The Ultimate Chicago Bucket List: Food, Activities, Places, and More.

July 22, 2022 / Destinations/Travel
Chicago Bucketlist

Has the pandemic made you keep aside your Chicago bucket list? Or are you bored of the monotonous work routine? Then, revive yourself with some most exciting and fun-filled vacations in Chicago. The city, known for its adventure activities and tourist destinations will help you find a work-life balance. 

Chicago is a diverse city with a thriving arts scene, numerous shopping districts, and many restaurants. The city’s public art and architecture are additionally worth seeing. Take in a Chicago River Cruise or visit Millennium Park for a quick look at the city’s skyline.

This article takes you on a trip through some of the best things you could do while in Chicago. 

Free Things to do in Chicago

In addition to being one of the most beautiful cities in the world, Chicago also boasts a wide variety of genuinely free attractions. From museums to ice skating in the city, you’ll never have to feel like you’re on a budget. There are plenty of spaces in the city, so take a break from monotonous routines and explore what it offers.

Here are a few places in Chicago you could enjoy and explore for free.

1. Explore the Chicago cultural center

The Chicago Cultural Centre is a historic site that hosts hundreds of free programs year around. Take a tour of the world’s largest glass Tiffany and check out the various exhibits and events that it has to offer. Also, keep up with the daily schedule of free seminars, film screenings, and dance performances.

2.Do not miss out on the Lincoln Park Zoo

The Lincoln Park Zoo is a must-visit for animal lovers in Chicago. This facility features several animals like tigers, lions, and gorillas in an immersive environment surrounded by tall buildings. The juxtaposition of these animals with the city’s tall buildings makes for an engaging experience.

3.Be part of the Chicago festivals and Social events

Looking for free things to do in Chicago? Festivals are a good bet. There is a variety of free events happening in the city, such as the Chicago Blues Festival and the Summer Dance. Besides being able to throw a party or a parade, Chicago also loves to host various holiday events. Some of these include the St. Patrick’s Day parade and the Christmas Lights Festival. 

4.Conservatories and parks

Make sure your Chicago bucket list does not miss out on the conservatories and parks in the city. Lincoln Park Conservatory, Garfield Park Conservatory, Humboldt Park and Millennium Park to name a few.

5.Buckingham Foundation and Navy Pier

These two are one of the best things to do in Chicago. Enjoy a free water show at the Buckingham Fountain. Take a tour of the Smith Museum of Stained Glass in Navy Pier and explore the park’s 50-acre playground.  Navy Pier Park hosts free fireworks show every Wednesday and Saturday night,


We always remember the food we eat at a place we visit. The Chicago bucket list will be incomplete without trying out the delicious hotdogs, pizzas and fried chicken.

While there are tons of great food options in Chicago, there are a few iconic food items that every diner should try. The diverse cultural backgrounds of Chicago’s dining scene have made it a vibrant and diverse place. There’s something for everyone in this city. Try some of the best bites from some of the city’s most prominent restaurants.


Although Chicago doesn’t have a rich history in the cocktail world, it has a few famous drinks that can be traced back to its past. Some of these drinks can be found in the city’s various bars and restaurants. Before Prohibition, the focus of most establishments was on pouring straight beer or whiskey. However, after the law was lifted in 1933, cocktail lounges started to appear all across the city.

1.A sip of Chicago with Old-Fashioned

The Old-Fashioned is one of the oldest and most famous Chicago cocktails. Although there is no evidence that this drink was invented in Chicago, this is one of the city’s best drinks.

2.Get zingy with the Chicago fizz

Although the Gin Fizz of New Orleans is more popular, the Chicago Fizz is a delicious alternative. It’s a bit unclear where this drink came from, but it was in Chicago before Prohibition began.

3.Something Mysterious, Mamie Taylor

The drink was named after Mayme Taylor, who was an actress from the 1890s in Chicago. It’s believed that the Moscow Mule was inspired by this drink. The drink with the actress’s name misspelt is a mystery.

4.Have a punch with Cohasset Punch

Although the Cohasset Punch is often associated with a town in England, it was invented by a Chicago bartender. 

5.The Infamous Mickey Finn

The Mickey Finn cocktail is one of the most famous drinks in Chicago. Although it’s not exactly known where it came from.

Chicago’s Music & Nightlife

There are numerous great neighbourhoods in Chicago that are perfect for getting away from all hustle-bustle and having a good time. From sports bars and dance clubs to comedy clubs and dive bars, there’s something for everyone in Chi-town.

