Chicago Series: What to do in Chicago

September 9, 2016
love you more too north dallas blogger plano lifestyle blogger travel bloger What to do in Chicago

Colton and I spent Labor Day weekend with some friends in Chicago to celebrate one of them turning thirty.  There are a few places I love to escape to on a three-day weekend, and Chicago is one of them.  Chicago is a city that has everything- great restaurants, fun nightlife, outdoor activities, and more.  Since we have been twice, I put together a list of what to do in Chicago.

Disclaimer: I was in Chicago with three photographers and two videographers, but we chose to be present with one another and took very few photos.  All of these were taken with an iPhone, so the quality is not the best.

What to do in Chicago

Getting to and from Chicago

On this trip, we booked the cheapest tickets possible and braved Spirit airlines.  Since O’Hare is an international airport, nearly every airline flies in and out of it daily, making it very easy to get to.

What to do in Chicago

I will sum up the Spirit experience for you with a list of positives and negatives.


  • Spirit has cool branding
  • Cheap flights
  • Seats don’t recline (I know this seems like a negative, but I never recline my seat and always end up with a seat in my lap from the person in front of me)


  • Don’t depend on being on time (I expect being late with every airline which is why Colton and I typically leave on the earliest flights).  Our flight was about 40 minutes late leaving but only about 20 minutes late at the gate.
  • You have to pay for everything (carry on luggage, checked luggage, picking your seat, water and sodas on board, snacks)
  • No in-flight entertainment, not even wifi
  • Very little legroom (unless you upgrade your seat) on the newer planes
  • Tiny tables on newer planes that would not hold a laptop

Overall, it was not the worst flight I have ever been on, nor was it the worst flying experience.  I would take Spirit again on short flights where the price difference is significant.

Where to stay in Chicago

The most popular area to stay in Chicago is the Magnificent Mile, on or right off Michigan Ave.  On our first visit, Colton and I stayed at the Inn of Chicago.  It was right in the center of everything, so it was a close walk to all kinds of restaurants, parks, and night life.

This time, our group rented an Airbnb in the South Loop near the Museum District.  I highly recommend going the Airbnb route because there are tons of great places to stay.  Our town home had 4 stories, a full kitchen, 3 bathrooms, 2 balconies and a terrace.  It was perfect for the 6 of us!  We took Uber/Lyft, Divvy Bikes, and the L train to get to where we needed to go.

What to do in Chicago

Touristy things to do in Chicago

Visit Millennium Park and take a photo with Cloud Gate or “The Bean”– The bean is one of the most recognizable sculptures in the world.  It is found in Chicago’s largest park, Millennium Park, a beautiful spread out park with a lot of green space.  Between the sculptures, exhibitions, garden, events and more, you will not run out of things to do.

What to do in Chicago

What to do in Chicago

What to do in Chicago

Wrigleyville– Wrigleyville is home of the Chicago Cubs and their fans are serious about baseball.  Wrigley Field is one of the oldest fields in the United States.  Wrigleyville is the area surrounding and including Wrigley field, so if you are a Cubs fan you will be in Heaven.  There are a ton of great bars and restaurants in the area to catch a game on TV if ticket prices are too expensive at the field.

What to do in Chicago

Navy PierThe Navy Pier is another Chicago landmark.  You can catch a ride on the ferris wheel or any of enjoy any of the attractions.  Navy Pier has a Shakespeare theater, children’s museum and more.  We enjoyed just strolling down the pier, catching a couple of songs from the live performance and the beer garden, and people watching.

Visit one of Chicago’s beaches– Chicago has a few great beaches to relax, read a book, play sand volleyball, throw a frisbee, and get some sun.  It is a great escape from the city life.  The water from the Lake is almost as blue as the ocean, so you forget you are in the city.

The Magnificent Mile– Michigan Avenue is full of shops and restaurants, so it is labeled as the Magnificent Mile.  You never know what you will see while shopping and strolling the mile.  The last time we were there, Colton saw Steve Harvey jump out of a giant, wrapped gift.

What to do in Chicago

What to do in Chicago

iO theater– Chicago has some of the best improvisational theaters in the country.  One of the many famous theaters where many favorite SNL cast members were trained and performed at is the iO theater. Our group had a great time catching a $5 late night show and some laughs.

Unique things to do in Chicago

No. 18 karaoke in Chinatown– Our friend Amanda found this hole-in-the-wall gem while looking for places to sing karaoke.  For $30 an hour, you can rent a private room and sing the night away.  We had a blast belting out all of our favorites, and we never had to wait for anyone else.  Many of the songs play the music video during the karaoke session, but a few of them had some hilarious videos to go with.  Although we didn’t have a reservation, we were still able to get a room for a couple of hours.

Divvy BikesDivvy bikes are a shared bike system that allows people to rent bikes for 24 hours, but in thirty minute increments.  This is my absolute favorite way to see the city of Chicago.  There are hundreds of drop off and pick up spots throughout the city.  Chicago is a bicycle-friendly city, so riding around the streets is safe and convenient.

What to do in Chicago

What to do in Chicago

We rode all over the city, but the best place to ride is along Lake Shore Drive.  You can watch the beautiful reverse sunset and enjoy the breeze.

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Kayak ChicagoKayak Chicago offers many different rental and tour options, so it will fit into any itinerary. Our group opted for the Architectural tour of the Chicago River, a three hour, 5-mile kayaking tour.  Our tour guides were charming, informative, and attentive.  It was a great way to see the buildings, riverwalk, and city.  I would highly recommend trying one of their tours while you are there.  (Be sure to check Groupon!  We were able to get a discounted rate for our group.

