The Best Time to Visit Chicago – A Month By Month Guide

Wondering what is the best time to visit Chicago? I have lived in Chicago for most of my life so I’ve put together a month by month guide to help you figure out the best time to go to Chicago depending on your interests and weather preferences.  I have broken down the best time of the year to visit Chicago by season and even further by month based on weather and festivals and events.

What is the best season to visit Chicago?

Not sure what season to go to Chicago? Here are some pros and cons about visiting Chicago in each of the four seasons. Once you have a general idea of what season you would like to visit, check out my month by month guide.

Visiting Chicago in the Spring

Spring is generally a great time to explore Chicago as temperatures start to increase making it more pleasant to walk around and sightsee. However, early spring weather can be very unpredictable, the temperatures can be more moderate and pleasant or they can be a continuation of winter.

Pros: Weather starts to warm up making it easier to walk around to explore.

Cons:  Spring weather is unpredictable so you might still encounter winter weather especially in March and early April.  Tourism starts to pick up in mid March for spring break and St. Patrick’s Day events.  Even if the temperature is warmer, it might rain so bring an umbrella.

Visiting Chicago in the Summer

Summer is the busiest and the most popular time to visit Chicago and usually has great weather (but some days can be very hot and muggy). The nice thing about visiting in the summer is that are always festivals, concerts and events going on around the city in the summer.

Pros: There are tons of festivals, concerts and events happening in the summer.  The weather is warm enough to go to the beach and spend time outdoors.

Cons: Some days the weather can be hot and humid, very busy with tourists so attractions are more crowded, higher prices, crime rate is higher.

Visiting Chicago in the Fall

Fall temperatures vary and can be less predictable but fall is usually the best time to visit in terms of good weather – the weather is usually more pleasant (still relatively warm and less likely to rain). Visitors to Chicago in early autumn (September and early October) can still enjoy many of the same outdoor activities that you can enjoy in the summer (architecture river cruise, outdoor festivals, the beach, dining at outdoor patios and rooftops) without the crowds.  Late Autumn (late October and November) might still be warm as well but even if it is cooler it is usually very pleasant.

Pros: Great weather making it easy to walk around to explore, less crowded because kids and students are best in school

Cons: No cons but weather is unpredictable so you might get a cold fall.

Visiting Chicago in the Winter

Chicago can be brutally cold- think below freezing temperatures and snow –but not always. Some winters can be mild in general and some days can randomly be warm. Even if you don’t enjoy cold weather, there are plenty of things to do indoors in the winter (museums, great restaurants, tall buildings, shopping, theatre, comedy clubs and more).  For those that hate cold weather, I would probably avoid Chicago in the winter. If you are able to book a trip more last minute, check the weather forecasts and book a trip if the weather is more mild.

However, if you don’t mind the cold, Chicago is a great place to visit in the winter as it is less crowded with tourists so everything will be less busy except between Thanksgiving Day and Christmas when people visit Chicago for holiday events and holiday shopping.

Pros: Lower prices on accommodation in January and February. This is low season so everything is less crowded (except right before the holidays).

Cons: Weather can be cold and snowy (but you might get lucky and get pleasant temperatures), river and lake is frozen (no architecture cruises etc.).

What is the best month to visit Chicago?

Hopefully you now have a general idea of the season you want to visit Chicago.  If you want to narrow it down further, here is a month by month guide based on weather and festivals and events (for more festivals and events check out this listing of all the festivals and events in Chicago.

Visiting Chicago in January

January is usually the coldest month in Chicago. The temperature will most likely be below freezing and there might be snow on the ground. However the last few years, January has been more mild so it is not rare to get lucky and have days where the temperature is in the 40s or even 50s. If you do not like cold weather, January is not a great time to visit. This is one of the two months with the fewer tourists and lower prices on hotels.

