This post of Amazing things to do when in Chicago, was guest written by Lake Country Family Fun reader, Heather Sorum, originally in May of 2018. It has since been updated in April 2024 by Samantha Bower, LCFF Team Member. And in January 2025 by Erin Guenterberg. *Parts of the experiences below were gifted by Chicago CityPass, 360Chicago, ExperienceFlyover, and Maggie Daley Park for the ice skating experience with skate rental.
Chicago is the third largest city in America and just a short car ride or train ride to experience all that the Windy City has to offer families. Please enjoy our tips and tricks for exploring Chicago with your family!
Step 1 – list out your Chicago visit with a map, to find your way around the best and be the most efficient in this big city.
Getting to Chicago and getting around:
To drive or to ride or to fly?
I mean, you can hop a flight from Gen Mithchell to O’Hare or Midway, but we think by car or train is better way to get from Lake Country south of the border.
Sam prefers to drive so she can control when they come and go. If having your own car or a rental – discover SpotHero, a digital parking app that can save you a lot of money on parking during your family trip to Chicago.
Once parked, most people do not move the car, as most places will not have in/out privileges. In Sam’s case, she had 5 places to visit not in walking distance, so she and her family ended up having to pay for parking a few times- using SpotHero. If you are doing a day trip, plan for a lot of walking. A LOT! Find some comfy shoes!
Our friend, Heather and myself, used most of the public transportation methods. This January 2025 visit was our first train ride in and out of Union Station. Super easy – highly recommend! Plus, kids ride half off! We got on and off at the MKA General Mitchell Airport location, which is a smaller station and super easy to navigate.
Once in Chicago, you can UBER or use the Chicago Transit Authority (CTA), which has a very user-friendly website. You simply input your destination and all the route options will appear. But, we just put our destinations into Google Maps, and the transit scheduled got us to where we needed to be! We didn’t purchase a Ventra card, just tapped our credit card at the rate of $2.50/adult. Kids were free! Super easy to get around and budget friendly!
PRO TIP from Heather: If you plan to take the subway, take a screenshot of the route before you get on, because you will lose service very quickly and not know where to get off (not that it happened to her…) Some routes also have express service depending on the time of day, which can make the trip much quicker.
Have you tried the water taxis? We did not go this route, but hear it is worth it and definitely worth looking into. The Shoreline water taxi that leaves from the Museum Campus and goes to Navy Pier and is what I’ve heard to be recommended. They also have a river route to see the Willis Tower. This is on our list for a summer Chicago trip!
Where to eat in Chicago:
On our most recent trip, we noticed that there were 10,000+ restaurants in Chicago! WOW! So many to pick from, and there are so many that we love. Here are a few of our favorites:
Eggy’s Diner was a big hit for breakfast. Fast service and reasonable prices, plus delicious food. The biscuit benedict and chocolate chip pancakes were absolutely fabulous.
Yolk for breakfast – there are multiple locations, and we ate at the West Loop Madison Street location. The El Torero Scrambler was delicious!
Wildberry Cafe was also a great breakfast spot. There are a couple of locations, we ate at the Prudential Tower one and it got really busy by about 8:30 with a business crowd (on a weekday).
Gyu-Kaku Japanese BBQ You are able to grill your own food on the table grill. If you go early enough, the happy hour specials are very good deals. The two person meals are more than enough for a family, and they now have s’mores for dessert. If you have adventurous eaters, we highly recommend trying this place.
Billy Goat Tavern is another fun spot and super casual. The paper hats and burgers are two things we love about this place.
Garrett Popcorn is a place we usually stop at as well for a snack. The Garrett Mix (cheese and caramel) is our favorite. They give you napkins and wet wipes too (you will need them!)
Gino’s East is a staple in Chicago known for their pizza, and VERY delicious too. We got the meat lovers thin crust pizza (not too thin) with a side of garlic sticks. I Absolutely recommend stopping here for lunch or dinner! Our kids loved it.
Giordiano’s is a Chicago pizza staple. We had their “special deep dish” stuffed pizza. YUM! We ate at the Navy Pier location. Because we had limited time, we ordered online, picked up and ate inside Navy Pier and it worked out perfectly!
So many more to visit! Don’t be afraid to venture out! Our rule on trips is no big chains or restaurants we can find back in Wisconsin 😉
PLACES TO VISIT IN CHICAGO:
*With all of these experiences, book your reservation in advance. Again, Chicago is the 3rd largest city in America and a tourist hotspot. If one of these attractions are on your must-do list – you may need to book your reservation well in advance.
If you do not have a Discovery World membership (which gets you in free to the Field Museum, Adler Planetarium, and Museum of Science & Industry), then you should consider a Chicago City Pass if you plan to explore more than one spot in Chicago. We did the City Pass, and I highly recommend. You will save a ton of money, you get priority entry, and the options are amazing! Check out Chicago City Pass and see if it makes sense for your family.
