Tips for traveling to Chicago with a toddler

Tips for traveling to Chicago with a toddler
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You may have heard that we recently took a family vacation to Chicago. It was a really fun trip and one that I learned a lot about the city on in a very short amount of time. Those lessons cost me a lot of extra money and time wasted though, so do yourself a favor and learn from what I already went through! Here are 11 tips for traveling to Chicago.

  1. Rent your car through Hertz and get a free carseat
    I booked an Advantage rental car through Expedia because it was a few dollars cheaper per day and thought I was saving some money. I found out at the rental counter there was an additional $15 per day charge for the carseat and some other fees that resulted in my final pay out more than $100 over what I was expecting to pay. Hertz gives you a free carseat for your kiddo so your quoted price is very close to the price you pay.
    tips for traveling to chicago with a toddler
  2. Buy a CityPass 
    It was $99 for me (and Zay was free to all the attractions because he was under 3 years old). The CityPass gives you access to Shedd Aquarium, Field Museum, Adler Planetarium, FastPass access to Sky Deck Chicago, and more. This is way cheaper than paying for each ticket outright. A Sky Deck FastPass on its own is $49 before taxes. The CityPass practically pays for itself with that alone and you can purchase it anytime within 6 months of your trip. You have 9 days to use all of the vouchers once you redeem the first attraction though.Save 53% on Chicago’s 5 best attractions with CityPASS. Shop Now!CityPass is available in several other major cities too if you’re traveling elsewhere: Boston, Tampa, Seattle and New York, just to name a few. Browse their full site for a list of all of the cities they operate in.
  3. Take your stroller 
    There is so much walking to do in Chicago. And while my Fitbit may not have been counting steps accurately while pushing a stroller, I know I easily walked several miles every day. Carrying a 2 year old or waiting for them to walk that distance would be so exhausting for everyone. Bring your stroller, you can gate check it for free and you get to skip long lines with it!
  4. Don’t overbook your day 
    Day 2 was a nightmare for us. I had big plans for the day and it was a total bust because of it. A cranky, hungry toddler was frustrating and killed my mood. Day 3 I scrapped our original plans and opted for a much lighter day. It was MUCH more fun for both of us. Do yourself a favor and don’t over schedule yourselves.
  5. Remember where you parked
    I got lost a dozen times, half of those times it was looking for my freaking car. I used Siri’s “Remember where I parked” function, and she failed me big time. The city parking is underground and there are lots of levels to the roadways. Then even when I found the entrance to the parking garage, I couldn’t figure out how to get back to my vehicle. In one garage I knew I parked in aisle 3G; I was on level 3 and doing laps around aisles 3A through 3E for 20 minutes. I couldn’t for the life of me find the rest of the rows; turns out they were tucked behind a cement wall and a poorly lit underground alley. Who knew?! Document how you get to the elevators AND how to get to the parking garage. It will save you hours.
  6. Order Giordano’s Pizza ahead so you don’t have to wait an hour for your food 
    During peak meal times, Giordano’s Pizza (at every location) has a wait just to sit down, then there’s another 45 minute wait for your pizza if you order a deep dish. And that time can increase with larger sizes or multiple pies per table. You can order ahead of time and still eat at a table though! Order online for pick up, then when you get there just put your name down for a table. It’s the perfect combination.
    girodanos pizza chicago
  7. Get to where you’re going before 9 a.m. to save a bunch on parking fees
    Parking is one of the most expensive parts of traveling to Chicago, yet it is still more efficient and cheaper than getting an Uber or other rideshare car depending on where you’re staying. We were in an AirBnB about 20 minutes outside the city, so for us, it was cheaper to rent a car. I quickly found there were plenty of money-saving opportunities if you arrive early on weekdays, you also secure better spots close to attractions!
  8. Skip the FastPass on the Centennial Wheel, but not for Sky Deck Chicago
    There are a dozen different lines when it comes to the Sky Deck. One when you first walk in the door to get onto the elevator to the ticket counter, one at the ticket counter, one for photos, one for turning your ticket in, one for the elevator up to the top and one to stand on the deck itself. And guess what? Each of those lines is stupid long. FastPass lets you bypass allllll of them except the final one onto the decks. And fortunately those are the shortest ones anyways. But all those other lines? OH MY GOD, NO. Fortunately, this FastPass is included in your CityPass purchase anyways. Save money and time.The Centennial Wheel on the other hand was a single, short line and the FastPass was a waste of money just to skip 4 people. And once you buy the ticket, you can’t return it or exchange it for the cheaper option. Save here and splurge elsewhere.
    Sky Deck Chicago
  9. Have at least 4 full days available for fun blocked into your schedule
    There is so much to do in Chicago for adults and kids. To get the full benefit of your CityPass and explore other parts of the city as well, you need at least 4 full days of activity.
  10. Don’t go to Shedd Aquarium on a weekend day
    We unknowingly scheduled our aquarium visit on a free-for-Illinois-residents Friday. It was packed, definitely, but not nearly as bad as when we passed the same facility on Sunday. Sunday there was a line a mile long out the door, just to get inside. I can’t imagine the madhouse it was once you were through the doors. All in all it was a really nice aquarium, but it wouldn’t have been a good time had we gone when it was any more packed than it already was.Shedd Aquarium
  11. Visit the Field Museum on a Sunday
    The weekends are crazy everywhere in Chicago, so save some sanity by visiting the Field Museum on a Sunday and some of the more popular attractions during a weekday. The Field Museum was active, but not insanely crowded. It’s also PERFECT for kids. Honestly I didn’t think this museum was going to be conducive to tiny, inquisitive hands. We only went for the Jurassic World exhibit, but once we arrived I realized how wonderfully it’s designed for children, even 2 year olds. We walked the whole museum and he was actually interested in almost everything, but of course the dinosaurs were the biggest hit.Field Museum Dinosaurs

At the end of the day, Chicago is an amazing place for a family vacation and children of all ages, but especially young kids. There are so many perks when you have a little one with you. They will also enjoy their time because there’s a million fun activities that are just perfect for them.

This post contains affiliate links where I make a small commission on any purchases you make. All thoughts and suggestions are my own and I never endorse a product or service that I do not whole-heartedly support. 

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