Chicago's Best Visiting Months: When To Explore The Windy City

Chicago is a city of extremes, with beautiful summers and frigid winters. But when is the best time to visit? The answer depends on what you're looking for. If you're after good weather, the best time to visit Chicago is between May and October, when winter subsides and summer sunshine dominates. During these months, you can expect warm temperatures, less rainfall, and plenty of outdoor activities to enjoy. However, if you're looking for cheaper prices, the period from November to March (excluding the holiday period) is considered the most budget-friendly time to visit, as accommodation rates are lower and there are fewer tourists. The shoulder seasons of late spring (April and May) and early fall (September and October) are also great for avoiding crowds while still enjoying pleasant weather. So, whether you're seeking good weather, budget-friendly travel, or crowd-free experiences, there's a perfect time to visit Chicago that suits your needs.

April to May: warm temperatures, manageable crowds, and a variety of festivals

April and May are excellent months to visit Chicago. The temperatures are warm, the crowds are manageable, and there are a variety of festivals to enjoy.

In April, the weather can be unpredictable, so it's a good idea to bring a travel umbrella as it is one of the rainiest months. However, by mid-April, spring flowers start to bloom, making the city more photogenic. There are also plenty of events to enjoy, such as the Chicago Cubs home opener and the International Exposition of Contemporary & Modern Art.

May tends to be one of the most pleasant months in terms of temperature. It is a great time to visit before the summer crowds arrive and the busy summer season starts. You can enjoy the warmer weather in Chicago's parks, lakefront trails, and beer gardens. There are also several festivals to enjoy, such as the Belmont-Sheffield Music Festival and the Sueños Music Festival.

Overall, April and May offer a great balance of warm temperatures, manageable crowds, and a variety of festivals and events to enjoy in Chicago.

September to October: warm weather, fewer tourists, and plenty of outdoor activities

September and October are excellent months to visit Chicago. The warm weather persists, there are fewer tourists, and there's a whole host of outdoor activities to enjoy.

September is considered one of the best months to visit Chicago, weather-wise. The temperature is usually warm, and it is also the driest month, so rain is unlikely. You can enjoy summer activities with smaller crowds, and hotels with outdoor pools are still likely to be warm enough to swim in. The beaches are officially closed to swimming after Labor Day, but there's still a chance of warm weather, and the river cruises are enjoyable. Restaurants will still be using their outdoor seating, and the gardens and fountains will be in full flow.

October is also a great month to visit Chicago, with very pleasant walking temperatures. Early October might still have summer-like temperatures, and mid-to-late October sees fall temperatures set in. The fall foliage is at its peak in mid-to-late October, and there are plenty of Halloween-themed events to enjoy.

Both months offer a good mix of pleasant weather and fewer crowds. You can enjoy the outdoors without the summer rush, and there are still plenty of festivals and events to enjoy.

June to August: peak season with hot weather, festivals, and outdoor events

June, July, and August are the peak tourist months in Chicago, with high temperatures, a packed festival calendar, and bustling crowds. The city's summer vibe is lively, with people flocking to the beaches, parks, and rooftops to enjoy the hot weather.

Weather

Chicago's summer months are hot and humid, with temperatures often reaching the 80s. June is the beginning of summer, with an average temperature of 68.9°F and a high of 79.7°F. July is the hottest month, with an average temperature of 74°F and a high of 84.1°F. August is the second-hottest month, with an average temperature of 72.4°F and a high of 81.9°F.

Festivals and Events

Summer in Chicago is all about outdoor festivals, concerts, and events. The city's pride celebrations in June are particularly spirited, with people partying despite the rain that falls on a third of the days.

July is the month Chicagoans wait for all year, with festivals rocking the city's neighbourhoods every weekend. Lollapalooza takes top billing, with Millennium Park hosting concerts every night. Taste of Chicago attracts visitors worldwide, and fireflies glow everywhere.

August is another busy month, with warm to sizzling weather and events like Lollapalooza, Northalsted Market Days, the Chicago Air and Water Show, and the West Loop Art Fest.

Tourism and Pricing

Summer is Chicago's peak tourist season, so expect high prices for hotels and vacation rentals. Restaurant reservations and theatre tickets should also be booked well in advance.

Advantages and Disadvantages

The warm weather and abundance of activities make summer an attractive time to visit Chicago. However, the high temperatures and humidity can be uncomfortable, and the crowds and long lines may be off-putting.

June, July, and August are ideal months to visit Chicago if you want to experience the city's vibrant summer atmosphere, enjoy the hot weather, and participate in the numerous outdoor festivals and events. However, be prepared for high prices and large crowds.

November to December: festive events, holiday shopping, and low hotel prices

If you're happy to brave the cold, November to December is a great time to visit Chicago. The city is famous for its icy winters, but the chillier temperatures mean you'll be able to take advantage of low hotel prices and fewer crowds.

The Magnificent Mile Lights Festival, which takes place in November, marks the start of the festive season. The city is adorned with millions of twinkling lights, and holiday shoppers fill Michigan Avenue. You can also catch the Chicago Thanksgiving Day Parade in November, which is followed by the opening of the Christkindlmarket, a German-style bazaar in the middle of the Loop.

In December, you can enjoy the festive cheer of the city's holiday markets and outdoor ice-skating rinks. The holiday season is also a great time to indulge in some of Chicago's famous deep-dish pizza.

If you're looking for a bargain, January and February are the best months to visit Chicago. The city experiences its lowest temperatures during these months, so you'll be able to find excellent deals on hotels and airfare. Just be sure to pack your warmest coat!

January to February: cold weather, low tourist numbers, and indoor activities

Chicago in January and February: Cold Weather, Low Tourist Numbers, and Indoor Activities

January and February are Chicago's coldest months, with temperatures often dipping below freezing and snow covering the ground. However, in recent years, the city has experienced milder weather during these months, with some days reaching the 40s or even 50s Fahrenheit. If you're not a fan of frigid temperatures, you may want to avoid travelling to Chicago during this period.

On the upside, January and February are typically the least crowded months in Chicago, with fewer tourists taking on the cold. This means you can take advantage of lower prices on hotels and accommodations. It's the perfect time to indulge in Chicago's famous deep-dish pizza without breaking the bank!

Despite the cold, there's still plenty to do in the city. You can start by exploring Chicago's renowned museums, such as the Art Institute of Chicago, one of the world's largest and most prestigious art museums. The winter season is ideal for this, as the museums are less crowded and you can easily find your way around.

If you're feeling adventurous and want to brave the cold, bundle up and head to Millennium Park, which marks the start of a chain of parklands along the banks of Lake Michigan. The icy scenes along the lakeshore are truly magical, with trees and bushes encrusted in ice. Just remember to dress warmly, as the wind chill can make it feel much colder than it really is!

Chicago also offers plenty of indoor activities to keep you entertained. Warm up in one of the city's many arcade bars, or find refuge from the cold in a cosy restaurant or café. If you're visiting in late January, you can even take part in the Chicago Polar Plunge, a unique and exhilarating event!

February continues the chilly trend, with temperatures often below freezing. But don't let that deter you from enjoying the city's events, such as the Chinese New Year Parade, Cupid's Undie Run, and Chicago Theatre Week. You can also celebrate the Lunar New Year in Argyle and Chinatown, savouring delicious cuisine and enjoying cultural performances.

So, if you don't mind the cold, January and February can be great months to visit Chicago. You'll find cheaper accommodations, fewer crowds, and plenty of indoor activities to keep you busy. Just be sure to pack your warmest clothes and embrace the winter wonderland that Chicago becomes during these months!

Frequently asked questions