you should plan on arriving to the Willis Building 30-45 minutes before sunset.

Best things to do in Chicago
Field Museum (photo courtesy of Michele from Endless Family Travels)

Field Museum of Natural History

By Michele from Endless Family Travels

One of the many impressive attractions on the Lake Michigan shorefront is the Field Museum. This world class natural history museum was built in 1921 and the grand building holds an equally grand collection.

As you enter, the huge Stanley Field Hall holds an enormous Titanosaur skeleton – the largest dinosaur ever discovered. Walk deeper into the museum, and you find a massive taxidermy collection – an old method of natural history display – and one that really illustrates the scale and look of the animals. In particular, learn about the Tsavo Man-Eater lions that terrorized railway workers in Africa over a hundred years ago; and see many other displays that teach you about the natural world.

Alongside the historic exhibitions, the Field Museum has 3D and interactive exhibits – keeping the museum relevant and modern. For example, walking up and inside a three-story replica of a Mastaba tomb to being exploring Ancient Egypt. Alternatively, “shrink down” to 1/100th of your actual size to explore the under ground world. You can purchase all-access passes which cover any temporary and 3D exhibitions on display plus the permanent displays.

Don’t miss a walk around the Field Museum building and along the Lakefront Trail. The classical early century architecture and columns make the Field Museum a very beautiful part of the shorefront museum complex. The Field Museum, Adler Planetarium and the Shedd Aquarium are all within walking distance of each other, and make for a brilliant day out on your family vacation in Chicago.

best things to do in downtown chicago with teens
Lake Michigan (Photo courtesy of Pixabay)

Lake Michigan

By Nicole from Go Far Grow Close

One of the coolest things about downtown Chicago that is different from most other major cities in North America is the close proximity to sandy beaches and other waterfront activities. From the stores on the Michigan Mile or Maggie Daley Park, Lake Michigan is less than a mile away. If you are visiting the Shedd Aquarium, Field Museum, or the Adler Planetarium, Lake Michigan is literally steps away.

Chicago’s 26 miles of beautiful lakefront includes public parks and gardens and more than two dozen free beaches that open every summer in Chicago.

Rent a bike, walk or run along the 18 mile paved Lakefront Trail from Ardmore Ave. on the north to 71st Street. Stop and spend the day at the many beaches swimming or boating (like kayaking and paddle boarding). Enjoy one of the many beach cafes and restaurants with stunning views of the city skyline or sunrises and sunsets.

Oak Street Beach is the closest to the Michigan Mile (a 6 minute walk to 360 Chicago). You can rent chairs, bikes, and play beach volleyball.

Spending time at Lake Michigan is one of the best things to do in downtown Chicago with your teens and they will love it. You can easily go to the beach, visit a museum, and do some killer shopping all in one day.

best things to do in chicago
North Avenue Beach (photo courtesy of Jessica from Uprooted Traveler)

North Beach Avenue

By Jessica from Uprooted Traveler

Located in the Lincoln Park neighbourhood, the beach is about a mile north of the famous John Hancock Center and Water Tower Place and offers some of the best views of the Chicago skyline. It is a 20 minute walk along the Lakefront Trail from Oak Street Beach and one of the more popular spots for tourists and locals alike. It is also near Lincoln Park, one of the coolest neighborhoods in downtown Chicago, and Lincoln Park Zoo. The beach is usually open daily from the end of May through Labor Day.

Besides beach lounging, there are designated areas for beachgoers to grill and a bike path along the waterfront. There are also plenty of bike rental shops nearby. During summer, you can check out sunrise and sunset beach yoga or for a chance to truly get up close and personal with the turquoise waters of Lake Michigan, consider renting a wakeboard or paddle board.

Food And Drink Options

If you need a break from the sun, you can mosey over to Castaways Bar and Grill to get a scoop of ice cream (make sure you don’t miss their rooftop patio, which always feels like a party!) For those who prefer to have a bougie-er experience, The Shore Club Chicago is the place for you. It offers handcrafted cocktails and world-class service overlooking the beach and the city’s iconic skyline. 

