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Best Time to Visit Chicago, IL

Written by Anietra Hamper
Dec 27, 2019

While it is easy to make a Chicago vacation a year-round option, the weather plays a part in determining the best time to go. Chicago weather is fickle: winters can be beautiful but brutal, with blowing snow and ice. Spring brings flowers and occasional rain; summers are hot in the festival season, and the winds coming off Lake Michigan make it blustery most times of the year. Each season brings unique opportunities to experience the best of Chicago, so it is important to time your visit when it suits your plans, interests, and budget.

No matter when you visit Chicago, you will experience its world-class museums like the Shedd Aquarium, jaw-dropping architecture, and sports and entertainment, which all add to the many opportunities and things to do in Chicago. Even with occasional inclement weather in Chicago, it is easy to fill the agenda with indoor attractions like the Field Museum or the Adler Planetarium or cozy up with some famous deep dish pizza until the skies clear.

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Best Time of Year to Visit Chicago

A sightseeing cruise through downtown Chicago

The best time of the year to visit Chicago is between April and October during the shoulder season and the high-tourist summer season, when the selection of things to do is the most abundant.

During the busy summer tourist season, Chicago can be quite warm, especially in the concrete jungle of downtown. June, July, and August have the most festivals and convention activity, and that is when the Navy Pier is buzzing. The summer crowds are big, so you may experience wait times on the observation decks at the Willis Tower and TILT, which tips you over the Magnificent Mile at 1,000 feet in the air. Be aware that the high tourist season also comes with high tourist prices at hotels.

The shoulder seasons of April and May are great times to visit, too, in the small window between spring and summer, September and October are also good times to go to Chicago, between the summer heat and the onslaught of winter. During these times the temperatures are warm, and Chicago attractions are still in full swing. These are the best times, especially for outdoor activities like strolling through downtown to the stores along the Magnificent Mile and snapping a selfie at The Bean in Millennium Park. The bonus to a shoulder season visit is that hotel rooms will be less expensive than in the summer months.

Spring: Spring is a beautiful time to visit Chicago, when the flowers and gardens are in full bloom and the city is awakening after the cold winter. Activity at the parks and lakefront is picking up, with walkers and bicyclists. Spring weather in Chicago is mild, with low humidity and comfortable daytime temperatures, from in the 50s Fahrenheit in March to the 70s by late May. These are perfect temperatures for walking around downtown and enjoying outdoor activities.

While springtime weather in Chicago is comfortable, it is also unpredictable-rain showers are likely, so pack a poncho or umbrella. The spring months have fewer crowds and lower prices, with the exception of mid-March when spring break tourists and St. Patrick's Day revelers flock to the city.

Summer: Summertime in Chicago is busy, and it is one of the most exciting times to visit. It is also hot and humid in Chicago in the summer. That is easy to remedy with an iced tea at one of the many open-patio restaurants and rooftop terraces. Summer temperatures range from the high 70s to the mid 90s Fahrenheit and feel even warmer with the humidity. You can also get storms in the summer, with June being the wettest month in Chicago.

Summer is the most popular time to visit Chicago, so expect large crowds everywhere, high prices for hotels, and long lines and wait times at restaurants. If you like being where the action is, summer is the best time to go to experience the festivals, outdoor music, and events. Some things, like the free fireworks at Navy Pier twice a week, you can only enjoy during the summer months. Summer hotel availability is tough to come by, so it is best to book far in advance.

Fall: If your vacation goal is comfort and being able to maximize your time then the fall is the best time to go. The city is still active, and attractions and outdoor activities are still buzzing, but the temperatures start to drop, making it nice to walk around or sit in the stands at a Chicago White Sox baseball game. Daytime temperatures in the fall average in the 60s and 70s Fahrenheit. Restaurant patios are still open this time of year but with less crowds and without the summer vacationers competing for space.

Some attractions, like Lincoln Park Zoo and Navy Pier, may have reduced hours later in the fall season, but you can still enjoy the outdoor venues, city parks, and the lakefront. This is also a great time of year to experience the many cultural activities in Chicago with live theater and comedy performances and special exhibits at places like The Art Institute of Chicago.

