A Long Weekend in Chicago – Days 2&3

I’m back to tell you more about how to spend a long weekend in Chicago with our day 2 and 3. If you missed day 1, check it out here.

Day 2:

We woke up and walked over to L to head back downtown to check out the Art Institute. This place is huge so you could go a dozen times and not see everything. It has one of my favorite paintings, A Sunday Afternoon on the Island of La Grande Jatte by Serat, which is worth seeing for sure! Funny story, I did a report on Serat in high school so when we went to Chicago, I made my family go to the Art Institute just to see it. Story of my life, the whole room was under construction so I didn’t even get to see it! It is full of famous works of art as well as beautiful but lesser known works as well. They have all their most famous paintings marked on the map so you can’t miss them! I will say, only try to see 2-3 areas (modern, Asian, Renaissance, etc) unless you want to spend the whole day there! The main reason we went there was to see a special exhibition called Van Gogh’s Bedrooms. The exhibition had his art arranged according to where he lived when he painted it which was really interesting! The main focus was his famous Bedroom painting of which he did 3 different versions. I didn’t know that! This was the first time all 3 paintings have been in the same location at the same time. Unfortunately, it only runs until May 10th so sorry if you miss it!
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest

After the Art Institute, we were starving so we jumped on Yelp to guide us to food. We found Brightwok Kitchen which I’m so glad we did! To explain it, it’s kind of like a Chipotle for Asian food. You got to pick your protein, sauce, noodles or rice and veggies. After lots of burgers and cheesy eggs, it was good to have something fresh! If you go to the Art Institute, I would highly suggest lunch here afterward!

Photo via

We then hopped in an Uber to get us over to the Shedd Aquarium. Most of my favorite animals are sea creatures… so 4 of my favorite animals (otters, beluga whales, dolphins and penguins) all in one place made me a happy camper.  I probably could have sat and watched the beluga whales all day. We got there later in the day which saved us from huge crowds. There is also a cool view of the skyline all the way to Navy Pier so don’t forget to check that out.
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest

To note, there is a pass you can buy that includes entrance fees to several Chicago attractions. Since we only went to the Art Institute and the Shedd Aquarium, we decided to skip it. Just an FYI if you are planning a trip there and want to check it out!

That night (Monday) we called ahead and reserved a table at Pequods Pizza! You definitely need to try Chicago style pizza while you are here and I would say this is one of the best. You may have heard more about Pizzeria Uno or Giordano’s but I think Pequod’s takes the cake pie.  😉 What makes them better is they caramelize the crust, which really takes it to the next level. While we sat down pretty quickly, pizza perfection does take time. Especially when it’s deep dish. So take my word for it and order the garlic bread as a starter because you’ll be waiting a bit for your pizza. I didn’t take any photos because I was too busy stuffing my face so I borrowed a couple from Google.

Day 3:

At this point, we were pretty tourist attraction-ed out so we decided to wander around different neighborhoods. We checked out parts of Lincoln Park that we hadn’t been to yet included Glazed and Infused donuts and Chicago Bagel Authority. I don’t think we needed to eat one right after the other but what can you do? When in Rome Chicago, right? All I can say is my waistline would not be able to handle living so close to these delicious places.
How to Spend a Long Weekend in Chicago - Due Midwest
How to Spend a Long Weekend in Chicago - Due Midwest

Next, we hopped on the brown line again to check out the Southport neighborhood which is conveniently the same name as the stop! We just wandering around and stopped in different shops along the way. This area has a combination of national chains (Anthropologie, J Crew, etc) as well as really cute local boutiques.


We hopped back on the L to go check out my brothers old neighborhood, Logan Square. This neighborhood is not as gentrified as Wicker Park or Lincoln Park so you will get a lot more international cuisine and unique local shops. Some shops we stopped in worth mentioning are Wolfbait and City Lit Books. Wolfbait was a cool store with stuff from lots of different local artists. There were t-shirts, jewelry, and lots of quirky gifts so definitely go check it out! City Lit books was so amazing. Just wandering around, you could tell this store was created and run by people who love books. I went up to the woman behind the register to ask a question about a book I was interested in. It was by an Icelandic author and said it was a prequel. She took the time to look up the series for me and read a review to me that the book could stand alone. So helpful and kind. Highly recommend stopping in here!


We grabbed some lunch in Logan Square before heading back to Lincoln Park to get our bags and head to the airport. I hope you enjoyed my little guide of our time in Chicago! I can’t wait to go back!


If you want more suggestions on what to do in Chicago, check out this post from The Local Tourist!

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  • Reply Beth

    I haven’t spent nearly enough time in Chicago, this is making me want to go!

    May 6, 2016 at 6:03 PM
  • Reply Slavka

    Good itinerary. I haven’t been to Chicago yet, but plant to change that soon. I am bookmarking this and will follow your footsteps, also with the Day 1 post.

    February 12, 2020 at 5:24 PM
    • Reply duemidwest

      I wouldn’t recommend going in the winter 😉 but I hope my suggestions help you in your visit!

      February 12, 2020 at 8:06 PM

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