Embarking on your Chicago adventure and craving an unforgettable experience? Dive into my curated Chicago Bucket List, brimming with must-visit places, delicious cuisine, and iconic attractions in the heart of Chicago. While tackling every item on this list during a single weekend might be ambitious, consider it a small glimpse of what Chicago has to offer, enticing you to return for more! Here are over 30 must-do and must-see items on the Chicago Bucket List:
The first iconic Chicago Bucket List item is an Italian beef sandwich. An Italian Beef is the juiciest a sandwich you’ll ever have; thinly sliced roast beef cooked in its own juices on a French roll. The next question you should ask yourself is whether or not you want this dipped or dry? The price for an Italian beef can vary from $9 to $15.
Take a free walking tour around one of Chicago’s neighborhoods.
One of the best ways to explore Chicago, Illinois is on foot through the residential areas. Adding a free walking tour to your Chicago Bucket List will allow you to find some hidden gems that you couldn’t find on Google before. The price for these tours is free; there are no cost.
One of my favorite sandwiches in Chicago is called a Jibarito. A Jibarito is usually a steak sandwich with flattened and fried green plantains instead of bread; some of the toppings include garlic, mayonnaise, cheese, lettuce and tomato. The sandwich is totally filling and worth a Chicago Bucket List item; it is usually accompanied by rice and gandules (pigeon peas). The price for a Jibarito is around $11.
Plan for one of Chicago’s summer festivals.
There’s so much to do in Chicago during the summer and that’s especially true if you’re a fan of festivals. With over 20+ festivals happening this summer, you can expect multiple live shows every week. Fill your Chicago Bucket List with delicious food, community and live music this summer with Chicago’s festivals. The price for Chicago’s summer festivals can vary; the price can range from free admission to $25 tickets per person.
Another iconic spot on the Chicago Bucket List is Rainbow Cone! This delicious ice cream has been a tradition in Chicago for over 95 years so you should definitely make it a tradition to stop by every time you visit. The Original Rainbow Cone is a combination of five delicious flavors, these cones include: chocolate, strawberry, Palmer house, pistachio and orange sherbet. The price for a Rainbow Cone ice cream in a waffle cone can vary from $6 to $9 dollars.
Admire Buckingham Fountain.
Located in the South Loop of Chicago, within Grant Park is Buckingham Fountain. This gorgeous fountain is one of the biggest fountains in Chicago and even has a water display about every hour. Even if you aren’t there for one of the water displays, admiring the fountain and the Chicago skyline around it gives you a pretty view of Chicago. The price to see Buckingham Fountain is free; there is no cost.
Referred to as world famous, Garrett Popcorn is another spot that you should definitely try when you complete your Chicago Bucket List. Their classic cheddar and caramel popcorn mix is my favorite combination, but they do have other flavors like chocolate strawberry and buffalo ranch. The snacks are preservative free and cooked daily. The price for Garret Popcorn can vary from $6 for a bag to around $40 for a tin.
Even if you are not a huge fan of sports, I recommend adding a basketball game to your Chicago Bucket List. The Chicago Bulls are an iconic Chicago team and depending on when your complete you Chicago Bucket List you may find reasonably priced tickets. The price to a Chicago Bulls game is around $50-$100 per person.
Take your photo in front of the Bean.
The Chicago Bean, or a Cloud Gate, is located in Millennium Park. Measuring over 66 feet long and 33 feet high, the Chicago Bean is an iconic attraction to visit and worth a Chicago Bucket List item. Made up of 168 stainless steel pieces, it’s reflective surface shows the skyline in a fun and pretty way; perfect for a photo. The price to see the Chicago Bean (Cloud Gate) is free; there is a curfew in the area that takes affect at about 11 PM.
Located 8 miles away from each other is Guaranteed Rate Field and Wrigley Field. If you’re located near the north side, I recommend stopping by a Cubs’ game and if you’re located near the South side then a Sox game would be closer to you. Of course both fields deserve a spot on your Chicago Bucket List. The prices to the baseball game can vary, but Cubs’ games are generally more expensive; I can expect to spend at least $45-$100 per person.
Try finding the Alphabet Monster.
If you’re a fan of photo walks, finding the Alphabet Monster near Lincoln Yards is a fun activity to add to your Chicago Bucket List. The Alphabet Monster is a photo project painted by Merlot that consists of the alphabet letters located in random spots between Bucktown and Sheffield Neighbors areas. The price to finding and take a picture of the Alphabet Monster is free; this photo walk is no cost.
Walk around one of Chicago’s parks, like Humboldt Park.
One of my favorite thing about Chicago is the green spaces we have available here. In a city full of buildings, it’s comforting to be able to reconnect with nature easily. I recommend adding as many parks as possible to your Chicago Bucket List, but especially my favorite park Humboldt Park on Chicago’s west side. The price of admission to Chicago’s parks is free; there is no cost to walking around and enjoying nature.
Admire the Chicago skyline.
Chicago has a gorgeous skyline and it’s one of the most iconic features of the city. With some of the tallest buildings in the world, these skyscrapers are worth admiring. Finding your favorite view of the skyline is a great Chicago Bucket List activity. The price to see the Chicago skyline is free; there are some awesome paid locations that offer views too though like rooftop bars.
With over 300 acres, there’s always something to do in Grant Park. If you are traveling to Chicago in the summertime your Chicago Bucket List should include checking out which music is playing so that you can have some live entertainment. These festivals are outside so expect some time in the sun. The price for enjoying a music festival in Grant Park is free; these events are no cost.
Walk the Chicago Riverwalk.
