Best Time to Visit Chicago for Weather, Prices, and Crowds

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A city skyline with buildings and trees in the background and a body of water
Chicago can be visited all year round, with different experiences offered each month

Known for its iconic skyline set to the backdrop of Lake Michigan, Chicago is the largest city in Illinois. It's also one of the most popular travel destinations in the United States.

Great to visit all year round, Chicago comes alive during the summer months of June through September. Warm weather elicits a plethora of outdoor events as tourists flock to the city's parks and public spaces.

But is summer the best time to visit Chicago? Not for everyone. Each month and season offers a different experience. There are many great reasons to visit the city throughout the year.

January and February bring rock-bottom prices, while April and October are a happy medium between the busy peak and cold off-seasons.

By the time you've finished this comprehensive guide about the weather, prices, and crowds, you'll have all the information you need to plan the best possible Chicago trip for you.

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Chicago Vacation Planning Questions

An aerial view of a city with many tall buildings and a body of water in the distance
Planning a visit to Chicago based on the activities you prefer
A field of flowers and grass with a city in the background
April is when local flowers bloom in Chicago

When is the best time to visit Chicago?

While summer (June-September) is the busiest season for the city, many tourists consider Chicago the most enjoyable during April and October.

Prices are lower and crowds are fewer than during the peak summer travel months. As a bonus, the weather is more pleasant than during the winter (December-March).

April is when local flowers bloom and October is the best month to catch the leaves changing from green to red.

For value-focused travelers, however, the winter months of January and February offer the lowest airfares and hotel rates. But even though the weather keeps most tourists away, events like Chicago Theatre Week provide those who do visit with plenty to do indoors.

A road with streetlights and snow on the ground
During winter, few travelers come to Chicago because of the colder weather

When is the worst time to visit Chicago?

For most tourists, winter (December-March) is the worst time to visit Chicago. This is when temperatures are at their lowest--peaking at 30 degrees Fahrenheit most days--and few travelers are inclined to vacation at this time.

There are plenty of indoor activities to engage visitors, although outdoor events like the Chicago Polar Bear Plunge attract their fair share of attendees as well.

Other travelers, however, prefer to avoid Chicago during the summer (June-September) when huge crowds (and higher prices) descend upon the city.

During these months, temperatures in the 80s degrees Fahrenheit and heavy rainfall are common, making outdoor activities uncomfortable for some.

A building with a decorated tree in front of it and the US flag
Visiting Chicago in winter can get you great rates at the nicest hotels

When is the cheapest time to visit Chicago?

January is the best month to go to Chicago if you want to get great rates at the nicest hotels in the city. That's because the winter (December-March) weather keeps tourist visits low and prices at a minimum.

Serial travelers who have done their homework know to visit in January as the city hosts the Chicago Travel and Adventure Show. The annual multi-day event showcases the hottest destinations and tour providers around the globe.

February offers prices as inexpensive with the bonus that the weather reaches into the 40s degrees Fahrenheit by the end of the month.

Value travelers also find early November, before the holiday crowds begin, to be an affordable time to visit Chicago.

A group of airplanes at an airport with a tower in the background
The best time to visit Chicago for flight deals is in January or February

When is the cheapest time to fly to Chicago?

The cheapest time to fly to Chicago from most places is in January or February. Tourism is in its off-season and airlines are dropping prices to fill their planes.

Plan for indoor activities if you're visiting during these months, though, as the weather is likely to be cold and windy.

November is another cheap month for visiting Chicago--especially if you're just flying in to see Chicago over a weekend.

The summer (June-September) crowds are gone but the cold winter (December-March) weather isn't quite here yet. However, holiday travel sees prices rise by the end of the month.

Getting in a last-minute cheap trip before the holiday season kicks off? Check out the Magnificent Mile Lights Festival held the weekend before Thanksgiving.

Sonja Weiss/
A view of buildings and the city from the Skydeck
Skydeck Chicago is best visited early in the morning or later in the evening

When is the best time to visit Skydeck Chicago?

