I’m a Chicagoan born and raised. No matter where I live whenever someone asks me, “Where are you from?”, I proudly say Chicago. And in my opinion, there is truly no better time to visit my hometown than Summer!


Summer in Chicago is all about soaking up the sun on the sandy beaches of Lake Michigan, rainy day visits to a museum, and catching a baseball game at either Chicago baseball stadiums. Summer is a truly special time to visit Chicago with kids and I’m sharing all of my local insider travel tips for a great family-friendly visit.



From exploring Millennium Park to riding on the 200 ft. tall Ferris wheel at Navy Pier, these are some of my favorite Chicago destinations to visit with kids!


Immerse Yourself in Art 

For a limited time, experience art like never before – lose yourself in 500,000 cubic feet of flawless projections animating Vincent van Gogh’s famous artwork. The exhibit features moving images that highlight brush strokes, detail, and color, and is fun for all ages. The Immersive Van Gogh exhibit hit Chicago earlier this year and tickets are on sale through the rest of the summer. 


Play at a Children’s Museums 

Scattered throughout the Chicagoland area are TEN different children’s museums that are dedicated to hands-on exploration and are the perfect place to spend a day with younger kiddos. While downtown, visit the Chicago Children’s Museum located at Navy Pier. Just west of downtown is Wonder Works Children’s Museum which is an easy 30-minute “L” train ride from downtown and located in beautiful Oak Park where you can plan a day of shopping, playing, and dining. Other popular children’s museums include Dupage Children’s Museum in downtown Naperville, the Kohl Children’s Museum in Glenview, and SciTech Hands-on Museum in Aurora.


See Animals at a Chicago Zoo

Chicago has not one but TWO different Zoos to visit – they’re both fun but completely unique from one another. Lincoln Park Zoo is a FREE zoo located North of downtown near the lakefront and some of the best Chicago neighborhoods such as Wrigleyville, Lincoln Park, and the Gold Coast. Brookfield Zoo is the larger of the two and located in the nearby suburb of Brookfield. It’s massive and popular so plan to spend the day there since you’ll want to get your money’s worth.


Enjoy the Beauty of Millennium Park

Whenever I’m back in my hometown, Millennium Park is one of my first stops and literally one of my favorite places on this planet! There is SO MUCH to do and explore – from taking a selfie at “The Bean” to splashing around in the massive Crown Fountain, to walking the tranquil green spaces. Check out a FREE concert at the Millenium Park Summer Music Series located at the architecturally beautiful Pritzer Pavillion. And be sure to visit the Play Garden at Maggie Daley Park! It’s a stunning 3-acre kid’s fantasyland with climbing walls, huge slides, a giant climbing ship, and more!


Explore Navy Pier

Navy Pier is a massive waterfront playland and one of the most popular tourist destinations in the city! Jetting out into Lake Michigan, Navy Pier is a place to play, shop, and dine and the home of the iconic Centennial Wheel, a 200 foot tall Ferris wheel that is SO worth a ride! 


Tour the City by Boat 

This one is a MUST DO! Chicago is known worldwide for its architecturally stunning buildings and there is no better way to take in the magnificent views than by boat. There are many boat tour options available along Lake Michigan where you’ll find breathtaking views of the Chicago skyline. But for a more up-close look at Chicago architecture and towering skyscrapers, take a boat tour along the Chicago River – it is one of the best ways to experience the beauty of the city (Chicago’s First Lady is my personal favorite)!


Shop the Mag. Mile 

The Magnificent Mile is THE ultimate shopping and dining district downtown. From shopping at the world-famous Water Tower Place (home to the American Girl store and the Lego store) to braving the TILT 360 Chicago Observation Deck at the John Hancock Center, the Mag. Mile is a fun way to see some of Chicago’s best attractions. 


Day at the Beach 

Pack your swimsuit because no visit to Chicago is complete without a day spent at the beach. The city is perfectly situated on the sandy shores of Lake Michigan and has 24 FREE public beaches! Some family-friendly options include the popular North Avenue Beach which has a picture-perfect beach house and is within walking distance of Lincoln Park Zoo. Oak Street Beach is another kid-friendly beach and popular with local families. Ohio Street Beach is a great beach located next to Navy Pier along with 12th Street Beach which is in the museum district and near Northerly Island


Visit a Museum

The museums in Chicago are world-famous – from the Art Institute of Chicago to the Field Museum and the Shedd Aquarium, you can spend DAYS visiting museums. For science lovers, check out the Adler Planetarium or the Museum of Science & Industry. For animal lovers, visit the Field Museum or the Shedd Aquarium. For lovers of art check out The Art Institute or Chicago’s Museum of Contemporary Art. For nature lovers visit the Garfield Park Conservatory, Chicago Botanic Garden, or The Morton Arboretum. And if you plan on visiting multiple city museums/attractions, be sure to get a CityPASS for cost savings! 


