12 Best, Fun and Unique Things to do in Chicago

Things to do in Chicago


Planning a trip to Chicago, and you are thinking of the memorable things to do while in the city? Then pack those bags because you will have a fantastic time, especially with friends and family. 

Chicago! The city of the Willis Tower is incredibly fascinating with its magnificent edifice, towering and breathtaking. It implores tourists with beautiful side attractions that only leave unforgettable memories. This spectacular city is located on the Southwestern shores of Lake Michigan and is refreshed by two great rivers, the Mississippi River and the Great Lake Watersheds.

Grab your swimsuits because the sandy beaches beckon with a flowing passion that gives you summer vibes. Visiting the lakes and waterfront sheds is a beautiful remarkable sight, one of the fantastic things to do in Chicago. If you are a music enthusiast, a front-row seat at the Chicago Symphony Orchestra will make your day.

Chicago city is structurally beautiful and has scenery that wows your sight. So, if you are looking for things to do in Chicago while on a trip, then just follow this article, and we will give you a tour of the city.

Here is a list of all the fantastic things you can do in Chicago

Things to do in Chicago for Couples

1. Sail the Lake Michigan

This is one of the most romantic things to do in Chicago with your partner. Set sail on a luxury yacht or cruise ship and take in the beauty of the lake from a vantage point. Immerse yourself in the beauty of the calm waters and delight in the view of the outstretched water.

At Lake Michigan, tourists can tour the lake using the 148ft Windy of Chicago or the 114ft Manitou. These spectacular ships take you on a voyage of bliss, giving the couples a mesmerizing perspective of the city’s skyline.

2. Enjoy a theatrical evening at the Chicago Theatre

Chicago is known for one prominent feature, and that is its magnificent high-rise landmarks. As a result, couples can enjoy a date night, snuggling up to each other to the delight of show-stopping performances.

The Chicago Theatre is a magnificent edifice that touches French Baroque architecture and gives tourists a grand view of its interiors. So, settle into the luxury displayed in the designs of the building and just relax in the dreamy atmosphere.

The Chicago Theatre offers couples a lifetime experience full of memories and sweetness: date night, honeymoon, or casual outings.

3. Lounge at the Green Mill Jazz Club

Settle into a jazzy atmosphere at the Green Mill Jazz Club and enjoy an evening of pleasant outdoor experience. It is a fantastic spot for romantic dinners, cocktail parties, and a live jazz session.

Couples can lounge at the jazz club and enjoy an evening of warmth and passion. The soft tune filtering from the live band gives a dreamy ambiance that melts the heart. The Green Mill Jazz Club features a great meal and soulful musical performances on Broadway Street.

Combining music and tasty food is a cocktail of pleasure that would surely delight any couple.

4. Take a walk in the Chicago Botanic Garden.

Nothing beats a walk in the most pleasant garden of Chicago. Stroll with your partner and enjoy the fresh smell of flowers from the arms of nature itself. There are various gardens to explore and fabulous scenery to enjoy.

The Chicago Botanic Garden is a large expanse of green vegetation filled with 25 gardens that are always on display for tourists. In addition, tourists can visit the Bonsai Gallery, the Regenstein fruit and vegetable garden, the Elizabeth Hubert Malott Japanese Garden, and the Railroad Garden.

This is one of the loveliest things to do for couples in Chicago as it inspires the appreciation of nature and all its beauty.

Things to do in Chicago for free

5. Cycle around the Lakefront Trail

Cycle your way through the famous Lakefront Trail and put your sporty side to display. The 18.5-mile trail can be used for walking, skateboarding, cycling, and running. It is a paved path that allows tourists to indulge in sporting activities that can double as recreational as well. 

The Lakefront Trail offers a free tourist visit and will surely provide visitors with a memorable encounter. So, grab your sports gear and work up some sweat walking those trails.

6. Take a trip to the Chicago Cultural Center.

I bet we all love a bit of history, and what other way to do it other than taking a trip to a center that holds this history within its walls? A visit to the Chicago Cultural Center is one of the most exciting and educational things to do when you are in the city.

