Chicago Travel Guide

This past weekend, we celebrated our anniversary in Chicago! Alex had never been to Chicago and I had not been since I was about eight, so we were both eager to explore the city. I received so many great suggestions on Instagram from you all, and we did our best to eat, see and do everything we could in five days. I have compiled a Chicago travel guide based on your recommendations!

Where to stay: We stayed at the LondonHouse by Hilton and had the best experience (read my full LondonHouse Chicago review).

Where to eat: Our trip started with lunch at the LondonHouse Rooftop. The weather was not great outside on the 22nd floor so we dined inside on the 21st floor. We visited the 22nd floor later in the week to enjoy the incredible view both during the day and night.

I received a ton of suggestions for deep dish pizza (Uno’s, Gino’s East, Girodano’s) and we decided to give Labriola Cafe a try. While we decided that we are more thin crust people, the Danny’s Special deep dish pizza was delicious and so so filling!

We mainly ate breakfast at our hotel (Land & Lake Kitchen), but did venture to Beatrix – River North one morning. We both enjoyed breakfast cocktails as well as the oatmeal and pancakes. I would love to go back and try their dinner menu, because the brunch menu was so yummy and creative.

After walking all around town, someone (couldn’t possibly be me) started getting hangry and lunch quickly became a priority. Fisk & Co. was not our original plan for lunch but it ended up being a much better option. We enjoyed the Spring Chowder (surprisingly light), the sautéed gnocchi and prime cheeseburger. Noyane was the most recommended sushi spot in Chicago and we loved the rooftop atmosphere! Their craft cocktails were very unique and the sushi was creative and delicious. We loved the acevichado roll, tuna nigiri and a classic California roll. Shaw’s Crab House was another unexpected lunch spot (we had time to kill before our flight) and ended up being one of our favorite neighborhood spots. The atmosphere had a very 1960’s east coast vibe that made you feel like a Kennedy. We devoured the crab cakes in seconds and added a generous amount of Tobasco to our seafood gumbo. Hampton Social was another highly recommended spot and while the food and atmosphere were great, our service was horrible. We visited the Streeterville location and would not go back but might try the River North location next time.

All of our dinners were incredible, starting with Celeste. We sat in the deco and enjoyed the tahini hummus, Iggy’s original lemon butter pasta and seared salmon. To celebrate our anniversary, Alex made reservations at RL Restaurant by Ralph Lauren. This was probably one of my top three dinners ever! Everything about RL was just as expected. Our service was perfect, the food was delicious and it made a great first anniversary memory. Our favorite things on the menu were the lobster bisque, mushrooms and key lime pie (currently trying to recreate the gingersnap crust), but our steaks were delicious as well. Fig & Olive was also a great dinner choice and we will probably try to visit the Houston location next time we are there. The truffle risotto with scallops made the list of my favorite dishes!

Other highly recommended restaurants we did not have time for include: Restoration Hardware’s Rooftop Garden, City Winery at the Chicago Riverwalk, Le Colonial, Drumbar, Cindy’s Rooftop, Au Cheval, Bongo Room, The Second City, Summer House Santa Monica, The Signature Room at the 95th, The Vig, Parson’s Chicken & Fish, and Violet Hour.

What to do: We went to a comedy show at the Comedy Bar and most of the comedians were funny. Amateur stand up is always hit or miss but the Comedy Bar had a very intimate vibe and is above a Gino’s East pizza if you want dinner before or during.

One of our favorite experiences was the Skydeck, the fast pass is totally worth it if you visit on a weekend. Your time on the skyjack is short and I wouldn’t look down, but the views are unmatched and you can really see all of Chicago.

The Art Institute Chicago and the Chicago’s First Lady Cruise were my two favorite things on the trip. I could have spent hours in the Art Institute looking at the wide range of art, especially the modern collection. The First Lady Architecture Cruise was one of the most informative city tours I have ever been on. Not only did Alex learn a great deal about architecture, but we also received a full history lesson on the city of Chicago.

Towards the end of our trip we felt like doing some more touristy things, and spent some time exploring Millennium Park. We caught part of a concert at the Jay Pritzker Pavilion (they run these all summer), stopped by Cloud Gate for a photo and saw Buckingham Fountain. We also walked the Navy Pier, which was not very exciting but great exercise.

For happy hour we checked out Three Dots and a Dash speakeasy, Centennial Crafted, District Brew Yards and On Tour Brewing.

Some of the highly recommended activities we did not have time for include: North Avenue Beach, The Museum of Contemporary Art, The Field Museum and Wrigley Field.

Watch our short recap and shop everything I wore during our trip to Chicago below! xoxo