Not sure what is the best time to visit Chicago? I have lived in Chicago for most of my life so I’ve put together an updated month by month guide to help you figure out the best time to go to Chicago in 2025 and 2026 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 as well as festivals and events.
Finally, I have a summary of the best time to visit depending on your interests and my overall top pick for most people.
I suggest bookmarking this blog post as it is regularly updated with new events. I also update this post every week with the best events for the upcoming weekend.
Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.
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 for more detailed information.
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 uncomfortably hot and humid). There are always outdoor festivals, concerts and events happening around the city in the summer – and many of them are free! Navy Pier has free fireworks twice a week during the summer only. You can also enjoy eating and drinking outside at Chicago’s many rooftops and patios.
Pros: Many festivals, concerts and events take place in the summer. The weather is warm enough to go to the beach and spend time outdoors.
Cons: The weather might be too hot and humid on some days, more tourists are in town so attractions are more crowded, higher prices for hotels, 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). During early fall (September and early October), you can still enjoy many of the same Chicago outdoor activities that you can enjoy in the summer (architecture river cruise, outdoor festivals, outdoor dining) without the crowds. Late autumn (late October and November) is a bit more unpredictable-temperatures can feel like summer, fall or even winter.
Pros: Fall usually has the most pleasant weather. Attractions are less crowded because students are back in school.
Cons: Fall temperatures can vary a great deal from year to year. You might get fall days with colder than average temperatures that feel more like winter.
Visiting Chicago in the Winter
Chicago can be brutally cold – think below freezing temperatures and snow – but not always. Some years winters can be mild and even on a colder winter some days can randomly be mild or warm. For those that hate cold weather, I would probably avoid Chicago in the winter if you are able to visit another time. But if winter is your only option, even if you don’t enjoy cold weather, there are plenty of things to do indoors in Chicago (museums, great restaurants, tall buildings, shopping, theater, comedy clubs and more). If you are able to plan a last minute visit, check the weather forecasts and book a trip if the weather is not too bad.
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 for the holiday season between Thanksgiving weekend and New Year’s Eve) when people visit Chicago for holiday events and holiday shopping. Even if you don’t mind cold and snow, keep an eye on the weather forecast for major snowstorms which happen once or a few times each winter (usually January or February). Snowstorms can make it difficult to get around and you might have to deal with flight cancellations on your way in or out of town.
Pros: There are many holiday events and things to do in Chicago in December and early January. During low season (January and February), attractions will be less crowded and accommodation is usually cheaper.
Cons: Weather can be cold and snowy (but you might get lucky and get pleasant temperatures), the river and lake might be frozen (which means no architecture river cruises, lake cruises, or water taxis), hard to enjoy outdoor activities.
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 celebrations. Even if the temperature is warmer, it might rain so bring a travel umbrella.
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.
Visiting Chicago in June
Summer has started but the temperature is not too hot yet. Some years, June can still be cold. 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
June Events and Festivals: Chicago Blues Festival (June 5-8, 2025), Ribfest Chicago (June 6-8, 2025), Wells Street Art Festival (June 14-15, 2025), Old Town Art Fair (June 14-15, 2025), Chicago Pride Fest (June 21-22, 2025), Pride in the Park and Chicago Pride Parade (June 29, 2025).
Here are the best things to do in Chicago in June.
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. July is a busy month with visitors in Chicago with a lot of events and festivals going on including celebrations for the 4th of July.
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
July Events and Festivals: Hyde Park 4th on 53rd Parade and Free Festival (July 4, 2025), NASCAR Chicago Street Race (July 5-6, 2025), Windy City Smokeout (July 10-13, 2025), Chicago Gospel Music Festival (July 12, 2025), Roscoe Village Burger Fest (July 18-20, 2025), Summer Tequila Tasting Festival (July 26, 2025), Chinatown Summer Fair (July 26-27, 2025) and Lollapalooza (July 31-August 3, 2025).
Here are the best things to do in Chicago in July.
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
August Events and Festivals: Lollapalooza (July 31-August 3, 2025), Northalsted Market Days (August 9-10, 2025), Chicago Air and Water Show (August 16-17, 2025), Summer Whiskey Tasting Festival (August 23, 2025), ARC Music Festival (August 29-31, 2025) and North Coast Music Festival (August 29-31, 2025).
Here are the best things to do in Chicago in August.
Visiting Chicago in September
I consider September to be 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 to mid September is a great time to visit. Late September is usually still warm but it starts to get a bit cooler at night. If your hotel has an outdoor pool, September is usually warm enought to swim outside and will probably be less crowded than summer. Overall September is my favorite month in Chicago, except I would avoid visiting the weekend before Mexican Independence Day (September 12-14, 2025) as the celebrations cause traffic and street closures.
