3 Nights In Chicago with a Toddler

When we moved to Indiana (almost a year ago – you can read more about that here), one of the activities that we were looking forward to most was the ability to travel to so many fun cities in this part of the country.  Obviously this hasn’t happened yet, but we are starting to venture out and one of the first cities on our list of getaways has always been Chicago.

Bryan and I visited Chicago in the Spring of 2015.  We went to a Cubs game, had a blast in Wrigleyville, ate and drank our way through the city, saw a show, shopped, and were up late in some amazing pubs and restaurants.  We have wanted to go back ever since!  

This trip was a ‘little’ different!  With Eloise along for the ride and some level of uncertainty as to what exactly we were walking into – given all that has been going on recently – we did a bunch of research and decided to go see with our own eyes.  No, this wasn’t an easy decision, but yes, we were confident in our safety on all fronts.  We wouldn’t have brought Eloise (or gone ourselves) if we weren’t.  

First step: find an amazing hotel.  We stayed at the Gwen on Rush Street right in the middle of Michigan Avenue (shopping, restaurants, walkable to the Bean, & tons to do nearby).  It’s a Marriott affiliated hotel for those that use Bonvoy and it exceeded all of our expectations.  The staff was extremely friendly, the room was spacious and had all the amenities you’d expect, and the location is perfect for everything that we wanted to do.

Most importantly – it was extremely clean.  All employees had masks on.  The gentleman we spoke with when we checked in was behind a screen.  Bottles of sanitizer are all over the place.  Our room had been cleaned by a housekeeper then checked with some sort of UV light device.  The door was then sealed and marked with a note to verify it had been cleaned.  TV remote was brand new, in a sealed plastic bag.  Towels, sheets, everything – very clean.  

Any of our questions or concerns around the hotel and its cleanliness and preparedness for Covid were eased very quickly.  

Our drive from Indianapolis was just about three hours, so we got there in time to get settled at the hotel and head out to dinner.



First Stop: Pizza.  It’s what we were craving and Eloise will happily have a slice or two of cheese pizza!  This can become a bit of a hot button item if you ask someone from Chicago “where to get pizza” as there are definitely loyalties and strong opinions.  We’ve eaten at three or four of them, but opted for Lou Malnati’s this time around.  Amazing deep dish pizza, good beer and wine list, and a comfortable spot to take a two year old.  We have a Lou’s opening up locally and are very excited about it!

On our walk back to the hotel, we stopped for a treat at Jojo’s Shake Bar.  They make ice cream and shakes that look more like works of art than dessert.  It’s pretty incredible!  The shakes were good, but we all didn’t have much of an appetite after eating pizza – but it’s a fun spot to check out.  If you are looking for a “scoop of vanilla”, this is not the place.  We asked, they don’t do that.  Fun spot, but I wouldn’t go out of my way to get back.



Day two had two major agenda items on it: Shedd Aquarium and RPM Italian.  Bryan and I joke about ALL that we used to try and cram into itineraries during vacations.  Slowing down to accommodate Eloise is amazing.  No, we don’t see quite as much, but we see everything with her, which makes every minute that much more enjoyable.  A two hour afternoon nap also allows for us to catch up on some work, take a breather, and re-group for the evening.  We need a quick recharge too because between these events she is the energizer bunny!

Shedd Aquarium: Bryan and I have been here as well, without Eloise, and knew that she would love it.  You have to make reservations ahead of time.  We were there on a Tuesday and we hardly saw other people (other than employees) while we walked around. Every room is one way traffic, masks are required (2 years and up), and there was constant cleaning.  Seemed like there was an employee in almost every room with sanitizing spray wiping down surfaces.  Two year olds like to touch things, so we were ‘on it’ in terms of our own sanitizer, but the aquarium more than did their part to ensure a high standard of cleaning.  

This aquarium is amazing!  Tons of cool fish, amazing exhibits, and lots to see.  We spent a good amount of time upstairs watching several beluga whales eat and play.  They are huge and incredibly smart!  Eloise was on cloud nine watching them swim and show off!

All in all, would highly recommend the aquarium to anyone (especially those with kids) heading to Chicago.  

RPM Italian: We’ve been looking forward to eating here again since our last trip.  We’ve been to several cities in Italy, and I’m not kidding, this food stacks up against the best we’ve ever had.  It’s amazing.  We started with Burratta and artichokes and their delicious focaccia bread.  All so good, but you have to pace yourself because your main dish is going to be so worth it.  I had the bucatini and Bryan had butternut squash gnocchi.  Eloise had the kids butter noodles.  We ended up with three empty plates!  



The morning of day 3 we walked to Cloud Gate (also known as The Bean) – was about a 10-15 minute walk down Michigan Avenue.  It’s such a unique sculpture and was really fun to watch Eloise try and figure it out.  It is blocked off currently by fences, so you can’t get closer than about 50 feet away, but still fun to go and check out.  

We had also intended to go to Navy Pier that day, but a quick google search revealed that it is currently closed. Great travel tip, no matter what the location, worth a quick search before to make sure all is good.  

We stopped for a donut (hey, it’s vacation, what carbs?) at Stan’s Donuts on our walk back to the hotel.  This was an awesome “stumble upon” spot that is definitely Instagram worthy. Amazing donuts, fun selection, all were happy!

A quick 15 minute drive from the hotel and we were off to the zoo!  Lincoln Park Zoo is free to the public (reservations required) and very close to downtown.  If you are having the debate of “should we bring the stroller” the answer is “yes.”  Definitely a good walk to get across the zoo, which was great for us after carb fest and helps encourage toddler nap time as well!  Again, all one way traffic, tons of sanitizer, no big groups of people – we felt very safe.  We are spoiled with the Indianapolis zoo, but this one was fun.  They had some different animals including a polar bear which was the highlight for Eloise.  This was a good place to get outside, spend a couple of hours, and explore.  

For lunch we headed back to another one of our favorites: The Purple Pig. After some brief confusion (the restaurant moved about 50 yards up the street) we were so excited to have some lunch!  Everything that we’ve had here has been incredible, but the whipped feta is not to be missed.  It comes with toast and vegetables and we clean the plate.  It’s amazing!  We ordered some other appetizers to share and shared a few plates.  (The gnocchi was some of the best we’ve had!). A very fun place to have a delicious lunch in the heart of downtown.

Eloise took a great nap while we caught up on work.  We didn’t have a dinner plan that night so we looked around for something close to the hotel and ended up finding Doc B’s Fresh Kitchen.  I had the brussel sprout salad, which was absolutely one of the best salads I’ve had.  Still trying to figure out how to recreate that one at home.  We shared some sweet potato chips with guacamole that were delicious and had a great dinner! I would go back to this place as well!  Great for kids, but you could also take a date here for a drink or for dinner.  

The next morning we stopped at Yolk for breakfast.  It’s a chain and we keep seeing it in new locations, but have never tried it.  We were both impressed!  Food was good, service was excellent, and it was exactly what we needed to get going for the day.  We made a quick stop at Garrett Popcorn – not to be missed in Chicago, and of course the Disney store, and were back on the road to Indiana.  











All in all, I understand that not everyone will agree with the choice to travel currently.  I respect and understand everyone’s opinions.  We chose to take a trip and were pleasantly surprised at the amount of things open, the health and safety precautions taken in all establishments that we were in, and the amount of people out and about.  We are saddened by the amount of boarded up windows throughout the city – Michigan Avenue in particular but were happy to see the businesses open and getting customers.  

Bryan and I agree that we felt safe, clean, and other than masks and some boarded windows, there is a lot of life still happening – even in major cities.  We’d go back anytime!


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