A Family Guide for a Weekend Getaway to Chicago with Children

As one of the largest cities in the U.S., Chicago is a premier bucket list destination for families in the Midwest. Situated on Lake Michigan, Chicago is famous for its deep dish pizza, striking architecture, and vast cultural attractions and museums.

With literally hundreds of Chicago family activities to chose from it can be a bit overwhelming to narrow down all the possibilities, especially when you’re visiting for a quick weekend trip. To help you out, we’ve rounded up our Top Things to Do in Chicago with Kids for a 3 day weekend getaway.

My husband and I have visited Chicago on many occasions as a couple and with friends, so we were thrilled during Spring Break to introduce our four children to the Windy City and allow them to experience the best of Chicago.

Honestly, we would have appreciated an additional day to squeeze more in since we only brushed the surface, but because of time constraints we were limited to 3 days. With endless activities, a robust food scene and striking views of skyscrapers accentuating the horizon you could easily spend a week exploring.

So let’s jump right in -here are the unmissable attractions in Chicago for families. Hopefully this will make your job easier when trying to choose where to stay, what to do and where to eat when vacationing in Chicago with kids.

3-Day Chicago Itinerary

DAY 1 Visit Field Museum on drive in/ Check into Hotel/ SkyDeck or Chicago 360/ Dinner at Lou Malnati’s for Deep Dish Pizza/ Swim at Hotel Pool

DAY 2 Walk to Navy Pier (Children’s Museum) / Walk to Water Tower Place (Lego Store/ American Girl Store), Treat yourself to JoJo’s Shake Shop/ Swim at Hotel Pool

DAY 3 Walk to Millennium Park (The Bean, Maggie Daily Park)/ Drive to Hyde Park and grab sandwiches at Cafe 53/ Drive short distance to Science and Industry Museum/ Head Home

*If you have additional days, I would highly recommend adding the zoo, a baseball game, architectural boat tour or a Broadway show to your itinerary.

Spend the day exploring the field museum — Spend the day at the Field Museum in Chicago

This post contains affiliate links. I may earn a small commission for purchases made through the links, at no additional cost to you. All opinions expressed are my own.

Tips for Planning Your Visit

Most of the museums, zoos and cultural attractions close at 5:00 pm, leaving your evenings with less to do. We found the Skydeck and Water Tower Plaza, which holds the American Girl Store and LEGO store, were open later till 7 or 8 pm, depending on the day. Add in dinner and swimming at the hotel pool to close out the night, we guarantee your kids will drop into their beds exhausted, but with huge smile on their faces.

Where to Stay in Chicago with Kids

Choosing where to stay in Chicago can be a bit daunting with it’s exuberant choices, but it’s crucial to save yourself time, miles of walking and money on Uber rides or parking fees. In my opinion, the best area to stay is North of the River and South of Water Tower Place if you desire walkability around the city. This allows you to be centrally located to many of the popular, unmissable attractions. Bookings.com offers tons of affordable options in downtown Chicago. I think it goes without saying, expect a lot of walking when visiting the city so the key to success is location, location location. Here are three great options for hotels in downtown Chicago.

Hampton Inn and Suites Chicago is an ideal location

Hampton Inn and Suites Chicago Downtown Located on West Illinois, we stayed in a spacious family suite with a sofa bed and kitchenette area for our family of six. It included an impressive FREE breakfast spread. The make-your-own chocolate waffles with all the fixins-strawberries, caramel syrup, cool whip was a favorite with our children. Maxing out the warm 95 degree pool was apart of our evening routine, as well as overusing the the revolving entry door to go around, and around and around. The hotel has Valet parking for a fee, but it’s a nice feature if you don’t want to try and secure self parking.

Hilton Garden Inn Chicago Downtown/ Magnificent Mile

In River North, two blocks from the Magnificent Mile and close by to Navy Pier and "The Bean", Hilton Garden Inn in Chicago Downtown is a great pick for families. Enjoy an indoor pool, fitness center, free WiFi, and an attached Weber Grill Restaurant.

Embassy Suites by Hilton Chicago Downtown River North In a ideal downtown location, with a pool and continental breakfast included, the Embassy Suites is another good choice for families.

Find Deals

Every time you Uber or taxi someplace, it cost more money. By carefully planning out your routes, you can easily walk to many of the locations. I’ve included a map created on Wanderlog with our favorite spots in Chicago to help you get a bird’s eye view and layout of the city.