Winter: While winters in Chicago can be brutal there are unique experiences during the colder months that can make for a fun vacation, especially around the holidays. Chicago winter weather usually means lake-effect snow up to 37 inches and average daytime temperatures below freezing. If you do not mind the cold weather then a few layers of winter clothing and a heavy coat will have you prepared to explore Chicago easily.

Winter in Chicago means indoor museums, theater, and shopping. The holiday displays in the store windows and festive lighting throughout the city creates a nice ambience that you can only experience during the winter. Since this is the low tourist season, you will find cheaper hotel rates and airfares. Keep in mind that the weather frequently causes flight delays in and out of Chicago in the winter, so it is best to pad your agenda with extra travel time.

Best Month to Visit Chicago

Buckingham Fountain in Grant Park, Chicago

There is so much going on in Chicago, and while the peak tourist months are during the summer, the best months to visit for optimal weather, open attractions, and value are April and October. During these months you will be able to dodge the heat, crowds, and highest hotel rates. The other months of the year have some advantages that range from nice weather, great prices, or events that only happen during certain times of the year.

January: The month of January generally has snow on the ground, and it's the coldest month in the Windy City. Not surprisingly, it is one of the months with the fewest tourists, so you can get cheap rates on hotel rooms and find airfare for a steal. Since it is not a popular tourist month, you will have plenty of space at the attractions that are open. Daytime temperatures average below freezing, but there are many indoor museums to visit.

February: Conditions in February in Chicago are similar to January with cold, wet, and snowy conditions. On a rare occasion, the month of February will have a couple of mild days, but you will still need a heavy coat and winter gear, even to get from point A to point B in the city. This month is sparse when it comes to tourists, so you do not have to worry about lines at attractions or long wait times at popular restaurants.

Thousands of people are drawn to Chicago in the month of February for the annual Chicago Auto Show. You can find great hotel rates this time of year to take in the largest auto show in North America or hit the diverse theater scene.

March: The Chicago scene takes a turn in March as spring starts to make an appearance. March weather in Chicago is unpredictable, so be prepared for possible snow and rain. Temperatures are usually above freezing in March, so you can get out and walk the city streets comfortably with a light jacket. While you can find some lower hotel rates than the summer season, March in Chicago is a popular spot for families on spring break, and the St. Patrick's Day holiday brings in many tourists.

The beginning of spring marks the beginning of some festivals, like the Chicago Flower and Garden Show at Navy Pier, the St. Patrick's Day Parade, and the famous event of dyeing the river green. If you plan to visit in March, you are advised to make hotel and flight reservations well in advance, as it is a popular time of year for visits.

April: April is one of the best months of the year to visit Chicago. Daytime temperatures hover around 50 degrees Fahrenheit, and the weather feels nice for walking around downtown. Since it is in the shoulder season there are fewer crowds at the attractions like the observation decks. Be advised, though, that there could still be some spring break crowds at the beginning of April.

The temperatures begin to warm up in April, but it is also one of the months with the most rain. It is still a great month to go because outdoor events are getting underway, like the opening day for the Chicago White Sox and Chicago Cubs. Chicago is a convention city, so you will likely find other events underway in April that have to do with the visiting conferences or music festivals.

May: May in Chicago is a comfortable month weather-wise. The winter weather is gone, and the summer heat is just around the corner, so May is a weather sweet spot in the Windy City. The average daytime temperatures are around 60 degrees Fahrenheit, so you can easily walk around with a t-shirt. This is a great month also to visit the Chicago attractions before the summer rush starts when kids are out of school. The number of festivals increases in May, and you can enjoy local events at the lakefront and local parks.

June: The month of June kicks off the high summer tourist season in Chicago. If you are looking for a month with lots to do both indoors and outdoors, June is it. The June weather is warm, averaging close to 70 degrees Fahrenheit during the daytime but it does not have the sweltering heat and humidity that comes later in the summer.

June is a great month to target for outdoor festivals, which draw both tourists and locals. Many of the notable June events have been happening in the city for decades. The Chicago Blues Festival is a June staple at Millennium Park. The 57th Street Art Fair is a must-experience for anyone in town in June, as it showcases artists and is a great way to experience the local scene. The Chicago Gospel Music Festival is another major draw that celebrates the music scene of Chicago.

