Chicago – The stunning windy city

If you are looking for a family getaway with many free activities to do with the kids, then a visit to the windy city of Chicago is a must.

With an array of amazing sightseeing and views, skyscrapers, architecture, food heaven, museums, and fascinating neighborhoods, to playing in the park, going to see a Cubs game, and eating Chicago’s deep-dish pizza, there is something for everyone.

Language English

The currency US Dollar

Best time to visit Chicago

Chicago is known for its cold weather. The best time to visit the city would be during the summer months of June through August when it gets warm and pleasant.

If you are there in early May or late September, do not expect sunshine. You can experience rain and even snow!

On the other hand, the winter season can be quite chilly. It is not advisable to visit Chicago from November through February because of the freezing temperatures that drop below zero degrees Celsius. Unless you love the cold and snow and they still do have some nice winter markets happening.

The city hosts hundreds of events and festivals throughout the year. If you are here for one, make sure to check it out because this is when Chicago comes alive!

You can find a full list of events on their official website. Here are some upcoming activities that I want to highlight:

If you are a foodie, the Taste of Chicago is a must-go event! It is the largest food festival in the city that takes place every year from July through August. There are over 70 restaurants participating and you can enjoy dishes from all around the world.

Although this is a post for fun things to do with the kids while you are in Chicago, sometimes the parents may want to have a little fun, given you can have the kids cared for of course.

For the parents only– Chicago also has a vibrant nightlife. If you want to experience some of the best clubs and bars in the city, check out the list below:

• The Underground (downtown)
• The Mid (West Loop)
• Martini Park (Near North Side)
• Green Street Local (West Town)
• Schubas Tavern (Lakeview)

Getting around Chicago

Chicago is a huge city, with plenty to see and do. Here are some tips for getting around:

-The Chicago Transit Authority (CTA) operates the city’s buses and trains; Chicago has the train system “EI” (elevated train). Tickets can be purchased for trips of one day, seven days, or even up to 30-day tickets, you can grab your tickets from the CTA website and they have maps and schedules of all routes. You can also buy your tickets at vending machines or from bus drivers. Using the CTA public transport is most likely your cheapest option.

If you’re staying in the Loop, you can walk to most places. The city is also very bike-friendly; there are plenty of bike lanes and racks throughout downtown, you can hire a bike from Divvy Bikes that offer electric bikes and standard bikes.

Be sure to take a walk or bike ride along the Lakefront Trail. The trail stretches for 18 miles and is one of the city’s premier attractions.

Water Taxis are another great option to get around the city and see some beautiful architecture, you can check out the water taxi website here.

If you need a taxi, there are several companies operating in Chicago. You can hail them on the street or call for one. Uber and Lyft are also popular ride-sharing services that can be summoned through an app on your phone.

Another option is to take a tour bus, which will show you the city’s most popular sights. There are many companies offering tours, so make sure to compare prices and schedules before booking one for yourself.

There are a lot of great free and budget-friendly things to do in Chicago with kids to keep them from saying “were bored” but there is also as much fun to be had if you were traveling without the kiddos too.

Where to stay

There is an abundance of accommodation throughout Chicago. If you are looking to stay one, two, or more nights, you can book here with Booking.com

If you like staying in Hostels, you can book your hostel here with HostelWorldwide. I stayed at the HI Chicago Hostel, it is situated in a great location and makes exploring easy being so walkable to everything.

Explore the many parks around Chicago

The city’s parks are perfect for a relaxing walk or bike ride. You can enjoy the fresh air and beautiful scenery while getting some exercise at the same time. Plus, there’s plenty of room to explore, so you can really get away from it all.

Below is a list of some of the beautiful parks around the city of Chicago for the whole family to enjoy and relax.

Lincoln Park – Take a trip to Lincoln Park Zoo the home to over 1300 animals from around the world and has plenty of activities and playgrounds to keep you busy.

Garfield Park Conservatory – Take a walk or ride your bike on the trails at the 60-acre Garfield Park Conservatory. Explore the four indoor gardens, which include a desert, temperate forest, aquatic, and tropical house.

Brookfield Zoo

A great place to visit if you’re looking for an animal-themed day out. You can see everything from elephants and lions to gorillas and pandas, and there are plenty of activities available too, such as boat rides and train rides enough to keep the family entertained for the whole day. The zoo is open every day of the year except Christmas Day, so there’s no excuse not to go!

The zoo has been around since 1934 when it was opened by Brookfield businessman Edward Renwick. It’s now one of the largest zoos in North America with over 3000 animals from all over the world. Brookfield Zoo also houses a children’s area called the Hamill Family Play Zoo, which is packed full of fun activities for the little ones.

Enjoy a picnic in Millennium Park. This park features various gardens, fountains, sculptures, and more! It’s also home to Cloud Gate (a huge stainless steel bean sculpture) AKA the bean as well as Jay Pritzker Pavilion where you can hear live concerts during the summer months.

