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How to Visit Chicago in Spring

Ernest Hemingway once wrote in his book, A Moveable Feast, “When the spring came, even the false spring, there were no problems except where to be happiest.” People often assume that this quote is about Heminway’s time in Paris, while others assume he is reflecting on the happy times at his home outside of Chicago in the Spring. But in either case, half of the quote is missing that perhaps reveals the truth: “The only thing that could spoil a day was people and if you could keep from making engagements, each day had no limits. People were always the limiters of happiness except for the very few that were as good as spring itself.”

Now if the idea of spending a long weekend in Chicago worries you due to the crowds, we get that! According to Lynn Osmond, the President & CEO of Choose Chicago, “The hotels were packed, the streets were full, the attractions were busy. And this fall we’re actually doing very well. We’ll probably end the year somewhere around 82% of 2019!” Since more than 60 million tourists visited the city in 2019, that is a lot of people to have to wade through.

So, what do you do if you have the amazing sports, incredible architecture, or cultural attractions on your Chicago Bucket list? Or paraphrase Hemingway, if “the only thing that could spoil a day” in Chicago “was people”, how do you manage crowds during a long weekend in the Windy City? 

Well, perhaps the answer is as simple as to visit Chicago in Spring!

The best weather for a less crowded Chicago

Now depending on what is on your Chicago bucket list will most likely direct you on when you will want to visit. For example, if you want to go swimming in Lake Michigan then Summer might be your only option since only then the average lake temperature is 70°F. But with warm summer days comes crowds of people looking to explore the various indoor Chicago Tourist attractions as they look to escape the heat.

Of course, the best season to visit Chicago is the beginning of autumn, from early September to mid-October. But with football season, the leaves change colors, & tons of food Festivals, the city becomes packed with visitors.

But if you really don’t care about specific events or seasonal outdoor adventures, then visit Chicago in the Spring, especially from mid-April to late May. Now the weather may be a bit unstable. For example, with an average of 59°, one day it might be a cold windy day and the very next day might be a sunny 86 °F. Perhaps, it is this unreliability in the weather that keeps the crowds a bit thinned.

How do you experience the incredible architecture, cultural attractions, or food experiences the Windy City has to offer while avoiding the crowds? Perhaps the answer is as simple as to visit Chicago in Spring! #ChicaGOandKNOW #Chicago Click To Tweet

The Best Activities when you Visit Chicago in Spring

Darcee and Eric Standing on the DuSable Bridge over the Chicago River during their visit to chicago in spring

When adding items to your Adventure Activities & Experiences Bucket List, Chicago has a lot to offer. From amazing museums and cultural activities to unbelievable food and drinks, it’s hard not to find something for any type of traveler. Plus, most of the popular items are easy to tick off during a long weekend in Chicago in Spring. So let’s dive into some of the best Chicago Bucket list items you can find.

The Wonderful World of Chicago’s Sports

Darcee & Eric Standing outside Wrigley Field to see a Cubs Baseball Game when they went to visit chicago in the spring

With spring comes baseball! There is something magical about watching either a White Sox or Cubs game in the Windy City. But for those with a Baseball Stadium Bucket List, Wrigley Field offers a magical step back in time. Of course, catching a pre-season game is ideal in the 100+ year old stadium, but if the team isn’t playing, don’t fret. Wrigley Field tours take place regardless of the weather & is ideal for those wanting to avoid the crowds. Just make sure you check the weather and dress accordingly because being so close to Lake Michigan can bring cold winds.

The Amazing Art Scenes in the Heart of America

A Sunday Afternoon on the Island of La Grande Jatte

Vincent Van Gogh Self Portrait

Little Dancer Aged Fourteen – by Edgar Degas

From major art exhibits to local history, there are tons to explore and see when you visit Chicago in the spring. With so many different types of museums you are bound to find something that piques your interest. But with fewer crowds, you can easily tick off some of the best the Second City has to offer. Plus, with a Chicago City Pass, you can gain admission to five of the city’s top attractions with priority entry like The Art Institute of Chicago.

Top Art to See in Chicago:

Crown Fountain in Chicago

  • The Art Institute of Chicago: With 2 gigantic lions guarding the entrance, this amazing art museum has over 300,000 artworks in its permanent collection from some of the greatest artists from history.
  • Museum of Contemporary Art: One of the largest museums in the world, this gallery is packed with art from local and international artists alike.
  • The Field Museum: Okay, so this isn’t an Art Museum. But this museum of natural history museum has tons to see from around the world. Make sure you see SUE, the world’s most complete Tyrannosaurus Rex.
  • Cloud Gate: Also known at the Bean, this outdoor sculpture was created by British artist Anish Kapoor between 2004 and 2006. On a perfect spring day in Chicago, it reflects the city’s famous skyline and those looking at it.
  • The Crown Fountain: Nearby the Cloud Gate is an interactive video sculpture created by Spanish artist Jaume Plensa. The fountain is two towers at each end of a reflecting pool that projects video images of Chicago citizens.
  • The Hemingway Birthplace Museum: Located about 1 hour via the Chicago L from downtown Chicago in Oak Park, Illinois, the once childhood home of Ernest Hemingway is now a museum that explore the author’s life.