Weather:  Average Temperature 27.7 °F, Average High Temperature 31 °F, Average Low Temperature 16.5 °F, Average Number of Days With Precipitation 10.5, Average Number of Days With Snow 8.2

Festivals and Events: Chicago Ale Fest, Soxfest, Chicago Restaurant Week

Visiting Chicago in February

February is usually the second coldest month in Chicago. The temperature might be below freezing and there might be snow on the ground. However the last few years, February has been more mild so it is not rare to get lucky and have days where the temperature is in the 40s or even 50s. If you do not like cold weather, February is not a great time to visit.  This is one of the two months with the fewer tourists and lower prices on hotels.

Weather: Average Temperature 27.7 °F, Average High Temperature 35.3 °F, Average Low Temperature 20.1 °F, Average Number of Days With Precipitation 8.8, Average Number of Days With Snow 5.9

Festivals and Events: Chicago Theater Week, Chicago Auto Show, Chicago Chinese New Year Celebration

Visiting Chicago In March

March weather is very unpredictable. The weather might start warming up or you might still encounter winter weather and even snow. Tourism starts to pick up especially the weekend right before St. Patrick’s Day which is huge in Chicago. In late March, tourism starts to pick up because many schools have spring break.

Weather: Average Temperature 37.9 °F, Average High Temperature 46.6 °F, Average Low Temperature 29.2 °F, Average Number of Days With Precipitation 11.1, Average Number of Days With Snow 4.2

Festivals and Events: The Chicago Beer Festival, Southside Irish Parade, Northwest Side Irish Parade, Chicago Flower & Garden Show at Navy Pier, St. Patrick’s Day Downtown Parade & River Dyeing

Visiting Chicago in April

By April weather has probably started to warm up a bit but the weather is unpredictable. April is one of the months with the most rain. Early April can be crowded because some students are still on spring break.

Weather: Average Temperature 48.9 °F, Average High Temperature 59 °F, Average Low Temperature 38.8 °F, Average Number of Days With Precipitation 12, Average Number of Days With Snow 0.9

Festivals and Events: Chicago White Sox Opening Day, Baconfest Chicago, Chicago Cubs Opening Day at Wrigley Field, C2E2: Chicago Comic and Entertainment Expo, One of a Kind Show and Sale Spring Show, CIMMFEST: THE Chicago International Movies & Music Festival

Visiting Chicago in May

May tends to be one of the most pleasant months in terms of temperature. It is a great time to visit Chicago before schools go on summer break and the busy summer season starts.

Weather: Average Temperature 59.1 °F, Average High Temperature 70 °F, Average Low Temperature 48.3 °F, Average Number of Days With Precipitation 11.6

Festivals and Events: Chicago Beer Classic, Chicago Kids and Kites Festival, Chicago Craft Beer Week,  Bike The Drive, Belmont-Sheffield Music Festival, Mayfest

Visiting Chicago In June

Summer has started but the temperature is not too hot yet. Unfortunately, it is more likely to rain in June than later in the summer.  Summer is peak season to visit Chicago- tourism starts to pick up and there are more festivals and events going on, especially outdoors.

Weather: Average Temperature 68.9 °F, Average High Temperature 79.7 °F, Average Low Temperature 58.1 °F, Average Number of Days With Precipitation 10.2

Festivals and Events: Chicago Blues Festival 57th Street Art Fair, Chicago Gospel Music Festival, Ribfest Chicago,Gay Pride Chicago

Visiting Chicago in July

July is usually the hottest month in Chicago in terms of temperature and the weather might be very hot and humid. It is a busy time to be in Chicago with a lot of events and festivals going on.

Weather: Average Temperature 74 °F, Average High Temperature 84.1 °F, Average Low Temperature 63.9 °F, Average Number of Days With Precipitation 9.8

Festivals and Events: Taste of Chicago, Rhythm World Festival, Square Roots Festival,  Millennium Art Festival, Southport Art & Music Fest, Pitchfork Music Festival,  Sheffield Music Festival & Garden Walk, Chicago Craft Beer Festival

Visiting Chicago in August

August is usually the second hottest month in Chicago in terms of temperature and the weather might be very hot and humid. It is a busy time to be in Chicago with a lot of events and festivals going on.

