39 Best Things to do in Chicago to add to your bucket list

Are you visiting Chi-town and looking for the best things to do in Chicago? Chicago has lots of free as well as paid attractions including the Bean at Millennium Park, Crown Fountain, Shedd Aquarium, etc and it’s really hard to know where to begin. Read our recommendations on the best architectural cruises, best views from above, what to eat, and where to go in Chicago in this epic guide. You may also like our post on 22 Best City Breaks in the USA.

Chicago is love. Chicago is home. Chicago is where the heart is. At least for us. Chicago is where we first set foot in the country. The first US city that we ever called home. I could go on forever, but you get the idea.

We love Chicago. And we are so excited to share our favorite spots and things to do in Chicago with you!

Here’s where you come to know all of Chicago’s secrets. Like the best watermelon ice cream that you will ever find and the best time to visit the Bean. And the best deep dish pizza. Hint: it’s not Giordano’s. 

Did you know that the Ferris wheel was invented right here in Chicago? The first Ferris Wheel was built in 1893 to amaze visitors to the Chicago World’s Fair!

Chicago has been inspiring innovators, architects, writers, celebrities, locals, and tourists for decades. The Windy City rose from its own ashes, like the mythical phoenix, after the Great Chicago Fire and continues to soar into the sky even today.

Chicago skyline as seen from Navy Pier

Chicago is truly awesome. Even in the winter. Yes, you heard that right. I will always remember the time I first saw Chicago. The Willis Tower Skydeck had zero visibility, I didn’t feel like getting out at many locations of our Hop-On Hop-Off Tour, tiny snowflakes were flying everywhere, the Magnificent Mile lights could not make it up for the howling wind, my winter coat weighed a ton – honestly, I can go on – but still I loved Chicago.

I loved it for the architecture that I saw through my watery eyes and for the way the locals braved the cold. If you are planning a Christmas trip to Chicago, then read our post on 16 Best Things to do in Chicago in the winter.

Top 4 Best Selling Attractions in Chicago – Purchase your tickets now!
Chicago Ultimate Architecture River Cruise 1.5 hours
Chicago River Cruise 45 mins – perfect for kids and families
See the T-Rex Sue at the Field Museum – Buy tickets now
Chicago Art Museum – the premier art museum in USA

And then, I lived there – through the winter and spring – and experienced summer. Concerts, festivals, beaches, cruises, fireworks, fountains, outdoor restaurants, gardens – you name it!

Chicago blossoms in the summer and this is the best time to visit. There is so much going on and so many activities that you will be hard-pressed to choose between them. And that brings us to our list of the best things to do in Chicago. Expect a little bit of both, popular and off the radar attractions. Expect to be awed, expect to be enchanted. This is Chicago. 

Chicago Navy Pier on a beautiful summer day

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“She is novelty; for she is never the Chicago you saw when you passed through the last time.”
– Mark Twain

What to pack for Chicago

Are you wondering what to bring to Chicago? What you should bring depends on the season you are visiting.

If you are traveling to Chicago in the summer (the best season!) then your bag will resemble a beach getaway bag. For the summer, I will recommend packing shorts, skirts, and cute summer dresses in all lengths.

Best carry on bags for Chicago

Throw in some t-shirts, tank tops, a silk blouse for dining and clubbing, plus a cardigan or light jacket for the nights, and you should be good. Add sunscreen sunglasses, and a hat if you want. You will need a good pair of walking sandals or sneakers since you will be walking a lot in Chicago.

If you are looking for a new pair of sandals or sneakers (always!) then let me introduce you to my 2 favorite companies – Blowfish Malibu and Plaka. Blowfish has some of the trendiest sneakers – I own 3 different styles and they are very comfortable to walk.

If you had to pick one I would recommend the Play sneaker or the Marley sneaker. Both of these are pull-on styles, which I personally love as they get me faster through airport security.

Plaka makes amazing sandals: they are waterproof and hardy but look cute! Win-win! Their palm-leaf sandals are my favorite – they go very well with summer dresses. And last but not least, I love these mesh walking shoes. They come in over 12 vibrant colors.

My favorite warm weather travel shoes

For spring and fall, carry a mix of long and short sleeve shirts, denim pants, sweater dresses, scarves, and a thicker jacket. And yeah, pack walking boots. Chicago is quite trendy so you will see a lot of mustards, olives, and rusts in fall but mints, baby blues, and rose gold shades dominating the show in the spring.

