What’s the ideal time to visit Chicago?

Known for its frigid winters, sweltering summers, and bustling festival scene, Chicago offers excitement throughout the year. Each month brings a new atmosphere, but the city’s vibrant nightlife, rich museums, and dynamic neighborhoods make it a worthwhile destination anytime.

Events like Lollapalooza and the Chicago Blues Festival have earned the city a spot on the national festival circuit, yet there’s something happening every month, from thrilling sports events to unique museum exhibitions, cultural festivals, and community gatherings.

Chicago truly shines in summer, with warm, humid days complemented by numerous lakeside beaches and parks where you can enjoy a refreshing breeze. The serene spring and autumn seasons have their own allure, while winter brings fewer tourists and a magical landscape of snow and ice along the lake.

For a city getaway rich in stunning art and architecture, exceptional global cuisine, and vibrant festivals, Chicago offers plenty to explore at any time of year. Here’s our guide to the best times to enjoy the Windy City.

From November to April, you can find the best deals.

While winter temperatures in Chicago typically hover around freezing, the biting winds from the lake can significantly lower the perceived temperature due to wind chill. Trees and shrubs by the lakeshore become coated in ice, and steam rises from the skyscrapers.

Although the cold may deter some tourists, it creates opportunities for great bargains, especially on accommodations. Visitors will have plenty of options for deals at hotels throughout the winter, and securing a table at popular restaurants becomes much easier.

As late November and December arrive, the holiday season transforms Chicago with dazzling light displays at places like Lincoln Park Zoo, along with holiday markets and outdoor ice-skating rinks. The frosty landscapes by the lakeshore add a touch of magic to the city. Museums become less crowded during this time, making it an ideal season to explore the Art Institute of Chicago, one of the largest and most visited art museums in the world.

Michigan Avenue buzzes with holiday shoppers, and downtown sparkles with countless twinkling lights. Winter is the perfect occasion to indulge in some Chicago deep-dish pizza and weigh in on the ongoing debate about the city’s pizza rivalry with New York.

January marks the coldest month in Chicago, with temperatures plummeting to as low as 22ºF and icy winds swirling through the downtown skyscrapers. It’s also the snowiest month, averaging around 10 inches of snowfall annually. It’s best to stay cozy indoors and savor the local food and drink.

February sees Chicago still entrenched in winter, yet numerous events abound to keep you entertained, including the Chinese New Year Parade, Cupid's Undie Run, and Chicago Theatre Week. For breathtaking views over the icy lake, visit the observation deck of the former John Hancock Center.

By March, many Chicagoans are left wondering if the sun will ever make an appearance again. This month, known for its dreary gray skies and strong winds, rarely sees temperatures rise above 37ºF. However, festive events like the renowned St. Patrick's Day parade lighten the mood, as the Chicago River gets a vibrant green transformation with biodegradable dye.

As spring unfolds in April, expect unpredictable weather. Be prepared for sunshine, snow, or rain—sometimes all in one day. This doesn’t deter sports enthusiasts, who eagerly gather at Wrigley Field and Guaranteed Rate Field for the start of baseball season.

May and the months from September to October are perfect for savoring culture without the hustle and bustle of crowds.

Chicago experiences two shoulder seasons—in late spring and early fall—when the city transitions from winter's chill or prepares for it. Both periods are fantastic for visits, especially if you're looking to explore the city's museums.

Temperatures range comfortably from 50ºF to 70ºF, creating a lively atmosphere in the city, though rain may still be in the forecast. Budget-conscious travelers can find great deals on flights and accommodations, but be mindful of the calendar; major sports events and festivals can drive prices up.

In May, warmer weather ushers in spring, prompting locals to flock to Chicago's parks, lakeside paths, baseball fields, and beer gardens. Beaches open for the season during Memorial Day weekend, attracting an influx of visitors. The improved weather leads to vibrant community festivals like Mole de Mayo and Sueños Chicago filling the streets.

As September arrives, children return to school and beaches close after Labor Day, signaling the wind-down of Chicago's peak tourist season. However, the cultural scene remains vibrant with events such as the Chicago Jazz Festival, Riot Fest, and the launch of the Chicago Architecture Biennial lighting up the city.

As temperatures dip to an average of 53ºF in October and the baseball season wraps up, basketball and hockey take center stage by month's end. Chicago Bears games and tailgating remain popular, while the more athletic crowd gears up for the Chicago Marathon.

From June to August, Chicago buzzes with festivals, beach activities, and baseball.

The warm weather and a bustling festival schedule make summer the prime season to explore Chicago. As schools close, families flock to Chicago's beaches for sun-soaked fun, and local museums become hotspots for both residents and tourists. Expect high rates for hotels and vacation rentals, and be sure to reserve popular restaurant tables and theater tickets well in advance.

As June arrives, schools close and festival season kicks off. Temperatures approach 80ºF, though rain graces about a third of the days. Nevertheless, Chicagoans celebrate with lively pride festivities.

A favorite summer activity is taking a boat tour, particularly the one hosted by the Chicago Architecture Center. Don't miss out on the city's abundant parks – Millennium Park begins a scenic stretch of parklands along Lake Michigan's shores.

July is the highlight of the year for Chicagoans. Every weekend features neighborhood festivals, with Lollapalooza leading the charge. Concerts light up Millennium Park nightly, while the Taste of Chicago draws visitors from all over, with fireflies illuminating the evenings. Despite the heat and humidity, the festivities make it all worthwhile.

August brings warm, sometimes sweltering days filled with concerts, festivals, baseball games, and beach fun. The city remains a hotspot for tourists, leading to higher lodging costs and longer lines. Excited Cubs fans fill Wrigley Field or claim seats on the Wrigley Rooftops for a view of the action.