Our whole family has the travel bug and we’ll always take the first chance we have to go somewhere, whether it be a small, little known destination or one of the big tourist hotspots. Like many people, we spent 2020 and the majority of 2021 at home dreaming of all the trips we’d like to take but hesitant to make any plans as things were (and still are) ever changing.
As things finally started opening up, we decided to take a girls’ trip, just my mom and I (sorry Dad!) and Chicago was the perfect choice since my mom had never been and I had only gone for work or to visit some friends. We visited in October and although it was a little chilly (but still sunny), the usual throngs of people you see in the summer weren’t there so we enjoyed almost no crowds at most of the touristy places.
We wanted to stay in the heart of the city so it would be easy to get to all the city highlights without having to Uber everywhere – LondonHouse Chicago was the perfect choice. Not only is it centrally located, but it has the most amazing views of the river and the beautiful Chicago skyline. We were lucky enough to get a room with a coveted river view. This hotel also has an amazing rooftop bar which would be a great place to hang out during the summer (it was just a bit too cold in October). Even with the cooler temperatures, there was a line to head up to the roof, so make a reservation in advance if you’d like to visit.
Recently, Chicago ranked as the number one most beautiful city in the world, beating cities like Paris and Vienna, and after visiting this city, I’m not surprised. The architecture, both old and new, is beautiful with the newer buildings seamlessly fitting in with the older skyscrapers, but each being unique and standing on its own. This beautiful skyline sits on the background of Lake Michigan and has the Chicago river flowing through the center of the city. We highly recommend walking along the river – you can get some great views of the buildings and there are some cafés that you can grab a drink or snack at.
Things to Do
Here are some of the highlights of our trip and our brief thoughts on each:
Millennium Park and Cloud Gate
The famous “bean” sculpture sits in this vast park that’s also home to the summer music festival, Lollapalooza. We went here mid-day on a weekday when it was unusually cold and kind of rainy so there wasn’t as much of a crowd which allowed us to take tons of pictures and appreciate the area without a lot of people getting in our way. We were really impressed by the Jay Pritzker Pavilion which was designed by Frank Gehry. Next time we’re in Chicago, we’d definitely like to attend a show here.
Willis Tower
The iconic skyscraper that once held the title of being the tallest building in the world. Previously known as Sears Tower, this is a must do if you’re visiting Chicago. We would recommend going up to the top when the weather’s clear so you can get amazing views of Lake Michigan and the surrounding mid-West landscape. Coming from the west coast, we were quite shocked by how flat the landscape is – you can see for miles! The main attraction here is the Skydeck where you can step out into a clear glass observation box that extends out from the building so you get unobstructed views from every direction, including down. Being scared of heights, I thought I would feel dizzy but it wasn’t bad since you’re fully enclosed and the views are breathtaking. One note, this is a super popular Insta-worthy photo op area so they time you on how long you can spend in the Skydeck.
Art Institute of Chicago
This was probably one of our favorite places we visited in Chicago and we highly recommend it for any art lovers. The Impressionism collection, especially their Monet and Van Gogh collection, is very impressive. My favorite exhibit is the Thorne Miniature Rooms where different rooms from different eras are intricately recreated at a 1:12 scale. I had never seen anything like this before and it felt like I was looking at an incredibly detailed doll house.
Chicago Riverwalk
This is a great way to spend the afternoon, walking along the river, enjoying the architecture and city life. There’s always something fun going on, especially on the weekends. We saw several photo shoots for weddings and many street performers.
Chicago’s First Lady Cruises – River Cruise
We originally hadn’t planned on doing this and added it to our plans very last minute and boy, was it worth it! We did the Chicago Architecture Foundation Center River Cruise which is a 90-minute ride in the river with a very knowledgeable docent guiding you through all the buildings along the river. They take you out into the lake at the end of the cruise and you get an awesome view of the Chicago skyline. This is definitely a must-do when visiting Chicago!
Magnificent Mile
Another way to spend a free afternoon. This stretch is filled with upscale shops, great restaurants, and fancy hotels. This area was definitely the most crowded while we were in Chicago. We’re not big shoppers, so this was an afternoon of window shopping for us, but it’s worth a visit at least once.
Navy Pier
This is a great place to visit, especially if you have kids. There are lots of activities like carnival games and rides and a children’s museum. The giant merry-go-round is a huge attraction for everyone. We intended to visit the Crystal Garden, an atrium with an indoor garden, but unfortunately it was closed for maintenance. The area is right on the lake and you can get some great views of the city from here.
Tribune Tower
A historic building, located on the river along the Magnificent Mile, that is not only beautiful but also has a unique feature where different fragments of famous historical sites are embedded into the walls of the skyscraper. Some famous sites that we noticed were the Taj Mahal, the Great Pyramid, and the Great Wall of China.
Places to Eat
Any time we visit a place, we not only like to hit the highlights of the city in terms of architecture, museums and things to do, but we also like to enjoy the food. Chicago has an amazing food scene and some notable up and coming chefs cooking up innovative dishes.
Here are the restaurants we visited and some of the dishes we recommend at each place:
Omakase Yume
This was our first omakase and we must say, it’ll be hard to compete with the outstanding experience we had here. Omakase is a Japanese phrase that literally translates to “I’ll leave it up to you” so the chef will make the courses on what ingredients are available that day and what they feel like making for you. We had 17 courses (set menu) and each dish and piece of fish was unique and had its own flavor profile. What made this experience even more special was the small group seating. There are only eight seats per seating with each seat getting a front row seat to the artwork the chef is creating (I’m not exaggerating when I say art – each piece of sushi was as beautiful as it was delicious). This is definitely a splurge dinner, but definitely worth it.
Aba
This is a Mediterranean restaurant serving up small plates with a cool rooftop patio to sip on their amazing cocktails. Getting a reservation (even a month before our trip), was a struggle, so definitely plan ahead. We were able to snag a table outside for two at 9 PM (thankfully we were still on west coast time!). For drinks, I would recommend going with their cocktails over wine since that’s what their known for, and trust us, they were really good. Some dishes that stood out to us were the muhamarra with warm pita bread and the salmon kebabs.
Avec West Loop
We came here for brunch and ooh, it was really good! We weren’t trying to go for a boozy brunch since we had a whole day of sightseeing ahead of us, so we started out with their coffee, which hit the right spot on the cool Sunday morning. Then we shared the patatas bravas, shakshuka, and French toast. Each dish was absolutely delicious. Next time we’re in Chicago, we’d definitely want to come back and try out dinner here. Not only was the food delicious, but the service here was top-notch. Our server was very knowledgeable and attentive and made us feel like family here.
Proxi
We had dinner here the day before we were flying back home and it was the perfect way to end our trip. Everything from the drinks to the food was excellent. I would highly recommend having one of their Spanish gin and tonics (my mom and I have a sweet spot for G&Ts). They come in these giant glasses and are so refreshing. We definitely had a few of these here. The food is served as small plates so you can try various things on the menu and you’ll definitely want to. All the menu items are some kind of fusion, taking flavors from Asia, Europe, and America and creating unique dishes with flavor profiles that I’ve never had before. I recommend getting the khanom krok which are coconut milk pancakes with shrimp and a chili jam. And don’t forget dessert: get the brown butter cake, it was so, so good. I’d come back here just to have this dessert again, but everything we had was delicious.
Overall our trip to Chicago was a great getaway, especially after staying home for so long. If you’d like any more information or have questions about our time there, feel free to drop a comment or reach out to us on Instagram!