If you have time after your stop at the beach, be sure to explore Lincoln Park. It is home to a bevy of cool bars and restaurants, like The J. Parker for swanky vibes and rooftop views. Fons, the world’s first all-vegan empanada shop, is also worthy of a stop, with mouth-watering plant-based varieties of the South American delicacy. 

lincoln park chicago
Lincoln Park (Photo courtesy of Unsplash)

Lincoln Park

By Nicole from Go Far Grow Close

Lincoln Park is a nature lover’s dream — manicured gardens, a hidden lily pond, an indoor botanical garden, and lots of lakefront green space with stunning city views. It is also home to Lincoln Park Zoo, one of the oldest free zoos in America. For a fantastic day with your teen, consider heading a few miles away from downtown Chicago and exploring all it has to offer.

The Lincoln Park Zoo was founded in 1868. It has a remarkable collection of animals and it is a wonderful way to spend a few hours, although you could easily spend the day there.

The Lincoln Park Conservatory is an indoor attraction that showcases a wide range of exotic plants and flowers in four different display houses. When it is cold and snowy, you will welcome the heat and greenery of this indoor tropical oasis. Admission is free.

old town in chicago with teens
Old Town (Photo courtesy of Unsplash)

Old Town

By Lina from World of Lina

Besides the shopping and commerical district with all the tall skyscrapers (the Magnificent Mile, for example), Chicago offers many other lovely nearby neighborhoods that are worth a visit.

One of them is Old Town, a charming area with Victorian-era buildings, quaint streets, cool shops and old-school pubs. You may not believe you’re still in Chicago as this neighborhood more closely resembles a town somewhere in Britain than a section of a major American city. However, you are! It is 20 minutes’ walk to North Avenue Beach and Lincoln Park Zoo.

One of the best things about Old Town is there are lots of nice coffee shops to sit and people watch. However, the best one is the 3 Arts Club Café inside the grand central courtyard of the enormous and gorgeous Restoration Hardware furniture store.

Crystal chandeliers hanging from a glass ceiling, a fountain in the middle of the room, and plants in every corner make this café look like a wedding venue in a romantic movie. From a good hot cappuccino with perfect milk foam to fancy Chai Latte – there’s something for everyone’s taste! There’s also a snack menu with delicious choices.

When you and your teen want to take a break from the crowds and traffic of the Magnificent Mile, come to Old Town. Shop and explore, then sit beneath those breathtaking chandeliers and enjoy a refreshment.

Second City Stage with teens
Second City Stage (Photo courtesy of Nicole from Go Far Grow Close)

Second City

By Nicole from Go Far Grow Close

If you are looking for the title of coolest parent ever, then take your teen to see a show at Second City in Old Town. It is one of the best things to do in downtown Chicago with your teen.

Second City is an improv and comedy club that opened in 1959. It has hired, trained or featured some of the most iconic comedians of the last 30 years – Steve Carrell, Steven Colbert, Tina Fey, Amy Poehler, Fred Willard, just to name a few.

However, these shows are unfiltered. Be prepared for adult language. I don’t think there is a topic that is off limits. So, come with your sense of humor and a “I have no idea what is going to happen but that’s what makes this exciting” attitude, or avoid at all costs.

A full bar and snacks are available during the show. Before or after the show, there are dozens of fantastic restaurants and bars in the area so you can make a night of this.

best things to do in chicago
U-505 German Submarine at Museum of Science And Industry (photo provided by Martin Soto from Travel Explorator)

Museum of Science And Industry

By Martin Soto of Travel Explorator

The Museum of Science and Industry is one of Chicago’s most famous museums and one that teenagers love. It’s also one of the biggest science museums in the world, measuring nearly 400,000 square feet. You can easily spend a day (or two or three) walking around the museum, seeing all sorts of interesting things and trying cool interactive exhibits. It’s perfect for families, couples, and even solo wanderers and should be included in any Chicago itinerary. It feels like you can learn something about everything – from world history, aviation history, biology, animals, and all sorts of other crazy stuff. 

The museum truly has it all. It’s famous for the captured U-505 German submarine from WW2. The WHOLE submarine is on display and you can take a guided tour of it. Tickets must be separately purchased for the tour and you might want to book several days in advance in order to secure your time.

If you don’t have time for the tour, simply entering the exhibit is amazing. You are constantly bombarded with sounds, music, original footage, and other World War II weapons and memorabilia that keeps you constantly engaged. It is a must see popular attraction in Chicago.

Another unique experience is exploring a mine. You actually descend in an elevator to an underground mine. It is amazing. Alternatively, try the Interactive Flight Simulator that lets you experience what it’s like to be a pilot. If you go on the right days, you’ll also be able to experience live science experiments. Please check out the website for a schedule of the day’s events.