Packing for Chicago in winter is tricky. The #1 item I recommend packing is a soft and warm thermal underwear. Get one that isn’t scratchy or you will be uncomfortable the entire day. I have these fleece underwear and they are excellent at keeping me warm and toasty even in the worse weather.

You need to layer the thermal underwear with long sleeve shirts or blouses and add a thick winter jacket. If you feel colder than most people than add in a layer of sweater under the jacket. Add scarves, hats, and gloves – I personally love these touchscreen phone gloves – they are both cheap and stylish.

My favorite winter walking shoes for Chicago

Best free things to do in Chicago

Chicago has all kinds of free attractions from indoor gardens to public sculptures. You can browse goods at outdoor flea markets or window shop famous brands on Michigan Avenue. You can enjoy the breeze and splash in the cold lake water.

For families, Chicago has free play areas and splash pads for kids. Navy Pier is a whole big free amusement park. Add in the free days at most museums and cultural institutions and you are spoiled for choice. Check out our awesome list of free things to do in Chicago.

In this article, we cover the best things to do in Chicago year-round. For winter travel to the Windy City, check out our post on Best Things to do in Chicago in winter. 

Grant Park

Not many people know but Grant Park is the large urban park which is home to individual attractions such as the Millennium Park, the Art Institute of Chicago, and Buckingham Fountain. It extends all the way down to the Museum Campus and up to Lake Michigan. Most of the free things to do in Chicago are located within Grant Park.

The park is largely built on reclaimed land and is one of the finest urban parks in the country. Grant Park also hosts Chicago’s top cultural events including Taste of Chicago food festival, Lollapalooza, and the Chicago Jazz festival. As locals, we used to walk to Grant Park every evening and had fun attending the many events. 

Cloudgate or the Bean reflecting the skyline in winter

Millennium Park

The northern section of Grant Park has been redesigned as Millennium Park – a large public park with sculptures, fountains, and open-air stage. During Christmas time, Grant Park is where you will find Chicago’s Christmas Tree. Cloudgate, Crown Fountain, Lurie Garden, and Pritzker Pavilion are some of the most popular attractions in Millennium Park.

Here’s a little known fact: the park is located on the roof of a parking garage and hence is also known as the largest rooftop garden in the world. Since it’s completion, Millennium Park is among the top-visited tourist attractions in the country. From Millennium Park, you can see beautiful views of the Chicago skyline. During winter, you can skate under the Chicago skyline in the Millennium Park ice rink. 


Cloudgate in Millennium Park is more famous as ‘The Bean’. This steel sculpture by artist Anish Kapoor resembles a giant bean and has a shiny mirrored exterior that reflects Chicago’s beautiful skyline. This is one of the most Instagram worthy places in Chicago – tourists love to take a variety of photos with the Bean.

We recommend walking around the Bean as well as under it to appreciate this unique sculpture. The architectural and engineering work that has gone into the making of this extremely heave sculpture makes it an extraordinary artwork. The Bean is mostly crowded at all times – to get photos without the crowds you need to visit early in the morning or late at night. 

Crown Fountain

Crown Fountain in Millennium Park is one of the most unique fountains that you will ever see. The fountain consists of a black reflecting pool between two 50 feet tall towers. The towers display digital videos of human faces that open and close their lips. Water continuously cascades down the sides of the tower as well as spouts from between the lips of the faces in sync with the digital animation.

The fountain is active from May through October. Crown Fountain is extremely popular with kids in the summer as they can splash in the water. Our kids love to play in the reflecting pool and walk under the spray of water with other kids. If you are planning to visit with kids, then bring along swimsuits or spare clothes. 

Crown Fountain

Lurie Garden

Lurie Garden is one of the hidden gems of Millennium Park. Visitors often overlook this beautiful garden which has pretty flowers in summer and spring, beautiful landscaping year-round, and stunning views of the skyline. You will also find butterflies, bees, and birds in the Lurie Garden. 

Jay Pritzker Pavilion

The stunning Pritzker Pavilion in Millennium Park is designed by the famous modern architect, Frank Gehry. The acoustic shell is in keeping with his deconstructivist style of architecture. Many music festivals, concerts, and events take place in the Jay Pritzker Pavilion. These summer concerts are one of the best free things to do in Chicago. 

