Choose Chicago: 30 Must-Dos In The Windy City - Updated 2024

Choose Chicago: 30 Must-Dos In The Windy City - Updated 2024
Contributing Writer
| 12 min read

Chicago is a vibrant city filled with art, architecture, culture and food. There is just so much to see and do, from going all the way up the tallest building in America to visiting the beautiful Chicago Cultural Center, or even eating a Chicago-style hotdog. So here’s a list of the top 30 things you should not miss out on while in Chicago:

Lincoln Park

1. Visit the zoo!

Siberian Tiger Lincoln Park Zoo (17562834949)
Source: Photo by Wikimedia Commons user Mobilus In Mobili used under CC BY 2.0

Lincoln Park Zoo is a wonderful place dedicated to connecting people with nature by allowing them to get up close to animals they don’t encounter every day. Lincoln Zoo is home to more than 200 different kinds of species from all around the world. The zoo also showcases state-of-the-art habitats for guests to literally come face-to-face with nature. Don’t miss out on this wonderful wildlife experience, right in the heart of Chicago. And the best part is, admission is free.

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2. Peggy Notebart Nature Museum

Rice Paper Butterflies
Source: Photo by Flickr user Benny Mazur used under CC BY 2.0

The Peggy Notebart Nature Museum is dedicated to the natural history of Chicago, in a way that allows both adults and kids to learn in a fun way. There are many different colourful exhibitions to see, including the Butterfly Haven, the City Science House, Water Lab, and Wilderness Walk habitat exhibits. The Butterfly Haven in particular features more than 200 species of native and exotic butterflies. The museum also offers an array of educational programmes (over 100 in fact) about natural sciences, catering to both adults and children.

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3. North Pond Restaurant

Editor's Note: Photo taken from the establishment's official social account

The latest addition to the a la carte menu at North Pond: Poussin! Grilled Spring Chicken, Baby Carrots, Charred Red Onion Salsa Verde, Schmaltz “Tamale," Lime, Pistachio Mazapan Crumble.

Posted by North Pond on Friday, April 14, 2017

When you go to North Pond Restaurant, it’s really so much more than just enjoying a plate of food. It’s truly an entire food experience. The North Pond Restaurant is located within Lincoln Park, and it serves up modern, creative American food made with the freshest local ingredients. The cuisine is beautiful and complements Chicago’s modern skyline and the peaceful setting of Lincoln Park. The food also reflects the interior artsy décor of the place, creating a whole complex experience in a very subtle yet memorable way.

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4. Follow the yellow brick road to Oz Park

Dorothy & Toto Statue in Oz Park
Source: Photo by Flickr user Ingrid Richter used under CC BY 2.0

Oz Park is exactly what you think it would be, a park that celebrates the Wizard of Oz theme. It’s located in the Lincoln Park community. It’s a great place for parents to bring their children. The “Dorothy’s Playlot” playground is filled with play equipment for little ones to climb, swing, and run. In the “Emerald Garden”, families can enjoy a leisurely afternoon among the beautiful flowers. Throughout the park, there are statues of the Tin Man, Scarecrow, Cowardly Lion, and everyone’s favorites, Dorothy and Toto. It’s a great place for kids, and for parents who were kids themselves when they watched this timeless classic.

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5. Chicago History Museum

South Side Elevated Railroad car 1
Source: Photo by Wikimedia Commons user JeremyA used under CC BY-SA 3.0

The Chicago History Museum is located at the south end of Lincoln Park. It cares for, showcases, and interprets millions of authentic pieces of Chicago, along with U.S. history in general. The museum’s immaculate ability to illuminate the past is a reminder of what really happened once upon a time, sheds light on the present, and compellingly informs of the future. It’s a great place for history enthusiasts, or people who just want to learn more about America.

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6. Have a fern-tastic time at the Lincoln Park Conservatory

Lincoln Park Conservatory
Source: Photo by Wikimedia Commons user Alanscottwalker used under CC BY-SA 3.0

The Lincoln Park Conservatory is a place filled with lush and green flora all year round. From tropical palms to ancient ferns, you can experience it all right in the heart of Lincoln Park. This place is must-see when in Lincoln Park. It offers visitors a wholesome experience with four different display houses, namely the Palm House, the Fern Room, the Orchid House, and the Show House. Each comes with something different, from technicolour flower shows to serene greenery, it’s sure to make you feel transported away. The best part: admission is free for all.

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Old Town Chicago

7. Buy a painting at the Art Fair

Old town art fair 2014 Chicago
Source: Photo by Wikimedia Commons user victorgrigas used under CC BY-SA 3.0

As you can tell from their wide range of museums, Chicago is a city that really celebrates the arts. And believe it or not, there’s always an art fair happening in some part of Chicago, and there’s a way you can navigate exactly where it is. The Art Fair Calendar displays all the current or upcoming art exhibitions and fairs, making it easy for you to visit and be delighted.

