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I won't even pretend to tell you that the things we did are good for Chicago in January. We were blessed with Chamber-of-Commerce Weather on a September weekend (I swear, one of my superpowers is good-weather-on-trips), but I'd say it would still be good for March to October. Chicago gets crazy-cold crazy-fast (I tried living there for a year, but I didn't make it through the winter -- weak, I know).
|Marvelous Suite at the W Hotel, Lakeshore.|
Normally, my suggestion is to rent an apartment if you are traveling with a kiddo. There are tons of great places on AirBnB and similar sites, so plenty of options there. This time around, however, we cashed in some of David's many Starwood points (the perk of having a job that requires a lot of travel) and managed to get upgraded to a Marvelous Suite at the W Hotel on Lakeshore Drive. It was a gorgeous modern room -- not ideal for a kiddo, as the bedroom part of the suite was separated only by a curtain and not a door. But the TV in the living room didn't wake him after bedtime, so it was comfortable and definitely felt luxurious. Having somewhere to hang that didn't have a sleeping baby was definitely a bonus.
|Having a little bit of "nursies" at Navy Pier.|
I know, I know, this is an obvious destination if you're traveling in Chicago with kids. We weren't 100% sold on it, but our hotel looked right out onto the Ferris Wheel. The boy was intrigued, so we walked over one afternoon after nap. The Wheel has fiberglass on all sides, and I think the gates are too close together for him to slip through. I was nervous most of the ride, but he liked it. If I'd been super nervous, I would have insisted we carry him in the Ergo baby carrier, so I guess I wasn't totally paranoid. He like the Ferris Wheel, but in the end perfered the carousel. Each ride is $6-7, but he was free (under three).
|Carousel at Navy Pier.|
You don't actually need to spend any money at all on Navy Pier -- there are plenty of sights to see just by sitting down and people-watching. We wandered all the way to the end of the pier where we caught a country cover-band rocking some Steve Earle. The wee boy danced, while I enjoyed a froofy beach-style daiquiri drink, and we all got a nice break. We also just sat on a bench and watched sailboats for a good while, which was a nice combination of beach-vacation-mentality without getting sand in your butt. There is a great Children's Museum there, but we didn't bother. The weather was nice, and there was plenty of activity on the pier itself.
|Gino's East deep dish cheese pizza.|
The line for the classic deep dish pizza places is always insane. Some hotel concierges can get you a FastPass type thing to skip the line, but we forgot to ask. Instead, we opted to skip the line and order carryout from Gino's East, the preferred pizza place of every Chicago native I know. While we were waiting (deep dish takes 45 minutes), we wandered around the block to the Seneca Playlot Park and let the Wee Boy run, climb, and slide with the neighborhood kids. Then we collected our Deep Dish Pie and walked back to our hotel. It would have been fun to just eat the pizza in the park, but we were tired and ready to crash early after a long day of sightseeing.
|The private balcony of a swanky suit store.|
We were staying near Michigan Avenue and were on a mission to buy David a new suit. I will be the first to admit that I hate shopping. But I love cities, and I love people-watching. Michigan Avenue is must more interesting than a mall, so I had a good time. We brought the umbrella stroller, and the Wee Boy enjoyed popping in and out of stores. Of course we popped into the Lego Store and a few toy stores (none of which blew my mind). We ended up at SuitSupply, where the staff was incredibly nice to us while David tried on several suits. They have an entire outdoor patio that is owned by the store, but only used for special events. The saleswoman allowed me and the Wee Boy to go outside and run around, which was a great way for him to get his wiggles out in a safe space and also get a really cool view of the city, while his daddy tried on suits in peace.
The best thing we did was take our time and take lots of breaks. We popped into cafes for snacks and drinks, making an adventure out of everything, even when it was just to rest our feet.