At a little over a mile, the Chicago Riverwalk is a gorgeous area where you can observe activities along the river, shop or admire the city skyline and it is perfect for a Chicago Bucket List. There is something to do in the area for everyone whether you’re interested in playing in the water in kayaks or cruises or leisurely enjoying the afternoon. The price to hangout at the Chicago Riverwalk is free, but the water sports do vary in price.
See plants at the Lincoln Park Conservatory.
If you’re a huge fan of plants your Chicago Bucket List should include a visit to the Lincoln Park Conservatory in Lincoln Park. This Victorian era glass house was built in the 19th century is filled to the brim with exotic plants from around the world. The price of admission for Lincoln Park Conservatory is free, but you may have to reserve tickets online.
Take a Chicago street art tour.
Another great way to explore Chicago, Illinois is there a street art tour. With so much street art around the city, you don’t need a formal tour guide in order to make this a fun Chicago Bucket List item. There are some must-see locations like the Greetings from Chicago Mural, the Robin Williams Mural, the iconic Cheshire Cat and so much more. The price to enjoy a street art tour is free; there is no cost to take pictures of street art in Chicago.
If you are a foodie, checking out The Taste of Chicago should definitely be on your Chicago Bucket List. Over the course of multiple days Grant Park is home to one of the worlds’ largest food festivals and you can find a lineup of delicious Chicago restaurant as well as live music. The admission to taste of Chicago is free, but you do have to purchase whatever food you want to eat; there is no cost to be in the Grant Park area during Taste of Chicago.
Another bucket list experience in Chicago is riding the centennial Ferris wheel in Navy Pier. While Chicago has had a Ferris wheel since 1893, the Ferris wheel we have today made its debut in 2016. At almost 200 feet this iconic piece of the Chicago skyline gives you such a beautiful and unique perspective of the city and the lake. The price to ride the Centennial Ferris Wheel is about $18 per person.
Originally carved in secret, the Secret Mermaid is now a gorgeous carved rock located in Chicago’s south side. Previously just being a lakefront rock in Burnham Park, the secret project was discovered in the early 2000s and then re-displayed in 2007. This Chicago Bucket List item is located near Oakwood Beach. The price to visit the Secret Mermaid is free; there is no cost to visit Oakwood Beach.
Located on the north side of Chicago within Lincoln Park is Lincoln Park zoo. This free admission zoo is supported by members, donors and the purchases of visitors and worth a spot on everyone’s Chicago Bucket List. With their mission of care, conservation and community you can find that it’s easy to support Lincoln Park zoo and all their projects. The price to visit Lincoln Park zoo is free; there’s no cost to walk around the zoo and admire the animals.
Located in Humboldt Park is the National Museum of Puerto Rican Arts and Culture. Located at the western gateway of Paseo Boricua, this museum exhibits beautiful artwork from the Puerto Rican diaspora. Not only do I recommend seeing the exhibits, but it is worth checking out what events they have available to as well. The price to visit the National Museum of Puerto Rican Arts and Culture is free; there is no cost to visit this museum.
Hosted every year since 1959, the Chicago Air & Water Show is one of the oldest air and water shows in the United States. This two day event happens above the lake in front of North Avenue Beach and can draw in well over 1 million people every year. You don’t need to be on the beach to enjoy the show, but if that’s where you want to go show up early. The price to watch the Chicago Air & Water Show is free.
Another Chicago Bucket List experience is checking out a Chicago Blackhawks game at the United Center. The Chicago Blackhawks are Chicago’s hockey team and totally worth a Chicago Bucket List item. The price to attend a Blackhawks game can vary between $75 and $140.
The Montrose Bird Sanctuary is another location worth a Chicago Bucket List spot. The Montrose Bird Sanctuary is a resting space for migrating birds along the lakefront. If you enjoy birdwatching or listening to the sounds of nature, I recommend walking around the Montrose Bird Sanctuary in the mornings/evenings for full effect. The price to check out the Montrose Bird Sanctuary is free; there is no cost to walk the trails.
Hike near Riverbank Neighbors Park.
Add a hike to your Chicago Bucket List by stopping by Riverbank Neighbors Park. Riverbank Neighbors Park was once an area full of trash until locals to the area filled it with Illinois native plants & designated trails. The price to check out Riverbank Neighbors Park is free; there is no cost to walk the trails.
Take the train around the Loop.
Another Chicago Bucket List experience is taking public transportation around the city and more specifically the train around the Loop. The price to take the train is $2.50.
Of course seeing a Chicago Bears game must be on your Chicago Bucket List. The Chicago Bears is Chicago’s iconic football team. Not only is watching a live football game a great experience, but seeing a game in the gorgeous Soldier Field area is even better. The price for Chicago Bears tickets is around $75-$150 per person.
The Chicago Pedway is a series of tunnels under the Downtown area of Chicago. This pedestrian walkway connects the buildings, stores, hotels and the train, but underground. If you’re completing your Chicago Bucket List in the winter time, this walkway is a great way to stay warm from the weather. The price to walk around the Chicago Pedway is free; there is no cost to walk through the area.
Another iconic food you need to try for your Chicago Bucket List is a Chicago style hotdog. This beef hotdog on a poppyseed bun is topped with mustard, onions, sweet pickle relish among a few more toppings; fries make a great partner. The price for a hot dog is around $3.
Another holiday tradition in Chicago is walking around the Christkindlmarket. The Christkindlmarket is a holiday market that offers shopping, food and fun for the whole family. You can find food like roasted nuts, bratwurst, hot spiced wine and cute Christmas decorations making it the best Christmas Chicago Bucket List item. The price to walk around the Christkindlmarket free; the food does cost a lot of money though.
Another fun holiday Chicago Bucket List tradition is trying to spot to CTA holiday train. During Christmas time the CTA holiday train includes food that’s going to be donated to charity, but also a very festive display that includes Santa waving to riders on the platform.