Maggie Daley Park

From Millennium Park, take the beautiful BP Pedestrian Bridge to access Maggie Daley Park. This park is a favorite with children and has a roller-skating (summer) / ice skating (winter) ribbon, q rock climbing wall, tennis courts, lawn areas, a huge children’s play area, and walking paths. While we lived in Chicago, the hubby worked on and designed some of the structural elements in this park – pretty cool! 

Buckingham Fountain in Grant Park

Buckingham Fountain

Chicago’s Buckingham Fountain is one of the largest fountains in the world. Operational from April to October, this fountain has a central jet that shoots 150 feet in the air. Water shows happen throughout the day and if you visit in the evening, you will be treated to a lights and music water show.

We recommend sitting on the benches near Buckingham Fountain and enjoying the water show. You can also see the blue lake behind the fountain and boats sailing by. This is also one of our favorite places to people-watch in Chicago. In the summer, you can find ice cream carts near the fountain – try one of their fruit pops, they are delicious! 

Chicago Cultural Center

Chicago Cultural Center is located opposite Millennium Park. Tourists often overlook this free attraction but it needs to be on your Chicago bucket list. Originally this was the Chicago Public Library building and you will still find literary inscriptions on the top floors. Currently, the building hosts cultural events, exhibitions, and can be seen on a free self-guided tour.

The building is beautiful inside out: it’s Italian Renaissance architecture with Doric columns is striking while the inner two stained-glass domes are breathtaking. The larger 38 foot long Tiffany Dome in Preston Bradley Hall is the largest in the world and a stunning work of art. 

Start of Route 66 sign

The Historic Route 66 Begin sign is a must for road trippers. You will find the sign across the Art Institute of Chicago at Michigan Ave and Adams St (next to the Starbucks). Chicago is where the Mother Road begins before traveling for 2400 miles to end at the Santa Monica Pier in Los Angeles. Road trippers have put stickers on the sign, adding to its unique charm. For more Midwest road trip ideas, read this guide.

Beautiful Tiffany dome inside Chicago Cultural Center

Chicago Riverwalk

The Riverwalk is my favorite part of Chicago and it is wonderful to see how this area is continuously expanding from the unused space that it once was. It is a 1.5 miles vibrant walkway along the Chicago River that extends all the way from Wacker Avenue to the Navy Pier. The entire walk takes about 2 to 3 hours at a leisurely pace.

Along the way, you can photograph Chicago’s iconic architecture and the skyscrapers located along the Riverwalk. Some of the famous buildings along the pathway include the Marina Towers, Trump Tower, etc. You will also find bars, restaurants, boat cruises, landscaped gardens, sculptures, and places to relax along the Riverwalk.

Be sure to check out attractions such as the Vietnam Veterans Memorial, the River Theater, McCormick Bridgehouse, and Chicago River Museum, etc. The Riverwalk is a great place for a date night, people watching, and boat watching. 

One of the most-watched events of the Chicago Riverwalk includes the St. Patrick’s Day River Dyeing Ceremony. Chicago’s St. Patrick’s Day Celebrations are one of the biggest in the world outside of Ireland and attended by tens of thousands of people.

The Chicago River is dyed green and everyone dresses up in green. The bars in the city serve green beer and parades are held downtown. To know more about the March 17th celebrations, check out our guide to celebrating St. Patrick’s Day in Chicago.

Navy Pier

Some call Navy Pier touristy, some call it overrated but Navy Pier is, without doubt, one of the most vibrant and popular places to visit in Chicago. The Navy Pier has both a mix of free and paid attractions including the Crystal Gardens, the Navy Pier Centennial Wheel, kids splash pads, etc. The Navy Pier is also undergoing improvement and we definitely love some of the changes- including the much larger beer garden!

We love riding the Centennial Wheel, the views from the 360-degree glass gondolas are beautiful. If you are looking for an alternate view of Chicago from above – try the Centennial Wheel. Navy Pier is the starting point for many of Chicago’s cruises. We also love seeing the Navy Pier fireworks during summer and the holiday season. If you are looking to eat – check out Giordano’s, Bubba Gump, and Harry Carey’s Tavern. 

Crystal Gardens

This attraction on Navy Pier deserves a special mention because not many people know of its existence. Crystal Gardens is a beautiful indoor tropical garden with lush palm trees, fountains, an enormous glass ceiling, and cozy places to sit. You can also see beautiful views of the lake and skyline from Crystal Gardens. 