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
September Events and Festivals: Taste of Chicago (September 5-7, 2025), El Grito (September 13-14, 2025), Riot Fest (September 19-21, 2025), Chicago Gourmet (September 25-28, 2025) and World Music Festival (September 26–October 5, 2025).
Here are the best things to do in Chicago this September.
Visiting Chicago in October
October is also a great time to visit Chicago in terms of weather. The temperature has started to cool a bit so it is very pleasant to walk around and explore Chicago. Early October might still have summer like temperatures if you enjoy warm weather. Temperatures start to cool mid to late October with fall temperatures. The best time for fall foliage is around mid to end of October. If you enjoy Halloween, many Halloween themed events take place all month. Overall October is one of the best months to go to Chicago, but keep in mind that Columbus Day weekend is very crowded as the Marathon always takes place on the Sunday before Columbus Day.
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
October Events and Festivals: Lincoln Square Ravenswood Apple Fest (October 4-5, 2025), Bank of America Chicago Marathon (October 12, 2025), Chicago Fashion Week (October 9-19, 2025), Arts in the Dark Halloween Parade (October 18, 2025), Open House Chicago Presented by Chicago Architecture Foundation (October 18-19, 2025) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2025).
Here are the best things to do in Chicago in October.
Visiting Chicago in November
If you enjoy moderate or cool temperatures, November is a great time to visit. Weather can be a bit unpredictable, and although snow is rare, there is a possibility of snow in November. Attractions are less crowded in early November. However, starting around mid-November tourism starts to pick up with visitors coming to Chicago for Thanksgiving, holiday shopping, tree lighting ceremonies and other November holiday events. The holiday season starts around mid-November with the opening of Christkindlmarket, ZooLights at Lincoln Park Zoo and other holiday attractions.
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
November Events and Festivals: Whiskey Washback (November 7, 2025), City of Chicago Christmas Tree Lighting Ceremony (November 21, 2025), Magnificent Mile Lights Festival (November 22, 2025) and Chicago Thanksgiving Day Parade (November 27, 2025).
Here are the best things to do in Chicago in November.
Visiting Chicago in December
You might encounter cold and snowy weather in December but the weather is usually still not that cold. If you are staying downtown, there will be traffic and it will be crowded with people doing holiday shopping or visiting 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
December Events and Festivals: One of a Kind Show (December 4-7, 2025), Chicagoland Toys For Tots Motorcycle Parade (December 6, 2025), TBOX (Twelve Bars of Christmas) Bar Crawl (December 13, 2025) and New Year’s Eve Fireworks at Navy Pier (December 31, 2025).
Here are the best things to do in Chicago in December.
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. January is one of the two months with 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
January Events and Festivals: Tomorrow Never Knows Fest, Chicago Cubs Convention, Chicago Polar Plunge, Chicago Restaurant Week and Chicago Boat Show (January 26-February 1, 2025).
Here are the best things to do in Chicago in January.
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
February Events and Festivals: Chicago Restaurant Week, Chicago Theatre Week, Chicago Auto Show, Chicago Irish Film Festival and Argyle Lunar New Year Celebration.
Here are the best things to do in Chicago in February.
Visiting Chicago In March
The Chicago River dyed green for St. Patrick’s Day
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 in March especially the weekend right before St. Patrick’s Day which is a big deal in Chicago. There are also more visitors in town because many schools in the US are closed for spring break at this time.
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
March Events and Festivals: Chinese New Year Parade in Chinatown (March 1, 2026), St. Patrick’s Day Downtown Parade & River Dyeing (March 14, 2026), Shamrock’n the Block (March 14, 2026), Southside Irish Parade (March 15, 2026), Northwest Side Irish Parade (March 15, 2026), Shamrock Shuffle (March 22, 2026) and C2E2: Chicago Comic & Entertainment Expo (March 27-29, 2026).
Here are the best things to do in Chicago in March.
Visiting Chicago in April
By April weather has probably started to warm up a bit, but the weather can still be unpredictable. April is one of the months with the most rain so bring a travel umbrella. Early April can be crowded because of spring break vacations. The city becomes more photogenic around mid-April when spring flowers (like the tulips on Michigan Avenue) start to bloom.
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
April Events and Festivals: One of a Kind Spring Show (April 24-26, 2026) and The International Exposition of Contemporary & Modern Art (Expo Chicago).
Here are the best things to do in Chicago in April.
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
May Events and Festivals: Mayfest, Belmont-Sheffield Music Festival (May 23-25, 2025), Mayfestiversary (May 24-25, 2025), Sueños Music Festival (May 23-24, 2026), Maifest and Do Division Street Fest.
Here are the best things to do in Chicago in May.
