What To Do In Chicago

What To Do In Chicago

Chris and I took our first trip to Chicago recently and it was amazing! The weather was great and the city was absolutely beautiful; truly a postcard at every turn! We were just there for a long weekend so we couldn’t fit everything in that we wanted to do, but we did a lot!

Here are my recommendations if you’re looking into visiting Chicago for the first time.

1) Do the Loop

The Chicago Loop is an area of downtown that’s full of restaurants, shops, theaters and parks. It’s named for the elevated ‘L’ train tracks that loop around the area – yes, you look up and you’ll see a train going by! We stayed at the Renaissance Hotel on the north side of loop overlooking the river. It was an excellent location. Everything was within walking distance; there were a lot of uber drivers around if you didn’t feel like walking, and the train was just around the corner as well.

2) Go to a Cubs Game and Take the Train

Chicago is an epic sports city, not only for the Cubs, but the White Sox, Bulls, Bears and Blackhawks too. I didn’t realize how much of a sports city it was until I remembered those teams and saw all the sports fans around town in their favorite gear. It’s true that the sports history runs as deep as the fans are passionate. We were able to go to the Cubs vs. Mets game at Wrigley Field and it was so fun! We took the red line train that was around the corner from our hotel, and got off right at the stadium.

3) Take the Architectural Boat Tour

We did the Chicago’s First Lady Cruise. It was a 90-minute slow ride down the Chicago River, and the boat had an air-conditioned lower deck with a full service bar. The guide was extremely knowledgeable about all the different architectural styles and history behind each building. We loved it.

Also just strolling the Riverwalk is fun. You can grab a coffee at one of the little restaurants and keep strolling and people watching.

4) Shop Magnificently

Ok, so this was my favorite. The “Magnificent Mile” is a 13-block stretch of Michigan Avenue and it was just around the corner from our hotel (trouble!). It had THREE indoor malls and hundreds of stores. There are the high-end designers (Burberry, Coach, Louis Vuitton), major retail chains (Banana Republic, Disney Store, Nike) and department stores (Bloomingdale’s, Macy’s, Nordstrom). I shopped mostly the retail chains and department stores and stayed away from high-end which Chris appreciated.

5) Take in the View at the Hancock Building Signature Lounge

To take a break from sightseeing and shopping, go to the 95th floor of the Hancock Building. It doesn’t cost anything to go up, but you do have the option of ordering food and drinks once you are up there. The view is breathtaking! Signature Room is a full restaurant and the Signature Lounge overlooks the restaurant and has a smaller menu. The Signature Room would definitely get my vote for the “Most Romantic Restaurant” ever – just don’t wear shorts, they have a strict dress code.

6) Eat, Eat, Eat

Chicago is home to some of the world’s most elite chefs and restaurants. There are literally thousands of places to eat and every type of food you can imagine! We kept it pretty simple this trip since we wanted to spend most of your time sightseeing. We ate deep-dish pizza at Giordano’s our first night and steak at the Chicago Chop House the next night. We highly recommend both of those places!

There are a ton of things we wanted to do that we didn’t get to this trip. Here’s what’s on our list to check out the next time we visit:

Just to name a few….


Chicago is definitely a city full of life and beauty. Definitely go if you get the chance! You will love it!

Walking along the river, so pretty!

Go Cubs Go!

View from Hancock Building.



  1. October 2, 2017 / 11:45 am

    thanks for sharing, really informative,well writen and fun to read.

    • Carli Best
      October 11, 2017 / 5:41 pm

      Thank you Roamy!

  2. October 2, 2017 / 11:56 am

    I love to read about other people’s visits. Sounds like you had a whirlwind weekend of fun!

    • Carli Best
      October 11, 2017 / 5:42 pm

      We sure did! Thanks Sally-Jane!

  3. October 3, 2017 / 12:20 am

    Unstoppable pics. Thanks for a fun post!

    • Carli Best
      October 11, 2017 / 5:43 pm

      Thank you! It was so beautiful!

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