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8. Go shopping at the Magnificent Mile

Source: Photo by Flickr user Bert Kaufmann used under CC BY 2.0

A 5-minute drive from Old Town is Chicago’s world famous Magnificent Mile, a 13-block stretch of upscale hotels, amazing mega-malls and some of the best restaurants in Chicago. They have the best boutiques, departmental stores, and shops, to ensure you’ll find whatever you desire, from fashion and food to gifts and everything in between. Most of these stores are unique to Chicago as well. Have an authentic Chicago shopping experience and enjoy a spot of retail therapy.

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9. Grab a pint at the Ale House

Old Town Ale House
Source: Photo by Wikimedia Commons user Seth Anderson used under CC BY-SA 2.0

When visiting Old Town, you have to visit the Old Town Ale House. It’s the only surviving thing that closely resembles Old Town in the 60s and 70s. The interior has tons of personality and stories to tell (if walls could talk!). The owners painted a bunch of very satirical portraits of politicians, and hung them all over the place, including the famous Ale House wall mural, which was painted in 1971. It is a neighbourhood​ landmark, and it’s a classic Chicago joint and a pub you wouldn’t want to miss.

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10. Smell some unique oils at Old Town Oil

Editor's Note: Photo taken from the establishment's official social account

Posted by Old Town Oil on Sunday, November 8, 2020

Old Town Oil makes and sells an array of speciality oils and vinegar, which act as great gifts. They also offer customers a hands-on, interactive culinary experience. Customers can sample, mix, and match from their selection of premium oils and vinegars, and you can even customise​ your creations with your own label. It’s a perfect idea for a gift or a souvenir. All in all, Old Town Oil is really a playground for your palette.

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Lake View Neighborhood

11. Watch a magic show at Uptown Underground

Editor’s Note: Establishment is permanently closed

Uptown Underground features fantastic performances from the best Chicago offers, from cabaret, magic, and burlesque to a whole variety of entertainers. They also have a range of delicious cocktails at the bar, as well as craft spirits, beers, and wines. With all these drinks, it’s obvious that Uptown Underground only allows entry for people 21 and above, so be sure to bring your identification.

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12. Graceland Cemetery

Getty Tomb Graceland Sullivan side window
Source: Photo by Wikimedia Commons user mindfrieze used under CC BY-SA 3.0

It may seem kind of morose and unusual to visit a cemetery while on holiday, but this one is steeped in historical significance. The Graceland Cemetery is tucked away in a quiet intersection between two major Chicago cross streets, Clark and Irving Park. It is the final resting place of many prominent giants in Chicago, from politicians to athletes and even architects whose vision and dedication led to the thriving city that we know today. The cemetery itself was designed by some of the best architects in the country, so while it shows visitors a glimpse of the past, it also alludes to the promising future of Chicago.

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13. Take a bike ride along Lake Shore

Divvy bike Skyline
Source: Photo by Flickr user Danny Navarro used under CC BY-SA 2.0

Riding on a bicycle might be one of the best ways to experience Chicago. It has some of the best cycling routes and it is very bicycle friendly, with many parking areas and roads cordoned off for bikes. Marvel at the beautiful sunrise over Lake Michigan, hear the birds chirp, and enjoy the views of Chicago’s skyline as you experience the best of the city by bike.

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14. Have a Chicago-style hotdog

Mmm... Chicago style hot dogs
Source: Photo by Flickr user jeffreyw used under CC BY 2.0

An all-beef frankfurter, on a pillowy poppy seed bun, topped with mustard, onions, relish, tomato slices, a spear of pickle, and sprinkled with a healthy dash of celery salt; these are the essentials that make the iconic Chicago dog. Lake View has some of the best, authentic Chicago dogs to offer. In particular, be sure to check out Flub A Dub Chub’s and Murphy’s Red Hots.

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15. Gill Park

Editor's Note: Photo taken from the establishment's official social account

The Sandlot will be starting shortly! Grab some snacks and come join us!

Posted by Gill Park on Friday, July 12, 2019

Gill Park is a fully air-conditioned field house, containing everything you need to be entertained; a fitness centre, indoor swimming pool, a gym, a field, and a playground. It’s a great place that focuses on fitness and just old-fashioned sports in general. There are even some aquatics programmes available. During the summer, they have continuous camps for kids to enjoy.

