15 Fun And Best Things To Do In Chicago


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 at fantastic restaurants and bars, staying in gorgeous hotels, and of course, enjoying everything that Chicago has to offer. With 4 kids, we have also found some spectacular family activities and experiences in Chicago. So, when people ask me what are the best things to do in Chicago, I have an opinion or two.

And so do a lot of other travel bloggers! In this article, I share not only what I think are the best things to do in Chicago, 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 Great American Cities

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, it 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 Chicago. 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 Chicago

Here are the 15 best things to do in Chicago. They range from amazing outdoor experiences to world renowned interactive museums, and from budget-friendly to splurge-worthy. Most are family friendly, close to downtown and easy to get to with public transportation. All have parking options, but in most cases, parking is expensive in downtown Chicago so consider other means to get there.

The Magnificent Mile

By Lisa of Planning Away

The Magnificent Mile 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 beach, Navy Pier, the Chicago Art Institute, among other things, are only a short walk away.

Best Hotels in Chicago near Magnificent Mile

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 the Magnificent Mile 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. If you are looking for more of an adult experience, or prefer contemporary styling, then I’d recommend booking your stay here.

For stays at either hotels, or other options nearby, take a look at this interactive map and the great prices offered by

Millennium Park

By Trisha and Modi from Try Wandering More

best things to do in Chicago
The Bean in Millennium Park (photo courtesy of Trisha and Modi)

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

This 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 given regularly!

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.

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

Parking And Public Transportation Recommendations

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.

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.

“360” Chicago

By Kylie from Between England and Iowa

best things to do in Chicago
View from “360” Chicago (photo courtesy of Kylie Neuhaus)

One of the best things to do in Chicago 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) 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 360 Chicago experience is ‘Tilt’. This is a section of windows where visitors hold on to hand rails and are tilted 30 degrees out over the side of the building, looking 1030 feet below to the street. For visitors who aren’t thrill seekers, Bar 94 has a large section of cocktails, beers, wine, hot and soft drinks where you can sit and enjoy 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 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.

Museum of Science And Industry

By Martin Soto of Travel Explorator

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

The Museum of Science and Industry is one of Chicago’s most famous museums. 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 and seeing all sorts of interesting things. It’s perfect for families, couples, and even solo wanderers. 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 have always wondered what it would be like to descend into and explore a mine, you can also do that here.

Another must-see exhibit is 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 (which kids will love). 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 or public transportation.

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 these iconic buildings.

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 take you onto Lake Michigan to give you some fantastic views of the Chicago Skyline. Try to take one of the later tours, so you have the chance to see the sunset. However, be warned, this portion can be a little chilly. If you are wearing shorts, t-shirts, summer dresses, or anything light like that, you should bring a jacket.

Wendella’s office is located at 400 Michigan Avenue. You can purchase your tickets online or from the ticket office, the price is the same.

By Jennifer from Family Trip Guides

best things to do in chicago
Navy Pier

Navy Pier is a “can’t miss” experience on your Chicago trip. 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 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, an enormous live performance stage offering a variety of shows for all audiences 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 6 story glass atrium. 

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.

Shedd Aquarium

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 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, kids 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.

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.

Attend A Cubs Game At Wrigley Field

By Sydney From A World In Reach

best things to do in Chicago
Wrigley Field (photo courtesy of Sydney)

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.

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.

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

If you’re 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, where you can then take a free shuttle to and from the stadium.

Field Museum of Natural History

By Michele from Endless Family Travels

Best things to do in Chicago
Field Museum (photo courtesy of Michele)

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 exhibitions – keeping the museum relevant and modern. 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.

Art Institute of Chicago

James Ian from Travel Collecting

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

The Art Institute of Chicago is the second largest art museum in the United States (after the Met in New York City) and 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, of course, and 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 at the entrance or 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, but if you drive, there are underground parking areas a block away. 

Buddy Guy’s Legends Blues Club

By Hannah Henderson from Hannah Henderson Travel

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

One of the best things to do in 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. A visit to Buddy Guy’s Legends is one of the best things to do in Chicago, whether you are into blues music or not. It is just a really cool experience.

Situated on S. Wabash in the Loop, 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.

North Avenue Beach

By Jessica from Uprooted Traveler

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

When you think about Chicago, you may not think of beaches, but it’s actually full of them (26 in all in fact), thanks to its location perched along the shores of Lake Michigan. Out of Chicago’s selection of beaches, though, North Avenue Beach is a favourite of locals and tourists alike and one of the best things to do in Chicago to enjoy some of its natural beauty.

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 city’s skyline. The beach is usually open daily from the end of May through Labor Day, with swimming permitted when lifeguards are on duty.

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. Even when the Windy City’s infamous weather isn’t quite conducive for donning a bikini, the paths along the lake shore are wonderful for walking and allowing you to soak up the expansive lake and skyline views. 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!) or if you prefer to have a bougie-er experience, The Shore Club Chicago is the place for you, offering 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, home to a bevy of cool bars and restaurants, like The J. Parker for swanky vibes and rooftop views, and Fons, the world’s first all-vegan empanada shop, with mouth-watering plant-based varieties of the South American delicacy. 

Garfield Park Conservatory

By Leslie from Backpackers Thailand

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

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.

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.

American Writers Museum

By Claire from Claire Pins Travel

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

The American Writers Museum is a smaller museum located right in downtown Chicago, which 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 one of the best things to do in Chicago.

This well-curated museum highlights a range of writers, including novelists, playwrights, poets and more, and traces their 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 and 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, which 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, as the museum is located across the street from Millennium Station on the second floor of an office building and elevators are available. 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. 

Old Town And 3 Arts Cafe

By Lina from World of Lina

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

One of them is Old Town, a charming area with Victorian-era buildings, quaint streets, small 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.

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 almost look like a wedding venue in a 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.

Sitting beneath those breathtaking chandeliers and enjoying a good cup of coffee is definitely one of the best things to do in Chicago!

Last Word

Chicago is a fantastic destination for any age and for any length of time. There are truly endless activities and experiences to do both indoors and out. You can also find ways to have lots of fun without spending a lot of money. The next time that you are considering your next weekend getaway or family trip, keep Chicago in mind.

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