Worst Time to Visit Chicago
I don’t think any time is a bad time to visit Chicago, but if I had to pick the worst time to visit Chicago, it would be in the middle of winter when the temperature is usually the coldest and it is most likely to snow.
The period between the end of the holiday season and the weekend before St. Patrick’s Day is considered low season in terms of tourism. While there are still plenty of events in Chicago during this time, there is not as much to do as there is the rest of the year.
What is the Best Time of the Year to Visit Chicago For…
Good Weather – Weather is very very unpredictable in Chicago especially in the spring and fall. While you can use the average temperature as a guideline what to expect, sometimes the temperature can be much higher or lower than average for that time of year. The temperature can also change drastically from day to day and even hour to hour. For example, you can have a day with a high temperature in the 70s and the next day the weather is only in the 30s.
The months that typically have the worst weather (cold and snow) are January and February but winter can start as early as November and end as late as March or April.
The months with the best weather in Chicago are typically September and early October when the weather is warm but usually not too hot and humid like it can be in the summer.
If you are looking for more predictable temperatures, I recommend visiting mid summer (July and August) when it is guaranteed to be hot (but it might be as hot as the 90s or more pleasant temperatures in the 70s).
Avoiding Crowds – Chicago is a popular tourist destination year round but the busiest times in terms of tourism are: mid-March to mid-April (for St. Patrick’s Day and spring break), summer (from Memorial Day weekend to Labor Day weekend) and the holiday season (mid November to early January).
If you want to avoid fellow tourists at popular tourist attractions, visit in the low season (mid-January through early March).
Shoulder season (mid-September through early November and mid-April through mid-May) is a good mix of not too many crowds but pleasant weather.
Foodies – While Chicago is a great place for food lovers year round, foodies might want to keep the following events in mind: Taste of Chicago (September 5-7, 2025), Chicago Gourmet (September 25-28, 2025) and Chicago Restaurant Week (January/February 2026).
Architecture Lovers – Architecture lovers should not miss Open House Chicago Presented by Chicago Architecture Foundation (October 18-19, 2025) for a behind the scenes inside buildings. This is also a good time to join an architecture river cruise while enjoying the beginning of fall colors.
Music Lovers – While Chicago is a great place to listen to live music year round, many outdoor music festivals take place in Chicago in the summer and early fall when the weather is warmer.
Popular outdoor music festivals include: Chicago Blues Festival (June 5-8, 2025), Windy City Smokeout (July 10-13, 2025), Chicago Gospel Music Festival (July 12, 2025), Lollapalooza (July 31-August 3, 2025), ARC Music Festival (August 29-31, 2025), North Coast Music Festival (August 29-31, 2025), Riot Fest (September 19-21, 2025) and World Music Festival (September 26–October 5, 2025).
Chicago also has ongoing concert series where you can listen to free music in the parks all summer including the Grant Park Music Festival.
Party Animals – If partying is your thing then you might want to visit Chicago during the weekend right before St. Patrick’s Day when people start drinking from the morning. Bars and clubs are busiest between St. Patrick’s Day weekemd and Halloween – they are less crowded during the winter months. Lots of bars and restaurants have outdoor patios and rooftops which are best during the warmer months (May/June to September/October).
Low Prices – You are most likely to find hotel bargains in January and February because there are fewer tourists visiting Chicago. Make sure to avoid large events and conventions which result in higher hotel prices on those dates. Hotels are usually more expensive in the summer, Columbus Day weekend and Thanksgiving Day weekend and other major holidays.
Best Time to Visit Chicago – My Overall Recommendation
While I think Chicago is a great place to visit year round, most people would enjoy visiting Chicago in the fall. In early fall 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 warmer 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 late April and early May) is also a good time to visit for more pleasant temperatures and pretty spring flowers.
If you enjoy hot weather and outdoor activities, then summer is the best time to visit. The are more bucket list worthy things to do in the summer including many outdoor festivals and events.
If you want to visit Chicago on a budget and want to avoid crowds, then consider visiting mid-winter but you might have to brave the cold and snow or stick to mostly indoor attractions.
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.
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I visit Chicago frequently when I am flying into or out of the midwest. The last two years I visited in January/February. This year wasn’t too bad at all, but the year before it was brutally cold! I was living in Russia and Chicago felt 10 times colder, lol! But I agree that it is a nice time with fewer tourists and we got some good deals on hotels.
I’ve been to Chicago a couple of times and both times it was during the Winter months. I would love to visit in May where the weather seems the most pleasant and most likely with no surprises of cold weather 🙂
I didn’t know you lived in Chicago!! That place has always been on my list of places I want to visit in the US! I am definitely taking note of the less busy times to visit! January and February actually works best for me!