Navy Pier Beer Garden

Lincoln Park Zoo

Lincoln Park Zoo is one of the last free zoos in the country. The zoo is home to more than 1100 animals and over 200 species meaning you will find penguins, polar bears, zebras, camels, kangaroos, antelopes, gorillas, flamingos, and more. The Bird House has many colorful tropical birds and is one of our favorite things to see at the Zoo. Also, don’t forget to take a stroll on the Zoo’s Nature Boardwalk – you will see amazing views of the skyline. 

Lincoln Park Conservatory

Located next to the Lincoln Park Zoo, the Lincoln Park Conservatory is a large free indoor garden. That’s right, there are so many gardens in Chicago that it is a paradise for nature lovers. Within the conservatory, you will find four distinct areas – Palm House, Orchid House, Fern Room, and the Show House – which displays beautiful floral arrangements.

The Fern Room is by far my favorite – it seems enchanting, tropical, and primeval at the same time. And somehow reminds me of the Fern Canyon hike (featured in Jurassic Park) in Northern California. Once inside the conservatory, you will forget that you are in Chicago! 

Lakefront Trail

Lakefront Trail is a hit with locals as well as tourists. This 18.5 miles trail connects the Edgewater Beach in the north to South Shore. Using the Lakefront Trail, you can run /walk/bike to many attractions including the Navy Pier, Millennium Park, Grant Park, Museum Campus, etc.

Along the way, you will see stunning views of the lake and the skyline as well as have to access to the beaches. I have walked the trail in summer as well as winter and it is a great workout year-round. 

Kangaroos in Lincoln Park Zoo

Magnificent Mile

The Magnificent Mile is an upscale shopping and dining district in Chicago along Michigan Avenue. While walking on the Magnificent Mile, you will see high-end fashion brands including Armani, Chanel, Burberry, Gucci, Prada, etc.

If you have children, be sure to step inside the Water Tower Place. Inside you will find the American Girl store and Lego store – a hit with my kids.

Some of Chicago’s most famous buildings are also located along the Magnificent Mile, including the Chicago Water Tower, and Tribune Tower. John Hancock Center and it’s famous observation deck is also located along the Magnificent Mile. 

Oak Street Beach

Chicago has many beaches including the Ohio Street Beach, North Avenue Beach, and South Shore Beach but my personal favorite is the Oak Street Beach. This beach is located a short distance away from the Magnificent Mile and can be easily reached. It has great views of the skyline and in spite of the crowds, you can almost always find a free spot.

Additionally, right across the street, you will find Lou Malnati’s Pizzeria on North State St – our favorite deep dish pizza in town. Don’t get us wrong, we love Giordano’s too but adore Lou Malnati’s a tad more!

Beautiful views from the beach

Frank Lloyd Wright Historic District

Frank Lloyd Wright Historic District in Oak Park is a must-see for architecture lovers. While you need to buy tickets to see his home and studio, the Historic District contains many other famous commissions of Frank Lloyd Wright which are free to see from the outside.

Oak Park is a stunning neighborhood with lots of beautiful houses – a staggering 25 of which are designed by Frank Lloyd Wright himself. Here you can see first-hand how his architectural style evolved from Queen Anne cottages to his signature Prairie School of architecture. You can also visit the nearby Unity Temple, which is a UNESCO World Heritage Site. 

“Eventually, I think Chicago will be the most beautiful great city left in the world.”
– Frank Lloyd Wright


Chicago’s Chinatown is the third-largest in the country after New York and San Francisco. We would recommend a stroll in Chinatown if you have the time. It is a fascinating look at the Chinese immigrant culture in the US.

There are many things to see and do in Chicago Chinatown including the Nine Dragon Wall, the Chinese-American Museum, Ping Tom Memorial Park, etc. You can eat dim sum and dumplings, buy rice cakes at the bakery, and shop for lanterns, lucky bamboo plants, and more on Chinatown. 


This is one of Chicago’s hidden gems and my favorite place to go for saganaki. In the old days, Greektown was the heart of Chicago’s Greek community but today it is largely commercial with lots of restaurants and eateries serving delicious Greek food.

Walking through Greektown, you will find blue and white colors of the Greek flag and statues of Greek gods located atop Doric columns. Our favorite eateries include Artopolis Bakery, Athena, and Zeus. Try the gyros and the flaming saganaki….while saying Opa! 

