Amazing Things to Do When in Chicago

Amazing Things to Do When in Chicago

This post was guest written by Lake Country Family Fun reader, Heather Sorum.

We love heading to Chicago for a big city getaway.  It’s so close, but feels a world away from Lake Country.  We have taken our boys since they were young; please enjoy our tips from our visits there.

Getting to Chicago and getting around:

We prefer to drive so we can control when we come and go, and also to not deal with hauling bags any further than we have to.  We recently discovered ParkWhiz, which saved us a lot of money on parking this past trip.  We paid about half as much as we would have if we had used the hotel’s parking, and ended up in the same ramp the hotel used!

Once we are parked, we do not move the car, as most places will not have in/out privileges.  We do a lot of walking in Chicago, but now that the boys are older, we also use Uber for further distances. (Once your kiddos no longer nap, WOW! It’s like a whole ‘nother world of freedom.)

We have also used most of the public transportation methods and the boys love them.  The subway is their favorite. Chicago Transit Authority (CTA) has a very user friendly website. You simply input your destination and all the route options will appear. TIP: you will want to purchase a Ventra card before your first trip leg, so you may need to alter your route for a station that sells those.  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 us…)  Some routes also have express service depending on the time of day, which can make the trip much quicker.

Another fun mode of transportation is the water taxis.  They run about $5 per ride. For my boys, who are too young to appreciate a river boat architecture tour, the water taxi takes almost the same route for way less money and a much quicker ride.  We recommend the Shoreline water taxi that leaves from the Museum Campus and goes to Navy Pier.  The views of the city are amazing! They also have a river route to see the Willis Tower.

Where to stay:

We have stayed at a lot of different hotels over the years, and almost all are very nice.  We tend to go by price and location when we decide. We prefer a location right near the river and Michigan Avenue, this allows us to walk to Millennium Park and all the shops & restaurants on Michigan Avenue easily.  We have stayed further north as well (River North neighborhood), and the disadvantage here is that you will be more dependent on public transportation to get to the Museum Campus and Millennium Park.

You may also want to consider if you want breakfast included, to have a kitchenette, or a suite set-up.  An indoor pool is usually the biggest wish list item for us. Typically the breakfasts are not that amazing, and we find that eating a big breakfast out at a local restaurant saves us from needing lunch. (We bring tons of snacks.) So, we still save money.

We have found that there are too many things we enjoy seeing to not stay at least one night, but you definitely could pick one or two major attractions and make a day trip out of it.

Where to eat:

On our most recent trip, we noticed that there were over 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.

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).

As I said before, we tend to pack snacks and sometimes sandwiches so we can avoid having to stop for lunch.  This often means you can hit attractions while everyone else is still eating! In addition, we are then usually ready for dinner earlier than the crowds and can get in without much of a wait – a necessity when traveling with kids!

Pizza is usually a must have in Chicago.  We have tried pretty much all of the major names, and they are all good.  You need to allow 30-45 minutes for deep dish pizza so an appetizer/salad will be a must to hold the kids over.  Also, try to arrive by 4:00 pm to beat the dinner crowds. Waiting for a table, and then for a pizza does not go over well with my hungry boys!

Emilio’s Tapas is a favorite stop for us, and we took the boys for their first trip last month.  There were plenty of options for them to enjoy and the atmosphere is just lovely.

Gyu-Kaku Japanese BBQ is my boys’ favorite dinner spot.  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 my boys 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!)

These are just a few spots we enjoy.  You can find any type of food you want, so don’t be afraid to venture out!

What to do:

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.  Costco also sells a similar card called the Explorer Pass for even less money, but it does not include the Shedd Aquarium.



Field Museum of Natural History is a must see for dinosaur lovers.  The look on my boys faces as they entered Dinosaur Hall was priceless.  SUE the T-Rex is currently off exhibit until early 2019, and a new dinosaur will be arriving in the main hall as well.  There are still plenty of dinosaurs to see even without those two.

Adler Planetarium is perfect for space explorers.  The views of the city and lake from this vantage point are some of the best.  We have not seen a planetarium show here but it was a good half day place to visit.

Shedd Aquarium is the third museum that rounds out the “Museum Campus”.  This is an amazing aquarium, definitely one of the best in the US.  Unfortunately everyone knows this, so it is usually very crowded. If you get a City Pass, you can gain priority admission which will help for sure.  Also, be sure you are not going on a free day-there are many of these for IL residents. Make sure you arrive about 10 minutes before opening as well so you can get in and get tickets to the shows you want right away.  There are very few deals ever on admission and it is expensive. Our last visit was incredibly crowded and it seems to be getting more crowded each time we go. The dolphin and whale show is worth seeing, and the 4D movies are quite good (but make sure to check the description-they can be very scary for younger kids).  

Museum of Science and Industry is our favorite.  We have been multiple times and find something new to see each time.  The Great Train Story is for my train lovers, and the Science Storms section is a fascinating look at weather.  In addition, there are lots of pop-up desks with museum staff demonstrating something or with a display. We looked at a penny, nerve cells, and blood cells under the microscope this last time, and joined in a challenge to build a better skyscraper.  Everything is hands on and encourages touching. There is an area for younger children (under age 10) called The Idea Factory that is really cool. You can see baby chicks hatch, visit a coal mine, tour a submarine, and see Giant Dome movies as well. Plan a full day for sure!



Millennium Park is a must-see spot.  Cloudgate (“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.

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.  


Other things to do

If you do not have the City Pass (which offers a chance to go to the top of the Willis or Hancock buildings), then there is another option.  The Signature Lounge is on the 96th floor of the Hancock building, and offers 360 degree views of the city.  The kiddie cocktails come with stir sticks shaped like the building (huge hits for our boys) and with drinks for our family, it is less than half the price of the observation deck and much more relaxing!  Be sure to check out the women’s bathroom too-a surprise awaits!


There are so many things to do and see in Chicago, but these are the ones we have done many times and recommend for sure.  Hope you venture down there for a trip soon! – Heather


For more resources on fun in Chicago with your kids, check out Lake Country Family Fun’s partner sites:

Toddling Around Chicagoland
Little Lake County
Stem Kids Chicago
Eat the Burbs

If you don’t want to make the travel plans yourself, check out Lovejoy Travel Agency to book your hotel stays for you.

Happy Exploring!

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