In terms of parking, you can park in their underground garage, but it’s expensive – it can cost as much as one entry ticket. Consider taking an Uber, Lyft or public transportation. It is too far to walk from the Michigan Mile.

architecture river cruise in chicago with teens
Chicago River Architecture Tour (Photo courtesy of Pixabay)

Chicago River Architecture Tour

Lindsey Puls from Have Clothes Will Travel

Do you know what Chicago means? Or why it’s called “The Windy City” (and it’s not because it’s windy!)? Cruising on a Chicago River Architecture Tour explains this and more. This tour also offers a unique perspective of Chicago, as the tour takes place from a boat, cruising along the Chicago River.

Chicago has a rich history of architecture from the 19th century and 20th century. On this tour, you will learn about this history and see many of the iconic buildings from that period. What is particularly nice for you and your family is all of it comes without any effort. You sit back, enjoy the views, and listen.

If you are also interested in seeing the Chicago Skyline, then book your tour on Wendella. They are one of the original architectural tour boats. Their guides are fantastic, and their boats also come equipped with a full-service bar for drinks and snacks.

Toward the end of the tour, the boat will also take you onto Lake Michigan to give you some fantastic views of the city skyline. Try to take one of the later tours, so you have the chance to see the sunset.

For the price and everything included, it is one of the best attractions to do with your teens in downtown Chicago. In addition, be warned, if you go later on a summer day, it could get a little chilly. If you are wearing shorts, t-shirts, summer dresses, or anything light like that, you should bring a jacket just in case. The rest of the year, dress in layers.

Most river cruise operator’s are located right off the Magnificent Mile, under the Dusable Bridge, on the Chicago River. You can purchase your tickets online or from the ticket office.

Chicago riverwalk with teenagers
Chicago Riverwalk (Photo courtesy of Pixabay)

Chicago Riverwalk

By Nicole from Go Far Grow Close

The Riverwalk transformed the Chicago River’s riverfront from an industrial area for shipping barges to a waterfront oasis. It is pedestrian-friendly and stretches 1.25 miles from Lake Michigan to Lake Street.

There are tons of fun activities that you can do with your teen on the Chicago Riverwalk. You can rent kayaks and explore on your own. Alternatively, you can take guided excursions and learn about the history of the city. You’ll paddle under historic bridges, past cool riverfront patios, and beneath some of Chicago’s most iconic buildings.

You can also fish for free at the Chicago Riverwalk. You’ll just need your own gear and an Illinois fishing license. Cast your line from the Riverwalk’s fishing-friendly areas: Lake Shore Drive near the Lake Street Bridge and the Jetty at Wacker Drive between Wells & Franklin.

You can combine fantastic cocktails or dinner at one of the many restaurants and bars on or near the Riverwalk (like City Winery) with Art on theMART. This is the the largest permanent digital art exhibition in the world. Beginning in early April each year, you can view nightly at 8:30 and 9:00 pm colorful immersive multimedia art projections along the wall of the Merchandise Mart building. They are created by artists from all over the world on a variety of themes and are free to watch.

best things to do in Chicago
Wrigley Field (photo courtesy of Sydney From A World In Reach)

Attend A Cubs Game At Wrigley Field

By Sydney From A World In Reach

Even if you’re not a big baseball fan, one of the best things to do in Chicago is attend a Cubs game at Wrigley Field. Cubs fans are loud and proud, and the atmosphere in Wrigley Field on any game day is electric. Attending a Cubs game is fun for all ages and one of the best things that you can do with your teenagers on a visit to Chicago.

Wrigley Field is located in the aptly named Wrigleyville neighborhood in Chicago’s North Side. With Wrigley Field as its centerpiece, Wrigleyville is home to a number of fantastic bars and restaurants, many featuring food and drink specials on game days. Grab a bite and a drink at a restaurant like Aurelio’s Pizza or Sluggers before heading to the stadium. Even if you plan to have lunch or dinner elsewhere, make sure you leave some time before the game for a quick drink to experience this unique neighborhood and the excitement of Cubs’ fans.

If you’re planning your visit to a Cubs game in advance of arrival, it’s best to purchase your tickets from an official retailer. However, if you’re coming last-minute and looking for cheap seats, check out resale sites like StubHub or Tick Pick, where you can sometimes find deeply discounted tickets.

