Best Time to Visit Chicago

When Is the Best Time

Chicago is an excellent year-round destination with countless must-see attractions. However, the weather can be unreliable, and every month is different in terms of crowds and hotel rates. Our unique Chicago guide provides you with unique tips from a local for every activity and detailed monthly advice.

The best time to visit Chicago is from April to October when the weather is mostly pleasant. The shoulder seasons are ideal for all outdoor activities and exploring the must-visit attractions.

This article was written by our Chicago resident! Make sure to read our monthly tips later, with links to our complete guides for each month (including more clothing tips and the best things to do for each month)!

Best Time to Visit Chicago For Great Weather

May, June, September, and October are the best months for visiting Chicago for great weather. These are the months that are warm enough to do outdoor activities without getting overheated. You’ll also find a lot of events occurring during these months.

Expect the weather to be generally in the 50s-70s in these months. Many people who visit Chicago cannot handle the cold of the winter and the hot and humid weather in the summer. By staying during these months, you’re avoiding the extreme temperatures on either end of the spectrum. This will make sure your visit is more enjoyable.

Best Time to Visit Chicago With Family and Kids

The best time to visit Chicago with family and kids is during the springtime (April and May) and fall time (September). During these months, the parks and museums are open, so your kids will have ample entertainment. Plus, the weather is not too hot to cause the kids to want to stay in the air conditioning all day.

These months also help avoid some of the crowds as most children are still in school. You’ll start seeing better accommodation rates in the fall time as people most often visit during the summertime. Head out earlier in the morning to avoid crowds when you visit.

If you decide to visit on a normally crowded holiday – like spring break, check out smaller and lesser-known spots to avoid crowds. For example, try heading to smaller museums instead of the most frequented ones.

Or, head to activities during the weekday to avoid crowds as most people will be at work.

Best Time to Visit Chicago for Cheap and Fewer Crowds

The best time to visit Chicago for cheap while avoiding the crowds is November through March. Due to the low temperatures, many tourists will avoid Chicago in the wintertime. This allows for accommodation rates as well as flight rates to be lower during these months.

You’ll also find fewer crowds more as even the Chicago natives will also avoid being outside for too long. Especially during days when the temperature dips into the negatives (in Fahrenheit).

Best Chicago Tours

Book your tickets in advance via GetYourGuide (see the tours above). You will get a mobile voucher and a printed voucher (whichever you like). It’s very comfortable and you avoid waiting in line.

Best Times of the Day to Avoid Crowds in Peak Season

The best time of the day to avoid crowds in peak season is in the early morning. Usually, activities and locations start getting crowded around 11 am and later. If you can get to a spot when they first open (8 or 9 am), you should be able to find smaller amounts of people.

For morning coffee – you’ll need to get up quite early to avoid crowds (think 5 am). This is the best time for the fewest crowds in the city. However, not many other places are open at this time. Though, in the summer months, you can walk along the shoreline in the early morning and watch the sunrise.

Of course, Chicago is a large city, so you will always find people out and about. There is not a time where you can avoid all crowds.

Best Time to Travel to Chicago for Fall Colors

The best time to travel to Chicago for fall colors is in September and October. These are the prime months for seeing beautiful fall colors in the leaves around Chicago. In September, you can catch the leaves starting to turn red at the end of the month.

October brings yellow, red, and orange leaves to the trees in Chicago. This is also when the leaves are falling, so you’ll see quite a few on the ground as you explore the city. October is also the month when many fall activities are available to do with your family.

Best Time to Travel to Chicago for Museum Visits

The best time to travel to Chicago for Museum visits is in May, September, and October. These months, children are in school so you’ll be able to avoid crowds. Also, the weather is delightful, and most people will be enticed to spend their time outside instead of inside.

The museums are open year-round. However, you’ll find them to be quite busy in the winter months and during June-August. Chicagoans and tourists will often crowd museums during these times to get a break from the weather – both cold and hot temperatures.

Best Time to Visit Chicago for Outdoor Activities

The best time to visit Chicago for outdoor activities is in April, May, September, and October. These are the months that offer the best weather – warm and pleasant without being too hot. This makes it the perfect time for outdoor activities.

April and May are ideal for visiting the gardens and parks as flowers will be blooming in these months. September is excellent for visiting beaches and taking outdoor walking tours. October is, of course, the best time to explore Halloween activities like outdoor pumpkin patches.

Best Time to Visit Chicago for Architecture River Cruises

The best time to visit Chicago for architecture river cruises is April through October. Most architectural river cruises are open and running during this time. In colder months, most tours shut down as the water will be frozen in some areas, and the temperatures will be too frigid.

Chicago is known for its architecture, and seeing it by cruise is the ideal way. You’ll get to enjoy the beautiful skyline while learning about the architecture of the area. The best cruise for this experience is the Architecture River Cruise.

Book your tickets as early as possible to ensure you get the day and time you want. Cruises/water tours can get pretty busy.

