How to Spend a Weekend in Chicago

I am lucky enough to have had the opportunity to spend a whole month living in Chicago in the month of May. My rotations for pharmacy school took me to Chicago and I was able to spend a month living with my family there and explore the city. While there are still many things in Chicago that I did not get to see and plan on visiting during future trips, I do think I have a pretty good sense of how to spend 2-3 days in the city and what the main attractions are for the Windy City. My engagement pictures were taken in Chicago as well, so I am definitely pretty fond of the place.

Most of the places I will talk about are all centered around downtown Chicago. There are definitely things to  check out further outside the city (Chicago Botanical Gardens for example and the fashion outlets) but if you only have a weekend to explore, I wouldn’t recommend venturing out too far. There is plenty to do downtown.

There won’t be any food recommendations featured here because there are so many restaurants in Chicago and a month isn’t nearly enough time to narrow it down to the best ones. I would trust an expert for that category (aka an actual Chicago native). I will mostly focus on places to go and things to see.

Millennium Park


This is the place where my fiancé and I chose to have our engagement pictures taken and the reason is, Millennium Park is a pretty unique place. The Cloud Gate aka “The Bean” is located in Millennium Park and is definitely one of the defining structures of Chicago. You can’t go to Chicago and not stop by and see The Bean for yourself. One of the most common questions I get about my engagement pictures is how we were able to get the park all to ourselves and the answer is we had to be there at 5 am, right at sunrise, to be able to achieve that. It was definitely worth it looking back at the pictures, but I did not enjoy getting up at 3 in the morning to get ready. Millennium Park during the summer also has a large field/pavilion area in front of a stage where you can watch free concerts at night time. Those concerts are part of a summer series and are a popular gathering place during the week. If you chose to go during the winter, you can find the city’s biggest Christmas tree at this park.  You can also ice skate at Millennium Park during the holidays.

Signature Lounge at John Hancock Center


While many people choose to spend a lot of money and go either on top of the John Hancock center to the Observation Deck or to the one on Willis Tower, I believe the better way to see an amazing view of the city is to go to the Signature Lounge on the 96th floor of the John Hancock building. Choosing to go this route you only end up paying for your drink while still seeing the view whereas if you just go to the observation deck, you’re paying just to stand up there, without a drink – now how is that a better deal? I also recommend going to the lounge about an hour before sunset. The wait will be about that long and this way you will get to see the city while it’s still light outside and then get to watch it light up which is a beautiful view. The picture above was taken from the Signature Lounge.

Boat Architecture Tour


During the warm months, an architecture boat tour is definitely something I recommend doing while in Chicago. There are numerous tours that are offered and most of them are about the same quality. The tour I went on  (Wendella Boat Tours) was about an hour long and I learned more about the city of Chicago on that tour than from any other source.  To buy the tickets you should go to the Trump Tower and walk down to the river walkway and you will see the booth that sells tickets for the tours. You can also buy the tickets ahead of time online but we didn’t have much of a wait buying tickets in person and that’s saying something considering it was Memorial Day Weekend and the city was swarming with tourists.

Shopping on Michigan Avenue

I highly recommend going shopping on Michigan Avenue because Chicago has a lot of stores that other cities do not have such as Zara, Uniqlo, Topshop and Mango. This is also referred to as the Magnificent Mile and you can find a list of all the stores in this area on this website:

Navy Pier



Here is another location that we chose to be part of our engagement pictures. Navy Pier is where the Ferris Wheel is located among other attractions. It is located on Lake Michigan and is full of parks, restaurants, and shops and is definitely a place you can spend quite a bit of time exploring. It just celebrated its 100th anniversary this summer and is considered one of Midwest’s top tourist destinations.

The Chicago River

While you are downtown, just spend some time walking along the Chicago River. You will stumble upon restaurants, shops and just beautiful views of the city just by following the River. If you are lucky enough to have good weather while you’re in Chicago then definitely take advantage of the fact and walk around as much as possible. This city is really unique and full of history so you can see a lot just by walking along the river.


That’s all I have for my recommendations for what to see in Chicago if you’re only there for a few days. There are definitely more in depth travel guides out there and depending on what you want to see while you are there, I would recommend doing a lot of research for places to eat and how to find events while you’re there. I hope I was able to at least provide some ideas of what to see during your stay.

As always, thank you for reading and I hope this was informative and helpful!


6 Comments Add yours

  1. itsgeorgiaxoxo says:

    Chicago looks sooooo gorgeous!! & you and your man look very cute together (:

    Liked by 1 person

    1. Thank you so much! 🙂 It is a gorgeous city! Definitely one to check out!

      Liked by 1 person

  2. sarahscupofbeauty says:

    Beautiful! xoxo Sarah

    Liked by 1 person

  3. I live just north of Chicago and we go on a architecture boat tour every summer. If you go on one of the later tours and it is a nice day you can see the sunset with the reflection on the skyscrapers. I look forward to it every year. Thanks for the post.

    Liked by 1 person

    1. I really enjoyed it! I think it’s a great way to learn about the city!


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