Aerial view of Chicago

July: July is in the height of the summer tourist season, so hotel rates will be at their highest and so are the temperatures and humidity. July is usually the hottest month in Chicago. Temperatures average in the high 70s to 90s degrees Fahrenheit, but factor in the humidity, and outdoor events can feel sweltering. While the weather is hot this month, at least the weather is predictable compared to other times of the year.

You can expect large crowds at all of the attractions and outdoor venues. You can also expect an array of events, from music and food festivals to cultural festivals. The big event in Chicago in July is the annual Fourth of July fireworks show. Expect hotel rates to be exorbitant around the holiday.

August: August is the second hottest month in Chicago but an exciting time to be in the city. This month is in the busy summer tourist season, so there will be many crowds at events and often long lines at some of the attractions. For attractions that require tickets, buy them early to ensure that you can work them in during your stay. Average temperatures are in the 80s Fahrenheit in August with high humidity.

Outdoor music concerts and festivals are big in Chicago in August, so plan ahead with cool clothing and plenty of water as you get out and about in the city. This is a great month for water activities on the lake or a river cruise.

September: September is one of the best weather months in Chicago. The temperatures are starting to cool slightly from the summer highs, and it is one of the driest months, so you most likely will not have to deal with rain. September has fewer crowds since kids are back in school, and the summer vacationers taper off after Labor Day. The nice weather makes it easy to enjoy the outdoor festivals that are still underway in the city.

October: One of the premier months to visit Chicago for weather is October. The cooler fall air is pleasant, and it is a perfect time to walk Michigan Avenue and enjoy the Chicago Riverwalk downtown. The daytime highs are in the low 60s degrees Fahrenheit, and the humidity has lessened from its summer peak. Nighttime temperatures can start to dip into the 40s Fahrenheit, so you will want to bring a light jacket for evenings.

October has fewer crowds since it is in the shoulder season, and you will be able to find discounted rates on hotel rooms. This is a great time to visit to enjoy the outdoors around the lake and see some of the fall foliage in the region.

November: The November weather in Chicago can be a little unpredictable, but overall it is a decent month to visit, as the temperatures are cooler and the blast of winter has not yet arrived. The holiday crowds start to pick up in late November with holiday shopping and the Thanksgiving Day holiday.

Chicago in November is a festive time. Two notable experiences this month are the Thanksgiving Day Parade downtown and the Magnificent Mile Lights Festival, which kicks off the official start to the holiday season in Chicago.

December: Although December is chilly in Chicago, the holiday festivities and sights around the city are exciting. The average December temperatures are in the 30s Fahrenheit, so you will need a coat to walk around, but the experience is worth it. Stroll down Michigan Avenue to see the millions of holiday lights and traditional holiday store window displays on State Street.

You can visit the Christkindlmarket in Daley Plaza, which is a large open-air German holiday market or see the ZooLights at the Lincoln Park Zoo. There are Chicago Trolley tours that go throughout the city to see the lights, and holiday dinner cruises that depart from Navy Pier. December is a busy time with quite a few tourists for the holidays and New Year's Eve.

Cheapest Time to Go to Chicago

The Bean in downtown Chicago

Your best time to find bargains in Chicago is during January and February. The winter months, with the exception of the holiday season, have the cheapest hotel rates and best availability. If you do not mind the frigid winter weather, you can score a cheap vacation and fill the itinerary with some of the great indoor activities in the city. You will not have crowds to contend with during these months.

Worst Time to Visit Chicago

Ice skating in the winter in Chicago

Since the Chicago experience is so weather dependent, the months of January and February are the worst times to visit. While they are the cheapest times to visit the city, you run the risk of canceled flights and some attractions that are closed. While January and February are typically the months with the worst weather, the snowfall can start in November and extend as far as April.

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Where to Stay in Chicago: There are many types of hotel options in Chicago in every range, from luxury and boutique to budget. Chicago has many pet-friendly hotels available, but be prepared to pay a premium to pamper your pet, as they are not cheap.

Things to Do in Chicago: If you plan to stay in Chicago, you will probably have more options of things to do than you have time to do them. If you have more time in your schedule and want to explore some of the other attractions in Illinois, you might want to base yourself in the city and explore Starved Rock State Park or one of the other nearby attractions. You might also want to build in day trips or an extended vacation to cities like Springfield, Rockford, or Naperville.

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