Unforgettable Family Vacation in Chicago
Are you thinking about a Chicago vacation? Chicago is a major city with tons of incredible places to visit, explore, and enjoy. Let us tell you the top things to see in Chicago, when to visit, how to get to Chicago, top places to eat in the city, and so much more. We’ve got tips and tricks for you to enjoy your trip to the Windy City. Plus we’ve pulled together a 3-4 day itinerary to get you started exploring. Whether you want to explore the iconic bean at Millennium Park, eat a deep-dish pizza, explore a German U-boat, explore impressionist art, or marvel at the white beluga whales in one of the largest aquariums in the world – Chicago is your place for an unforgettable family vacation!
Family Vacation Chicago
Chicago is a vibrant city that should definitely be at the top of your travel bucket list! From iconic landmarks like the Willis Tower and Millennium Park to world-class museums like the Art Institute of Chicago, there is something for everyone in the Windy City. One of the highlights of visiting Chicago is the incredible food scene. From deep-dish pizza to gourmet hot dogs, there are endless options to tempt your taste buds. Plus, Chicago is home to some of the best breweries and cocktail bars in the country, making it a foodie paradise. But it’s not just the food that makes Chicago special. The city is also known for its stunning architecture, with famous buildings like the John Hancock Center and the Chicago Water Tower dotting the skyline. Exploring the city on foot or by boat on the Chicago River offers a unique perspective on its beauty. Like any major metropolis, there is a lot to see and experinece. You could easily spend over a week here, but I will try to help you find the very best spots you must see on your family vacation in Chicago.
When to visit chicago
If you are wondering when is best time to visit chicago, let me tell you. Chicago is in the midwest, it gets hit pretty hard in the winter with snow and more than anything cold – bitter, face-bighting, cold wind! So I would plan a visit in the spring (April), anytime in the summer, through fall (October) to enjoy the lovely shoulder season and beautiful, albeit crowded summer months.
How to get to chicago
Chicago is located on Lake Michigan, in the state of Illinois. You can easily get here by car or flying into one of the major airports: Ohare Airport or MIdway Airport. Because it is a major city there are many deals to be had flying into Chicago. You can also get here via Amtrak as there is a train station conveniently downtown. Our family has enjoyed leisurely train trips to/from Chicago and St. Louis, Louisiana, and other locations. Although you can technically walk around Chicago, there are some bad areas so I always prefer to drive. The museum area and fields are safe. So we drive in and drive out, or in your case to a hotel. If you are willing, staying outside the city will save you a lot of money, but that is up to you. There are many choices for hotels so browse Expedia or your favorite hotel booking site to find one that meets your individual needs. 
Top things to see in chicago
- Navy Pier: One of the main reasons to visit Navy Pier is the stunning views of the city skyline and Lake Michigan. One of the main reasons to visit Navy Pier is the stunning views of the city skyline and Lake Michigan
- Millennium Park: Snap a selfie at the iconic Cloud Gate sculpture, also known as “The Bean,” and stroll through the beautiful gardens and fountains. The park hosts a variety of festivals, events, and activities throughout the year, making it a lively hub for both locals and tourists alike.
- Lincoln Park Zoo: Admission to the Lincoln Park Zoo is free! With over 1,100 animals, there is so much to see and do! The lions, dolphins, and penguins are some of the most popular animals.
- Shedd Aquarium: Not only is the Shedd Aquarium home to over 32,000 animals, but it also offers interactive exhibits, live animal presentations, and behind-the-scenes experiences that will leave you in awe of the wonders of the ocean. From white beluga whales to a massive 5 million US gal tank, penguins and an amazing reed exhibit – you will want to spend all day here!
- Adler Planetarium: Discover the mysteries of space and astronomy through interactive exhibits and shows. Don’t miss out on a chance to see breathtaking views of the Chicago skyline from the Adler’s unique location along Lake Michigan.
- The Art Institute of Chicago: Introduce your family to the world of art with a visit to this renowned museum featuring a diverse collection of works. One of the highlights of the museum is its collection of Impressionist and Post-Impressionist masterpieces, including works by Monet, Renoir, and Van Gogh.
- Maggie Daley Park: This park is unlike any other you’ve ever visited, with its imaginative playgrounds, beautiful gardens, and breathtaking views of the city skyline. Let the kids run around and play in this expansive park featuring playgrounds, rock climbing walls, and mini-golf.
