Why Early Fall Was the Perfect Time for a Visit to Chicago

Have you ever been to Chicago in the fall? I can’t wait to share my early fall visit to Chicago and why I felt it was the perfect time to experience everything there was to see in the famous Windy City.

view of Chicago from the Swissotel

I’ve always wanted to visit the Chicago area.

So when my husband told me he was going to be traveling there for work last year, I knew it would be a great way for me to finally visit one of the incredible cities on my bucket list.

view of the Chicago River

My good friend Candice and I flew out for a few days in late September 2021 on our own, and then my husband joined me on the day she left. I loved spending time with each of them individually.

As an Amazon affiliate, I earn from qualifying purchases at no extra cost to you. My blog contains other affiliate links for your convenience as well. Click here to read my privacy policy.

room service in the hotel looking at the Chicago view

Our Hotel in Chicago

We stayed at the Swissotel which is only an 8-minute walk to the Riverwalk.

What I really loved about the room we stayed in was that the view was constantly changing depending on the time of day and the weather.

As you can see, every capture was stunning in its own way. We could sit in front of the window and just stare outside, and not do much of anything else.

It was the perfect place to just unwind and take in the beauty of the moody sky.

view of the Chicago River

Why is fall a great time to visit Chicago?

There are so many reasons why I loved taking a trip to Chicago at the very beginning of fall last year. Here are just a few…

  • The brilliant fall colors are spectacular.
  • Our weather still allowed us to experience outdoor activities.
  • We missed the peak season so we didn’t spend all our time waiting in lines.
impatiens and fall flowers and foliage in the center of the Chicago street

Brilliant Fall Colors

In my opinion, fall is the best time to visit Chicago. The autumn season filled the streets and parks with brilliant fall colors that took my breath away.

When I talk about fall colors, I saw them mostly in the flowers and fall foliage throughout the city.

As far as the vibrant autumn leaves that a fall visit to Chicago would feature, we were a bit too early for that. But I have heard how stunning the colors are later in the season.

Everywhere I looked there were beautiful autumn blooms and foliage lining the streets.

I was surprised to see the bright and stunning plants as I walked down the streets of downtown Chicago and the gorgeous fall flowers they had already planted.

The Magnificent Mile Association Beautification Award

The Magnificent Mile Association

Beautification awards were handed out as well. It was so fun to see the beauty that was created in these outdoor spaces.

a sailboat full of green outdoor plants for fall contest

Check out this amazing sailboat full of incredible plants.

I shared quite a few pictures of these stunning fall garden combinations.

Their beauty was overwhelming and a shocking but welcome acknowledgment that you can create garden spaces just about anywhere.. even among the many tall buildings and concrete sidewalks.

early budding mums and cabbages planted between streets and sidewalks

Here you can see that these garden mums were just planted and only had tiny buds. Can you imagine how vibrant they looked a few weeks later when they fully bloomed?

It made me smile to see how garden spaces were created where you wouldn’t imagine them to be.

view of the Chicago River

The Weather Allowed Us to Enjoy the Outdoors Still

Skip the sweltering summer heat and blustery winters and visit Chicago in the fall.

There were several outdoor activities in Chicago that we were able to enjoy because of the nice weather. The average temperature for this time of year is a high of 74.8°F and a low of 54.3°F. You can’t complain about those mild fall temps!

While we were there, the weather forecast called for a little rain and quite a bit of wind for the first few days, and then we had some amazingly warm temperatures after that so we could enjoy the city at its best.

I don’t know about the remaining fall months, but the crisp fall air we experienced in the early fall was so welcoming.

The Bean in Chicago

Enjoying Tourist Activities With Fewer Crowds

Traveling to Chicago in the fall season meant that we would miss all the crowds and lines that the summer season’s peak time experiences.

It was so much more enjoyable to have fewer crowds when sightseeing than during the summer tourism season.

view of the Chicago River and wooden boat on Riverwalk

There are So Many Fun Things to Do in Chicago in Early Fall

So many of the things we wanted to see and do were within walking distance from our hotel. We only needed to drive once to a restaurant we wanted to go to for dinner.

