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The last time we visited Chicago was almost 5 years ago, so we were eager to return and revisit the Windy City. As usual, we had a list of restaurants and bars to try during our stay. We planned a 3 night trip which was a mix of work and leisure. Some of the best things to do in Chicago is explore restaurants, it is a foodies heaven, enjoy the beautiful architecture and enjoy long walks or bike rides.
Where to Stay
We stayed in the Waldorf Astoria, we stayed here on our last visit and the location is unbeatable, plus most of the rooms have balconies with a great vista over the area. Located on East Walton Street you are within walking distance of Magnificent mile, the Lake and River, plus you are surrounded by all the designer stores and local restaurants. As Chicago is a large city there are many hotels to choose from as well as a good selection of Airbnbs.
Some other notable hotels:
St. Regis
Four Seasons
Viceroy
Peninsula
The Drake
Soho House
If you're not acquainted with Chicago, we consistently discover that it is a fantastic city to explore due to its location. It is so easily accessible with many flights both domestic and international every day. The city itself allow You to experience the urban atmosphere and enjoy the beaches as well. Another aspect that stands out to us when we are in Chicago is its cleanliness. The well-maintained streets create a pleasant environment for leisurely strolls or a snoop on some of the beautiful real estate.
Cocktails & Dining
There are a number of new restaurants that had opened up since we last visited and I had added these to my list. Ahead of traveling I always make sure to try and get the reservations for our top choices. We were lucky to snag a reservation at Omakase Yume, we always include an Omakase experience wherever we go as it is one of our favorite cuisines to enjoy. Sadly, we didn't love this Omakase experience, mostly down to the fact that the chef didn't interact with us at all and as there was only 8 guests there it created a slightly cold environment. That being said, some of the bites were amazing and this caviar and 24 karat gold nigiri is one of the most decadent nigiris I have ever had.
We were eager check out the newly opened St.Regis hotel where TreDita bar and restaurant is located and has been getting a lot of positive press. We had a smaller Italian restaurant called Ciccio Mio reserved, this was a local recommendation from some friends from Ireland who now live in Chicago. Luckily, we got to meet up with them while we were in town and Indulged in some great Italian plates.
We reserved for The Aviary which is an interesting experience and one I would recommend checking out for one drink, this bar concept is from the same group behind the world-renowned restaurant Alinea. There is a lot of theatre with every cocktail so it is worth visiting but it is not somewhere I would frequent. After enjoying some entertainment at Bar Aviary, we decided to explore a new spot called Bar Bisou. Situated in Fulton Market, this small 1960s Parisian inspired cocktail bar impressed us with its unique cocktails and welcoming staff. If you are a martini lover, then this bar is for you! Unlike many other bars in the area, Bar Bisou stayed open late, and they certainly knew how to make a mean espresso martini.
The St.Regis Hotel opened with a bang and as mentioned we had really wanted to see the property which overlooks the water. We didn’t get a reservation for dinner at TreDita but we wanted to make sure we checked out the hotel so we booked a late night bar reservation to be able to experience it. This is a great way to see more of the five-star hotels, while you’re visiting any city if you go and grab a pre-dinner or post dinner drink you will get the feel of it and have a luxury experience. You don’t need to be staying in a hotel to enjoy its amenities. This is definitely a travel tip I would recommend.
We returned to The Girl and The Goat, situated in the ever-famous foodie district Chicago's West loop. The restaurant has been open since 2010 and as usual it was absolutely humming and super busy. The food is great, the service is friendly, and it is definitely a Chicago staple.
For lunch, we went to Restoration Hardware. I fell in love with restoration hardware when I visited Chicago for the first time back in 2014, long before they ever had a dining offering and like all of the other Restoration Hardware restaurants, you don’t go for the food or the service or the drinks - you only go for the ambience, the vibes and being able to wander about the store and admire all of the beautiful interior pieces.
Shopping
As previously noted, our stay at the Waldorf was excellent due to its unbeatable location. While we didn't dedicate much time to shopping (who needs souvenirs when you have memories, right?), we did engage in some browsing during our visit. With stores such as Dior, Hermes and Chopard on the doorstep it would be rude not to practice our window-shopping skills! We didn't make any purchases, but safe to say you could easily do some damage.
Outdoor activities in Chicago
Fortunately, the weather was fantastic during our time in Chicago allowing us to enjoy several beautiful walks throughout our trip. What is amazing about Chicago is it is extremely walkable, there is the river walk plus you can actually walk all around the lake and throughout the day and evening we walked to ensure we got our steps in. During the Spring and Summer months, you will find people engaging in activities such as volleyball and biking down by the water.
Top Recommendations if Visiting Chicago for the First Time
If I was a first time tourist there is definitely a few activities I would recommend:
Architectural Boat Tour
Millenium Park - snag a photo with the Famous Bean (Chicago Athletics association has a great rooftop bar called Cindy's which I would recommend for a great view of the Bean)
Sky Deck - only recomened if you do NOT have a fear of heights
Walk Magnificent Mile
Riverwalk - a great walk to do with many casual restaurants and breweries along the way
Walk to the beach and along the water for a great viewpoint of the city skyline
Having visited Chicago previously and already experienced many of the typical tourist attractions, we were eager to simply wander around on foot this time and discover new neighborhoods.
Our visits to Chicago are always fantastic, and I can't wait to go back. What has been the highlight of your time in Chicago, and would you consider visiting the Windy City again?
I hope you enjoyed a little recap of our recent trip to Chicago.
Keva xox
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