The weather in Chicago can be unpredictable and extreme, but that doesn’t mean you should let it stop you from visiting.
There are many reasons to visit this beautiful city, but the best time of year to go depends on your interests.
Spring and Autumn will offer great opportunities for dining out and enjoying festivals like Taste of Chicago or
Oktoberfest if you’re a foodie or beer connoisseur. Spring is festival season with music festivals like Lollapalooza and Pitchfork Music Festival drawing huge crowds each weekend; there are also plenty of outdoor activities if the heat isn’t too intense (like sailing along Lake Michigan).
No matter what time of year you decide to visit Chicago, we have suggestions for how to make the most of your trip to the Windy City.
Best Time to Visit Chicago
The Chicago weather is one of the biggest impacts on what you can do in the city. For example, if there’s a foot of snow outside, it doesn’t make sense to go to an outdoor music festival.
Likewise, if it’s 90 degrees during Christmas, ice skating outside around Millennium Park probably won’t be very pleasant. So here are some suggestions for when each season is best to visit Chicago.
Spring is a great time for visiting Chicago because the weather’s warm enough for outdoor activities like biking, hiking, and boating without being too hot.
Many of the city’s top attractions also host special events during this time starting in early March like:
- Field Museum: April 20-November 2
- 3 Floyds Brewing Co.: Midwest Metal & Beer Fest May 20-21
- “Ride for Heart”: April 27-28
- Renegade Craft Fair May 19-21
Head to Wrigley Field around opening day to catch the Cubs’ first home game of the season. Or visit the Chicago History Museum to participate in free events, such as family-friendly scavenger hunts and movie screenings.
If you’re looking to get away from the hustle and bustle of downtown during Spring weather, be sure to check out what’s going on in Chicago’s neighborhoods like Logan Square.
The neighborhood is home to one of the city’s hottest music festivals during Spring include:
- Fit to Print: May 5
- Kinetic Sculpture Race: May 20-21
- Windy City Wine Festival: May 19
The warm weather during summer in Chicago is a major selling point for visitors, but it can get very hot, so you’ll want to carefully consider the outdoor activities, especially if you have kids with you. Some of the top events that take place in the city during summer are:
- Music festivals like Chicago Open Air & Lollapalooza
- Taste of Chicago July 6-10
- Beer Fest at Soldier Field June 24-25
The Shedd Aquarium is in full swing with its schedule of daily activities during the summer season, plus other attractions like the Art Institute of Chicago have special exhibits you won’t want to miss.
Many visitors know that summer is the best time to visit Chicago because of hotel bargains and discount rates due to the city’s high humidity.
Fall is a great time to visit because it’s usually milder than other seasons but still has lots going on, including many food and music festivals starting on Labor Day weekend as the summer rush ends.
Some of the top events that take place in the city during fall are:
- Oktoberfest at Wrigley Field September 16-17, October 7-8
- Chicago Marathon October
- Taste of Randolph Street September 2-3
If you’re visiting During Autumn to see the fall foliage, don’t miss the chance to check out the Chicago architecture by boat on one of these Lake Michigan Architecture Cruises.
In addition, the Chicago Marathon ends downtown, so it’s a great time to be in the city– you can even cheer on runners while they make their way down North Michigan Avenue.
Lincoln Square during the hottest month of the year can be a bit on the uncomfortable side, but it’s nice and cool during the winter and fall.
Winter is an option for visitors looking for fewer crowds during the coldest months, but it comes with its own set of challenges. Although there are plenty of holiday events in the city during winter, many attractions are closed for part of the season.
Some of the top things you can do in Chicago during winter are:
- Ice skating at Millennium Park: December 2-March 18
- Wizard World Comic Con: January 12-15
- “Light Up Night” to see the holiday lights: November 23-December 31
- Chicago Auto Show: February 11-20
Chicago is known for its many shopping destinations, but the Magnificent Mile Lights Festival is a great time to visit because of all the holiday decorations taking place downtown.
The end of November through New Year’s Eve is also full of activities in Millennium Park, including ice skating (December 2-March 18).
Even during the cold weather, Chicago offers plenty of activities to keep you busy. If you visit in winter, you can skate or go on a scenic boat tour or catch the Lolla-Palooza music festival– bring some extra layers of clothing to stay warm!
From early February until St. Patrick’s Day, the city is full of green. Celebrate by visiting some of the many Irish pubs and restaurants or stop by Shedd Aquarium for a glimpse at their playful resident green sea turtle Hatchimal.
Many visitors to take time to visit Chicago during the winter months can enjoy deeply discounted prices on theater tickets and indoor attractions from early December through mid-January.
In addition, from early November until late Spring, during the city’s worst weather, visitors can explore Chicago and enjoy its world-class museums and other events in the beautiful winter wonderland the blustery winters bring.
From the freezing temperatures during the winter months to the hot, humid days during the summer months, Chicagoans and visitors alike must deal with a lot of variety when it comes to the weather.
Chicago’s average temperatures during the holiday season make it the best time to visit.
Spring is mild, bringing temperatures in the 50s and 60s. Head to Wrigley Field around opening day to catch the Cubs’ first home game of the season.