For those taking public transportation to Wrigley Field, you can take the CTA Red Line to the Addison stop. If you’re driving, park your car in the free remote parking lot. You can then take a free shuttle to and from the stadium.

best things to do in Chicago
Buddy Guy’s Legends Blues Club (photo courtesy of Hannah from Hannah Henderson Travel)

Buddy Guy’s Legends Blues Club

By Hannah from Hannah Henderson Travel

One of the best things to do with teenagers in downtown Chicago is to indulge in the blues music that became famous in the clubs around the city. Chicago Blues is an urban style of blues that is a continuation of the Delta Blues, brought to the city during the great migration to the industrial north in the mid-20th century.

Buddy Guy played for blues legend Muddy Waters and many others, as well as having an illustrious solo career himself. He started Buddy Guy’s Legends music club in 1989, having promised Muddy that he would help to keep the Blues alive. If you love live music and even if you aren’t, a visit to Buddy Guy’s Legends is one of my favorite things. The music is amazing and the vibe of the place is very cool.

Situated on S. Wabash in the Loop (12 minute walk from the Art Institute), Buddy Guy’s is both a music venue and restaurant. It has memorabilia on the walls, many of Buddy’s own guitars, and their creole style food is delicious. Buddy still owns the place and plays regularly. He has been known to pop in and watch from the bar… and if you’re lucky, he might even play with the house band. If you are spending 2-3 days in Chicago, definitely put Buddy Guy’s Legends on your list of evening activities.

best things to do in Chicago
Garfield Conservatory (photo courtesy of Leslie from Backpackers Thailand)

Garfield Park Conservatory

By Leslie from Backpackers Thailand

Looking to escape the hustle and bustle of downtown Chicago? Located close to the intersection of Lake St. and North Central Park, Garfield Park Conservatory is a much-loved attraction and one of the best things to do in Chicago with teens.

Opened in 1908, the Conservatory has more than 600 species and 120,000 plants. They are organized into collections and climate-focused exhibitions, including palm house, outdoor gardens, desert house, fern room, aroid house, sugar from the sun, and others. Stroll along at your own pace and enjoy the beautiful plants. The Conservatory also hosts numerous temporary exhibits, children’s workshops, lectures, and even yoga sessions. Today, more than 250,000 people visit it annually.

It’s free to visit, but it’s recommended to leave a small donation to help with operating costs. Parking is also free of charge. To get there using public transportation, take the Green line to Conservatory-Central Park Drive, or bus 20, 52, 82.

best things to do in Chicago
An old fashion typewriter (photo courtesy of Claire from Claire Pins Travel)

American Writers Museum

By Claire from Claire Pins Travel

The American Writers Museum is a smaller museum located right in downtown Chicago (a few minutes from Millennium Park). It presents the legacy of America’s greatest writers through a variety of highly interactive exhibits and constantly changing special exhibitions. For anyone that loves to read, write or is intrigued by unusual museums, this is a unique attraction in Chicago to enjoy.

This well-curated museum highlights a range of writers, including novelists, playwrights, poets and more. It traces these writers’ cultural impact through the timeline of American history.  

The main exhibition is designed as an immersive experience with brightly coloured, floor-to ceiling book displays and numerous touchscreens, which provide a personalized and interactive experience. The fun and modern layout really makes this museum a great choice even for visitors who are more casual fans of American literature, or who may not be familiar with American literature at all, since you can tailor your visit to suit your interests. 

A particularly fun section of the museum hosts a number of old typewriters. Visitors are welcome to try them out and type up a page to bring home.

Younger visitors might enjoy reading a story in the designated children’s section. It is decorated with beautiful murals of famous book characters and hosts frequent story time readings. 

Literary fans can consider attending special events at the museum, such as lectures, book launches and talks by various authors. 

You can easily plan a visit using public transportation. The museum is located across the street from Millennium Station on the second floor of an office building. An average visit will last around two hours. Children aged twelve and under can visit for free and there are discounts for seniors and students. 

Last Word

Chicago is a fantastic destination for any age and for any length of time. However, if you are looking for a destination that will capture the attention of your teens, then look no more. There are countless activities and experiences to do both indoors and out. Most are either in downtown Chicago or a short walk away. You can spend lots of money enjoying fantastic and unique experiences, or create an exciting itinerary filled with lots of free things to do. Either way, Chicago is one of the best places to visit in the United States with teenagers.

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