- The Field Museum: Explore exhibits on natural history, including the towering T. rex Sue or the intricate mummies in the Ancient Egypt exhibit. My kids favorite is the Underground Adventure where you shrink down to the size of a bug and explore the world beneath our feet. This interactive exhibit is a hit with kids and adults alike.
- Chicago Riverwalk: Take a stroll along the river, enjoy stunning views of the city skyline, and stop for a bite to eat at one of the many restaurants along the way.
Top places to eat in chicago
- The Purple Pig – This Mediterranean-inspired restaurant offers a wide variety of small plates perfect for sharing with the whole family. Don’t miss their famous milk-braised pork shoulder!
- Portillo’s – Known for their mouthwatering Chicago-style hot dogs and Italian beef sandwiches, Portillo’s is a must-visit for families looking for classic Chicago eats.
- Lou Malnati’s Pizzeria – Serving up some of the best deep-dish pizza in the city, Lou Malnati’s is a Chicago staple that the whole family will love.
- The Rainforest Cafe – Take your family on a culinary adventure at The Rainforest Cafe, where you can dine among animatronic animals and enjoy a fun and lively atmosphere.
- 2Toots Train Whistle Grill offers a unique dining experience with seating around the tracks, serving up classic American dishes delivered by an electric train.
- Oberweiss is our family favorite ice cream shop of all time. They serve the creamiest, most delicious treats. Their chocolate peanut butter and mit chip is amazing!
Family Trip to Chicago
So if you are planning a family trip to Chicago here are some local tips/tricks to consider:
- Start your visit with a stop at Millennium Park to see the iconic Cloud Gate sculpture, also known as “The Bean.” This is a great spot for family photos and to enjoy the beautiful green space.
- Don’t forget to take a ride on the famous Navy Pier Ferris wheel for stunning views of the city skyline and Lake Michigan. There are also plenty of family-friendly attractions and activities to enjoy on the Pier.
- take a boat tour: See the city from a different perspective by taking a boat Tour on the Chicago River or Lake Michigan. Your kids will love learning about the city’s architecture and history while cruising along the water.
- Head to the suburbs to visit Brookfield Zoo, Morton Arboretum, LEGOLAND Discovery Center, or Kohl Children’s Museum
- Stick to well-lit areas: When exploring the city, especially at night, try to stick to well-lit and busy areas. Avoid dark alleys and isolated areas.
Chicago Family Vacation
That is a lot of information, so where do you start. You cannot possibly see everything around Chicago; I just gave you the highlights and it was probably a little overwhelming. The age of your kids, budget, and time you can allow will help dictate some of your trip paramaters. But here is my suggestion for a 3-4 day trip.
Day 1 – Get your Bearings and be a Tourist
Book a tour like a hop-on-hop-off bus, segway tour, or the hugely popular Chicago architecture boat tour. You will get to know the city, learn some fascinating information, discover some iconic buildings, and discover this beautiful city. Check groupon for some savings on popular activities.
- Make sure to go up the Skydeck Chicago or the Willis Tower for an amazing view.
- Grab some deep dish pizza at Lou Malnati’s Pizzeria (or something else that looks good)
- Stroll along the Chicago riverwalk or head to Maggie Daley park
- Looking for more food – the Walnut Room is pretty famous, grab lunch or dinner
Day 2 – Visit a Museum
Plan an entire day at one of the amazing museums that rival any world-wide. Which one you choose will depend on your family. The above mentioned Museum of Science and Industry, the Field Museum, the Chicago Art Museum, or the Adler Planetarium are some good ones to consider first. When the museum closes, take a stroll through Millinium Park and see the iconic “bean” and beautiful Buckingham Fountain.
Day 3 – Visit Animals
Choose one of Chicago’s amazing animal venues – Shedd Aquarium (one of the 10 biggest in the world), the free Lincoln Park Zoo, or head out of the city and visit the amazing Brookfield Zoo. When you the zoo closes, or you are done, walk along Navy Pier.
Day 4 – Visit More Museums
If you are lucky enough to spend another day in Chicago I suggest trying to see another museum from our list above. Not into museums, the Chicago Botanical Gardens are lovely, catch the Cubs playing baseball in historic Wrigley Field , watch the Bears play a game at Soldier Stadium, attend a Chicago Symphony concert, or head out into the suburbs for even more gems like the Morton Arboretum, Kohls Children’s Museum, Illiinois Railroad Museum, or Ravinia picnic with live concert. 
Chicago Vacation
As you can see there is more than enough to keep you excitedly exploring and tasting your way throught Chicago for at least 3-4 days, but more ideally a week. We hope you enjoy your Chicago vacation with your family!
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