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16. Try an authentic Chicago deep dish pizza

The Perfect Pie
Source: Photo by Flickr user Caribb used under CC BY 2.0

What makes a Chicago pizza different is the depth of it. The pizza has a characteristically high edge, and that deep surface packs more flavour, with chunky tomato sauce and large amounts of cheese. When in Lake View, be sure to try the stuffed pizza from The Art of Pizza. With its flaky crust and zingy tomatoes, it’s a perfect bite every time.

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17. Visit the home of the Bears and Cubs

2016-10-22 Wrigley Field hours before Game 6 of NLCS 2
Source: Photo by Wikimedia Commons user Arturo Pardavila III used under CC BY 2.0

When we mention the home of the Bears, it’s not actual bears! Rather, it’s the Chicago Bears! Wrigley Field is a baseball park on the North Side of Chicago, Illinois. This field is prominent and famous for its ivy-covered brick wall, and the iconic bright red marquee over the main entrance. It’s also the last major league park to have lights installed so that they can play after dark. It’s a great place – THE place in Chicago at least – to watch a game of baseball and just immerse yourself in the contagious energy of the crowds of supporters.

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18. Millennium Park

Source: Photo by Wikimedia Commons user Owenusa used under PUBLIC DOMAIN

Millennium Park is Chicago’s premier green space, with its stunning landscapes, state-of-the-art collection of architecture, hundreds of free cultural programmes like concerts, exhibitions, tours, and family-friendly activities.

The Bean is an iconic draw for visitors and locals alike. It’s awesome to take a crazy photo, and a great place to capture the Chicago skyline. There is always something happening at Millennium Park, and it literally is the heart of Chicago. It’s a must-see for all tourists.

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19. Navy Pier

Navy Pier - Chicago Skyline
Source: Photo by Flickr user Shelby L. Bell used under CC BY 2.0

After Millennium Park, the next stop is definitely Navy Pier! There are so many things to do. From cultural programmes, seasonal celebrations, special events, festivals, fireworks, and entertainment, to public shows in the exhibition hall space, there is always something happening here, winter, spring, summer and fall. Be sure to check out their IMAX theatre in particular, for a very unique movie-watching experience.

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20. Eat some Garrett Popcorn

Source: Photo by Flickr user snowpea&bokchoi used under CC BY 2.0

This world-famous chain store of decadent popcorn started out in Chicago in 1949. They make their popcorn fresh daily, and pop them off with amazing, trademark flavours like CaramelCrisp or Cheesecorn. Even better, you can combine the best of both worlds and order the Garrett Mix. If you buy a gallon’s worth, you can customize your popcorn tin to have the Chicago skyline on it, and you can keep it as a unique souvenir!

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21. Be drawn by the beauty of the Chicago Cultural Center

Chicago Cultural Center
Source: Photo by Flickr user JohnPickenPhoto used under CC BY 2.0

The Chicago Cultural Center sees hundreds and thousands of visitors every year, and for good reason too. The stunning architecture of the building is enough to attract visitors. This place of wonder was crafted by the world’s top architects using the finest materials; rare imported marble for the steps, polished brass and fine hardwoods, and all topped off with the world’s largest stained glass Tiffany dome. There is always something happening at the center, be it musicians playing live music, dance and theatre events, rare art films, lecturers, and of course, art exhibitions. Every year, the Chicago Cultural Center presents hundreds of free international, national, regional, and local artists, musicians, and performers, giving them a platform to showcase their talents in a place where the public will be able to enjoy and learn about the arts.

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22. Visit the Art Institute of Chicago

Art Institute of Chicago
Source: Photo by Wikimedia Commons user Tripp used under CC BY 2.0

The Art Institute of Chicago is one of the top art museums in downtown Chicago, attributed just to its wide repertoire of art pieces. In fact, to date, the Art Institute of Chicago is home to a staggering 87,000 pieces of art. From African to American and from ancient to contemporary, it is home to everything an art enthusiast could want. Even if you’re a layman, the free art tours provided by the museum are extremely comprehensive and engaging.

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23. Treat your sweet tooth at this whimsical candy store

Editor's Note: Photo taken from the establishment's official social account

Chicago candy lovers, rainy day got you down? Stuck at your desk? Need to send a quick gift? Whimsical Candy can come to...

Posted by Whimsical Candy on Wednesday, October 2, 2019

Whimsical Candy is Chicago’s very own fun and original artisan candy store. This candy store is the childhood dream of the owner, and is now a very fun candy shop selling artisanal candies that are a delight to eat as well as to see. The candies are very innovative, and the most unique and famous of all are their Lah Dee Dahs, a roll of hand-made nougat wrapped around a decadent sea-salt caramel, covered with a little chocolate on top. They even have instructions about the different ways you can enjoy this delectable dessert. Above all, stepping into the shop itself is an enthralling experience, so be sure to check it out!