Entrance to Chicago Chinatown

Best indoor attractions in Chicago

Chicago’s indoor attractions will leave you awed and inspired. Its museums are on par with those of New York, London or Paris, especially the Chicago Institute of Art. Apart from the cultural attractions, Chicago is also famous for its culinary and sports attractions as well as a hip party scene. Here are some of the best things to do in Chicago indoors. 

Art Institute of Chicago

The Art Institute of Chicago is one of the largest, oldest, and best art museums in the country. This museum is located in Grant Park and has a vast permanent collection of significant art pieces. Some of the most popular artworks at the museum include Picasso’s The Old Guitarist and Grant Wood’s American Gothic.

The collection also includes works by Rembrandt, Money, Van Gough, and other masters. Apart from the art collection, the museum also hosts many temporary exhibits and events.

The museum building is also worth a look: it was originally constructed in 1893 for the Chicago World Fair. The Michigan Avenue entrance is flanked by two bronze lion sculptures that are iconic of the building.

The museum’s South Garden on Michigan Ave is a beautifully landscaped tranquil space – we love to rest here after a busy day of exploring the museum and surrounding attractions. 

Art Institute of Chicago’s bronze lion sculptures

Willis Tower Skydeck

Willis Tower once held the title of the tallest building in the world and it is just as magnificent today! The tower is 110 stories tall and the Skydeck is located on its 103rd floor. I have been fortunate enough to live in an apartment with clear views of the Willis Tower as well as visited friends who work in Willis Tower – and checked it’s various floors – but my favorite view remains the one from Skydeck.

On a clear day, you can see as far as 50 miles and 4 states of Illinois, Indiana, Michigan, and Wisconsin. The highlight of the Skydeck visit is definitely the Ledge – a clear glass balcony that extends out of the building. Stepping on the Ledge is a thrilling experience as you feel that you are standing in space. The Ledge is also perfect for taking photos of falling in space! 

John Hancock Center

John Hancock Center on Michigan Ave is the fourth tallest skyscraper in Chicago. It is most famous for its 360 Chicago Observation Deck which is located on the 94th floor. 360 Chicago is much larger than Skydeck plus has a bar. In fact, they have a cocktail special package, in which you can sip a drink while enjoying the views. They also have the TILT ride which leans you 30degree over the city, making it seem as if you are falling!

Standing on the glass balcony of the Skydeck Ledge

Shedd Aquarium

Shedd Aquarium is one of the largest indoor aquariums in the country and has a large collection of marine animals. This is one of our favorite places to visit in Chicago with kids.

The Aquarium has a variety of exhibits and habitats including the Caribbean tropical reefs, Amazon river forests, open ocean reef, etc. Interactive exhibits allow children to touch stingrays, see Magellanic penguins, and watch 4D films about marine life.

The highlight of a visit to the Shedd Aquarium is the show featuring beluga whales, dolphins, penguins, sea lions, and more.

Field Museum

If you have a dinosaur crazy child, take the first flight to Chicago and visit the Field Museum of Natural History. This is one of the premier natural history museums in the world and contains a stunning variety of exhibits.

The highlight of a visit to the Field Museum is Sue – the most complete T-Rex skeleton in the world! Besides the T-Rex, they also have most skeletons that kids know about including Allosaurus, Apatosaurus, Brachiosaurus, Maiasaura, Stegosaurus, and Triceratops.

Other exhibits include ancient Egyptian mummies, world cultures, geology exhibits, and animal halls. We recommend keeping aside half a day to a day to see the entire collection. 

Coral Reef inside Shedd Aquarium

Adler Planetarium

While not as popular as Shedd Aquarium or Field Museum, Adler Planetarium has its own charm. The collection includes many space exhibits including meteorites, antique scientific instruments, and spacecraft.

It also has theatres and an observatory. There are a few sculptures located on the planetarium campus, the most famous of which is ‘Man Enters the Cosmos’. From the front of the Adler Planetarium, you can see beautiful views of Chicago. 

Museum of Science and Industry

The Chicago Museum of Science and Industry is an amazing place to take older kids and teens. Even adults love it for the sheer variety of exhibits and experiences including a replica coal mine, a captured German submarine U-505, the first diesel-powered train Pioneer Zephyr, etc.

The exhibits are present from different fields and display advances in space, agriculture, transportation, energy, genetics, anatomy, etc. We would recommend the submarine special exhibit – it is worth the additional fee.   

