A Weekend Getaway to the Windy City

I’m not really much of a city person. Give me ocean or mountain scenery over skyscrapers any day of the week. But there are a few cities that, for one reason or another, have really captured my heart, and Chicago is one of them. I’m not sure if it’s the friendly people (those stereotypes about Midwesterners being nice are real), the miles of lakefront that somehow make a city of almost three million people feel outdoorsy or the sentimental memories of childhood visits with my family, but Chicago and I just click. And since we now live just a couple of hours away and early fall is the perfect time to visit, it was an easy choice for a recent weekend getaway. My husband and I have both been to Chicago many times before and done many of the usual tourist activities, so this trip was a leisurely one, and we focused on soaking up the city, enjoying the beautiful weather and of course, finding excellent places to eat.


Our first stop was Lula Cafe in Logan Square. Although it was chosen mostly for its dog-friendly outdoor seating, the food and coffee here were absolutely fantastic. I can never say no to cornbread french toast, but I especially loved Lula’s perfectly seasonal version, with roasted plums, sweet granola and cinnamon-creme anglaise. My husband raved about his Royale breakfast sandwich, which had pork loin, winter squash and a fried egg. Four thumbs (and two paws!) up for Lula Cafe.


After a walk around Logan Square Park for the furry one, we headed into downtown and checked into our hotel, the super pet-friendly (no fees or weight restrictions) Kimpton Gray. The hotel is brand new and I was very impressed with it, especially the funky design touches (I love the way the turquoise doors pop against the dark blue hallway).


I know it’s tourist central, but I can never go to Chicago without visiting The Bean (the sculpture officially known as Cloud Gate). It’s a great spot to get a selfie or a photo of the reflected skyline. Unfortunately, that afternoon it was even more crowded than normal because of a food festival happening in Millennium Park, but it was still a fun stop, and the various lakefront parks nearby are a great place to hang out and enjoy nice weather.


I was eager to experience the Chicago fine dining scene I’ve heard so much about, so that evening we gussied ourselves up and headed to Acadia. This restaurant first caught my eye because of its name, which is a reference to my beloved National Park, but as soon as I looked at the New England-inspired tasting menu I knew it was a place I needed to try. Our meal here exceeded my very high expectations. It seemed like every bite that came out of the kitchen was better than the last, and so much thought went into the presentation of each dish (coordinated green bowls for the cucumber sorbet, chocolate ganache formed into spaghetti noodles) that they were practically works of art. I can’t point to a single disappointing dish, but if pressed to name my favorites I would have to go with the miniature lobster rolls that began the meal, the deconstructed salad made of ingredients grown on Deer Isle, Maine (where the chef has a family home) and the flaky biscuits with special high fat butter (yes, high fat butter is a thing and it’s as delicious as you would imagine).


We started our Sunday in a lazy fashion, strolling over to Do-Rite Donuts and Chicken for donuts and breakfast sandwiches. The verdict: don’t miss the donuts (both the Valrhona chocolate and blueberry crumble were outstanding); the sandwiches aren’t bad but I’d skip them so you have more room for donuts.


We walked home via Michigan Ave, the large boulevard famous as Chicago’s premier shopping destination, and the Chicago Riverwalk.



We picked up the pup and took a (long) walk up the lakefront to Navy Pier. The other spots I’ve mentioned aren’t exactly under the radar, but Navy Pier is incredibly touristy. With it’s giant ferris wheel and carnival funhouse, I’m pretty sure it’s a place tourists flock to, but locals avoid like the plague. Still, it’s not a bad spot to visit as an out-of-towner, especially for a first-time visitor to Chicago, if for no other reason than the fact that there’s a pretty nice view of the Chicago skyline from here.



We had a second reason for being at Navy Pier, however – it was the departure point for our architectural boat tour of Chicago’s waterways! I mentioned at the top of this post that I’ve done many of the traditional tourist things in Chicago, but one thing I’ve always wanted to do but never had the chance to is an architectural boat cruise. We cruised with Seadog who, true to its name, allows dogs on some of its cruises. In fact, we were not only allowed to bring Dancer along, we actually got a 15% discount on our tickets for having a dog in tow. We began by heading out onto the lake for a full view of the skyline (unfortunately with the sun not in the best position for photography) and a little bit of a thrill ride on the speedboat.



We then headed back past Navy Pier and into the lock that was built to reverse the flow of the dirty Chicago River away from Lake Michigan, which supplies Chicago and many other communities with their drinking water.



We cruised the river for about an hour, with our guide pointing out various buildings of note and telling us a little about their history and architecture. The weather was perfect for a boat ride, and I really enjoyed learning about some of Chicago’s most famous buildings, including the Wrigley Building, the corn cob-shaped Marina City towers (which have had a starring role in many movies, including Batman Begins) and, of course, the most famous Chicago landmark of them all, the Willis Tower (which will always be the Sears Tower to me).



We ended the trip with some delicious tacos on the patio at Big Star before hitting the road for home.


Until next time, Chicago!

2 thoughts on “A Weekend Getaway to the Windy City

  1. Okay, I want donuts now. (And I also want high-fat butter on something – I’ve never heard of it!) And how cool that your pup scored you a discount. I love that!


  2. Pingback: A Foodie Excursion to Deer Isle, Maine | Destinations & Desserts

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s