You have many options to explore the nightlife of Chicago, there are dance clubs known for their unique atmosphere. These clubs also display works inspired by great artists. Theatres that thoroughly modern take on the news that’s sure to make you laugh. The cast delivers shows both hysterical and entertaining at the same time. clubs featuring on-site stand-up comedy show that is known for hosting nationally acclaimed comedians. Arcade bars offer weekly themed games and an ever-changing selection of pop-culture-themed shows. These venues are known for their art gallery and live music. And cocktail lounges that feature a variety of live music and DJ sets, as well as weekly jazz series.


Chicago’s museums are known for their incomparable collections. From Egyptian mummies to Pacific white-sided dolphins, from literature to industry, and from art to industry, you’ll find something in one of the city’s cultural institutions. The city of Chicago is well-equipped to cater to both adults and kids. It also has a variety of museums that are designed to provide a fun and unique experience for both kids and adults. 

Experiencing the underwater world at the Shedd aquarium

The Aquarium’s aquatic offerings are anchored by some of the most popular animals such as snakes, frogs, and predator fishes from the Amazon, as well as sharks, rays, and turtles from the Caribbean. It also features various marine mammals such as sea lions, beluga whales, and penguins. The large facility features seven permanent exhibits. It’s easy to spend a day exploring the various sections of the facility.

The museums for contemporary art and contemporary photography, the Chicago art Institute, Smart museum for art, and Planetarium are all well-known attractions in the city of Chicago. Visit them to get the best experience of your trip.


In Chicago, you can choose your adventure. There are a variety of ways to get in some adrenaline-pumping, such as kayaking through a canyon, climbing a rock wall, or going over a glass-bottom observation deck.

1.Go-Karting on Ice

Thrill yourself and your friends as you drive across an ice-skating rink. This is a great way to have some fun with your friends and family while learning how to navigate through the various corners of the ice. There are many service providers offering karting on Ice.

2.Sunset Kayak on the River

Take a break from the city’s hustle and bustle and head to the Chicago River for a guided tour or a kayaking adventure. You’ll get to see some of the city’s most prominent landmarks, such as the Chicago Bridge and the skyscrapers of the city, while additionally enjoying the great outdoors. For an additional treat, try an evening kayaking trip, which allows you to catch the fireworks show on the lake.

3.Boat Party at the Playpen

One of the most popular events of the summer is the annual Lake Michigan party. People from all over the country attend this event each year. This event is free to the public and everyone is invited to join the party on the lake. Those who own a boat or jet ski are also allowed to join the party. The attendees are also encouraged to bring multiple food and drinks to last all day.

4.Stand-up Paddle Board

Chicago is a city that’s surrounded by waterways, and it’s a great place to explore. One of the most popular urban activities in the area is going on a boat ride on the Chicago River or Lake Michigan. Stand-up paddle boarding is a great way to get some fresh air and experience the city.

5.Learn to Wake Surf on Lake Michigan

If you’re a wakeboarding enthusiast, then Chicago is a must-visit destination. There are numerous places to try and experience this sport in the city, such as Lake Michigan. In addition to instructors, many other service providers can help you get the most out of your trip.

6.Cherry Blossoms in Jackson Park

The Columbian Basin in Jackson Park features around 160 cherry blossom trees that bloom each spring. These trees are located near the Japanese Garden and the Museum of Science and Industry. A short walk away from the basin is the Wooded Island Japanese Garden.

Things to do in Chicago at Night

In Chicago, varying evening activities are depending on the season. For instance, in the summer, there are a lot of cool things to do, but in the winter, there are only a few places that are truly ideal for chilling out.

You could go for a long stroll in the serene and vast parks made to entertain night tourists. The city also has various hangouts where you could enjoy your night. The Museums and art centres remain open late on certain days of the week. Several theatres and bars have live performances and music shows. The eating joints and restaurants function late at night to satisfy your tastebuds and the evening skyline is always mesmerising.

Best Time to go to Chicago

The best time to visit Chicago is from April through May and September and October. During these periods, there are a variety of festivals and events that are usually well-organized and free to the public. The start of spring is a great time to explore Chicago as it’s usually warm and pleasant to walk around. However, it can also be unpredictable. March is the time of year when people start to gather for St. Patrick’s Day celebrations.

Summers In Chicago, lets you enjoy a variety of outdoor activities such as drinking and eating on the city’s many rooftop bars and restaurants. The weather can be warm enough to go to the beach. However, on certain days, the temperature can get too hot and humid.


Everyone has a bucket list, but finding the time to complete it is a tedious task. taking a break from a busy life and enjoying moments for yourself or with your family is priceless. If Chicago is on your bucket list, then why wait to enjoy the summers at one of the coolest and most fun-filled cities in the world. be it art, food, adventure or nature the city offers a unique and versatile experience to all its visitors. Visit our blog, to know more about travel tips, destinations, and more.