Top 5 Things to See in Chicago

We have been lucky to be able to call Chicago our home for the past 4 years. During this time, we have been able to explore the city and all its beauty and we truly love everything it has to offer. Our favorite thing to do is to show our out of town guests around the city and share the top things to see in Chicago while they are here.

Kyle and I have been getting a lot of questions about what to see and do while visiting Chicago and thought we would round up our 5 top things to see in Chicago in a blog post for you!

We hope this helps you plan your next trip to Chicago and explore some places that may not have been on your list yet. If you're looking for the most Instagrammable indoor spots in Chicago, check out this post.

 

1. Top Things to See in Chicago: Architecture Tour with Shoreline Sightseeing

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

We have taken all of our out of town guests on the Shoreline Sightseeing Architecture Tour and it has easily been everyone's top thing to see in Chicago! It's a 75 minutes boat tour on the Chicago River where you learn all about the history of the windy city, and get some of the most beautiful views of the skyline.

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

Outift: Two Piece Set from Chicwish / Earrings from H&M

 

The boat tour has two different starting points: Navy Pier or Michigan Avenue. Both are really easy to get to and close to downtown Chicago. Shoreline Sightseeing will take you along the river through downtown,  underneath the iconic bridges, all the way to the North Branch of the Chicago River and will then turn around to share one of the most recognized buildings from the opening scene of The Dark Night: the post office!

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

In addition to getting incredible views of the city and great photo opportunities, Shoreline Sightseeing shares some interesting facts about the city and I learn something new every time I join my guests on the cruise - probably also because I'm always so focused on taking pictures, I forget to listen!

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

You can get your tickets online here or buy them at the booth on Navy Pier or Michigan Avenue before the tour. If you're visiting in summer, I would recommend you get your ticket a few days in advance as their tours will sell out.

 

Chicago Skyline from Shoreline Sightseeing Architecture Cruise

 

Thank you Shoreline Sightseeing for treating my friend Vivian and me to your Architecture River Cruise!

 

2. Top Things to See in Chicago: Have A Drink at the Signature Lounge

 

Top 5 Things to See in Chicago - View from Signature Lounge

 

If you are looking for incredible views of the city from above, without standing in line or paying admission fees for the Willis Tower, I can highly recommend going for a drink or two (or three!) at the Signature Lounge. The lounge is located on the 96th floor of the Hancock Tower in River North. While their cocktail prices might be a bit higher than what you're used to, you don't pay admission to get to the 96th floor. And the views certainly make up for the prices. A tip for all the female readers, by far the best view of downtown is from the ladies room in the Signature Lounge! You read that correctly, plan some extended time to powder your nose! 🙂

 

Top 5 Things to See in Chicago - View from Signature Lounge

 

If you're in town for a few days, try to visit the Hancock tower on a clear day right before sunset so that you get the best of the daytime views and nighttime city lights. You might have to wait in line to access the elevators on a busy weekend night, but I personally never waited longer than 15 minutes.

 

Top 5 Things to See in Chicago - View from Signature Lounge

 

Top 5 Things to See in Chicago - View from Signature Lounge

 

If you're looking for a unique place to eat, check out Machine Engineered Dining and Drinks and 3 Arts Cafe.

 

3. Top Things to See in Chicago: Take a Selfie at the Bean

 

The Cloud Gate, also known as the bean, is one of my favorite landmarks and probably one of the most well-known things to see in Chicago. You haven't truly seen Chicago without taking a selfie at the bean. The Cloud Gate is beautiful in its simplicity and I love the way it reflects the city and blue skies on a clear day. It is so iconic, it's easy to see why it's surrounded by tourists on any given day. You can find it in Millenium Park, off Michigan Avenue, between Washington and Madison Street and it is easily accessible if you take the "EL" (Elevated Train) to Washington and Wabash.

 

Top 5 Things to See in Chicago - Selfie at the Bean or Cloud Gate

Outfit: Top from Zara / Jeans from Mint Julep Boutique / Shoes from Aldo / Purse from Nordstrom

 

The best time of day to visit the bean if you want to avoid the crowds is early in the mornings around 7am. Kyle and I managed to get it all to ourselves on one Friday at 7am. During the cold and harsh Chicago winters, getting a reflection selfie in the bean without interruption is easier but you will still have the odd tourist suffering through the cold as well.

 

Top 5 Things to See in Chicago - Selfie at the Bean or Cloud Gate

 

Outfit: Top from Zara / Skirt from Chicwish / Shoes from Aldo / Purse from Nordstrom

 

 

While you're already there, you might also stop by the corner of Michigan and Adams, which marks the beginning of the historic Route 66. Route 66 technically started on Jackson Boulevard but because Jackson Boulevard is now a one-way street East, the landmark sign was moved one block north to Adams Street.

 

4. Top Things to See in Chicago: Enjoy the Skyline from the Adler Planetarium

 

The first time I visited Chicago in 2013, I was determined to find the best place to take pictures of the Chicago skyline and I stumbled upon a forum which talked about the view from the Adler Planetarium. Little did I know that a few years later, I would move to the city and live in the South Loop, biking past the Planetarium on my way to work almost every day.

 

Top 5 Things to See in Chicago - Chicago Skyline from Adler Planetarium

 

If you love skylines and observing the city from a distance as much as I do, you may not want to pass up this opportunity. On a warm sunny day, bring a picnic basket and enjoy the sunshine, the skyline, and the ocean-like Michigan lake.

Getting to the Adler Planetarium using public transport will involve a fair bit of walking. We recommend renting a Divvy bike and take the lakefront trail to get there (more on the trail below).

 

 

5. Top Things to See in Chicago: Bike Along the Lake Front Trail

 

Most people are surprised by the fact that Chicago has sand beaches and bike and pedestrian dedicated lake front trails. On a warm sunny day, rent a Divvy bike and bike along the lake front trail, and spend a few hours exploring the city starting at the Adler Planetarium, biking north past Navy Pier, North Avenue Beach, all the way to Lincoln Park. You'll get a completely different feel of the city - being away from the hustle and bustle and able to absorb its beauty from a distance. And to cool off after a lengthy ride, join the many Chicagoans on the beach dipping their toes in the lake.

Have you been to Chicago? What was your favorite thing to see? If you end up taking my advice and share your trip on social media, please tag me (@thenexttrip) in your picture! I would love to see how you enjoy the city and maybe share that drink or two!

 

Top 5 Things to See in Chicago - Chicago Skyline from Signature Lounge Hancock Tower

 

Pin this blog post to your Pinterest board to save all your ideas about the top things to see in Chicago!

 

Top 5 Things to See in Chicago

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2 Comments:

  1. You were an incredible tour guide! We’ll have to check out the other spots sooner than later!

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