Chicago holds a super special place in our hearts! Josh proposed on the Navy Pier there in July of 2005 and we were married exactly one year later. I’ve been back numerous times, both with him and with girlfriends, but we had never taken our kids. We had time to do it in between two other trips and decided to make it happen! You know we aren’t strangers to road tripping, so we planned to break up the drive by staying with family in STL on the way there. Then, we would do the drive straight through coming back, going through Des Moines.
We spent 3 days and nights in the “Windy City.” On Thursday we got into town and were starving! We headed to Little Goat in the West Loop for lunch. It’s a cute diner that serves comfort food with a gourmet take. The French toast with fried chicken was so delicious! Then we checked out the Museum of Science & Industry before going to check in at the 21c Museum Hotel. Our favorite exhibit was Science Storms but the Whispering Gallery was really cool too!
We went to dinner that night at Il Porcellino, a chic, classic, Italian restaurant in River North. They make a lot of their pastas in house. Many of their dark walls were gallery walls with old photos and most tables were covered with red checkered tablecloths. String lights and pendants hung everywhere. Everything was so delicious and our waiter, who had the best accent, couldn’t have been nicer! Shockingly, the gnocchi bolognese didn’t leave me any room for dessert. But I have no regrets. Ha!
We knew our view from the 17th floor was great when we checked in, but it wasn’t until we got back from dinner that night that we realized HOW great!
On Friday we had an early lunch at Au Cheval in the West Loop. It’s an upscale diner with big, tufted-leather booths, a long bar, and a cozy vibe due to the dim lighting. They don’t take reservations. It was recommended that for lunch, we arrive before they open at 11am. So glad we did because within minutes the place was full and a long line formed outside! Apparently the Food Network rated the restaurant as having the best cheeseburger in the US, so the wait time shouldn’t come as a surprise. We unanimously agreed that they may be the best we’ve ever had! A bit of advice: Singles actually come with two patties and doubles come with three. We all had singles and shared fries and hashbrowns. Definitely recommend adding bacon and/or an egg!
After lunch, we spent a few hours at the Shedd Aquarium. All the black & white stingray were very on-brand for me and we loved the dolphins and sharks. But I bonded with the beluga whales and they were the best!! Currently googling how to own a pet whale. I could’ve watched them for hours and loved how they always stayed in pairs!
We then walked through Grant Park and Millennium Park to take in the sights. Below you’ll see the moment I realized how old I am because my kids have no idea what “Married with Children” is.
On our way back to the hotel, we walked Michigan Avenue (known as The Magnificent Mile). We stopped to check out the Riverwalk and grab cold brew and hot cocoa at the Starbucks Reserve Roastery. I usually like to find local coffee shops when I travel, but the Reserve Roasteries are only in Seattle, Chicago, and NYC. It was around the corner from our hotel, so I feel it would’ve been neglectful not to stop in to see what it was all about so I could report back! The long line moved quickly and both drinks were yummy. So was the chocolate hazelnut tart I devoured before taking a picture. No shame here- I was killing it with my steps each day and declared it a Fed Girl Summer back in May!
After a long day of sightseeing, we headed back to the hotel to freshen up before walking to our nicest dinner of the trip at Joe’s Seafood, Prime Steak, & Stone Crab in River North. It’s a chain that’s known for their stone crab and key lime pie. In case you don’t preview menus before choosing restaurants (who even are these people), you know it’s going to be pricey when you walk through the doors and see every waiter in a tux. Every aspect of this meal was fantastic. The bread (Rowan even commented on it), drinks, seafood, dessert, and service were all amazing. I’m still thinking about my colossal lump crab cakes. Our waiter loved chatting with our kids and gifted us two desserts, so we purchased two and each had our own. Nothing brings me pure joy like not having to share my dessert!
Saturday we made our way to the Skydeck at Willis Tower before they opened. It rained off and on every day of our trip and we learned when we got there that visibility was basically zero, but we decided to go up anyway. We rode an elevator 103 stories and listened to the facts about the tower. We walked through a very well-done mini museum about the city and the tower. When we got to the end, we stood/sat on 1.5 inches of glass that protruded from the side of the building. I say we, but I think Josh’s feet/body made it onto the platform for a total of 18 seconds.
We then took the BP bridge from Millennium Park to Maggie Daley Park. The park was really well done, but most aspects of it were geared toward younger kids so it was a quick stroll through.
Lunch was at the South Loop location of Lou Malnati’s on State Street. Josh loved it, but the rest of us decided it wasn’t really our style. Personally, I don’t love deep dish or a lot of sauce, but I’m glad we tried it and I actually loved their house salad with the homemade sweet onion dressing.
There was a break in the rain when we got to the Navy Pier for our Hornblower Seadog speedboat tour. I was so glad I made a reservation in advance because the line was LONG. We did the regular 30 minute speedboat tour- not the extreme, which was good because we didn’t need to get MORE wet on this trip. Cool J, Swag, and Eric made for a great crew and we really enjoyed the ride along the lakefront!
Our last dinner in Chicago was at Aba, a trendy Mediterranean restaurant serving small plates in the West Loop. It’s gorgeous and often places that look really good don’t have really good food to match. Aba would be the exception. Even though the dining room is huge and there are two long bars and a sizable rooftop patio, it’s incredibly hard to get into. I can’t stress this enough: Make reservations as soon as they go live a month in advance. I initially wanted them for Friday but by the time I went online to put in for them at 7am, that day was completely booked for dinner a month away! I switched gears to Saturday and stayed up that night until midnight in order to grab a time for the Saturday a month from then. To my surprise, it was worth it. The lamb and beef kebabs, rice, and crispy potatoes were delicious. Because they serve small plates, we felt full but not stuffed and had plenty of room for dessert. The chocolate cake with caramel sauce was delicious! This restaurant had the coolest vibes of almost any I’ve ever been to!
Our night ended on the Navy Pier where we rode the Centennial Wheel and watched the fireworks. Everywhere along the pier you saw the celebration of Pride Month! The fireworks began while we were on the ferris wheel, which I couldn’t have planned but was so grateful for!
We stayed at the 21c Museum Hotel. The location was great and the rooms were clean and spacious with a gorgeous view and a sitting area. There’s even a museum on the first two floors. The only negative was parking. There are many garages within a block and they will only validate parking for some of them. Of course this isn’t a problem if you don’t drive there!
- Au Cheval
- Il Porcellino
- Aba- Book as soon as reservations go live for your date! Stay up late or wake up early to book- this is not a drill!
- Shedd Aquarium
- Willis Tower Skydeck
- Navy Pier Ferris Wheel & Fireworks- Currently, fireworks are on Wednesdays & Saturdays in the summer.
It rained a lot while we were there, which is funny because I can’t remember it ever raining the numerous times I’ve been there in the summer. We didn’t let it spoil our fun, but there were a few things it kept us from seeing or doing. Next time we will for sure visit Garfield Park Conservatory, the John Hancock Observatory, and Lincoln Park & Zoo. We may make time for the Field Museum as well.
It was so much fun exploring a big city with older kids! They are a blessing to travel with. They can walk a lot and keep up, care about the history of places and ask a lot of great questions, go with the flow, and are down for trying new foods. They still roll their eyes and complain about their feet hurting, but I’m good at blocking out that kind of negativity! Chicago in the summer is magic. The people have that midwest kindness, the temperatures are usually mild, the options for what to do are endless, the city is walkable, and we always felt safe. What more could you ask for?