The Cultural Center has an archive of remarkable concerts and historical performances. Tourists can also schedule to participate in free performances and concerts. Enjoy a tour of the auditorium and revel in its astounding view. 

7. Tour the Chicago Riverwalk

Thinking of exploring the South bank of Chicago, then a trip to the Chicago Riverwalk is the best idea to nurture. The place has a pedestrian trail that stretches 1.25 miles from Lake Michigan to Lake Street and gives tourists an eye-catchy tour of the scenery.

It is one of the pleasant things to do in Chicago because the venue allows you to enjoy various services, from food truck owners to museums, public art displays, and boat tours, among others.

You can dine and wine at the City Winery, a favorite spot on the Chicago Riverwalk, which allows you to relish the taste of signature wines and satisfy your palette with snacks while taking in the spectacular view of the waterfront resort. Explore the terrain and enjoy boat tours that provide an urban recreation experience.

8. Indulge your imagination at the Historic Water Tower

The Chicago Water Tower is a historic site that is prominent in the city. It is a famous landmark that plays a significant role in the history of Chicago. In addition, the building is notable for surviving the Great Chicago Fire of 1871.

Designed with great architectural skill, tourists can visit the tower to indulge their imagination at this historic water tower.

Things to do in Chicago on a birthday

9. Thrill your friends to Karaoke at Trader Todd’s

Celebrating your birthday could not be more fun at Trader Todd’s lively karaoke bar. This tropical paradise welcomes tourists with pomp and pageantry. Unique for its position in the heart of Chicago, it is a place that delights its guests with mouth-watering dishes and tropical cocktails.

Share the fun with your friends at this iconic location. Enjoy a karaoke session and entertain your guests with the seafood cuisines served by restaurants and food trucks. Make your birthday memorable with a visit to Trader Todd’s, and you will be pleasantly surprised.

10. Share a fun time with friends at the 360 Chicago Observation Deck

Get ready for this one because it is for the bold and daring. The 360 Chicago Observation Deck gives a grand view of the city from 1,000ft above the magnificent structure. Tourists can explore the deck to have a better perspective of Chicago city.

Get the adrenaline pumping when you get on Chicago’s highest thrill ride. Enjoy this panoramic view with friends while tilting from the thrill ride, which offers visitors a breathtaking experience. Enjoy this tour while chilling with beverages that delight your taste and celebrate the moment.

A visit to the 360 Chicago Observation Deck leaves feelings that are better experienced than told. It is indeed thrilling, fun, and adventurous. 

11. Tour the architectural scenery cruising on the Chicago River

Chicago is famous for its fantastic architectural designs and towering skyscrapers. To enjoy a better view of these towers, tourists can cruise on the Chicago River to grasp the magnificent structures adorn the city with beauty and elegance.

Make your birthday memorable by touring the city’s prominent landmark on a cruise ship. First, watch the skyscraper’s gigantic elegance and sail past the Willis Tower, East Bank Club, and several others. Then, settle down for a meal, drink with friends, and entertain yourselves with the brilliance of creative individuals who have built remarkable structures that have become Chicago’s legacy.

12. Entertain yourselves to indoor skydiving at the Chicago- Lincoln Park

This is one of the fun things to do in Chicago with friends. It is an indoor skydiving experience that gives you the vibe of taking a plunge from a real plane. The iFLY Chicago helps tourists create the courage to enjoy a simulated skydiving experience. 

Visit the Chicago-Lincoln Park with your friends and have a thrilling sky session with the instructors available to guide tourists on their visit. It is entertaining and filled with lots of fun. 

Feel the rushing wind on your face as you take a plunge from this simulated skydiving encounter, and you will feel quite energetic afterward.

When to visit Chicago

Chicago is a bubbling city, and as a great destination, it receives millions of tourists annually. For someone planning a trip to Chicago, the best time to visit this wonderful city is from April to May and from September through October.

This period of the year allows a tourist to enjoy all the spectacular landmarks within the city. In addition, it makes your traveling experience fun and eventful.