Trip map created using Wanderlog, a road trip planner app on iOS and Android

Explore Outside

Millennium Park

The Bean, officially named Cloud Gate, is an iconic fixture in the center of Chicago. This enormous reflective, stainless silver sculpture is near the entrance to Millennium Park and lavishly reflects the surrounding sky scrappers on a clear, picture-perfect day. Gaining it’s nicknamed “The Bean” from its similar shape to a kidney bean, it’s mirror-like exterior surface provides an ideal spot to grab a selfie picture.

Decked out in stainless-steel panels, the Frank Gehry’s winding BP Pedestrian Bridge is an adventure all it’s own as it leads you over the expressway to access Maggie Daley Park. It’s serpentine structure allows you stunning views of the towering buildings surrounding the area.

Maggie Daley Park

One of the most beautiful city parks to behold is Maggie Daley Park in the heart of the city. The eye-catching focal point is the expansive suspension bridge stretching across the middle of outdoor play area. All around the bridge structure, multiple slides slant downward into the spacious pit, spilling laughing children out into the center space.

Another reason why Maggie Daley Park is a true gem, is that no matter the season, there is something to enjoy at this epic park. On cold winter days, an ice skating path meanders through the park for a fun adventure. Whereas in summer months, the same path can be used for rollerblades, bikes and scooters. In addition, kids can cool off while splashing in the water areas, or try the rock climbing wall or mini golf course on warmer days.

Parents and kids will appreciate the beautiful landscaped area with flowering spring bulbs, magnolia trees and additional playgrounds featuring a lookout tower and saucer swings set against the backdrop of skyscrapers.

Additionally, Grant Park is a fun option to visit for some wide open space, including it’s eye-catching Buckingham Fountain.

Sky High View of the City

Two skyscraping opportunities exist in Chicago to experience the beauty of the city from among the clouds. Both 360 CHICAGO in the John Hancock and the Skydeck in the Willis Tower give you a unique sky-high adventure.

Skydeck View in Chicago, Illinois — View from Skydeck in Chicago

While visiting Chicago, an unforgettable experience is a trip straight up Willis Tower to view Chicago from the Skydeck. If you dare, walk out on the Ledge, where you can step into a clear, glass box to view the street below, while grabbing a truly Instagram-worthy picture. During your visit, informative exhibits about the history of Chicago can be found in the Willis Tower. This incredible view for miles is truly a unique experience, which my husband and I shared together on a previous trip. Unfortunately, we planned to share a similar adventure with our children at 360 Tilt.

The 360 is located close by to the Navy Pier area, since we were staying North of the River, it would reduce our walking time. It also has a one-of-a-kind adventure where visitors can hold on tightly to handles as they are tilted forward above the ground 1,030 feet below. With plans to visit this newer attraction, we were thwarted by cloudy/ snowy weather which kept us from experiencing it. Although it just gives us another reason to plan an additional family trip to Chicago!

Admission:

360 Chicago: $30 Adult/ $20Child

Skydeck: $32-$44 Adult
$24-$36 Child (3-11)

(prices change based on date and time.)

Unmissable Attractions in Chicago for Families

Navy Pier

Although a bit touristy, Navy Pier still provides gorgeous views and a ton of fun Chicago family activities for children. During warmer months, kids can ride all the attractions including the Centennial Wheel ($15/$18), swings or taking a boat tour through the Chicago River. The City Architectural Tour and the Tall Ship Windy are ideal in the sunny, warmer days when you’ll appreciate the cool winds of the water and sun on your face. During the ride, entertaining guides share the unique architecture and history of Chicago. Being on the water in early September was a highlight during one of my girl’s trips to Chicago, although it was a bit too cold during our trip over Spring Break in March.

In the evenings, Navy Pier is especially eye-catching with all the lights illuminating the area. Near the entrance, your eyes will most likely be drawn to the interactive fountain at Polk Brothers Park, which consists of jetted water streams that are programmed in different patterns. Kids will love splashing and playing in the illuminated space, especially at night as the ambience will make you want to dance and run among the colored LED lights.