September is the best month to visit the Skydeck Chicago. This attraction offers a magnificent aerial view of the city and is a must-see. The weather is drier and more moderate and clear skies provide some of the best viewing conditions.

But no matter what month you go, plan to be there early. The Skydeck opens daily at 9 a.m. and you should aim to be there before 10 a.m. if you want don't want to be overwhelmed and fatigued by standing in the queues that build up as the day progresses.

The evening provides an entirely different perspective of the city. Skydeck Chicago is very busy leading up to sunset but the crowds thin once the sun goes down and the glow of city lights takes over. It depends on whether you want to see Chicago through the lens of day or night.

Songquan Deng/
The best time to visit Chicago and the Navy Pier is in the summer
Navy Pier is open year-round but some venues are closed during the winter months

When is the best time to visit Navy Pier Chicago?

No matter when you visit, Navy Pier Chicago has something for everyone with its special events and 50 acres of attractions.

The busiest season for Navy Pier is the summer, from June to September. During these months you'll find crowds gathered at the Miller Lite Beer Garden for free concerts and unbeatable views of the twice-weekly fireworks displays.

For some travelers, the holiday season is the best time of the year to visit Chicago. From mid-November until January, Navy Pier hosts Light Up the Lake, the largest indoor lights experience in Cook County.

While Navy Pier is open year-round, be aware that many venues close during the slow months of January and February. You would be wise to do some research to avoid disappointment.

A river with tall buildings and a large boat with a clear blue sky
Chicago is a popular tourist destination in the summer months, with many activities

When is the best season to visit Chicago?

The summer (June-September) is the best season to visit Chicago according to most tourists. Prime weather--daily highs in the 70s and 80s degrees Fahrenheit--makes it a great time to be outdoors.

Plenty of events are held throughout the city, including Chicago Pride Fest and the long-running Northalsted Market Days.

Summer is also a great time to take a cruise down the Chicago River and check out some of the city's most famous buildings from the water.

If you're interested in fewer crowds and lower prices, visiting during April and October also provides an enjoyable experience.

A dome-shaped building with a glass front
Chicago has colder weather in January, but there are many indoor activities to enjoy

When is the coldest month in Chicago?

January is the coldest month in Chicago. The year starts with average highs in the 30s degrees Fahrenheit, although that will drop into the 20s by the end of the month. Nighttime lows remain below freezing.

If you're planning to visit Chicago in January--or any of the other cold winter (December-March) months, plan for most of your trip to be indoors.

You'll find plenty to do, however, from visiting the indoor gardens at the Lincoln Park Conservatory or Garfield Park Conservatory to animals, fish, and other exhibits at the Shedd Aquarium.

January also hosts the Chicago International Puppet Theatre Festival, which celebrates puppeteers from around the world. Performances are held at dozens of local theatres.

A city skyline behind a beach of blue water and sand
July is the hottest month in Chicago and a good time to visit the beaches

When is the hottest month in Chicago?

July is the hottest month in Chicago as the daily high reaches well into the 80s degrees Fahrenheit most days. The average evening temperature sits comfortably around 70 degrees Fahrenheit.

Although July is right in the middle of the city's wet season (April-October), it experiences less rainfall than other peak travel months.

July is a good time to visit Chicago if you plan on exploring the outdoors, such as hiking trails or relaxing on the many beaches along Lake Michigan.

Be warned that the busy summer tourist season is in high gear in July, thanks largely to the hot weather. This means higher rates and larger crowds throughout the city.

Antwon McMullen/
A restaurant sign on the sidewalk with a yellow and red building
Chicago experiences significant temperature variations throughout the year

What is the average temperature in Chicago?

Unlike milder, more tropical locations, the average temperature in Chicago will vary significantly throughout the year.

In the winter (December-March), visitors can expect daily highs in the 30s or 40s degrees Fahrenheit with nights often below freezing.

The spring (March-June) and autumn (September-December) can see high temperatures ranging from the 40s-70s degrees Fahrenheit.

The summer (June-September) brings consistently warm weather, with highs in the 70s and 80s and lows above 60 degrees Fahrenheit for the most part.

