We are lucky to be able to call Chicago our home for the past 4 years. During this time, we explored the city and all of its beauty, and we truly love everything it offers. 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 visit.
Kyle and I receive 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 be on your list just yet. If you're looking for the most Instagrammable indoor spots in Chicago, check out this post.
Table of Contents
1. Top Things to See in Chicago: Architecture Tour with Shoreline Sightseeing
We take 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. An added bonus is getting up close and personal with some of the most beautiful skyline views.
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 many iconic bridges. The tour continues all the way to the North Branch of the Chicago River, and then turns around to share one of the most recognized buildings from the opening scene of The Dark Night: the post office!
In addition to getting incredible views of the city and great photo opportunities, Shoreline Sightseeing shares some interesting facts about the city. I learn something new every time I join my guests on the cruise!
Tickets are available online here or buy them at the Navy Pier or Michigan Avenue booth before the tour. If you're visiting in summer, I recommend you purchase your ticket a few days in advance as their tours do sell out.
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! 🙂
If you're in town for a few days, visit the Hancock tower on a clear day right before sunset. This way 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.
3. Top Things to See in Chicago: Take a Selfie at The Bean
Cloud Gate, also known as The Bean, is one of my favorite landmarks in the city! It is also one of the most well-known icons of Chicago. You haven't truly seen Chicago without taking a selfie at The Bean. Cloud Gate is beautiful in its simplicity and I love the way it reflects the city and blue skies. Due to this beauty, 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.
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 much easier. You will still have the odd tourist suffering through the cold as well though!
While you're already there, you might also stop by the corner of Michigan and Adams. This marks the beginning of the historic Route 66. Route 66 technically started on Jackson Boulevard, but Jackson Boulevard is now a one-way street East. As a result, 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! I stumbled upon a forum which mentioned 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.
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, view, and beautiful Lake Michigan.
Getting to the Adler Planetarium using public transport will involve a fair bit of walking. Therefore, our recommendation is to rent a Divvy bike and bike 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 sandy beaches. Not only that, but there is a bike and pedestrian dedicated lake front trail for almost 20 miles. On a warm sunny day, rent a Divvy bike and bike along the lake front trail. You can easily 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. Another top tip is to cool off after your ride by joining the many Chicagoans 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 sharing 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!
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