Weather: Average Temperature 72.4 °F, Average High Temperature 81.9 °F, Average Low Temperature 62.9 °F, Average Number of Days With Precipitation 9.8

Festivals and Events: Lollapalooza, Northalsted Market Days, Chicago Jazz Festival, Chicago Air & Water Show, Chicago Hot Dog Fest, Logan Square Food Truck Social, Chicago Fringe Festival

Visiting Chicago In September

I think September is the month with the best weather. The temperature is still usually warm and it is also the driest month so it is less likely to rain. If you enjoy summer activities with fewer crowds, early (but after Labor Day) to mid September is a great time to visit. Late September is still usually warm but it starts to get a bit cooler at night.

Weather:  Average Temperature 64.6 °F, Average High Temperature 74.8 °F, Average Low Temperature 54.3 °F, Average Number of Days With Precipitation 8.3

Festivals and Events: Chicago Gourmet, Poetry River, Chicago Architecture Biennial, Fulton Market Harvest Fest, World Music Festival Chicago, Windy City Wine Festival,  West Loop Art Fest

Visiting Chicago in October

October is also a great time to visit Chicago in terms of weather especially if you do not like hot weather. The temperature has started to cool so it is very pleasant to walk around and explore Chicago.

Weather: Average Temperature 52.5 °F, Average High Temperature 62.3 °F, Average Low Temperature 42.8 °F, Average Number of Days With Precipitation 10.2

Festivals and Events: Chicago International Film Festival,  Chicago Marathon, Northalsted Halloween Parade, Open House Chicago Presented by Chicago Architecture Foundation

Visiting Chicago in November

If you enjoy moderate or cooler weather November is a great time to visit. Attractions are less likely to be crowded but starting after Thanksgiving tourism starts to pick up with visitors coming to Chicago to do holiday shopping and other holiday events.

Weather: Average Temperature 40.3 °F, Average High Temperature 48.2 °F, Average Low Temperature 32.4 °F, Average Number of Days With Precipitation 10.8, Average Number of Days With Snow 1.7

Festivals and Events: Magnificent Mile Lights Festival, Christmas Tree Lighting Ceremony, Christkindlmarket, ZooLights at Lincoln Park Zoo

Visiting Chicago In December

Winter has started so you might encounter very cold and snowy weather. Although it is winter, there are a lot of visitors to Chicago. If you are staying downtown, there will be traffic and it will be crowded with people doing holiday shopping or coming to Chicago for holiday events.

Weather:  Average Temperature 27.7 °F, Average High Temperature  34.8 °F, Average Low Temperature 20.7 °F, Average Number of Days With Precipitation 11, Average Number of Days With Snow 6.9

Festivals and Events: Renegade Craft Fair, One of a Kind Show, Randolph Street Holiday Market, Winter Wonderfest at Navy Pier, New Year’s Eve Fireworks at Navy Pier

What is the Best Time of the Year to Visit Chicago – My recommendation

I think Chicago is a great place to visit year round but overall most people would enjoy visiting Chicago in the fall because of the weather is still relatively warm and you can enjoy outdoor activities with fewer crowds because kids and students are back in school.  If you prefer warm summer like weather, September is a great month to visit. If you like more moderate and pleasant temperatures, October and early November are great times to visit.  Spring (especially May) is also a good time to visit for more pleasant temperatures. If you want to visit on a budget and want to avoid crowds, then you might want to visit in the winter but you might have to brave the cold and snow.

Ultimately when to visit Chicago depends on you so hopefully this guide has helped you make a decision on the best time to visit Chicago. If you are still not sure, feel free to ask me any questions in the comments below.