Ohio Street Beach
If you are uptight, you will hate this advice. Sorry, I'm a crunchy mom when it comes down to it, and probably more laid-back than most first-time-moms. My kiddo love swimming. It wasn't in our plans, or we would have brought a swim diaper and trunks, but he stripped down to his diaper and rolled around in the Lake. It's not dirty or anything (like rivers in the 1980s) -- there were hundreds of people swimming. You'll just inevitably need to clean sand out of, um, all the body parts. We were ill-prepared, so we just walked back to the hotel for a mid-morning shower. But the Wee Boy had a blast, throwing his cars in the Lake, rescuing them, blowing bubbles, making sand angels, and running up and down the beach. So. Much. Fun.
|Ohio Street Beach in early September. Chicago.|
|Vegetarian skillet at Wildberry Cafe. Chicago.|
It's my favorite meal of the day, but it's even more satisfying when your toddler wakes up at the crack of dawn. This means you can get to the über-popular weekend brunch spots before the lines form. I also like eating a huge breakfast, then a light lunch (hitting the grocery store saves loads of money) and simple dinner. We went to Yolk, Wildberry Cafe, and West Egg. All were delicious and family-friendly. Yolk was BYOB, as we learned as the child-free couple next to us emptied their second bottle of André. Wildberry is one of the most popular restaurants in the whole city -- yummy, but wouldn't have waited in the hour-long line that we saw after we finished (again, the perk of rising at 6am). If we'd found West Egg the first day, however, I'm not sure I would have gone anywhere else. The staff was incredibly kind to our rambunctious almost-two-year-old, and the coffee was superb.
We hit up Millennium Park after a leisurely breakfast at Wildberry Cafe. The Cloud Gate (or "The Bean" as my Facebook friends insist it is called) is a massive and cool public art piece where we spend a good thirty minutes running around, staring up, lying down, taking pictures, and making faces at ourselves. The kiddo was fascinated.
We also spent a good deal of time frolicking in the Crown Fountain (also in Millennium Park) near the Art Institute. (201 E. Randolph St., between Michigan Ave and Columbus Ave). The faces on the fountain appear year-round, but the water is available only mid-spring to mid-autumn. The water was cool and refreshing on a perfect 72* day. Again, crunchy mom here, but it was a blast. This time we were prepared with a swim diaper. We kicked off our shoes, parked the stroller, and splashed with lots of other families.
|The Cloud Gate aka The Bean in Chicago.|
|Playing in Crown Fountain in Millennium Park. Chicago in September.|
What toddler doesn't love "The Wheels on the Bus"? Seriously, if you're tired or it's raining or you just need to get somewhere, this is a great activity for toddler tourism. We took the bus from Millennium Park to the Lincoln Park Zoo.
Same as the bus, except it's a TRAIN!! The Wee Boy is in a serious train phase, so this was a great ride for us all.
Lincoln Park Zoo
It's free! It baffles me that the Art Institute is over $20/person, but the Zoo is free. But it is. Free activities are the best because you don't feel bad if you only stay thirty minutes, or if your kiddo falls asleep right after the sea lion training demonstration.
|The lion took a snooze. Lincoln Park Zoo. Chicago. September 2014|
Watching the Boats
We were able to see the boats docked from our hotel window, so that was an easy and relaxing activity. But it was just as easy to walk down to the pier by the Ohio Street Beach and count the boats (I wanted to rent one of those fun bicycle/wagon things, but we opted not to spend the money). Good, innocent fun.
There is so much more to do, but we were trying to do as much free and outdoors stuff as possible. All in all it was a really easy weekend, but packed with activity. I think the key, as with any trip with a toddler, is to go with the flow and only plan just enough. Naptimes or meltdowns can throw kinks in the best-laid plans.
And before anyone gets on my case, yes, I'm aware that I've only got one kiddo, so life is a lot easier than it could be. But we are still not afraid to travel. Thankfully, my kid loves adventures, and shaking up his routine actually makes him sleep better at night. (Seriously, I'm so thankful for this because routine makes me cranky. Maybe it's genetic.)