Or visit the Chicago History Museum to participate in free events, such as family-friendly scavenger hunts and movie screenings.
- Average Temperature: 52 degrees Fahrenheit
- Average High: 67 degrees Fahrenheit
- Average Low: 44 degrees Fahrenheit
Head to one of the city’s many parks like Lincoln Park Zoo or take a scenic stroll down Lake Shore Drive in the warmer weather during late April. You can also visit Shedd Aquarium during this time for spring break field trips.
Summer is hot, reaching highs in the upper 80s and 90s. The weather during summer in Chicago is typically sunny with high temperatures. The city hosts various festivals during this time, including Taste of Chicago in July.
There are also a few days each season that reaches over 100 degrees Fahrenheit.
- Average Temperature: 77 degrees Fahrenheit
- Average High: 88 degrees Fahrenheit
- Average Low: 69 degrees Fahrenheit
You’ll want to plan your trip around one of the city’s many festivals during this time, including Chicago Craft Beer Week in May and Taste of Chicago in July.
Plus, don’t forget to check out what the Shedd is up to during the summertime because it’s one of their busiest seasons!
Early fall is colorful, bringing temperatures in the 60s and 70s. The windy city is decorated with pumpkins, mums, and colorful trees for seasonal festivities during fall.
You can also catch a free show at Millennium Park or visit Navy Pier for its Fall Family Fun Fest from September 19-21.
- Average Temperature: 59 degrees Fahrenheit
- Average High: 72 degrees Fahrenheit
- Average Low: 52 degrees Fahrenheit
From mid-September until late November, Chicago welcomes a new wave of tourists during the month’s outdoor festivals. The best one to plan your trip around is the Chicago Film Festival in early October.
For fall fun, check out Navy Pier while it has its Fall Family Fun Fest going on from September 19-21 and the Magnificent Mile Lights Festival in November– a great time with pleasant weather to be in the city.
Winter is cold, reaching lows in the 20s and 30s. There are also a few days each season that drops below 0 degrees Fahrenheit.
If you’re traveling this time of year, there’s a good chance that you’ll be here for the holidays, specifically Christmas and New Year’s Eve. The entire city will be decked out in festive decor during the holiday season.
- Average Temperature: 33 degrees Fahrenheit
- Average High: 44 degrees Fahrenheit
- Average Low: 26 degrees Fahrenheit
If you’re visiting during the winter, make your trip all about shopping and taking part in some of the city’s holiday activities like ice skating at Millennium Park and “Light Up Night.”
Visiting Chicago for the Music
The town is renowned for its various styles of live music available year-round. There are plenty of ways to catch live music, from the Chicago Blues Festival every June to the Chicago Jazz Festival in August.
Chicago Blues Festival
The city hosts the Chicago Blues Festival in June, and it draws more than 400,000 people. The event features performances by blues artists like Buddy Guy, Koko Taylor, and Junior Wells. Plus, admission is free!
The festival started in 1984 and has been going strong ever since.
Chicago Jazz Festival
The Chicago Jazz Festival takes place in late August or early September annually at the Jay Pritzker Pavilion in Millennium Park for ten days. The event usually averages more than 100,000 people and features renowned jazz musicians like Herbie Hancock and Tony Bennett.
The Jazz Festival started in 1987 and is one of the city’s longest-running festivals. It’s also free to attend!
Chicago Summer Dance
Chicago Summer Dance is a free outdoor dance party every Friday night from June 21 to August 16 in The Spirit of Music Garden in Grant Park. Each week features a different DJ playing genres like swing, salsa, hip-hop, and more.
Chicago’s Theatre District
Along with concerts, the city offers plenty of year-round theatre options like Chicago’s Theatre District, which is home to 19 theatres, including The Private Bank Theatre and Cadillac Palace Theatre.
Chicago’s Theatre District is the largest in the country outside of New York City. There are musicals, plays, and other forms of entertainment year-round at venues like the Cadillac Palace Theatre and The Private Bank Theatre.
There are also comedy clubs, improv groups, and performance spaces around town for various kinds of stage entertainment all year round.
The city is home to museums year-round, including the Art Institute, Museum of Science and Industry, Chicago History Museum, Peggy Notebaert Nature Museum, and more! You can also check out free admission days or half-off discounts.
During October, the city hosts the Chicago Marathon and half-marathon. More than 40,000 runners come from all over the world to participate in this event. Runner’s World has called it one of the Top 10 Marathons worth traveling to attend!
Many tourist businesses offer day trips across the Chicago River nearly every time of the year. The river tours feature a variety of fun excursions, from food and drinks to architectural tours.
Many families avoid the crowds during the shoulder season between the end of March and the end of May. During this time, tourist companies offer discounts on tours, sightseeing cruises, and their hottest attractions.
Chicago Restaurant Week
The city hosts Chicago restaurant week annually during the end of January and the beginning of February. It’s also known as Restaurant Week Chicago, where participating restaurants offer special menus to attract tourists.
Chicago Restaurant Week is an annual winter foodie event in the city that features discounted multi-course meals at some of the best restaurants in town.