The Loop

According to Britannica.com, the loop is bounded by Lake Street (north), Wabash Avenue (east), Van Buren Street (south), and Wells Street (west).

The term loop is sometimes used to refer to downtown Chicago in general. This is particularly true for the area enclosed by the Chicago River, Michigan Avenue, and Congress Parkway. This area is basically the heart of the city and includes:

  • Chicago Riverwalk
  • Millennium Park
  • Theater District
  • Shopping along State Street
  • Historic architecture
  • River cruises
  • Dining options

Here are some of my favorite things to do in the windy city.

Views from the Riverwalk in Chicago

Chicago Riverwalk

I personally felt that the riverwalk was the best part of my trip.

The riverside pedestrian path features the most beautiful city views & delicious dining with an incredible ambiance.

selfies on the Riverwalk in Chicago

We had such a good time with very few lines for dining and the weather being warm enough to eat outdoors with those gorgeous water views.

View of the Chicago River from the Riverwalk

You know how I feel about boats, don’t you?

I really loved seeing the boats in the water while walking down the Riverwalk path.

Millennium Park entrance with fall flowers and foliage

Millennium Park

Millennium Park was such a great place to see with so many different attractions.

The fall flowers in this section of Chicago did not disappoint by any means.

Millennium Park

There’s my husband standing in front of the Millennium Monument.

The Bean at Millennium Park

A few selfies were taken in front of this contemporary sculpture nicknamed “The Bean”.

According to Free Tours By Foot, its real name is Cloud Gate, and was assembled with nearly 200 stainless steel plates, this sculpture cost $26 million dollars to complete.

Water feature at Lakeshore East in Chicago

Lakeshore East Park

The best way to describe this area is as a mixed-use development in the northeastern part of the Loop community area of Chicago.

Water features and walkway at Lakeshore East in Chicago

We found the most beautiful park with flower-lined walking paths and surrounded by tall skyscrapers.

There’s a children’s splash park, a dog park, fountains, and green grass.

A few restaurants and a grocery store nearby were so convenient and close to our hotel.

Chicago Theater

Magnificent Mile

Let’s talk about shopping! You wouldn’t believe all the fun I had at the department stores and boutique shops along The Magnificent Mile in Chicago.

The Magnificent Mile is a 13-block stretch of North Michigan Ave and has everything you could ever want. Besides the shopping, there are so many restaurants and bars, theaters, hotels, and so much more.

London House rooftop in Chicago

London House Rooftop

One of the best ways to see amazing sights and sweeping views is to go to the top of the building and spend some time on the rooftop of the London House.

London House rooftop in Chicago

This is about as good as it gets when it comes to viewing the stunning city of Chicago.

view from London House rooftop in Chicago

It’s a very good idea to make a reservation a month or two ahead of your visit. We learned this the hard way and were only able to go up for a few moments to take pictures but couldn’t sit down to have a drink and take it all in.

Chicago Architecture Foundation boat cruise

Chicago Architecture Foundation Boat Cruise

There really is no better place to see all that the stunning skyline of Chicago has to offer than by water.

We took a Chicago Architecture Foundation boat cruise for a 90-minute narrated tour of how the Chicago skyline came to be.

Chicago Architecture Foundation boat cruise

Here’s the boat going under one of the many Chicago bridges.

river cruise to see architecture
Willis Tower in Chicago

The Willis Tower in Chicago, which used to be known as the Sears Tower, is a 110-story building. It’s one of the tallest buildings in the world and the second-tallest building in North America.

It was the world’s tallest building until 1988.

Jeweler’s Building is on the left and the Chicago News Tribune building is on the right.

Wrigley building in Chicago

More Incredible Buildings in Chicago

Here are some of the other buildings around the city that I thought were extra special.

Above is the Wrigley building.

The Millennium Tower

The Millennium Tower is pretty stunning, especially in the evening with all the lights shining through the windows.

Carbide and Carbon building

The Carbide and Carbon building is another one of my favorites. Above is a full view from the river tour and below is the doorway as I was walking by it one day.

Carbide and Carbon building

The Residence at St. Regis Chicago is quite interesting and unique in shape.

relief scultures in Chicago

The relief sculptures that embellish the four bridge houses on the Michigan Avenue Bridge commemorate important events in Chicago’s early history. 

