The Best Time to Visit Chicago 2024: The Ultimate Guide

Published by: BouncePosted

Most people think the best time to visit Chicago is during the hopping summer months, and that may be true if you love large crowds and hot temps. However, Chicago really has a lot to offer throughout the year, not just during summer break.

While summer is a busy time in Chicago since it is the peak season, you may want to take a closer look at the shoulder seasons, spring and fall. The temperatures are generally milder and the humidity is most of the time lower, making outdoor activities much more enjoyable. Even a day trip to the lakeshore is better in the spring or fall because you miss the crowds.

Winter usually is not anyone’s favorite time to visit the Windy City, however, if you are looking to take a cultural trip where you plan a lot of museum hopping and art galleries, you just might want to brave the frigid temperatures and bone-chilling wind.

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From the green Chicago River in March to the Chicago Blues Festival in June, whenever you feel the best time to visit downtown Chicago (and beyond) is, you will find plenty to keep you on the move!

Is visiting Chicago in your future? No matter the season or what you plan to do, store extra gear or unneeded items with a luggage storage locker rather than carry them from place to place.

Whether pleasant weather awaits you or Chicago gives you a wet and windy day, be sure to see sights like Grant Park in the spring and stroll down Michigan Avenue to see the lights during the holiday season. The fall brings the Magnificent Mile Lights Festival and the freezing temperatures of a Chicago winter allow for fun on an ice rink. Visit Chicago any time for all the fun it offers!

Summer in Chicago: June-September

Chicago summers are always hot and extremely humid. The humidity is what will zap you quicker than anything, but summer is also one of the most popular times for people to visit. The average temperatures during summer in Chi-Town are in the mid to high 80sF (high 20sC) with the lows dipping down into the 60sF (15sC).

The summer season in Chicago sees a lot of outdoor events and festivals including live music, beer, food, and pretty much any other type of festival they can think of. Carnivals just outside the city and on Navy Pier are also popular as are concerts and movies in the park. There seems to always be something interesting and fun going on during summer.

If you are planning on spending time in Chicago during the summer, Navy Pier does fireworks displays two times a week throughout the entire season. It is free to come to the pier to enjoy the fireworks but many people grab a snack and head to the rooftops, decks, or patios to watch the technicolor explosions.

Lake Michigan is a busy place during the summer and the beach on the Chicago side is always crowded. Busy times are also evident when the Chicago Cubs and White Sox are making a run for the playoffs. But, remember, with an influx of tourists comes higher prices for hotels and travel.

August does see more rain than the other summer months so plan several contingent indoor activities in case your original plans get rained out. When it is not raining, though, check out one of the boat tours that are offered, they are fun and informative and get you away from the really big crowds.

There are several popular events that occur during summer in Chicago that you may want to check out. In June, attend LBGTQ Pride Chicago and Do Division Street Fest Sidewalk Sale. July brings Square Roots Fest, Taste of Chicago, and Lollapalooza Chicago. If you arrive in August, take part in Windy City Smoke Out or City of Chicago Presents U.S. Navy Blue Angels.

Fall in Chicago: October-November

Fall in Chicago sees the temperatures start to drop and the tourists head for home. While the average temperatures in the fall can vary significantly ranging from the low 70sF (20sC) to the low 80sF (mid 20sC) for the highs and the low 50sF (10sC) to upper 60sF (15C) for the low. The weather is generally less predictable but the falling temps make being out and about feel pretty good. 

Outdoor festivals are still pleasant and any other outdoor activities may require a light jacket due to the winds coming off the lake. Summer activities include the architecture river cruise, Centennial Wheel, Lincoln Park Zoo, and Navy Pier. Outdoor dining is less crowded and frankly more enjoyable without the long wait times. 

Hotel rates and travel prices begin to drop when the weather starts turning cooler, which means bigger savings for you. You will need to pack a variety of clothing since the fall weather in Chicago does fluctuate quite a bit and may feel summery but can also plummet and feel wintery. Check the weather forecast before stepping out for the day.

Spend some time taking in the breathtakingly vibrant fall foliage as the colors begin to change in early fall and only become more vibrant as the season advances. There are a lot of festivals that take place in the fall including the following. Oktoberfest Chicago, Chicago Gourmet, and Riot Fest are in September. October brings Bank of America Chicago Marathon and Chicago Beer Fest.

Winter in Chicago: December-February

Winter in Chicago can really be brutal, and the extremely cold weather is helped by the high winds coming off Lake Michigan. It can also be very snowy in Chicago making it probably a less-than-ideal vacation unless you are planning on spending the entire time indoors. There are times when the winter in Chicago is actually mild, but you generally do not know that until the season is in full swing.

