Do’s & Don’t of the Windy City

I’ve been to a lot of cities, but there is something unique about Chicago.  It’s a big city with a complete midwestern vibe.  It’s clean, easily accessible, and so so friendly.  For the past year my brother has been living just outside of the city.  He’s headed back to LA and so we spent his final days playing tourist.  I think he needed a vacation after having to play “substitute dad” for several days since Jimmy had to head back to work early. Apparently spending a week with my three is a phenomenal form of birth control.  Whatever that means.

We’ve ventured with our littles into this magnificent city a handful of times and never regretted it.  If you are headed to the windy city with kids, here’s my do’s and don’ts.


DON’T overpay for parking.

Get your phone out right now and download the app SpotHero.  Trust me. It will save you lots of time & money!   This app partners with different facilities throughout the city to provide you with parking options at a discounted rate.  Parking downtown is expensive.  But with SpotHero, you put in the location you want to park in, and SpotHero provides nearby options. Typically you park at apartment buildings or business garages that have available spots that they sort of “rent out” to SpotHero.    I’ve used it several times and never had an issue.  Here’s an example: to park at our hotel was $60 overnight.  With SpotHero, we parked across the street and paid $24.  Another time, we paid $8 to park all day, instead of the standard $25.  SpotHero is in a lot of cities, you can find a list on their website. We typically park and travel by foot through out the city.


DO have deep dish pizza.

There’s a reason Chicago is known for its deep dish pizza.  It’s delicious.   There’s a couple of classic deep dish pizza joints in the city.  Pizza Uno is one of them.  Here’s our little secret:  Visit Pizza Duo across the street (literally); it isn’t the original pizza shop but uses the same receipts and is a whole lot less crowded.  It is a tight squeeze for a stroller, but if you ask the host, they will store it for you.  Deep dish slices are thick and rich – you can’t eat as many of them as you would a standard pizza, so don’t over order.  Or do– can you say breakfast?  Pizza Duo address: 619 N. Wabash Ave


DON’T leave without eating at Portillos.  

You can’t buy happiness but you can buy Portillos and that’s pretty much the same thing.  I’m not sure where to start? The fries, the burgers, the hot dogs? I know, the cake shakes.  You guys there are actual pieces of their decadent chocolate cake (don’t even get me started on the cake) IN THE SHAKE.  Think DQ Blizzard but smooth and creamy and rich…I’m digressing.  Just get one.  You won’t regret it.  Portillo Address: 100 W. Ontario St.


DO see the sites

Our Favorites:

  • Millineum Park

We love the iconic “big bean” as my kids refer to it.

You will also find Crown Fountain in Millennium park.  I suggest brining a change of clothes, as the interactive video sculpture periodically shoots water and the kids love to play in it.   Millennium Park Address: 201 E. Randolph St.

  • Maggie Daley Park

This park is relatively new.  Google says it was constructed in 2014.  It’s a HUGE park with multiple play areas in the heart of the city.  The only downside is that the play areas are separated by age, so if your kids vary in age (like mine do) you will have to split up to keep an eye on everybody.  We love walking through the enchanted garden area, which has an “Alice in Wonderland” feel to it, with upside down trees and several different climbing and water features, .  If you have older kids, there are even several rock climbing areas to try out.   Maggie Daley Park Address: 337 E. Randolph St.

  • Museum of Science & Industry

A definite favorite.  The museum is filled with all sorts of different exhibits, most interactive.  If you want to see it all, it will take the majority of a day.  Base tickets are relatively inexpensive, compared to most museums, with a discount for buying online.  But here’s the catch:  All the extra exhibits require a separate ticket, and thats where the money adds up.  We’ve paid for three extra exhibits and here’s the honest truth.  It’s not worth it.  We’ve done the robotics exhibit and the lego exhibit.  Both were interesting, but not worth the price of admission.  Here’s the one exception, the coal mine exhibit.  That one was definitely worth the extra $ we paid.  It’s an interactive exhibit that transports you to another time during the height of the coal mining industry.  Museum of Science and Industry address: 5700 S Lake Shore Drive.

  • Shedd Aquarium

Pricey.  But amazing.  Again, lots of add on options to your base ticket. General admission starts at $39.95 for adults and $29.95 for kids.   There’s something for everyone here.  Apart from what you’d expect at an aquarium, there’s also an interactive, exhibit for each ecosystem of the world, with not just fish on display.  You’ll see marine mammals, reptiles, birds, even a few monkeys. The string-ray touch exhibit ($4.95) was a highlight for my oldest.  Plan for a full day here.   Shedd Aquarium address:  1200 S Lake Shore Drive.

DON’T stress about getting to Navy Pier or the Willis (Old Sears) Tower 

I know, I know, my native Chicagoans are yelling at me.  But hear me out.  IF, and only IF I was short on time, and couldn’t see everything, these are the two I’d skip, and I’ll tell you why.

Navy Pier:  It’s out of the way.  It’s a hike from the rest of the things on the agenda. And it’s pretty pricey.  If you decide to venture over, you’ll find the iconic ferris wheel (15$ tickets), Swings (8$), and a carousel ($5).  There is also a pretty neat climbing wall for only 8$ a climb with some pretty unique features.  The are a ton of shops and snack stops inside too.

Willis Tower:  If you take out the long lines and expensive ticket prices, the Willis Tower is pretty neat.  Base tickets start at $23 for adults and go up to $49 if you want to skip the lines.  When we went there, the line was about 45 minutes to get to the top, but I’ve heard it easily gets to 2hr.  Once at the top, you’ll find a room with glass windows, including the famous sky deck, which includes a glass floor and lends to some pretty neat photos.  Apart from looking out over the city, there isn’t anything else to do.  I’d save this attraction for older kids who can appreciate the views and won’t fall apart in the long line.


DO spend time on the lake front 

In my opinion, Chicago has the best lake front to all the great lake cities.  We love to walk along it and watch the boats.  We haven’t yet, but plan to bike with a picnic lunch during our next visit.  You’ll also find the classic Buckingham Fountain near the lake shore.  Buckingham Fountain Address: 301 S. Columbus Dr.

I can’t say it enough, Chicago is a wonderful city.  I hope you all make it there at some point.  For those of you who have already been there, I’d love to hear from you.  What are your Do’s and Don’ts?

“She’s always a novelty; for she is never the same Chicago you saw when you passed through the last time.” – Mark Twain


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