top of page

Hi, we're Georgina and Nathan, college friends turned travel partners. We're coffee and animal-loving adventure enthusiasts here to share our favorite travel tips with you! Our goal is to inspire others to get out and explore this wild planet by camping, hiking, or wandering around a fun new city!

5 Apps & a Free Planner

Join our newsletter to receive the 5 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf!

Free Travel Planner Printable!

free travel planner printable pdf.jpg

Grab your FREE travel planner printable below and get planning your next trip with Alpacka My Bags!

  • Georgina D'Angelo

The Best Time to Visit Chicago

When to Visit and What Each Season Brings in the Windy City

The Best Time to Visit Chicago

When you think of Chicago, you might think of cold, snow, wind, and frost, but this Midwest city actually has four lovely seasons to enjoy. And each of them makes for a great time to visit! So keep reading if you want to learn when to visit Chicago.

Start planning a city vacation to this incredible travel destination. Chicago is home to countless museums, restaurants, architecture tours, parks, and more. Yeah Central Park in NYC is very cool, but wait until you get to explore some of the best parks in Chicago during every season.

There truly is something great about every season in Chicago, so the best time to visit depends on the type of weather you prefer to travel in. Do you prefer traveling in warmer weather? Or colder weather? Do you want to enjoy the snow? Do you want to go to the beach? Keep reading to find out the best time to visit Chicago!

Chicago’s Seasons in a Nutshell


The weather in Chicago in spring typically begins warming up from the winter months. March through May is a nice time to visit as it's generally not freezing, but you can still wear cozy sweaters, boots, and cute hats. But be aware, it can still possibly snow in the spring in Chicago! Temps average around the 30s to 50s from March through May in Chicago.

Chicago in Spring


My favorite time of year to visit Chicago is in the summer. From June through August the temps average from the 60s to the high 80s. The trees are green, the beach is buzzing with swimmers and sunbathers, and all the ice cream shops make for the perfect pitstop. Be aware though, summer in Chicago is typically the busiest.

Chicago in Summer


The weather starts cooling down in Chicago in September. Throughout fall, September through November, the average temps are around the 40s to 70s. Local coffee shops make for the perfect place to stop and warm up with cocoa or coffee, and the museums are eager to be explored.

Chicago in Fall


Even though it gets icy cold, Chicago becomes a gorgeous winter wonderland. From December through February, temps average around the teens to 30s. In some winters, it will stay above the 20s, but check the temps before you go as there can be days where it stays in the teens or lower. Check out our winter packing list for Chicago too!

Chicago in Winter

Now you might have chosen exactly when you want to visit Chicago, or maybe you’re still trying to figure it out based on the different experiences available during each season. So let’s dive in deeper! When to visit Chicago not only depends on the weather you prefer but also on what activities you want to participate in while exploring the city.

Read Also: The Best Museums in Chicago

Swimming, sunbathing, and Lollapalooza…

Best Time to Visit Chicago

If you want to enjoy any of the above activities, then you definitely need to visit Chicago in the summer! With temps averaging in the 80s, June through August is the perfect time to go, enjoy the sunshine, explore Chicago outside, and go for a dip in Lake Michigan.

It was always so fun to spend the summers in Chicago while living in the incredible city. The streets are busier; everyone just wants to soak in the sunshine and have a good time, and fashion is popping in the warmer weather.

There are so many fun activities to partake in if you’re visiting Chicago in the summer. And if you’re not a fan of cold weather, this is most definitely when to visit Chicago.

Pumpkin patches, perfect weather, and deep dish pizza…

Best Time to Visit Chicago

Ahh, fall in Chicago is lovely. The weather is cool, but not freezing. The foliage is gorgeous if you catch it at the right time. And the city starts to slow down. You’ll find quieter streets in Chicago in the fall as the weather is cooling down.

You can catch a pop-up pumpkin patch in or just outside the city. Utilize public transportation, fyi. It’s so useful and cheap. Fall is also the perfect time to sit down and enjoy an entire deep-dish pizza. It’s so good you can’t skip it!

If you’re like us and love walking everywhere when traveling, then fall is definitely the best time to visit Chicago. Grab a light jacket, get your phone for maps, and hit the sidewalks! Chicago is a great, walkable city.

Winter wonderland, holiday lights, hot chocolate, and ice skating…

Ice Skating in Chicago in Winter

Maybe you’re a huge fan of winter! If you enjoy snow, festive and fun lights and decorations, and wearing cute beanies and winter coats, then you’ll definitely want to visit Chicago in the winter.

The city turns into a bright and bustling winter wonderland this time of year. There are so many fun activities to enjoy in Chicago in the winter, such as ice skating and Lincoln Park zoo lights. And if you’re a fellow coffee shop lover, this is the time to hunker down in a cute local cafe and sip on a large hot cocoa or chai latte.

Read Also: Best Coffee Shops in Chicago

Beautiful flowers, bike rides, and outdoor dining…

Biking in Chicago in Spring

Spring in Chicago is literally blooming! With tons of flowers coming to bloom all around the city, you’ll forget you’re in one of the busiest, biggest concrete jungles. For a big city, Chicago seriously does nature well. With a plethora of lush parks to stroll around, you can still get your fill of nature in Chicago.

There are also huge, gorgeous potted plants scattered around the city. Check out Alfred Caldwell Lily Pond if you’re visiting in the spring! This one park is only open in the warmer months, and spring is the perfect time to visit when everything is in full bloom.

The Best Time to Visit Chicago

Now you know what each season brings in Chicago. This city is incredible and is awaiting your exploration! When will you be planning a trip? There is something beautiful and great about every season in Chicago, so it truly depends on what you want to do while in the city. But if we were to give you a flat-out answer, the best time to visit Chicago is in the summer.

The Best Time to Visit Chicago - Alpacka My Bags

But do not let that stop you from visiting during another time of year! Winter is gorgeous with the powdery fallen snow. Spring is fresh with flowers blooming all around the city. And fall is cozy, the weather is perfect, and the city is quieter.

After reading all about the seasons, what would you say is the best time to visit Chicago? Will this be your first time to the Windy City? Let us know if you have any questions regarding the city as we love, love, love it, and have spent lots of time exploring it. We look forward to hearing about your Chicago travel plans!

Post: Blog2_Post

Ready To Book Your Trip...

Planning a vacation can be time-consuming and a little overwhelming. To help smooth this process for you, we've compiled our favorite travel planning resources.

From finding the best flights and hotels to the essentials you need to make the most of your trip, check out the Alpacka My Bags travel resources page.

5 Apps & a Free Planner

Join our newsletter to receive the 5 apps I use to plan a trip, my go-to travel essentials list, and a free travel planner pdf!

Alpacka My Bags Travel Blog.jpg


We're Georgina and Nathan, two adventure enthusiasts and creators of Alpacka My Bags. We're here for all of your travel and adventure planning needs! 


We've been exploring this insane planet that we call home together for over 3 years now. After college, we knew the "traditional career path" was not for us, and honestly the "traditional life path", in general, just wasn't for us.


We needed to travel and explore what this world has to offer, it sounds cliché but you do only live once. So we made going on adventures a priority, and soon realized that we wanted to share them with others so they can enjoy them too! 

Our passion is spreading the travel bug and showing others that travel is attainable and so worth it. From itineraries to camping tips to packing lists, Alpacka My Bags has you covered!

Join us, and often our dog, JoJo, as we find exciting adventures and travel recommendations for you! If you've been bit by the travel bug just as we have, we hope you find our tips useful for any and all of your future travels.

bottom of page