Visiting Chicago for the Year-Round Great Food
Chicago offers an array of places to eat throughout the city, featuring different cuisines at the city’s top restaurants.
Whether you’re in Chicago just for a day or are moving here, these are some places that you must try before leaving. In addition, many people come to Chicago for the food and music scene at specific times of the year with the best hotel rates.
However, Chicago year-round offers exciting opportunities to enjoy food and locally brewed beer at numerous locations, including:
- Beer Gardens & Breweries
- Revolution Brewing,
- Hopewell Brewing Company
- Half Acre Beer Company
The Windy City is home to more than 100 breweries and beer gardens. You can purchase a Chicago Craft Beer Passport for $40 that offers 52 different beers from breweries all over the city from September 1 through December 31. Plus, it’s half off from January – April!
There is no shortage of shopping options during each season in Chicago. Chicago has it all, whether you’re looking for a shopping mall, boutique stores, or big-name retailers!
Whether you’re in town for a few days or making this your new home, the best time to visit Chicago is during the off seasons.
However, many shoppers arrive from out of town during the holiday season to take advantage of deep discounts at popular retailers.
During April & May, area fashionistas are looking for deals on everything from shoes to clothes since stores are trying to get rid of old inventory before summer merchandise arrives.
Chicago also hosts Fashion Focus Michigan Avenue during October, when fashion brands offer designer apparel for up to 70% off. The shows offer a good mix of men’s and women’s clothing.
Tourists who want to take home a Chicago Bears jersey or other souvenirs should wait until the end of the regular season in December when these items go on sale and stores offer discounts.
The Bears play at Soldier Field, located near the Magnificent Mile and Navy Pier.
Chicago Cubs and Chicago White Sox
Baseball fans from across the nation arrive during the crowded time to watch Chicago’s two major baseball teams. These fans stay in the city for days at a time while enjoying baseball games, food, drinks, and other activities.
Since Chicago is home to several major sports teams, the best time to take advantage of ticket deals is off-season. For example, tickets for Bears games always go on sale later than most other pro football teams because they have a later start date.
Chicago Red Stars
During the summer, soccer fans worldwide come to see World Cup stars play on local teams at area stadiums. The Chicago Red Stars is a pro women’s soccer team that plays at Toyota Park in Bridgeview near O’Hare Airport and Midway Airport during April – September.
Chicago Shopping Events
Many people don’t realize that Chicago hosts several “Shopping Weeks” throughout the year, creating an excellent chance to enjoy discounts at some of the city’s finest retailers.
Seasonal Markets & Festivals
In addition to offering discounts on tours and events nearly every time of the year, tourists visiting Chicago enjoy holiday shopping during the winter months when the temperatures start dropping.
Avoid crowds during the exciting time of the holidays at seasonal markets and enjoy a special event among Chicago’s stunning architecture and waterways.
The famous Magnificent Mile hosts several large holiday markets and festive activities starting in early November and ending at the end of December.
If you’re visiting Chicago during the summer, there’s no excuse not to stay cool while enjoying food, drinks, and entertainment throughout the city. After all, there’s always something to do whether you’re looking for a night out on the town or a family-friendly day of fun.
Be a Tourist in Your Resident City: The Magnificent Mile
The Magnificent Mile is an excellent starting point if you’re looking for a place where trendy boutiques, restaurants, and hotels all converge.
You can enjoy shopping at popular brands like Louis Vuitton, Burberry, Longchamp, Tumi, Michael Kors, Movado, Kate Spade New York, BCBG Max Azria, Armani Exchange, and many more.
More than 100 shops offer an assortment of choices whether you’re looking for men’s or women’s wear. You can also find interesting gift ideas, such as a limited-edition Tiffany & Co. gift box containing one blue-gray silk ribbon with a sterling silver charm that offers “Paris” in script lettering.
In addition to having several shops, the Magnificent Mile hosts several events throughout the year that will keep you entertained. For example, in September, they host a fashion-focused event featuring designer apparel for up to 70% off retail prices.
The best time to visit Chicago is often based on whether to participate in the activities you enjoy, the discounted hotel rates, and fewer crowds.
The best weather is not always during the peak season during the warmer weather of the summer months or spring break.
Many people choose to visit Chicago during the winter holidays, especially around Christmas and New Year’s Eve.
If you enjoy shopping, attending events, participating in sporting activities, or simply enjoying the city streets of Chicago during the holidays is a great experience.
If you like to take advantage of hotel deals and discounted rates on activities, however, the shoulder season (between high and low season) is often the best time to visit Chicago.
The shoulder seasons typically include the weeks leading up to summer break and following summer break, winter holidays, and spring break.
As discussed in this article, if you want to avoid crowds during the holidays, attend special activities, and enjoy shopping malls or discounts on tours, the off season is typically the best time to visit Chicago.
More Information about Chicago
Chicago is well-known for hosting numerous annual events celebrating everything from art to science to sports all year round.
Make sure you take advantage of these opportunities when planning your trip, especially if you enjoy exploring new things or meeting interesting characters.