Chicago food scene

Chicago’s food scene is one of the best in the country. There are so many things to eat in Chicago that you need a minimum of 3 to 4 days to sample the top ones. Some of the must-eat items include the famous deep-dish pizza, Chicago style hot dog, Garett’s Mix popcorn, etc.

Here’s a tip about the deep dish pizza: it takes 30 to 40 mins to cook but at most places, you can preorder as you wait in line for a table. One of the easiest ways to sample Chicago’s best foods is to go on a good tour; you can check the best in our post on the best food tours in Chicago. 

Wright’s Arthur B. Heurtley House in Oak Park

Guided tours of Frank Lloyd Wright buildings

As we mentioned above, Frank Lloyd Wright has several famous buildings in Chicago. You can see many of them for free and even enter the famous Unity Temple but to experience the best of his works including Robbie House and Frank Llyod Wright Home and Studio in Oak Park, you need to buy tickets to a guided tour.

We have done many of FLW architecture tours even outside of Chicago and love them for the detailed information, opportunity to view structure in-depth, and friendly tour guides. If you had to select one, we would recommend the Home and Studio tour over Robbie House – it is an excellent look into the space that FLW designed for himself. 

Symphony Center

Chicago Symphony Center is home to the Chicago Symphony Orchestra. If you have time, watch the Chicago Symphony Orchestra perform. The production is fabulous and the musicians are extremely talented. The building itself is stunning from inside with ornate decor and good seats.

If you don’t have time to see the Opera, stop at Symphony Store – here you can purchase recordings and see pictures of musicians. The Symphony Center is a must for classical music lovers. 

“My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.” 
– Oprah

Chicago Theatre District

Chicago’s Theater District while no Broadway is magnificent in its own way. Located in the Loop, the district has historical buildings in flamboyant architectural styles and features all noteworthy Broadway shows.

The most famous building in the district is undoubtedly the Chicago Theatre and it is a delight to catch a performance at this grand venue. Other popular theaters include the Goodman Theatre, Oriental Theatre, and the Cadillac Palace. 

Jay Pritzker Pavilion at Millennium Park

Chicago Children’s Museum

Located in Navy Pier, the Chicago Children’s Museum is extremely popular with families. The museum’s Dinosaur Expedition is a hit with us, kids can dig for dinosaur bones and perform ‘archeological excavations’ to their heart’s content. Other activities include climbing area, small-town replica, fire station, water play activities, art, etc. 

Best outdoor activities in Chicago

In summer, Lake Michigan shines a brilliant blue. You will find people swimming, sailing, jet-skiing, and kayaking on the lake. Apart from water activities, there are concerts and festivals all over the city. This is also a great time to bike along the lakeshore trail or stroll along the Chicago Riverwalk. Here are our favorite outdoor things to do in Chicago in the summer.

Lake and River Cruise

Chicago’s lake and river cruises are very popular. The river cruise is a great way to know about the city’s architecture while I love the lake cruise for views of the skyline from the lake. There is nothing better than sit and enjoy a Chicago cruise on a hot summer day!

There are also several types of cruises available for both the river and the lake including booze cruises. If you aren’t interested in a cruise but still want to see the city from the water, you can also kayak or paddleboat or take the water taxi.

If you had to choose between them, we would recommend the dinner and fireworks lake cruise – totally romantic with superb views! For a detailed look at the selection of cruises and how to pick one, check out our article on Chicago River Cruise vs Lake Cruise: Which one should you do? 

Views along the Chicago River on St. Patrick’s Day

Wrigley Field

Wrigley Field is the home of the Chicago Cubs and a must for baseball fans. Enjoy a game with family and friends in this historic venue and experience the thrill of watching the Cubs play in hometown.

There are many pubs and restaurants located near Wrigley Field in Wrigleyville and these are perfect to catch up on the post-game excitement. This is by far one of the best things to do in Chicago in the summer. 

Mob and Crime Tour

Today’s Chicago maybe a beautiful, cultural center but the city’s history is laced with mobs, gang wars, and crimes. On these unique Mob and Crime Tours, you can trace the footsteps of major mobsters, hear the daring escapades of famous criminals, and even see a ghost if you are lucky. Depending on which tour you choose, you may also step into a prohibition-era bar or drink beer while listening to Chicago’s bootlegging legacy. Check out our favorite mob and Crime Tours here. 