Ice Skating in Millennium Park 

If you are visiting in the colder months the Millennium Park Ice Rink is open to the public from November to March. Admission is free for all ages and there’s always a great atmosphere and skate rentals are available on site. The rink offers a great opportunity for people of all ages to enjoy some winter fun in the heart of downtown Chicago. Skaters can take in views of the cityscape while enjoying a brisk skate around the rink.

The rink typically sees around 500,000 visitors each season, so be sure to visit early in the morning or later in the evening to avoid long wait times. The rink is open from Monday to Thursday from 11 am and closing time varies depending on the day of the week, and on the weekends Friday to Sunday from 11 am to midnight.

Ice Skating Tips

• Visit during the week if you can, weekends are the busiest.
• Be sure to dress warm!
• If you are a beginner skater, consider taking skating lessons or renting ice skates with blades that are shorter than normal (these will be easier to control).
• If you are not comfortable skating on your own, consider joining a skating group or hiring a personal skating coach. Always be aware of your surroundings and stay away from other skaters when possible. Happy skating!

Grant Park

Make sure you check the event schedule in Chicago to see if there is an event taking place at Grant Park that you would like to attend. Some popular events held at Grant Park are Lollapalooza and Taste of Chicago.

If there are no events taking place during your visit, you can still visit the site and check out the beautiful statues.

There are also a few fountains in the park that make for a great place to relax on a hot day. And of course, no visit to Grant Park is complete without checking out Buckingham Fountain! It’s worth taking the time to admire this Chicago landmark and every 20-minutes there is a water display.

I was lucky enough during my visit to Chicago in July that the Taste of Chicago festival was on, I got to taste many cuisines and listen to Stevie Wonder perform, so if you visit during the time of the “Taste of Chicago” you better bring your appetite and enjoy the culinary experience.

Spend time playing with your kids outside on any number of playgrounds located throughout downtown Chicago.

No matter which parks you choose, you’re sure to have a great time in Chicago!

Navy Pier

There’s plenty to do at Navy Pier, from rides and attractions to shopping and dining. You can explore the six-story Ferris wheel, catch a show at the Chicago Shakespeare Theatre, or take a cruise on Lake Michigan. There’s also a variety of shops and restaurants to choose from, so you’re sure to find something that suits your taste. Navy Pier is a great place to spend a day or evening with friends or family and take in the amazing views of the city.

You can also visit the Chicago Children’s Museum, which is located on Navy Pier. The museum has interactive exhibits and activities that are perfect for kids of all ages. Admission is free for children under age 15, making it a great option for families on a budget.

If you’re looking for a fun and affordable day or evening out, Navy Pier is worth checking out. You can buy tickets for individual rides and attractions or purchase a pass that gives you access to all the rides and attractions.  You can see a movie at Navy Pier IMAX Theatre during the summer months only (June-August).

Take a cruise along the Chicago River & Lake Michigan

A river cruise is a great way to see the city, saving your legs from doing all the hard yards. There are several different boat tours that you can take, so you can find one that fits your interests and schedule. The river offers beautiful views of the city’s skyscrapers and bridges. You’ll also get a chance to learn about Chicago’s history and architecture.

There are a lot of different boat companies to choose from. Here are some popular ones: I have made it easy for you to check availability with a tour with get your guide.

Chicago Line Cruises – This company has been in operation since 1991 and offers tours of the Chicago River as well as Lake Michigan. They offer many different options for groups or individuals. You can take a dinner cruise on the river, an architecture tour along the lakefront, or a fireworks cruise.

Chicago’s First Lady Cruises – This company offers narrated river tours of Chicago. They have several different boats to choose from, each with its own unique features. You can book a tour for just yourself or bring your whole family along.

Urban Kayaks – If you’re looking for something a little more active, check out Urban Kayaks. They offer guided tours of the Chicago River and Lake Michigan, as well as rentals for those who want to explore on their own.

Wendella Boats – This company offers several different options for your tour of the Chicago River. You can take a traditional sightseeing cruise or go on a themed tour such as a beer tasting, wine tasting, or architectural cruise. They also offer seasonal cruises, such as a Christmas time cruise or a fireworks cruise.

No matter which company you choose, you’re sure to have a great time on the Chicago River. So, grab your camera and get ready for some stunning views!

Chicago View from up high

Take in some spectacular views of the city skyline from atop Willis Tower Skydeck Chicago. The Skydeck is the third tallest building in the western hemisphere at over 1,300 feet, step out onto the ledge’s glass boxes that extend out of the building by four feet to get a better view.

Visit the John Hancock Observatory – one of Chicago’s most popular tourist attractions. You will find 360-degree views from 1000 feet up, including Lake Michigan, Grant Park, and Millennium Park. The Skywalk features a transparent glass floor and double-decker views.

The Observatory also has interactive exhibits and a multimedia theatre.

Admission for either the Willis Tower or the John Hancock Observatory are the same, so decide which tower you prefer, they both offer amazing views or visit them both. The prices are from $30 for adults, $20 for youths aged 3-11, and free for children under 3.