While rain is common throughout summer, reduced precipitation in September brings many travelers out and about for walking and food tours of Chicago before temperatures begin to fall.

Weather, Prices, and Crowds in Chicago

A city with tall buildings with a river running between them
Be mindful of the weather, prices, and crowds when planning a visit to Chicago

Chicago in January

January is the coldest month in Chicago as daily highs rarely get out of the 30s degrees Fahrenheit. Occasional snow or rain can be expected even though it's one of the driest months of the year.

You will find fewer crowds and cheaper hotel rates if you're traveling to Chicago in January. Tourism is in its off-season due to the winter (December-March) weather, but there's still plenty to keep travelers busy.

Chicago Restaurant Week kicks off in January with some of the city's highly-rated hot spots offering great deals on curated brunch, lunch, and dinner experiences.

Outdoor ice skating is big in January, with popular rinks at Maggie Daley Park, Millennium Park, and Parkway Bank Park in Rosemont.

Chicago in February

February is the best time of year to go to Chicago to enjoy the city's vibrant winterscape. Crowds (and prices) are still low and the weather is beginning to warm up. Days are reaching into the 40s degrees Fahrenheit by the end of the month.

You'll also find the lowest chance of precipitation in February with Chicago seeing just two inches on average.

Even though it's still winter (December-March), the city is still alive with events--mostly indoors, however.

Chicago Theatre Week takes place in February with more than 200 local theatres offering low-cost tickets to performances across all genres.

Then there's the Chicago Auto Show. It's the largest automotive show in the United States, taking up more than one million square feet of McCormick Place every February.

Chicago in March

The weather begins to improve rapidly in Chicago in March. The temperature will poke into the 50s degrees Fahrenheit by the middle of the month, and spring (March-June) showers become more frequent as well.

For many tourists, late March is a great time to come to Chicago to avoid the cold winter (December-March) and beat the summer (June-September) crowds.

The most popular event during March is St. Patrick's Day. The Chicago River is dyed green and revelers pack the city's Irish pubs for beer, whiskey, and music.

If you're visiting earlier in the month, check out the after-hours Brewsology Beer Fest at the Museum of Science and Industry.

Chicago in April

Many tourists visit Chicago in April as warming temperatures bring the highs into the 60s and nighttime lows into the 50s degrees Fahrenheit.

But you will start to see more rain this month as the wet spring (March-June) season gets fully underway.

On sunny days, however, the comfortable weather and fewer crowds make April ideal for checking out some of the famous landmarks in Chicago.

The International Exposition of Contemporary and Modern Art--commonly referred to as EXPO Chicago--is hosted annually at the Festival Hall on the Navy Pier in April.

Flowers are also in bloom throughout the city, revived by the month's wet and warming weather, making April a charming and colorful time to visit Chicago.

Chicago in May

May is the best time to travel to Chicago if you want to get ahead of the busy summer (June-September) travel season.

The weather is warm--often in the 70s degrees Fahrenheit during the day--but rainfall is at its peak for the year.

Don't let this put you off, as the chance of rain is only slightly higher than during the spring (March-June) and summer months.

You won't be bored visiting Chicago in May--even on rainy days. There's plenty to do indoors, from visiting the Chicago History Museum to catching a show at the Goodman Theatre.

At the end of the month, the busy Memorial Day weekend marks the unofficial beginning of Chicago's peak travel period.

Chicago in June

June is the start of the summer (June-September) travel season in Chicago as students are out of school and the weather sits comfortably in the 70s and 80s degrees Fahrenheit.

Chicago sees its second wettest month in June although rain chances decrease as the month goes on.

If you're planning a trip to Chicago in June, you should consider getting the Chicago CityPASS. It covers admission to many of the city's most popular tourist attractions and best of all allows you to skip the peak season lines.

The Chicago Blues Festival is a free festival held annually at Millennium Park and other smaller venues around the city in June. The weekend event boasts performances by blues legends and popular new stars.

Chicago in July

There's no better time than July to check out the beaches in Chicago. Air temperatures are in the 80s degrees Fahrenheit while Lake Michigan's waters average a comfortable 70 degrees.

