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The Best Time to Visit Chicago – A Month By Month Guide (By A Local!)

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.

Finally, I have a summary of the best time to visit depending on your interests and my overall top pick for most people.


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.

RELATED – Take a look at 3 Days in Chicago: The Perfect 3 Day Itinerary By a Local for the best things to do in Chicago year round, what to eat and where to stay.

Visiting Chicago in the Spring

cherry blossoms in 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.

Visiting Chicago in the Summer

Summer is one of the best times of the year to visit Chicago

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

Early fall is the best time to go to Chicago for great weather

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) can still enjoy many of the same Chicago outdoor activities that you can enjoy in the summer (architecture river cruise, outdoor festivals, dining at outdoor patios and rooftops) 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. Everything is 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

bean in winter best season to visit Chicago

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) 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.  They 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 during late November, 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 cruises, lake cruises, or water taxis), hard to enjoy outdoor activities.

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.

Please note that to current events, some festivals and events have been cancelled, postponed or changed to virtual. I suggest bookmarking this blog post as I will be updating it regularly with new events.

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. Here are the best things to do in Chicago in January.

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


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. Here are the best things to do in Chicago in February.

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

Visiting Chicago In March

St. Patrick's Day is the best time of the year to visit Chicago if you like to party

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. Here are the best things to do in Chicago in March.

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: Southside Irish ParadeNorthwest Side Irish ParadeSt. 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 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. Here are the best things to do in Chicago in April.

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 and Chicago Cubs Opening Day at Wrigley Field

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. Here are the best things to do in Chicago in May.

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:  Pivot Arts Festival (May 21-June 5, 2021)

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. Here are the best things to do in Chicago in June.

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 EventsOld Town Art Fair (June 12-13, 2021), Chicago Craft Beer Fest (June 18-20, 2021), Pride in the Park (June 26-27, 2021)

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. Here are the best things to do in Chicago in 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

Festivals and EventsWindy City Smokeout (July 8-11, 2021), Taste of Chicago To-Go (July 7–11, 2021), Southport Art Fair (July 10-11, 2021), Chicago Auto Show (July 15-19, 2021), Millennium Art Festival (July 16-18, 2021),
Chinatown Summer Fair (July 17-18, 2021), Belmont-Sheffield Music Festival (July 17-18, 2021), Jazz Institute of Chicago’s Latin Jazz Festival (July 23-24, 2021), Wicker Park Fest (July 23-25, 2021), Taste Of Lincoln Avenue (July 24-25, 2021), Lollapalooza Festival (July 29-August 1, 2021), Sundays on State, Grant Park Music Festival

If you are visiting Chicago in July or August, consider a day trip to one of several nearby sunflower fields for pretty Instagram photos.

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. Here are the best things to do in Chicago in August.

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: Grant Park Music Festival, SummerDance, Northalsted Market Days (August 6-8, 2021), Printer’s Row Art Fest (August 7-8, 2021), World Naked Bike Ride (August 14, 2021), Wells Street Art Festival (August 14-15, 2021), Gold Coast Art Fair (August 21-22, 2021), Chicago Air and Water Show (August 21-22, 2021), Taste of Greektown (August 27-29, 2021)

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 (but after Labor Day weekend) 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. Here are the best things to do in Chicago this September.

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: ARC Music Festival (September 4-5, 2021), North Coast Music Festival (September 3-5, 2021), AVP Gold Series, Chicago Open (September 3-5, 2021), Pitchfork Music Film Series (September 6-8, 2021), Pitchfork Music Festival (September 10-12, 2021), Printers Row Lit Fest (September 11-12, 2021), Riot Fest (September 17–19, 2021), Run Your Sox Off (September 18, 2021), Renegade Craft Fair (September 18-19, 2021), Lakeview Taco Fest (September 18-19, 2021), West Loop Art Fest (September 18-19, 2021), Hyde Park Jazz Festival (September 25-26, 2021), Chicago In Tune (until September 19, 2021)

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. The best time for fall foliage is around the second week of October. Temperatures start to cool mid to late October with fall temperatures. If you enjoy Halloween, many Halloween themed activities and events take place all month. Here are the best things to do in Chicago in October.

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 Pride Fest (October 1-3, 2021), St. Benedict’s Oktoberfest (October 1-3, 2021), Lincoln Square Greek-tober Fest (October 1-3, 2021), Chicago Wine Fest (October 2, 2021), WingOut Chicago (October 2-3, 2021), Lincoln Square Ravenswood Apple Fest (October 2-3, 2021), Lincoln Park Wine Fest (October 8-10, 2021), Chicago Beer Festival (October 9, 2021), Chicago Marathon (October 10, 2021), 57th Chicago International Film Festival (October 13-24, 2021), Open House Chicago Presented by Chicago Architecture Foundation (October 16-17, 2021), Arts in the Dark Halloween Parade (October 30, 2021) and Haunted Halsted Halloween Parade & Costume Contest (October 31, 2021)

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, it does sometimes snow in November. Attractions are less crowded in early November. However, starting in mid-November tourism starts to pick up with visitors coming to Chicago for Thanksgiving, holiday shopping and other holiday events. Here are the best things to do in Chicago in November.

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 EventsMagnificent Mile Lights Festival (November 20, 2021), Christmas Tree Lighting Ceremony, Chicago Thanksgiving Day Parade (November 25, 2021), ChristkindlmarketZooLights at Lincoln Park Zoo

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. Here are the best things to do in Chicago in December.

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: One of a Kind Show (December 2-5, 2021), C2E2: Chicago Comic and Entertainment Expo (December 10-12, 2021), ChristkindlmarketZooLights at Lincoln Park Zoo, Winter Wonderfest at Navy Pier, New Year’s Eve Fireworks at Navy Pier

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 to Labor Day) 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 to early November and mid-April to 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: Chicago Restaurant Week (March 19 – April 4, 2021) and Taste of Chicago To-Go (July 7–11, 2021).

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.

Some of the most popular outdoor music festivals scheduled for this year are:  Windy City Smokeout (July 8-11, 2021), Belmont-Sheffield Music Festival (July 17-18, 2021), Wicker Park Fest (July 23-25, 2021), Lollapalooza Festival (July 29-August 1, 2021), ARC Music Festival (September 4-5, 2021), Pitchfork Music Festival (September 10-12, 2021), Hyde Park Summer Fest (September 11-12, 2021), Riot Fest (September 17–19, 2021), and Hyde Park Jazz Festival (September 25-26, 2021).

Chicago also has ongoing concert series in the summer where you can listen to free music in the parks including: Grant Park Music Festival (July 2-August 21, 2021), Millennium Park Summer Music Series (August 2-September 16, 2021) and Chicago In Tune (August 19-September 19, 2021).

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 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.



Booking.com

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 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 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 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 in the 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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savvyglobetrotter

4 Comments

  1. Hello from France! Thanks for an inspiring post I was happy to look through.
    Me and my husband we are going to visit Chicago in October on business . We plan to spend 3 weeks there and we are searching something to spend our time on in our spare time. Festivals are ok, but we are in love with active ways of spending time. Maybe you know something special to pay attention to in October? We found a lot of different activities like kayaking and sailing on https://rove.me/to/chicago and some cultural stuff on https://travel.usnews.com/Chicago_IL/Things_To_Do/ but maybe you know something really FAN-TAS-TIQUE? And how are the prices in this period? Thanks in advance!

  2. 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.

  3. 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 🙂

  4. 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!

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