Take in a Baseball Game

Chicago has two GREAT baseball teams and both stadiums are easily accessible from downtown via the “L” train! The Chicago Cubs play at the world-famous Wrigley Field. Time and time again, Wrigley is named as one of the most iconic baseball stadiums in the country famous for its ivy-covered walls. The Chicago White Sox play on the Southside with affordable ticket prices and a fun Kids Play Zone


Enjoy Views at the Top of a Skyscraper!

The Willis Tower Skydeck is a must-do experience and WELL worth the cost! The views are the best in the city and the entire family will love stepping onto the completely clear glass balcony that extends 4 feet out and hovers at 1353 feet in the air! (Insider Tip: If you find yourself needing directions, some locals may look confused if you ask for help finding the Willis Tower. Locals call it by its old name, The Sears Tower). And for even more great views check out Chicago’s highest thrill ride at the 360 Chicago Observation Deck



There are tons of great neighborhoods to stay in during a visit to Chicago, so it’s hard to recommend just a few places but these hotels are family-friendly and in the best locations for getting to some of the most popular Chicago destinations. 


Stay Pineapple is a fun boutique hotel located in the heart of downtown and within walking distance of Millennium Park, Lake Michigan, and the Mag. Mile. For families, suites are available with separate living rooms and sleeper sofas. 


Embassy Suites are some of the best hotels for families – offering suites with separate sleeping and living areas, free breakfast, and an on-site pool. The hotel offers views of Lake Michigan and is conveniently located within walking distance to Navy Pier and Millennium Park. 


This budget-friendly hotel offers a great location, an indoor pool, and separate living and sleeping suites. 


The Four Seasons knows how to cater to kids – The Family Experience is the ultimate kid-friendly way to stay and includes a “welcome” toy at check-in, in-room visits from the ice cream man, and FREE access to the 32nd Floor Kids Club Room which has games, crafts, and movies.  


Located on the beautiful Chicago River with views of Lake Michigan, you can’t find a much better location! The Kids Suite at the Swissotel is worth the splurge and includes a two-room suite, complimentary movies, and FREE breakfast! Best of all, the signature Swissotel Kids Room is stuffed with age-appropriate toys, books, games, and more. 



Eating in Chicago is an experience in itself and Chicagoans take their food very seriously! We literally argue over who’s got the best beef sandwiches, the most authentic “Chicago dogs” (hotdog), and whether deep dish or tavern-style pizza is Chicago’s signature pizza! No visit to the Windy City is complete without grabbing a bite to eat from these delicious Chicago dining establishments.


Chicago-Style Hotdogs

  • Chicago’s hotdog game is no joke and a visit to the city isn’t complete without grabbing a Chicago-style dog! Superdawg Drive-in and Portillos are some of the more “nationally” recognized hotdog joints while Dowtown Dogs and Fast Track are kid-friendly and conveniently located downtown. Whatever you do, DO NOT ask for ketchup on your hotdog – you legit may get yelled at. 


Chicago Pizza


Italian Beef Sandwiches

  • An Italian beef sandwich is another essential Chicago meal. Order it “hot (or sweet, or both) & dipped” and be sure to assume “the Italian stance” so the juices of the sandwich don’t drip all over you! Conveniently located, Al’s Beef in Little Italy, Luke’s, and Buona Beef are great places to pick up Chicago’s favorite sandwich. 


Authentic Mexican Food


Food Hall


Italian Food

  • With the third-largest Italian population in the country, Chicago is not messing around when it comes to authentic Italian American food. Italian Village is the oldest Italian restaurant in the city, conveniently located in the heart of downtown, and a place my family has been visiting since I was little. Forno Rosso Pizzeria, Monteverde, and Eataly Chicago are all kid-friendly and delicious. 


Fun Themed Restaurants 


*Please be aware that certain attractions and destinations may still be impacted by Covid-19 restrictions. We recommend contacting specific locations to help you better plan your visit.  


Photo credit: Facebook



About Ashley Hubbbard-Porter

Ashley Porter is a Chicago native who now calls Birmingham home. Ashley and her husband Mike and son Jake love attending local festivals, exploring Detroit’s diverse food scene, and venturing outside of Metro Detroit to enjoy the natural beauty of Michigan. With a background in Early Childhood Education, Ashley loves connecting with and supporting families in her community, which is why she is so excited to be a part of LittleGuide Detroit.