Rain is still a common occurrence in July, although less frequent than it has been for the past few months.

July is the month for outdoor music events in Chicago as both Lollapalooza at Grant Park and the Pitchfork Music Festival attract big crowds to the city.

Another popular music and food festival, the Windy City Smokeout, brings the best BBQ, beer, and country bands to the United Center in mid-July.

Chicago in August

Chicago's weather stays comfortably in the 80s degrees Fahrenheit during most days in August, although the highs have begun falling from July's peak.

It's still the rainy season, which lasts from April until October, but it's a little drier than May or June.

Many visitors consider August the best month to visit Chicago and get the premier summer (June-September) experience. Compared with other peak season months, the weather is moderate, the rain less frequent, with fewer crowds.

The Chicago Air and Water Show runs every August. A local favorite since the 1950s, the event offers free admission to performances taking place on both Lake Michigan and in the skies.

Chicago in September

The weather is enjoyable in Chicago in September as the high temperature stays in the 70s degrees Fahrenheit most days.

This makes it a great time to be outdoors where visitors will find the leaves beginning to change from green to a delightful orange and red.

September also sees the least rainfall of Chicago's peak summer (June-September) months, which makes it ideal to take a tour of the city's skyline by helicopter.

September hosts the popular Chicago Jazz Festival. Held over Labor Day Weekend at and around Millennium Park, the event is the city's largest jazz celebration of the year.

September is the perfect time to check out some of the great things to do in Chicago at night before the weather turns cold for the year.

Chicago in October

The temperature starts dropping in October with daily highs falling into the 50s degrees Fahrenheit by the end of the month.

Rainfall also picks up for one last push before the April-October wet season comes to an end. However, there's still a lot happening in Chicago in October.

The Bank of America Chicago Marathon is one of the biggest draws of the year, welcoming more than 45,000 competitors from around the world.

October's Chicago International Film Festival is the oldest competitive film event in the United States while the Lincoln Square Apple Fest ushers in the autumn (September-December) season with delicious pies, cold cider, and plenty of other apple-centric goodies.

Chicago in November

November is the beginning of the dry season (November-March) in Chicago.

Rain chances aren't the only thing dropping as fall (September-December) temperatures dip as well. Average highs start the month in the 50s but will be in the 40s degrees Fahrenheit by Thanksgiving.

The Chicago Christmas Tree Lighting Ceremony takes place at Millennium Park in mid-November and is the city's kick-off for the upcoming festive season.

Lightscape at the Chicago Botanic Garden also gets started in November, welcoming visitors to its colorfully lit trails and displays.

Tourists often find this the best time of year to visit Chicago to get the holiday experience without the freezing weather and larger crowds of December.

Chicago in December

Although the holiday season brings many travelers to Chicago in December, the weather becomes increasingly chillier as daily highs average in the 30s degrees Fahrenheit for most of the month.

Chances of rain are low in December, although the cold weather can sometimes bring snow.

Many welcome the occasional snowfall, however, as it sets the mood for all of the month's seasonal events.

December welcomes holiday markets to neighborhoods across Chicago, but the most famous is the Christkindlmarket held annually at Daley Plaza.

Want to get in the holiday spirit but prefer to be indoors? Light Up the Lake at Festival Hall at Navy Pier provides a whimsical winter experience including access to a full-size ice skating rink.

In Summary

Chicago is a great destination no matter when you're planning to visit. You'll have a wonderful vacation any month of the year, as long as you know what to expect and are prepared for the weather, prices, and seasonal crowds.

If you're looking for a great time with fewer tourists like yourself, consider April or October. These shoulder season months offer a pleasant climate and lower rates.

But regardless of when you come--from the busy summer (June-September) months packed with outdoor events and festivals to the quieter winter (December-March) season punctuated by indoor attractions-–Chicago always has something exciting to offer travelers.

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Written by Jonathan Davis

JDavis WRITER Jonathan is a Florida-based travel writer who can't seem to stay in one place for long. With more than two decades of trips under his belt, Jonathan has a wealth of information to share about travel within the United States and abroad.

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