How to Spend a Weekend in Chicago

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Chicago is one of the hottest travel destinations in the United States. Once you spend some time there, you can easily see why.

This was my first time in Chicago but we had the best weather possible. Now, this was pre-Covid so we didn’t have to worry about any pandemic restrictions. It was in the 60s, it wasn’t windy and the sun was shining all day. After spending a weekend there, I love this city. It was by the water and seemed really chill. I would definitely like to go back and explore more of the city. I know this is a common theme on my travel posts… the lack of vacation days **sigh**

I never thought about Chicago as an outdoorsy city but I would like to go back in the summer. It looks like they have paddleboards and other water sports, and there is outdoor seating next to the river once it warms up.

As the biggest city in the midwest, there is a lot of things to see and do in Chicago. According to, “The name Chicago may have come from a Miami Indian word for the wild leeks that grew on the bank of the short Chicago River”. Chicago is also actually where the world’s first skyscraper was built in 1885. 

We stayed at the Residence Inn Chicago in River North. We picked this hotel because it was within walking distance to a lot of the tourist attractions and was relatively cheap.

My friends and I love having tea parties. Ever since we took a trip to New York City and had afternoon tea at the Plaza, we try to plan a trip to have afternoon tea in a different city each year. So the post consists of where to go for a fancy afternoon tea as well as some of the touristy things to do while you’re at it.

Doing all the Touristy things

The Bean in Millennium Park

The iconic Bean in chicago

We decided we had to go see the Bean first, technical name Cloud Gate. It is located in Millennium Park and a quick walk from our hotel on North Dearborn Street in River North. I’m glad we got to the bean early because there weren’t that many people taking the obligatory mirror selfie off the bean quite yet. It was so pretty with the city in the background. 

Buckingham Fountain

Once we were done taking our touristy pics, we headed towards the Buckingham Fountain in Grant Park. Grant Park and Millennium Park are right next to each other so this was a quick walk on a beautiful day. We walked through the garden but the flowers weren’t bloomed quite yet. There was an outdoor music venue right next to the bean that looks like it’s awesome in the summer. Another reason why I have to go back in the summer.

When we first got to Buckingham fountain, it wasn’t running so that was a little disappointing. We thought it was too early in the season to see it in action.  We sat on a bench and just relaxed in the sun. Buckingham fountain overlooks Lake Michigan so it was a really beautiful view. Then, randomly at like 10:23 am, the fountain turned on so we were pleased. The fountain is definitely a lot cooler (literally, it made the air cooler with all that water being shot up into the air) when it’s running. 

Buckingham fountain in Chicago.

So we watched the fountain for a little bit then we decided to walk along Lake Michigan. There was a great walking/biking path and the water is so blue. It is almost as blue as the Caribbean. I’m sure much colder though. The path along Lake Michigan leads you to the Chicago Riverwalk which was nice. 

A quick stroll along the Riverwalk

The riverwalk had a lot of things to do. I’m sure it’s really nice in the summer. They had a booth for kayaking and paddleboarding. I think you may even be able to bar hop on paddleboards in the summer. There was plenty of places to sit along the river, there was even an area with rocking chairs. This is why I really want to go back in the summer sometime. The common theme, I know.

Garrett Popcorn

logo of Garrett Popcorn. A popular destination for tourist and locals for popcorn.

After we were done walking the riverwalk, we headed to Garrett popcorn, a must-eat in Chicago. We got Buttery and CheeseCorn, which both are delicious and original flavors since the store opened. Back in 1949, a bag was only 5 cents! Garrett popcorn was actually created by a female entrepreneur who brought her own family recipe to the public. I definitely recommend it. Then we headed back to the hotel to get ready for our afternoon tea. 

Afternoon Tea

We had a tea party at the Drake Hotel. They also have a palm court like the Plaza. Queen Elizabeth has had tea here so we figured this must be a good spot to have an afternoon tea. It was really nice and the servers were really good. They even had a harpist.

The sandwiches were so good. We had a cucumber sandwich, egg salad, turkey and cheese (it was almost like a turkey salad sandwich, and grilled vegetables. Of course, afternoon tea is not complete without some scones and mini desserts. It was so filling and we were stuffed to the brim as usual. We also had two black teas and a white tea. We always go with a classic like early grey then we venture out. As you may have noticed, we go big at these tea parties. 

Picture from afternoon tea at the Drake Hotel. Includes a picture of a tea pot and a cup of tea, the outside of the menu labelled "Palm Court", and the inside of the menu, and the views of the seating at the Drake.