The Incredible Architecture of the Second City

the view of the Skyline from the Skydeck of the Willis Tower went to visit Chicago in the Spring

Known around the world for its beautiful designs and soaring skyscrapers, Chicago is an architectural delight. Of course, you can get lost amid all the amazing towering buildings. But throughout the Second City, you will find ornate fountains, wide European style bridges, & even a few gothic churches. 

Now when you visit Chicago in the spring, you should take note of the weather before you head out. Due to a mix of rain & cold weather on some days, some of the sights can be lost amid the fog. But overall, you will find  that most of the popular locations are open with little to no crowds.

Top Architecture to See in Chicago:

View from the Skydeck of Willis Tower in Chicago

Holy Name Cathedral in Chicago

Rocks of the Chicago Tribune Wall

Buckingham Fountain in Chicago

  • Skydeck Chicago at Willis Tower: One of the most famous buildings in all Chicago is the Willis Tower. Originally known as the Sears Tower, this building held the title of World’s Tallest Building for 25 years. Now, visitors can take in views of the city while sitting in a glass cube that hangs off the side of the building some 1,353 feet in the air.
  • The Chicago Tribune Wall: Perhaps one of the coolest buildings in Chicago is that of the Chicago Tribune. Along the Magnificent Mile, this building humbly stands amid its taller brothers. But what makes it unique are the 150 fragments of famous world architecture embedded in the outside wall. They have stones, bricks, and just random pieces from places like St. Peter’s Basilica, Pompeii, the Hagia Sophia, & even the White House.
  • Buckingham Fountain: Located in the center of Grant Park is one of the largest fountains in the world. Inspired by the Latona Fountain at the Palace of Versailles, the fountain performs water shows and evening colored-light shows. Fair warning though, the fountain is only turned on from May to mid-October.
  • The Holy Name Cathedral: For those who don’t know, most of Chicago was destroyed in the 1871 Great Chicago fire and a great rebuilding occurred, hence the name the Second City. Perhaps one of the beautiful results was building of the Gothic Revival style Cathedral in 1875. Though seemingly flawless, it does bear a unique scar of bullet marks from the murder of North Side Gang member Hymie Weiss, who was killed in front of the church.

Where to Stay when you visit Chicago in spring

A room inside the Acme Hotel

The Berkshire Room at the Acme Hotel in Chicago

Cocktails at the Berkshire Room at the Acme Hotel in Chicago

With so many hotels and places to stay in Chicago it can be a wee bit overwhelming. But during our long weekend in Chicago, we wanted a place close to downtown but away from all the crowds. So we were especially happy to find the Acme Hotel in Chicago. 


Located about 3 blocks from the Magnificent Mile and a block from the Red Line, it allowed us to easily explore Chicago. Plus, it was quirky fun. The hotel has an eclectic style with modern art everywhere and we mean everywhere. If you have an inner room, look out the window into the alley way to see random mannequins in unusual positions.


Another bonus to staying at the Acme Hotel is the Berkshire Room bar. Chicago bars are awesome but always crowded or worse, you wait in line for an hour just to get in. But hiding in the bottom of the hotel is an amazing speakeasy style hotel bar with unbelievable cocktails. 

Now Go to the Paris of the Prairie

Eric Gamble standing behind the Chicago sign during long weekend in Chicago with Darcee

Architect & urban designer, Daniel Burnham, originally called Chicago the “Paris of the Prairie” since he developed major changes to the city’s layout in a style that is similar to Paris. Perhaps that is why Hemingway felt so close yet so challenged by the people of both cities. But, if you too have issues with crowds then springtime might very well be the best time to visit Chicago.

But what do you think about visiting Chicago in the Spring? Which of the activities do you think are the best for you and your partner? Are there other things to do in Chicago over a long weekend that we forgot?

Let us know in the comments below and help someone else plan out their own long weekend getaway or bucket list adventure in Chicago today!

Don’t forget to Pin this to your Favorite Travel Bucket List Board! Pinterest Pin of 4 pictures of when Eric and Darcee Gamble went to visit Chicago in Spring

Disclosure: This post, “How to Visit Chicago in Spring”, does contain affiliate links. Using the links doesn’t cost you any extra, and it helps keep the site free, fun, and community supported! Eric & Darcee will never recommend a product that we don’t genuinely believe in, actually use ourselves, have researched, and trust. Please see the disclosure policy for more information.

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