The average daytime temperatures are in the low 30s (about -1C)to high 40s ( around 4C)and the nighttime temps can dip down into the single digits, but usually hover in the 20sF (-6C). Be sure to pack plenty of warm clothes, a winter coat, hat, scarf, and gloves so you are prepared to meet the cold head-on.

If you are one who does not like the heat and humidity of summer, you may actually like being bundled up and braving the cold and wind of winter. Hotel rates are usually at their lowest during the winter, and you can get pretty good deals. Restaurants and attractions around the city will offer discounts and deals during the winter season.

The best part about visiting the Windy City during winter is that you actually get to experience the brutal winds that gave the city its nickname. Visiting in the winter means the crowds are at their thinnest. There are also many fabulous indoor things to keep you busy and let you get to know the city a little better than if you were being jostled along with the masses.

The holiday season in Chicago is definitely festive and something you will want to see in person. The cold weather does not put a damper on the spirits of locals and they turn out for many amazing activities including the Magnificent Mile Lights Festival. Holiday shopping in Chicago with terrific bargains is also an experience you do not want to miss.

Christkindlemarket Chicago is a way for the city to showcase its strong German heritage. This German Christmas Market is held outdoors and is super family-friendly. Admission is always free so you have more money to spend on gifts and treats. Strolling through the market, your tummy will begin to rumble, and the smell of bratwurst, fresh pretzels, roasted nuts, and spiced wine will make your mouth water.

The vendors will offer anything from sweet treats to handmade and hand-painted ornaments. The festive, live music will have you tapping your foot as you shop. You never know what you will find as you wander through this unique and lively German market. There is even a section dedicated to the kids so they can make crafts and spend time with new friends.

Garfield Park Conservatory hosts the annual Spring Flower Show, which is one of the longest flower shows in the Midwest. The flower show begins at the end of February and runs through the first week of May. Blooms include hydrangeas, tulips, hyacinths, and daffodils, along with roses, lilacs, peonies, and so much more. You do not have to be a budding botanist to enjoy this flower show.

When you visit Chicago during the winter season remember to look out for fun. November brings Chicago Thanksgiving Parade and Christkindlmarket Chicago. In December, don't miss Chicago Comic & Entertainment Expo. If you like cars, the Chicago Auto Show is in February. And don't miss the St. Patrick’s Day Parade in March.

Spring in Chicago: March-May

If you are looking for pleasant average high temperatures with low humidity, you will want to visit Chicago in the spring. Temperatures begin to rise beginning in March but April and May are when you see the best temps. Vibrant flowers begin to bloom making the parks and green spaces come back to life after a long, dormant winter.

Average high temperatures can range between the low 50s (teens celsius)to the low 70sF (20sC). The temps then fall back into the high 30s (about 3C) and 40s(6-8C) at night, but are still pleasant enough to enjoy spending time out in the fresh air and checking out the different landmarks and parks.

With the warmer weather, the locals really start heading outdoors, but you still do not see an abundance of tourists. It is a fantastic time to explore and take walking tours through the city. Just remember, the weather is still pretty unpredictable so be sure to pack some warmer clothes and a jacket. Check the forecast each morning before you head out for the day sightseeing.

You do see an influx of tourists for spring break, which is usually in mid-March. Get ready for the St. Patrick’s Day celebrations held throughout the city. Expect to see a lot of younger people descend on Chicago during this time. Then, tourism wanes a bit until late May and Memorial Day.

Since Oktoberfest only comes around once a year, the German community decided years ago to have a festival in May to celebrate all things German-American. Maifest was founded as a way to promote the strong German heritage that runs deep in Chicago. Also called MayFest, admission is free and you can listen to live music and dine on German and American dishes and wash it all down with strong ale or craft beer. From February to May, enjoy the Garfield Park Conservatory Spring Flower Show. Runners will like to take part in the Chicagoland Spring Marathon and Half Marathon in May.

Visit Chicago at any time

 Whether you are in town for the Chicago Jazz Festival or checking out all the holiday events, each season in Chicago is as different as they can be. The average high temperature varies greatly from winter to summer and depending on your preference the Chicago weather just may dictate when you choose to visit this intriguing city.

World class museums beckon during the worst weather and the Art Institute of Chicago is one of the best indoor attractions and a great way to get in out of the cold or beat the heat during the hottest month in Chicago. Optimal weather in Chicago can be a bit difficult to find, but late spring is generally when the best weather occurs, with low humidity and warm temps.

Seeing this city is a treat, though, so deciding to explore Chicago is always a good idea!

Know what you want to do during your trip to Chicago? Check out these guides for inspiration!

The Best Hikes In Chicago
Chicago On a Rainy Day: Things To Do
Music Festivals in Chicago in 2022

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