Beatnik on the River in Chicago

Exploring Chicago Dining

I’m sure you can only imagine how many restaurants there are to choose from in the downtown Chicago area.

Beatnik on the River in Chicago

Beatniks on the River

My friend and I decided to try Beatnik on the River and I’m so glad we did!

According to their website, Beatnik on the River is driven by a fusion of 3 countries.

  • Morocco for its audacious combinations of color and passionate artisans
  • France for its music and artistic confidence
  • Italy for a healthy dose of polish and panache
Beatnik on the River in Chicago

This is the outdoor space overlooking the river where we sat. It was a bit cold that evening but totally worth it.

Their food and drink were exceptional and the staff took great care to create the best presentation possible.

The picture on the left was where I was sitting. The water was so close. It almost felt as if I was on a boat.

Beatnik on the River in Chicago

The beatnik bar shows off the eclectic style throughout the entire restaurant.

Eataly in Chicago


More than a market, Eataly is an experience where you can eat, shop, and learn.

There is a variety of restaurants, food and beverage counters, a bakery, retail items, and a cooking school. 

pizza at Eataly

We had some pizza for dinner.

And there was plenty to choose from for a little dessert.

RL Restaurant in Chicago

RL Restaurant

RL Restaurant opened in 1999 and features the vision and decor of Ralph Lauren and modern city-club cuisine.

The restaurant is located adjacent to the world’s largest Polo store, the Chicago Flagship on Michigan Ave.

We were able to eat outdoors because of the beautiful Chicago fall weather that day.

lunch at RL Restaurant

The food and the ambiance were above expectations and really were a special treat.

There were many other attractions that we would have loved to visit but we literally ran out of time. Here are some things we will try to see next time:

  • Navy Pier
  • Lincoln Park Zoo
  • Chicago Botanical Garden

I can’t thank you enough for following along to see how much fun our Chicago early fall visit was. If you’re thinking of taking a trip to the Windy City, this is such a great time to go.

Leave me a comment and tell me what you think.

Until next time,

Happy Traveling!


If you’ve enjoyed this blog post, please pin and share this on Pinterest.

Let’s Connect on Social Media

Similar Posts


  1. First, that combo of cabbages and the closed mums looks so cool!!! Love all the flowers…but all that yummy food got me!! Beautiful pictures you’ll have to start a travel blog on the side because you are so good at documenting your travels.

  2. Wow! These are stunning photos, they just knock your socks off. I grew up in Illinois and have been to Chicago several times, but not recently. This makes me want to go again, and I have pinned a lot of your info to my Chicago board. Thanks for this article.

  3. Kim ~ I have lived in the Chicago suburbs since I was a child. We love “our” city and I loved your post! It was fun to see the city through your eyes. Your pictures are wonderful. We did not know about Beatniks and we look forward to trying it! Thank you for this beautiful look at Chicago!

  4. I was born and raised about 35 miles southeast of Chicago. I worked in the Loop and Chicago was a highlight when we were kids, especially at Christmas. I have so many wonderful memories of looking at the decorated store windows and seeing the gorgeous Marshall Field’s Christmas tree. There are so many wonderful things about the city and its people. And you have captured almost all of them in your photos. The only drawback is you have to stay within the city. Believe me, you can walk a few blocks west of the Loop and think you were in a totally different world. Thank you for sharing all these wonderful photos of my favorite city in the whole wide world. It brought back a lot of wonderful memories.

  5. Kim, I love this post! I was just in Chicago in July to help my son move there. Surprisingly the weather was fabulous. He lives right next to Millennium Park and I stayed a short walk away near the theatre district. So many of the photos you shared are walking distance from his apartment. I love the location and I agree, that Chicago is a great place to visit. Unfortunately most people think Chicago is just a murder capital and so dangerous, but I never experienced that. And the plants and street maintenance is very impressive. Great post.

    1. Thank you for the compliment, Mary. I really had such a great time on our trip and couldn’t believe how many things there are to do there.

Leave a Reply

Your email address will not be published. Required fields are marked *