Weekend in Chicago

For last year’s 4th of July weekend, we headed to Chicago. I know a lot of people head to NYC for this weekend, but I always want to get away from the crowds and experience another city. I’ve been to Chicago many times before and have always had a good time in this city. There’s a charm about the Windy City that holds a soft spot in my heart. As always, we left on a Friday around noon and came back on Monday night. That gave us two full days to really explore and have some adventures!

We stayed near the Magnificent Mile and the 360 degree Chicago building in the Whitehall Hotel. The location was perfect because it gave us access to all of the neighborhoods while we were in the middle of it all. The hotel is more north of the major attractions, but it gave us an opportunity to check out the cool neighborhoods that are away from all the major attractions.

Since Chicago is a couple of hours behind NYC time, we landed with ample time to comfortably leave the airport and settle into our hotel before heading out. Our first night was fairly laid back while the rest of the trip was jam packed! Here is what we covered during a 3 day trip in Chicago:

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The infamous Chicago sign is a must see and picture capture while on a visit to the city. So many different movies, shows, and articles have this iconic sign somewhere in the background. Very cool to see and definitely recommended to happen upon!

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Beautiful old architecture is mixed in with brand new buildings. Our first night was spent wandering around the hotel area and grabbing dinner close by at an Asian Fusion restaurant. The city was looking good so far!

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I honestly don’t remember which night this was, but we happened upon a really cool wine restaurant in a hotel somewhere downtown. I’ll have to do more research on it and let you all know what it was. Such an adorable place with a wonderful selection of wines and charcuterie!

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The next morning, we woke up bright and early since we wanted to fit a lot of different sights in. We started out by walking along the streets to get to an opening of Lake Michigan. We got to a point where you could see the city skyline behind you and the view was beautiful!

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Here’s a panoramic view of the city. There were a lot of people just hanging out. Some were picnicking, others were chatting with friends, there were lots of bikes and roller blades. Locals and tourists both enjoy this stretch of space on the lake.

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We obviously had to visit Navy Pier and check out what the big hub bub was about. Pretty fascinating boardwalk with plenty of restaurants, rides, and benches to relax on. Depending on how windy it is, the pier isn’t suitable for all day.

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We caved and ended up riding on the Millennial Ferris Wheel! It was such a fun experience and provided such an unbelievable view!

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We were so famished by this time, so we decided to try out the famous hot dogs that Chicago is known for. We stopped by an establishment that had been around for a while and looked pretty busy. We definitely enjoyed them!

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This is the John Hancock building. We ended up dining in the Signature Room in the building with incredible views. The food on the other hand wasn’t great. It was a little bit of a disappointment.

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The next day we decided to walk the river walk and came upon amazing fountains.

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I’d say that the riverwalk had more people milling around than the boardwalk by the lake. People were engaged in all sorts of things around the river walks.

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It’s really cool to see all of the buildings that surround the Chicago River. There are plenty of outdoor dining spaces and tour venues set up to utilize while your around the area.

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We decided to check out the Chicago Art Museum since we love art. He also wanted to replicate Ferris Bueller’s Day off scene by looking at this painting. This was the highlight of the trip for him. Overall, the museum had great pieces that you won’t find elsewhere! This is a must visit if you enjoy art.

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Deep dish pizza. Chicago is known for that and we had to check out Lou Malnati’s deep dish pizza before we left. The pizza was delicious, but I can’t say that I’d eat it frequently if I lived in Chicago.

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The Bean. This is really infamous in Chicago as well. It was extremely busy around it and there were a lot of people trying to take pictures of it.

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The Buckingham Palace fountain was another famous scene from Ferris Bueller’s Day Off movie. The fountain wasn’t as large as I imagined it to be though in real life. Still really cool to check out!

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One of the last things we did was lounge on one of the many beaches that are around the city. This is such a cool part of Chicago that I couldn’t get over how it’s surrounded by all the skyscrapers to one side and then so much water to the other. A relaxing oasis (that also offers a beer pub) right in the city.

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We wanted to check out a suburb of Chicago right before we got on the plane. We’ve discussed moving to Naperville, Il on several occasions due to wonderful ratings online. I will say that the town was extremely charming and I’d consider moving there if an opportunity arose. One of my get-ups is how cold it was. Chicago is a cold city and I have no idea how locals manage during the winter months. I had a jacket/sweater on during the entire trip.

Overall, we had a wonderful time and were able to squeeze in a lot of sightseeing. We walked about 20 miles during the entire weekend though and it was a bit exhausting. I’ll have to write another post on all of the different food and restaurants we had the pleasure eating at in another post! Feel free to leave any comments on any other sights that are a must see in Chicago!

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