Children's museum in Chicago — Children’s Museum in Chicago

The weather was quite uncooperative when we visited. After exploring outside at Navy Pier for a bit, we headed indoors to the Family Pavilion, which is home to the Chicago Children’s Museum. ($21/ Person)

Water City Splash Area at the Chicago Children’s Museum

A highly impressive museum that fosters creativity and innovation, it was a favorite with our younger children. It’s geared for children 10 and under, but older children and parents are allowed on all of the climbing structures and interactive exhibits.

Learn and play with tons of hands-on exhibits, including digging for dinosaur bones, performing a circus act, splashing in the water area or crafting your own race car with recycled materials. On top of all that, experience being suspended above the mall in a maze called The Cloud Buster. Even my husband and I joined in the fun as we clamored through a series of tunnels and obstacles with our children.

Learn at a Museum

Chicago holds it fair share of impressive history, science and art museums that the whole family can enjoy

Science and Industry Museum

Learn in an awwwesome way as you explore science hands-on. Steer a submarine and climb inside a jet plane to see the inner mechanical workings. The museum includes permanent exhibits, including Science Storms featuring a swirling 40-foot tornado, to Numbers in Nature: A Mirror Maze, which kids can try navigating the dizzying maze of mirrors.

Other exhibits change periodically, like the Toy Maker 3000, where you can watch a toy on the assembly line be made from start to finish, utilizing modern automation and robotics.

Admission

Adult $25.95
Child ( 3-11 ) $14.95

Be forewarned, the museum has tons of add-ons which all cost additional money. As a parent, I am not a fan of this system. Their was additional fees for the mine tour, James Bond Movie, and to tour the inside of a submarine.

Field Museum

Upon entry, the magnitude of titanosaur, the largest dinosaur that paleontologists have ever discovered will astound your mind. If you have a dino-obsessed child, they will be in awe as they view the largest T. Rex skeleton in the world.

Rich history is immersed in every exhibit throughout the museum as you will learn about ancient Egypt, the Pacific Islands and China. The Mammal exhibit feels like your walking through a zoo featuring hundreds of taxidermied lions, wildebeest, giraffes and birds. If your children are rock hounds like mine, we spent a good portion of time viewing glittery jewels and meteorites.

Admission: Adult $30, Children $23

Animal Adventures in Chicago

It’s undeniable, kids can’t get enough of animals. Luckily Chicago has not one, but two different zoos to choose from, plus a butterfly garden and aquarium. Large families will especially love that the Lincoln Park Zoo is entirely free.

Lincoln Park Zoo

Few attractions are free in Chicago, so that’s why the Lincoln Park Zoo is a gem. With free entry and hundreds of exotic and wild animals to view, you’ll easily spend hours watching the antics of playful penguins, imposing lions and agile monkeys. Take a spin on the carousel or ride the train around the park.

Brookfield Zoo

A bit farther out in Chicago, is another opportunity to view animals at the highly regarded Brookfield Zoo. With a sprawling 216-acre nature park featuring a polar bear underwater enclosure and an impressive primate exhibit, adults and children alike will love this incredible zoo experience.

Admission

Adult: $24.95

Child: $17.95

Padan Peggy Notebaert Nature Museum

Explore the butterfly haven, as well as, attend unique events and programming like butterfly yoga or taxidermy 101 at the nature museum.

Admission $17/$10

Shedd’s Aquarium

When we were visiting Chicago, parts of the Shedd’s Aquarium were under construction, so we skipped this attraction. From speaking with others, the majority of families said if you have younger children, the Shedd’s Aquarium will appeal to them, whereas the Field Museum is better for older kids. If you do plan to visit Shed’s and the Field Museum they share a parking area ($20/park) so it will save you money. Additionally the aquarium is one of the more expensive attraction, so buying a City Pass can be a great option. ( I share about this later in the post)

Admission Adults: $39.95 Kids (3-11): $29.95

Shop at Water Tower Place

From the towering glass elevator to the kid-friendly shops designed with your children’s favorite toys, Water Tower Place is an unmissable stop when visiting Chicago. Got any LEGO maniacs in your family or maybe a child who loves American Girl Dolls, then make a stop at Water Tower Place. The LEGO store has life-size LEGO structures that are fun photo ops, plus many LEGO models completely assembled to peruse. For $9.99 you can select and create 3 of your own personalized LEGO figures to create, which my kids loved.

