9 Unmissable Activities in Chicago

We LOVE Chicago! Chicago, as a destination for families in the US, is great for a quick weekend getaway or for a longer stay.  We have never run out of things to do (especially on The Magnificent Mile:)), and have always found fun, discovery and a unique culture in Chi-Town!!  Chicago is famous for many things including their Chicago style hot dogs and Chicago style pizza (YUM!!!!).  It is also known for jazz music, interesting architecture, many wonderful museums and their loyal sports fans. We are breaking it down for you in a concise easy to follow Chicago guide of highlights so you don’t miss out when visiting the Windy City! Keep reading for the 9 unmissable activities in Chicago!

The Quintessential 9 Unmissable Activities in Chicago

1.Millennium Park 

Millennium Park is a beautiful green space set among the famous skyscrapers of Chicago.  It has tree-lined paths that give way to open areas complete with monuments and fountains and is located on Randolph Street between Michigan Avenue and Columbus Avenue.  It’s a great place to spend a short time or make a day of it. The famous “bean” sculpture, accurately known as Cloud Gate is located within the park and is always busy with people snapping photos and enjoying the area.  Millennium Park is a fun place for the whole family with plenty of area for kids to run around and get their energy out. It would be a great place for a picnic in warmer weather. There are free events and exhibits for the entire family as well.  The Park Grill Restaurant has a great menu and has outdoor seating in warmer months and ice skating out of their doors in colder months. Check their official website for more information about a visit.

2. Art Institute of Chicago

The Art Institute of Chicago is right next door to Millennium Park and is a fabulous art museum just waiting for you to wander and enjoy its treasures.  Highlights include its impressive Impressionist (there is some alliteration right there – HAHA!!) exhibit. I love Impressionist art and find myself soooo happy when viewing the likes of Van Gogh, Seurat, and Monet among others. You must not skip the modern and contemporary art as well as the collection of Neo-Classical and Roman/Byzantine. For families, there are art-making activities, self-guides, games and more. A visit here is always a highlight and is definitely on the top of the list of things to do in Chicago.  Book tickets online to avoid potential long lines. Even the casual art observer will find something they recognize and appreciate here.

3. The Magnificent Mile

Shopper’s nirvana right here! The Magnificent Mile is a 14 block stretch of Michigan Avenue from the river to Oak Street.  Here you will find upscale shopping as well as average big chains and everything in between. We have been on a few girls trips to Chicago and we consider it one of the best shopping cities in the country, maybe only second to New York.  There is enough shopping in this city to busy yourself for days…or until the money runs out.

4. Theatre

I am a theatre lover and always enjoy a good show.  I have never been disappointed with the quality of shows I have seen in Chicago.  Chicago has a rich, live theatre scene and I have personally felt they were on par with other great theatre cities.  On our latest trip, my husband and I scored tickets to Hamilton. We were blown away with the music, the performers, and the show in general.  The energy was off the charts and the crowd was engaged and the feeling was electrifying. It was almost rock concert status! Chicago may not have the sheer number of productions as other places like NYC may have, but the quality is superb.  See chicago-theatre.com or broadwayinchicago.com for more information.

5. The Navy Pier

Get out and play!!  Navy Pier is Chicago’s number one tourist attraction (which may or may not be appealing to you).  It is on the shoreline of Lake Michigan located in the Streeterville neighborhood. It offers 50 acres of parks and fun all on the edge of the lake.  You will find something for everyone in the group; rides, theatre, restaurants, shopping, attractions, gardens, and museums. It is a family-friendly area with a great view of the skyline of Chicago and Lake Michigan. The rates for the rides can be expensive, but YOLO!!!  Going in good weather is a plus and goes without saying.

6. The Lincoln Park Zoo

The very best thing about Lincoln Park Zoo is that it is free (although the parking is not).  You may need a free activity after you have been out to Navy Pier:). Let’s be clear that this zoo is not on the level of San Diego Zoo or other famous zoos, but it is lovely and worth a visit.  The animal exhibits are clean and well maintained and in general, the animals seem to be happy. The zoo is well laid out and easy to walk. You could spend an hour or the entire day… it’s all up to you.  It is open 365 days a year and a visit here may even make you forget you are in the city.

7. Architecture River Cruise

We have been on both Wendella and Chicago’s First Lady Cruises and can recommend either.  Even if you are not an architecture buff, you will still enjoy this cruise on the Chicago River.  You will enjoy floating by wonderful buildings, both old and new from the vantage point of the boat.  The cruises are narrated by knowledgeable guides who really make history and architecture come alive and the facts are fun and interesting.  The boats are clean and well maintained. Cruises range in length from 45 minutes to 90 minutes and all cruises are general seating so be early to get the best seats upstairs and on the outer edge of the boat.  Be mindful of the weather- whether hot or cold. Dress appropriately and you will enjoy the experience much more. An architecture cruise should for sure be on your list of “What to do in Chicago!”

We LOVE river cruises and include them on almost all of our European Itineraries as well :).

8. Wrigley Field 

It was my husband’s dream to visit this legendary baseball park, home to the Chicago Cubs and let me tell you… it did not disappoint.  This grand old park was built in 1914 and holds over a 100 years worth of history and nostalgia for baseball fans and sports fans in general.  Try to catch a game here and enjoy the excitement of the hard-core fans. If you are not able to catch a game, there are daily walking tours of the field. See their website for information.  Wrigley is not the nicest or biggest of the parks but it is one of the best-loved. The seats are really hard, old and rusty and the aisles are narrow but it’s all part of the charm. Just a note on the food; we found the concessions to be sub-par compared to other parks. Wrigley Field is an oldie but most definitely a goodie.  

9. Eat Chicago Style Pizza 

Oh, you must!!  When in Rome, right?  Chicago style pizza is thick and gooey, and oh so calorie laden!!  And it’s worth every one of those calories, you can count those calories tomorrow.  There are many restaurants claiming to have the best Chicago style pizza and we will continue to try them all but we have consistently had great experiences with Giordano’s.  There are multiple locations around the city. Check the website for a location near you. Do not attempt a meal here if you are short on time. A Giordano’s pizza order takes 45 minutes…let me assure you, it’s all worth the wait.

View our Chicago coloring page here!