Navy Pier – Experience Flyover is the best flight simulator experience we’ve been to, and we’ve been to quite a few! First, there are two options showing currently (2025) Believe Chicago and Legendary Iceland. We opted for Believe Chicago and I’m so glad we did. It included a storytelling element – 3 acts, with the third act being the final flight over the city of Chicago with breathtaking views. And the drop off from above a skyscraper to the ground below felt so real! It is 4d, so experience some light wind and mist at times. This is NOT included in the CityPass, but we enjoyed it. Highly recommend for a compelling city story and thrill of the ride!
Field Museum of Natural History is a must see for dinosaur lovers. We unfortunately did not make it to the Field Museum this trip, but plan to make it next time!
Adler Planetarium is perfect for space explorers. The views of the city and lake from this vantage point are beautiful. I highly recommend going right away when they open for the day, in order to secure your tickets for the shows! If you are not able to see a show, there are tons of exhibits to explore! I would plan about two hours.
Shedd Aquarium is the third museum that rounds out the “Museum Campus”. This aquarium is incredible, but also VERY crowded so be prepared for that. If you get a City Pass, you can gain expedite admission which will help. My kids especially liked the Star Fish Touch exhibit. the Penguin play area and the SHARKS! The dolphin show is worth seeing. It is short and sweet. If you do not care to see the Dolphin show, I would recommend getting a bite to eat while everyone else is watching the Dolphins. Something we did NOT know that I wish we did is you can bring in your own food if you have small children. Snack and a stroller/wagon would have saved us from a few melt downs. We could have been there all day if we were properly prepared.
*Please note that they have regular Illinois resident free days, where the museum will sell out. Always get a reservation before arriving!
Museum of Science and Industry is very cool. We visited when my children were very young, so we enjoyed exhibits geared towards 10 and under. We spent a lot of time in The Idea Factory. Everything there is hands on and interactive. Learn how to make gears move, there is water play, a book nook and tons of engineer like play. The Great Train Story is for my train lovers, and the Science Storms section is a fascinating look at weather. Do not forget to see the 40ft tornado! There are options for purchasing food here as well. Plan a half day or a full day if you have older children.
The Skyline is an absolute must see while in Chicago and is included in your City Pass (another reason to consider a City Pass.) You will take a quick elevator ride up to the top of Willis Tower, which was very exciting for a 4- & 6-year-old. Once you get to the top, IT IS BEAUTIFUL! You can walk around as long as you’d like, checking out the view and taking pictures. Before you leave, you MUST experience The Ledge. The Ledge is a glass balcony extending from the top of the Willis Tower at 1,353 ft! Don’t worry, it’s completely safe.
360 Chicago: TILT If the Skyline/Sky Deck isn’t enough, get tilted at the 875 North Michigan Avenue building, formerly known as the John Hancock Center for us Millennials 😉 The observation area has amazing views – breathtaking, overlooking Lake Michigan, Navy Pier, and the city of Chicago to the south, west, and north. AND TILT, tilts you over the ledge from the 94th floor! My girls and I braved it (ages 11 and 13) and thought it was so cool! Highly recommend! *The 360 Observation Deck is included in the CityPass; TILT is an add-on.
The Color Factory was Sam’s children’s favorite (ages 4 and 5). Located in the same building as The Skydeck, this interactive museum is NOT included in the City Pass, but well worth the entry fee. There are 14 interactive rooms to explore. From a confetti room to a giant ball pit room, you will not be disappointed. They also have complimentary photo booths throughout to capture your experience, with delicious treats along the way! We will absolutely be returning in the near future.
PARKS IN CHICAGO:
Millennium Park is a must-see spot. Cloud Gate (“The Bean”), Crown Fountain, and Maggie Daley Park are all here. In warmer weather, Crown Fountain is a lot of fun (bring a swimsuit, towel, and water shoes) and Maggie Daley also has water features. Plan to go to Maggie Daley early or late in the day to avoid the crowds and have one adult per child as it can be hard to watch where kids go with all the slides and towers. There are lots of vendors selling ice cream and other snack items.
AND we experienced the ice skating ribbon at Maggie Daley this January 2025 – highly recommend! We love our ice skating rinks in Lake Country, and this is so different! We skated at night in an 8:00 pm to 10:00 pm reservation timeslot, under the light of the skyscrapers, and it felt magical sliding around the ribbon, which has a slight incline and decline. For more insider tips and tricks, check out our sister site, KidList in Chicago.
Lincoln Park Zoo is just north of the city. We usually take the bus to get here, and then enjoy the walk back to the city along the lakeshore. The zoo is free! There are lots of picnic areas with gorgeous skyline & lake views. The giraffe exhibit is especially neat as you end up at their level as you wander through.
For more resources on fun in Chicago with your kids, check out Lake Country Family Fun’s partner sites:
Kidlist
Eat the Burbs
Toddling Around Chicagoland
Happy Exploring!
