Chicago Travel Guide: A Family-Friendly Winter Weekend

We just got back from a few days in Chicago, and decided it was one of our favorite trips yet! The girls had a blast, and we did a handful of things we’ve never done in Chicago before, which made it super fun! Let’s jump right into our travel guide to see our family-friendly winter weekend in Chicago!

Where we stayed

We were so excited to partner with Hilton again, and this time, experience a different area on Michigan Ave. We stayed at The Hilton Chicago Hotel, on the south end of Michigan Ave. The hotel had some MAJOR curb appeal. Adaline actually yelled out, “ARE WE STAYING IN A CASTLE?!” And, she wasn’t wrong. The hotel itself is massive. But we didn’t have an issue valeting, and the parking entrance is on a side street, so we were thankful to not have the stress of trying to park/unload on Michigan Ave (which is Dave’s least favorite thing!) So, right off the start, the hotel was a win.

 

We had adjoining rooms – both of which were very roomy! Our room had an amazing view of Grant Park and Lake Michigan.

Shop my outfit here. 

Dave and I were talking about how we gauge hotels on how they cater to children (and we don’t mean the “family resort” or “waterpark” style hotels – we mean the hotel’s ability to make children feel included, special, and welcome – and parents a little less stressed!) We always love the staff at Hilton Hotels.  You might remember our stay this summer, when one team member literally made the girls’ day each morning, by giving them a ride in and out of the hotel on the baggage trolly! At Hilton Chicago, the girls were so excited to see a GIANT Christmas Tree in the lobby, as well as a gingerbread replica of the hotel, and the parks nearby near the elevators. On Saturday morning, we walked out from breakfast, and were delighted to see the team setting up a cookie decorating station for kids!

 

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Home is where the heart is, and Christmas is where the cookies are ????????????⁣ ⁣ We are back hoke now, but i can’t get over this cute cookie station at @hilton_chicago_hotel!! They run it on Saturdays during the holiday season!⁣ ⁣ QUESTION! Are you a holiday cookie baker? Or are you team store-bought?⁣ ⁣ AD #ChicagoHiltons #heyitsjennatravels http://liketk.it/2HUST #liketkit @liketoknow.it #LTKholidaystyle #LTKfamily #LTKunder100 #chicago #windycity #hilton #suitelife #chitown #christmas #christmascookies #gingerbread #gingerbreadtrees #cookies

A post shared by Jenna (@heyitsjenna) on Dec 8, 2019 at 5:33am PST

Where we ate

Hilton Chicago

We enjoyed daily breakfast at Hilton Chicago. The buffet was amazing, and had a ton of options. Dave and I discovered a new love for breakfast chicken hash, which was on the buffet daily. It was SO good. They also had a made-to-order egg station. Dave and I were able to enjoy omelettes, while the girls were able to get freshly scrambled eggs!

I mentioned the desserts above, but guys. Hilton Chicago doesn’t mess around when it comes to treats! We were greeted with the prettiest cake ever when we checked-in. I almost didn’t want to cut into it, but I’m so glad I did – it was one of those fun cakes with M&Ms inside! For breakfast the last morning, we received a fun and festive dessert tray!

Herb N’ Kitchen is located in the lobby, and offers grab-and-go options, as well as drinks and coffee!

Formento’s

Friday night, we headed to dinner at Formento’s. Pro tip: snag a reservation on Open Table! The food and atmosphere was amazing, and our server was very fun and friendly. While they don’t have a dedicated Kid’s Menu, they did have crayons and coloring pages for the girls, and were able to do picky-kid-approved buttered noodles 😉

I had the lobster risotto (so yum!), and we had an assortment of gelatos to try for dessert – we highly recommend the apple cinnamon!

Shop my dinner outfit here.

What we did

Winter Wonderfest

We got into Chicago Thursday for Winter Wonderfest at Navy Pier! When you stay at any Chicagoland Hilton hotel, you’ll score 20% Off Admission for up to 4 people at Winter Wonderfest as well as: 20% Off Parking at Navy Pier, a $5 Winter WonderFest Food Voucher (one per room reservation), and 10% Off Photo Package! (read how to redeem here)

Winter Wonderfest was SO fun. They had giant inflatable slides, bumper cars, carousels, a few “big kid” rides, ice skating, aerial acrobats, lots of fun photo-ops, a cute little train, and Santa and Mrs Claus!

You can shop the girls’ outfits here. 

The entire event was pure magic!

Millennium Park

Millennium is a short walk from Hilton Chicago. If you haven’t been in the winter, it is SO fun (cold, but fun!). Again, you get some major perks if you’re staying at any Chicagoland Hilton hotel!! Score two pairs of free ice skates when you show your Hilton confirmation email at the skate rental desk to redeem! (and read the details on how to redeem here)

I can’t think of many things that are more perfect for a December afternoon than ice skating, while enjoying the view of the Chicago skyline and the Bean! We also found a massive Christmas Tree, which made the perfect photo-op!

Shop our looks here.

Maggie Daley Park

We wandered across the street from Millennium Park, and stumbled upon the cutest park. There were so many cute little play gardens, divided by age. Maggie Daley Park also had a giant climbing wall, mini golf, and an ice skating rink!  The girls had a blast running around and playing on the swings and the pirate ship in the play garden.

I imagine the park is the place to be on summer day, but we enjoyed mostly having the park to ourselves!

Shopping

Because it’s just not possible for us to go to Chicago and not pop into a store or two, haha! We surprised the girls with a trip to the American Girl Doll Store, which was such a treat for them! Definitely recommend checking their website prior to your visit, so you can see if there are any fun events planned! They have a cookie baking event coming up that sounds adorable!

You also can’t beat the views, just walking around Michigan Ave, seeing the pretty Christmas lights and decorations!

Christkindlemarket

We walked over to Christkindlemarket from Hilton Chicago. In hindsight – and with 3 kids – I would opt for a Lyft or Uber, but we made it there and back! It was SO magical but also SO crowded. While I absolutely loved looking from booth to booth, I would recommend not bringing kids along. Lines were huge, and it was shoulder-to-shoulder packed, and hard to navigate through.

I did score the cutest new ornament for our tree and some tasty chocolates and treats, though!

Swimming

Hilton Chicago has a pool! Woo-hoo! The girls loved it, and it gave us something to do once it got dark/colder in the evening! The pool area also had pretty views, and a seasonal sundeck. Obviously, we didn’t hang out on that, but in the summer, that must be gorgeous!

The Art Institute of Chicago

Before we left the city, we decided to pop into the art museum. Andy Warhol is one of my favorite artists, and the Art Institute of Chicago currently has the Andy Warhol – From A to Be and Back Again Exhibition, and it did not disappoint. The exhibition is open through January 26th!

The art museum also had a fun area called The Family Room, where the girls could do a craft, and make their own art guide (which was basically a fun scavenger hunt to get them engaged in the art)! Very cool!

 

Chicago never disappoints, but I feel like this was just such a fun, family-friendly winter weekend overall! We did so much, and with all the festive holiday magic sprinkled throughout, it’ll be a tough trip to top!

Have you been to Chicago around Christmastime?! What’s your favorite thing to do?

Thank you again, to Hilton for hosting us. All content and opinions remain our own!