American Girl Store at Water Tower Place

The three story American Girl Store is a young child’s dream. Every imaginable doll is possible from hair color, clothing, to adorable pets or even a wheelchair that can be customized to every child’s unique character traits, interests and passions. During your visit, you can have your American Girl Doll’s nails done, eat at the diner or visit the hospital for repairs.

Sometimes the simplest things entertain kids the most, riding the glass elevator and heading up and down the series of escalators amused my kids for quite some time.

We topped off our visit at JoJo’s Shake Shop, which has the epitome of milkshakes. With several locations throughout Chicago, these epic shakes, although pricey, included all the fixings like cookies, cotton candy, marshmallows etc. Both the Unicorn and Girl Scout were huge and chocked full of yumminess!

Restaurants

Cafe 53

Located in Hyde Park, we stopped here on a whim when visiting the nearby Science and Industry Museum. Featuring oven baked sandwiches loaded with flavorful meats, cheeses and unique sauce blends, plus the phenomenal Dutch crunch bread hit it out of the park. The portions are generous, my children all split a sub. Although the one downside is the seating area is basically nonexistent, so take it to go. We ordered the Chicken Pesto, Sumac and Honey Barbecue Chicken, all of which were delicious.

Lou Malnati’s

No trip is complete without savoring a slice or two of Chicago style deep dish pizza. Lou Malnati’s is one of Chicago’s oldest local pizza places, and in our opinion the best. Perfect blend of fresh cheeses and toppings combine to make this pizza amazing, but the real star of the pizza is the sauce bursting with flavor from the basil, garlic and Roma tomatoes. As a large family, we appreciated being seated right away and had minimal wait for our meal, especially compared to some other famous Chicago pizza places.

Portillo’s

If you have picky eaters or just want relatively quick Chicago street food, Portillo’s is an easy option. With tons of seating, this 2-story warehouse style restaurant in River North has Chicago street food so you can choose from a gamete of options - Italian beef, Chicago hotdogs, spaghetti, and burgers to name just a few. Plus it allows your children to try Chicago classics, on a budget. While visiting we learned a Chicago Style hotdog includes mustard, relish, celery salt, freshly chopped onions, sliced tomatoes, a kosher pickle, and peppers stacked onto a warm poppy seed bun.

Experience the Fine Arts

Spectacular shows like the Blue Man Group at Brier Street Theater or a Broadway musical, allow your children to be exposed to the fine arts. On a past trip we saw the vibrant Wicked in Chicago, which was incredible. Many theaters downtown in the Chicago Loop offer discounted tickets through the rush program. Basically, on the day of the show, tickets go on sale at a large discount on a first come, first served basis.

How to Save Money in Chicago

I did a ton of research before visiting to see if it was worth purchasing a Chicago City Pass or GO Chicago cards for differing locations. Here’s my take- If you plan to pack in multiple expensive attraction- keyword expensive- then it does end up saving you money. For reference, some of the more expensive entry fees for attractions are Shed’s, SkyDeck, and the Science and Industry Museum. Unfortunately, we were visiting attractions that weren’t as expensive, plus because of rainy/ cloudy weather forecasted, we were nervous about pre-buying if we wouldn’t be able to get good views at Chicago 360.

So all that being said, it really depends on the attractions you select. If you plan to do 5 attractions, there are greater discounts. Additionally, if you’re an out of town visitor, prices are increased for non-residents of Illinois. In summary, the Chicago CityPASS can reduce your ticket costs, shorten your wait in line and is a great value if you visit 3 or more of the higher priced attractions or museums.

Chicago C3 CityPASS Cost

Adult – $139
Child (3-11) – $109

Examples of attractions included: Shedd Aquarium, Skydeck Chicago, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Shoreline Sightseeing Architecture River Tour, Centennial Ferris Wheel at Navy Pier, Field Museum and the Adler Planetarium

FAQ

Is Chicago a good place to visit with kid.

Yes, there are so many wonderful museums, zoos and stores that kids will love exploring.

Closing Thoughts

Chicago makes a wonderful adventure for families who want to experience a big city. Chocked full of family-friendly attractions, hands-on museums and gorgeous outdoor parks, there is truly something for everyone. Hopefully this guide helped whittling down the vast array of options to choose between and reduces decision fatigue for you. Don’t forget to Pin and Save this post and follow Discovering Anew on Facebook for more family travel, vacation guides, and camping recommendations. If you found this content helpful, share it with a friend!