Soldier Field

Bears, Bulls, Cubs, and Hawks! Chicago is fanatic about its sports teams and football fans must visit Historic Soldier Field on the Lakefront near Museum Campus. This is the home of Chicago Bears. During game season, you will find fans camped around Soldier Field – tailgating and having fun irrespective of the weather – the Chicago Bears play well into December! 

Chicago – the beautiful!

United Center

United Center completes the trio of famous sports fields in Chicago and is home to two sports teams: the Chicago Blackhawks (hockey) and the Chicago Bulls (basketball). United Center is located in West Loop and is popular for its atrium with Michael Jordan’s statue. The team store in the United Center is also huge and you can buy all kinds of team merchandise from jerseys to glasses. United Center also doubles up as a live music venue and hosts concerts when there’s no game. 

Maxwell Street Market

Saving the last for the best. Come Sundays and we drop everything and hotfoot it over to the flea market. This is our absolute favorite tip for one of Chicago’s best hidden attractions: the Maxwell Street Market.

This outdoor market in Chicago has everything from delicious Mexican food to antiques and produce! You will also find live music performances and other events. The street market is a long-held Chicago tradition and is open year-round on Sundays from 9 am to roughly 3 pm. If you happen to be in Chicago on a Sunday then this is an absolute must. 

If you are planning to buy anything then haggle, haggle, haggle. I have scored awesome finds in the past including an old Chicago marquee sign for $10! If visiting in winter, then the hot tamales feel like comfort food.

In summer, you NEED to eat the fruit ice creams. Taste the watermelon or guava or Mangonada and your life won’t be the same again. We mean it – since moving to Houston, we have tried about half a dozen different taquerias but found nothing to compare. 

Chicago Downtown as seen from Willis Tower

In addition to the year-round activities and attractions, Chicago has some really awesome festivals and celebrations including St. Patrick’s Day River Dyeing Ceremony, Lollapalooza music concerts, Taste of Chicago food festival, and the stunning Chicago Air and Water Show. We recommend planning a Chicago trip around these events or adding them to your bucket list for a future trip. 

Did you like our epic list of things to do in Chicago from a locals perspective? Did we miss out on anything awesome? Let us know in comments if a new must-see attraction pops up in the Windy City! 

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23 thoughts on “39 Best Things to do in Chicago to add to your bucket list”

  1. Chicago is a very good city. The performances in the Chicago theater are the most interesting performances I have ever seen. The beach scenery in Chicago is also very beautiful. I plan to go to Chicago again in March. Thank you for sharing the attractions, which are very helpful to me !

    • Yeah, many tourists order the deep dish in a hurry and then are disappointed on realizing it takes so long to cook! But it’s definitely worth the wait!

    • Hi Kristin! Yepp, you just have to visit the Bean. You can skip Willis Tower if you don;t have a head for heights. But IMHO the view is stunning and a complete must-do!

  2. Gorgeous photos! I’ve been to Chicago a couple of times for work but never really explored the city for fun! This totally made me want some Giordanos though, omggggg yummmmm!

  3. I’ve been to Chicago many times.. well the airport that is! I’ve never really had the chance to look around properly. Your blog makes me want to make sure I do next time…

    • Emma, hope you were at Midway rather than O’hare! O’hare is such a nightmare and always super busy. Do plan a trip to the city this summer, it’s really beautiful.

  4. Cool post! Chicago has always been on my bucket list, although I haven’t had the chance to actually explore the city. I’ve driven through it multiple times and live in Minnesota so I’m not too far away but luck has never been in my favor to visit! I’ll get there soon. Thanks for sharing how to spend the perfect day there!

    • You should definitely visit Chicago, Sophie. Doesn’t the skyline look pretty when you drive down the I-90? Minnesota, that’s cool. I have been to the Twin Cities and enjoyed the trip.

  5. Love this post Ketki. I absolutely fell in love with Chicago when I visited in 2013. Additionally to all the great recommendations in your post I also loved hanging out at Navy Pier. Also Pizza at Giordanos is absolute perfection. My couchsurfing host took me there and I almost died and went to Pizza heaven <3 <3

    • Thanks Madeline. I know, isn’t Chicago absolutely gorgeous?! Navy Pier is fun with the funny mirrors and ferris wheel, though touristy. I’d definitely recommend it if you are in the city for more than a day. You are bang on about pizza heaven!

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