A Quick Weekend Chicago Travel Guide


Happy November everyone. Last month my cousin and I took a quick weekend trip to Chicago. It was both our first time visiting the windy city. We decided to visit on the first week of October, and we couldn’t have picked a better time. The weather was absolutely beautiful. The leaves were turning a pretty golden color and fall was in full swing. We did not make it to all the recommended places but we had a blast exploring the city. For this post, I though it would be a fun idea to share some of our favorite places around Chicago.

We landed pretty late on Thursday so we checked into our Airbnb for the night. The Airbnb was located in this beautiful quiet neighborhood around Logan Square. I would recommend staying in this area as it was close to the city but far enough to enjoy a quiet walk in the neighborhood. Our adventure started Friday morning at Chiya Chai. It’s a small place with ten tables including outside seating. They have small plates and curry dishes that are all so amazing. Their coconut chai tea latte is the best I’ve ever had. I would definitely recommend this place.

With the weather in the 70s, we spent most of our time walking around the city. The river walk is truly one of my favorite spot in Chicago. You can find many chic, instagrammable restaurants with outside seating overlooking the river. We spent most of our mornings here snapping pictures and watching all the boat tours go by.

One of our favorite restaurant was The Hampton Social. The decor was beautiful, the dishes excellent and ofcourse we had to snap some pictures in front of the ‘Rose ALL Day” sign.

Another restaurant I would suggest is the London House Rooftop. This rooftop has one of the best views in the city. I suggest reserving your table in advance since they are booked weeks ahead. We were lucky to get a table.

Other restaurants to check out include the Beatnik on the river for lunch, Fremont for their Sunday brunch, Pizzeria Portofino by the river for dinner, and Hub 51 in downtown.

Don’t forget to see all the famous landmarks if you have time. The bean in millennium park is fenced off due to Covid-19 but you are close enough to get your pictures. It was not crowded like we anticipated. Buckingham fountain next to the park was not on but it was a beautiful place to visit. We rented some bikes to tour the city and stumble across the Chicago sign. Don’t forget the concrete beach. It was easily my favorite place to sit and people watch.

Other things we didn’t get a chance to do that are highly recommended include the Sky deck at Willis tower, the architecture boat tour and all the museums.

I’ve been told that this city is magical in the winter with the ice rink next to the Bean but I am not sure that will happen this year. Hope you guys enjoyed this blog post.

Leave a comment below if you like this post and if you have future plans to visit Chicago.

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