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24. Explore the nightlife

Chicago River at Night
Source: Photo by Flickr user R Boed used under CC BY 2.0

Downtown Chicago has a lot to offer, but it truly comes alive at night. The streets are lined with nightclubs and bars, and they don’t just offer you a sloppy drink, it’s a whole experience. The bars have their own takes on signature cocktails, but also are sure to put a twist on old favorites, and they each have at least one invention for you to try. The accompanying food is also of good quality. Unlike oily pub food, the bars in Chicago serve some top-notch grub, to turn your night into a gastronomical experience. Be sure to check out The Northman and the Mezcaleria Las Flores in particular.

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25. Soldier Field

The Refurbished Soldier Field
Source: Photo by Wikimedia Commons user Johnmaxmena2 used under CC BY-SA 3.0

Soldier Field is an American football stadium on the South Side of Chicago. It opened in 1924 and has been a venue with a lot of historical significance since then. Apart from football games, the stadium also hosts a variety of shows, live performances, and all things fun. If you’re in town and an artist is performing at Soldier Field, don’t miss the opportunity and be sure to watch the show and experience the electric atmosphere of this place for yourself.

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26. Get the best view of the city on top of the Willis Tower

View From The Top Of Willis Tower
Source: Photo by Flickr user Andrew Wilkinson used under CC BY-SA 2.0

The Willis Tower is a 108-storey, 1,451-foot (442-metre) skyscraper overlooking the city of Chicago. It is, in fact, America’s tallest building and a global icon, and of course it’s in Chicago, the city known for its stunning architecture. You can take the elevator all the way up to the top floor, and marvel at the crazy view of the entire city and beyond on the Skydeck. It’s a fantastic place to take photos, because the Skydeck is completely transparent. It’s not for the faint-hearted, but it still is a must-see for all.

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27. Float!

Editor's Note: Photo taken from the establishment's official social account

Everyone takes vacations to relax, and at Float Sixty, relaxation takes on the next level: through floating. Although this may seem strange and foreign, floating is actually a unique relaxation tool that has been around for a long time. Every session lasts for 60 minutes, in a very inviting ‘float room’. The modern suites are equipped with a private shower. The floatation equipment holds 10 inches (25 centimetres) of water, and 1,000 pounds (453.6 kilograms) of Epsom salts, which are guaranteed to calm you down. The whole room is very calming and serene, it’s sure to make you feel relaxed and recharged.

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28. Visit the famous Magnolia Bakery

Magnolia Bakery cupcakes
Source: Photo by Flickr user Alexi Ueltzen used under CC BY-SA 2.0

This bakery that started out in New York has gone on to expand nationwide, and of course, there’s one right in Chicago. From its inception, this bakery has been loved and praised for its hand-made baked goods, vintage décor complete with a pastel colour scheme, and the generally warm atmosphere of the store. They are exceptionally famous for their banana pudding and the vanilla cupcakes.

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29. Borrow some time for the Harold Washington Library

Serenity Library Skylight Chicago Panorama at Harold Washington Library Winter Garden
Source: Photo by Flickr user Spiro Bolos used under CC BY-SA 2.0

Located on the South Loop, Harold Washington Library Center is CPL’s main library. The public library’s main branch features a mix of classic and modern architecture and a winter garden. It’s a great place to escape from the hustle and bustle of the city and to grab a quiet corner in this oasis and sit under the sky-lit area to enjoy your read.

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30. Enjoy a cruise along the Chicago River

Downtown Chicago, Chicago River
Source: Photo by Flickr user Jeffrey Zeldman used under CC BY 2.0

The city of Chicago has some of the best architecture, and what better way to explore and revel in all these man-made wonders than cruising along the Chicago River? The river cruise is truly deigned with the needs of the tourist in mind. You are able to move freely around the boat, to see the buildings from every angle you desire. The water tour will also pause three times, for you to snap picturesque photos of yourself or your friends against the beautiful Chicago city skyline. And now, this river cruise is offered at twilight as well. The city’s architecture really takes on a whole new perspective and energy against the serene setting sun. You’ve got to see it for yourself.

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There's a Chicago for everyone

The city of Chicago is very versatile, and every street has a surprise or a hidden gem. Gastronomic food experiences. Historic museums. Stunning architecture. And enough shopping for days. There really is a Chicago for everyone, so be sure you find yours when you get there. Chicago is beautiful.

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Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


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Kirthana is currently studying at the National University of Singapore, pursuing a degree in Political Science. In her free time, she enjoys writing for leisure and loves to travel whenever the...Read more

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