Cocktails and Jazz

After the tea party, we went to get drinks at the signature lounge in the John Hancock building. It is on the 97th floor so the views are spectacular! The drinks were super expensive so this is definitely not a budget-friendly place. I had a gin and tonic then took pictures in the bathroom because honestly, it had the best views (and you can’t tell we’re in the bathroom at all). 

View of Chicago from above at the Signature Room. You can see water and skyscrapers.

Later that night, we went out to this jazz club by our hotel. It had a $10 cover but it was a cool experience and within walking distance from our hotel. The jazz club was called Andy’s jazz club.

A little background on the jazz and blues scene in Chicago. During the Great Migration, many African Americans from the south moved to Chicago and brought blues and jazz to the Windy City. What started in the south side soon attracted some of the great jazz musicians like Louis Armstrong. “Chicago-style” jazz is a mix of the Mississippi Delta and New Orleans Dixieland. 

Chicago Cub Game and Deep Dish Pizza

collage of my trying a Chicago-style hot dog, the view of the baseball field from our seats, the view from the front of the stadium, and a sign of the words Chicago.

The next day of our trip was all about the Cubs game and deep-dish pizza. After we finished breakfast we went to find the CTA (Chicago’s train) to get to the stadium. It’s pretty easy. Chicago has a loop in the downtown area and then the different routes shoot off in every direction. You have to take the red line to get to the Cubs game. It was fairly easy because we just followed everyone else who was in baseball gear and it was a fairly short train ride. 

One thing about the Midwest is that people are a lot friendlier, we had several random strangers strike up conversations with us. I strongly recommend taking the CTA if you are staying in the city because Wrigley field is right off the subway station. I didn’t see a huge parking lot and the stadium just seems kind of plopped down right in the city so I could see parking being hard. You could literally see the stadium from the platform. 

I know I raved about the weather earlier but it was pretty cold when we went to the game. Also, fun fact, the only seats in the sun at Wrigley field are the real close ones or in the bleachers. We weren’t so lucky. We were way up top and there was an awning covering the seats, which is probably really nice in the summer and when it is raining but not in windy 50-degree weather. 

One thing we found interesting was that the Cub stadium seemed to have more cocktail booths than beer. We usually get a beer at Phillies games (which is my home team) but I swear they didn’t have much other than craft beer. So we all got mixed drinks.

Chicago Style Hot dog

We also got a Chicago-style hot dog and let me tell you. It was so messy! I was skeptical about it from the beginning since I’m not a fan of half the toppings but I figured I would get it a go… when in Chicago, right? 

A traditional Chicago-style hot dog is an all-beef frankfurter on a poppy seed bun with yellow mustard, chopped white onion, green sweet pickle relish, a dill pickle spear, tomatoes (sliced or wedged), pickled sport peppers, and celery salt. It’s important to put the ingredients on in that order according to locals. 

I took one bite and it literally fell apart! The hot dog part was good but I think that may have been my first and last Chicago-style hot dog. 

I’ll just stick to a good old fashion hot dog with ketchup from now on. Which apparently, ketchup is a big no-no for Chicagoans. In my defense, I don’t like pickles or mustard that much soooo this hot dog didn’t have my favorite toppings on it, to say the least, but I had to at least try it! We didn’t stay for the whole game since it was so cold but it was fun while it lasted. 

Where to get Deep Dish Pizza

After we rested up for a little bit at the hotel, we went to eat what we came to Chicago for… deep dish pizza. We were going to try Lou Malnati’s but the wait was over an hour so we went to Gino’s East whose wait was 35 mins, so they said. It actually took 50 minutes but you win some, you lose some. But we did finally get some deep dish pizza.

After having one slice of deep-dish pizza, we were all done. It was so filling, I don’t think I’ve ever been so full in my life. It was so much cheese and dough. Delicious but the food coma was real. 

We planned to go out afterward but we had to take a nap in between pizza and going out since we were so full so plan accordingly. The nightlife on Hubbard street was pretty cool. We started at this place called three dots and a dash and it was Polynesian-themed. The line to get in was in an alleyway which seemed kind of sketchy but there were a lot of people waiting in line so we decided to go for it. It was fun but I expected it to be better honestly. I had more fun at Howl at the Moon which had a dueling piano set up and they covered a bunch of popular songs. 

And that’s everything we were able to do over a weekend. Between walking around, eating all the food, and seeing a Cubs game, I had a lot of fun. I would like to come back in the summertime and see the city fully open. 

What are your plans for Chicago? If you’ve been, what is your favorite thing to do?

Until next time,

How to Spend a Weekend in Chicago

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