Visit some of Chicago’s famous neighborhoods

There’s no better way to see a new city than by taking a trip out into some of its famous neighborhoods. Chicago is blessed with an abundance of them, from artsy Wicker Park and eclectic Lincoln Park to historic Hyde Park and leafy Rogers Park. Each has its own unique character and attractions that are worth exploring.

To find a good neighborhood to visit, check out Choose Chicago for more information and to plan your trip.

• Wicker Park – for artsy shops, restaurants, and bars
• Hyde Park – for historic homes and the University of Chicago campus
• Lincoln Park-for Zoo, nature museum, botanic gardens, and more
• Rogers Park – for beaches, Loyola University, and a diverse community

During my visit, I was able to see the Chicago Gay and Lesbian hall of fame carnival, It was a great day out exploring some of the outer neighborhoods.

Check out the many Museums in Chicago

The Museum Campus is a beautiful location on the shore of Lake Michigan. There are also gardens and a nature walk. The museum campus is home to Adler Planetarium; Shedd Aquarium; Field Museum and the Museum of Science and Industry.

The Field Museum is one of the most famous museums in Chicago of Natural History and has exhibits on dinosaurs, ancient civilizations, and more. It is home to Sue the giant Tyrannosaurus Rex skeleton.

The Field Museum has a large collection of natural history artifacts and specimens like dinosaur skeletons! It also hosts events throughout the year for families with kids such as sleepovers at night or scavenger hunts during daytime hours.

Shedd Aquarium The aquarium is home to over 32,000 animals with fish, penguins, and other aquatic creatures. You can even feed them!

Adler Planetarium was founded by Max Adler as a planetarium to teach astronomy and now it’s a museum with exhibits on the solar system and space exploration.

Museum of Science and Industry If you want to learn more about Chicago’s history, head over to the Museum of Science and Industry. It is located in Hyde Park on Lake Michigan’s south side near downtown. The museum offers exhibits on topics like engineering, transportation systems, energy production technologies as well as natural sciences like astronomy or genetics.

There are also several museums in Chicago that are worth a visit.

Visit The Art Institute of Chicago is one of the oldest and largest in America. The museum is home to over 300,000 works from various periods including contemporary art.

Chicago Cultural Center The center has free performances and educational events for kids of all ages throughout the year including music, dance, storytelling, and more and it is free.

If you’re looking for a fun family outing, I highly recommend visiting the Museum Campus. It’s a great way to learn about science and history while having a lot of fun!

See a local sports team

Chicago is home to the Chicago Cubs and the Chicago White Sox baseball teams, If there is a game playing on your visit, it would be great to feel the Chicagoan vibe, the explosive atmosphere, and the love for the sport, it will be an outing not to forget.

If you are more into Football Chicago is home to the Chicago Bears and the Chicago Bulls if you are a basketball fan and Chicago Fire for soccer fans and let’s not forget the Chicago Blackhawks if you love Hockey.

Eat like a local

Chicago is home to some of the most delicious food you can eat and are very well known for their famous deep-dish pizza, Italian beef sandwiches, the Chicago hotdog, and let’s not forget the brownies that originated from the windy city.

There are many places you can get the famous deep-dish pizza, but a couple I enjoyed was at Giordano’s and Lou Malnati’s which are spread across the city.

If you’re a food lover a food tour may just be the thing for you.

Go shopping on the Magnificent Mile 

The two main shopping streets in Chicago are Michigan Avenue and State Street. Both have a lot to offer for tourists, whether you would like to shop at big department stores or upscale boutiques.

Michigan Avenue is home to some of the biggest department stores in the city, including Macy’s, Saks Fifth Avenue, and Bloomingdale’s. If you’re looking for something more unique, State Street has a lot of small boutiques that offer one-of-a-kind items. There are also plenty of places to eat and drink on both streets, so you can make a day of it!

Some other great shopping areas in Chicago include the Magnificent Mile, the Gold Coast, and the Loop. The Magnificent Mile is especially popular with tourists, as it has some of the most famous stores in the world. No matter what your style or budget maybe, you’re sure to find something great to buy in Chicago.

See a show at one of the many theatres downtown

There’s always something new and exciting playing at one of the theatres downtown in Chicago. You can see everything from big-name Broadway shows to experimental theatre productions, so you’re sure to find something that interests you. Plus, downtown theatres are typically smaller and more intimate than their counterparts in other parts of the city, which means you’ll get a more personal theatre-going experience.

Check out the theatre’s website to see what’s playing and buy tickets online, if you don’t want to see a show, you must stop by the Iconic Chicago theatre for a photo. You won’t regret it!

Some popular theatres in Chicago include:

• The Chicago Theatre
• The Goodman Theatre
• Bank of America Theatre
• Auditorium Theatre of Roosevelt University
• Joffrey Ballet Theatre of Chicago
• Blue Man Group Chicago.

If you are interested in theatre, you can even do a behind-the-scenes tour.

There are so many amazing things to do in Chicago whether you are a family, single, or a couple, you could easily spend a few weeks or even months here and not run out of new activities to try. Be sure to check out some of these great ideas the next time you’re visiting Chicago!

Do you have any favorite activities to do with your kids in Chicago? Let us know in the comments below!