What to do in Chicago

What to do in Chicago

Explore neighborhoods– Chicago has a variety of neighborhoods, each with their own style and charm. Along with Wrigleyville and Magnificent Mile, we explored Chinatown, Lakeview, Lincoln Park, Little Italy, the Loop, Wicker Park and Bucktown.  We saw several other neighborhoods as we rode around on our Divvy bikes.

What to do in Chicago


Click here to check out Post 2, Where to Eat and Drink in Chicago.

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What is your favorite thing to do in Chicago? Now that you know what to do in Chicago, the next question is when will you visit? Leave me a comment below!

  • Krista Williams September 9, 2016 at 6:31 am

    It looks like you had the best time babe.

    I love Chicago! This was a perfect re-cap!!


    • Jessica September 12, 2016 at 11:42 am

      Thanks, Krista! It was a blast. I love going places with friends and Chicago is one of my favorite places.

  • Lee Anne September 9, 2016 at 8:37 am

    Love all of this, and the photos are great! Looks like so much fun

    Lee Anne

    • Jessica September 12, 2016 at 11:43 am

      Awh, thank you Lee Anne. I always get nervous posting cell phone photos. Fortunately, there were several of us, so we could collaborate.

  • Renata September 9, 2016 at 10:25 am

    I am glad you enjoyed Chicago, pictures look amazing!! Next time let me know when you are in town.


    • Jessica September 12, 2016 at 11:44 am

      I will!! I absolutely love your city. It is one of my favorite places.

  • Logan September 9, 2016 at 3:04 pm

    Next time I’m there, I am totally going to do the bikes! I loved going to a cubs game last time. Chicago is a fun city!

    • Jessica September 12, 2016 at 11:44 am

      The bikes were the best! I wish we had something like that in Dallas.

  • Chelsea September 9, 2016 at 3:10 pm

    I love Chi town so much. As tourist-y as it is,I love going to see the Bean!

    • Jessica September 12, 2016 at 11:49 am

      Agree! It never gets old. One of the coolest sculptures I have ever seen.

  • Neely (@Neelykins) September 9, 2016 at 3:12 pm

    Chicago is one of my fav cities to visit. I almost moved there before i met Andrew.

    • Jessica September 12, 2016 at 11:50 am

      It’s wonderful! They tell me I would hate the winter, but I think I could survive it for the culture. 😉

  • Jessy September 9, 2016 at 3:23 pm

    Looks like a great time! We love heading to Chicago for long weekends! So much to do and see 🙂

    – Jessy

    • Jessica September 12, 2016 at 11:50 am

      Agree! I wish we could go there more often. 🙂

  • Kristen Kavan September 9, 2016 at 5:52 pm

    i LOVE chicago! Looks like you had so much fun! Ive never been in the summer and am dying to go to their beach!

    • Jessica September 12, 2016 at 11:51 am

      It was a lot of fun. I wish we had more time on the beach.

  • Lisa September 9, 2016 at 6:11 pm

    Sounds like a fantastic trip and some great ideas for the next time I visit!

    • Jessica September 12, 2016 at 11:51 am

      Thanks, girl! I hope you get to go again soon. 🙂

  • Shann Eva September 9, 2016 at 8:59 pm

    Chicago is one of my all time favorite cities. I live about 2 hours from it by train, so we try to get there every once in a while. I love the idea of using Airbnb for a place to stay. The bike riding looks like a lot of fun too.

    • Jessica September 12, 2016 at 11:53 am

      Lucky!! I would love to live so close to Chicago. 🙂

  • ashleigh September 9, 2016 at 11:06 pm

    This is so great! I just moved to the Northern Suburbs and have been trying to find new stuff to do in the city. Thank you for sharing, looks like you had an amazing time!

    • Jessica September 12, 2016 at 11:54 am

      It was amazing! I hope you found some things that sound good to do. 🙂

  • Adaleta Avdic September 10, 2016 at 2:31 pm

    I would love to visit Chicago, as this looks absolutely incredible and I’m a fan. My boyfriend went for a work conference a few months ago, and loved it! xx Adaleta Avdic

    • Jessica September 12, 2016 at 11:54 am

      It really is a fun city. I know it won’t be our last time to visit. 🙂

  • Melissa September 10, 2016 at 4:17 pm

    I haven’t been to Chicago in forever. Hopefully, I will have the opportunity to get back there. If I do, I will know what to do.

    • Jessica September 12, 2016 at 11:57 am

      I hope so too. It is so much fun!

  • Rebecca Hicks September 10, 2016 at 10:37 pm

    It looks like y’all had a lot of fun in Chicago!! I would LOVE to do a bike tour of a city, and I think it’s so cool that they are growing in popularity.
    Also, thank you for your honesty on Spirit airlines! I’ll have to remember them next time I am booking a short flight.

    • Jessica September 12, 2016 at 11:58 am

      I have heard a lot of crap about Spirit, but it was definitely not the worst experience if you know what to expect. I read that drinks weren’t included so I carried on my own water bottle. Problem solved.

      I love the bike fad. 🙂

  • Lecy | A Simpler Grace September 10, 2016 at 11:05 pm

    Love these ideas! I’ve never been to Chicago, but have always wanted to visit!

    • Jessica September 12, 2016 at 11:58 am

      I hope you get to go soon! It is a great city!

  • chanel van reenen September 12, 2016 at 11:33 am

    Chicago is high on my list of places to go! Everything you listed sounds like so much fun. Just bookmarked for future reference!

    • Jessica September 12, 2016 at 12:00 pm

      I hope you get to go! It really is a blast! 🙂

  • Denise September 12, 2016 at 4:40 pm

    I’ve been to Chicago a few times but have yet to do any of the activities you mentioned. Looks like I’ll have to go again sometime soon! Looks like such an adventure! Thanks for sharing.

    • Jessica September 12, 2016 at 6:17 pm

      Of course! There are so many great things to do. 🙂