Best Time to Visit Chicago for Festivals

The best time to visit Chicago for festivals is June-July. These are the months with the most popular festivals – both music and food-based. You can never go wrong with music or food-centered festivals.

June hosts the Chicago Blues Festival, while July hosts Lollapalooza and the Taste of Chicago. All three festivals should be attended at least once as these are some of the best Chicago festivals. Both the Chicago Blues Festival and Lollapalooza boast big-name performers.

The Taste of Chicago offers food from all around the city in one convenient spot so that you can try as much of the local food as possible. This is an event that is highly anticipated each year.

Both of these months offer warm weather, so dress accordingly, drink a lot of water, and find a shady spot to take a break under if possible.

Chicago Hotel Deals



  • Temperature: Average High 32°F (0°C)
  • Rain: 5 Days on average
  • Crowds and Hotel Rates: Low

January in Chicago has an average high of 32°F. When the sun is not out, the daytime temperatures are even chillier. Chicago is nicknamed the “Windy City” for a reason.

During the winter season, the wind can be frigid, making it feel even chillier outside. Rain is rare in January, as it usually turns into snow due to the temperatures.

What to Wear

In January, you’ll want to bundle up. If you’re visiting here, plan to bring a thick winter jacket. If you can find one that is longer and covers your legs as well, that is ideal. Of course, you’ll also want to wear thick gloves and a hat.

The keyword for dressing in winter is layers. Add layers of shirts or a shirt and sweater underneath your jacket. For your bottoms, you can add tights or long johns under your pants.

When looking for shoes to wear in January, opt for boots with a good amount of grip. The sidewalks are usually pretty clear in regards to snow. However, if a large amount of snow occurs, it may take longer for the streets and sidewalks to be cleared off.

Boots that extend higher would work well in case of significant snowfall. The grip on the bottom will prevent slipping as there is also occasional ice on the ground. January in Chicago gets very chilly at night – you’ll want to bundle up, especially at night, as temperatures can hit negative numbers during this time.


Chicago is usually a bustling city. In January, you’ll find the crowds to be much smaller and manageable. You will see much fewer people outside than you would in the warmer months.

There will still be a lot of crowds inside, though. The chilly weather keeps most people inside in the wintertime – especially in January. You will find the bars and restaurants in the area to be more busy than usual.

Other indoor activities like movie theaters, indoor performances, and even grocery stores will be more filled with people.


Hotel rates in January are usually low. With the winter temperatures, fewer visitors typically come to the area. With lower demand, there come lower rates. If you visit in the warmer months (spring through fall), you could expect rates to be 1.5-2x what they are in wintertime.


  • Temperature: Average High 36°F (2°C)
  • Rain: 7 Days on average
  • Crowds and Hotel Rates: Low

February has an average high of 36°F. It is another very chilly month in Chicago. There is less of a chance of below-freezing temperatures during this month. The past few years have shown warmer and more pleasant weather in Chicago during February.

During this month, there is a chance you may see rain when the temperature peaks over 32°F.

What to Wear

In February, you’ll still be bundling yourself up. During the days when the sun is out, and the temperature is in the higher 30s, you can forego a hat if you’re feeling brave. At nighttime, once the sun is gone, you’ll still need to keep your hat and gloves on during outside commutes.

The key to Chicago is making sure you have many layers on; this can be tricky when walking into a store or bar where the heat is blasting. Make sure to wear easy-to-take-off layers (like a scarf) to make the transition from inside to outside easier.


In February, the crowd levels are still lower. As the temperatures start to rise, more people will be out and about. Towards the end of February, you will begin to see more people on the sidewalks.


Hotel rates in February are also low. They will be similar to January rates. If you’re concerned about hotel costs – this is a great time to visit.


  • Temperature: Average High 45°F (7°C)
  • Rain: 5 Days on average
  • Crowds and Hotel Rates: Low – starting to increase
What to Wear

March in Chicago is still on the colder side, with an average high of 45°F. When the temperatures are at this point, you may start seeing Chicagoans loosening upon layers.

You may see fewer hats during the day. It’s best to bring sunglasses, a warm jacket, thick pants, boots, and gloves.

Since it gets frigid in the winter, as soon as the temperatures start to warm up, locals like to enjoy the weather as much as possible. This usually includes a few Chicagoans wearing shorts on the warmer days beginning in March, which is not advisable.

Tip: If you are planning to visit during this month, read our in-depth guide for Chicago in March (Weather, Clothing, Things to Do)


The crowds during March are still very light. Most people during this month continue to stay inside, and public outdoor places like gardens are easy to traverse through as there are not as many people there.

This is a great time to explore outdoor areas that are typically packed, like Millenium Park. Check out the iconic “bean,” also known as Cloud Gate, in the middle of the park. This is a must-see for visitors.

You can often find people taking pictures in front of this shiny, mirror-like art piece.


Hotel rates are still reasonable and relatively low during March. The rates at this time are just starting to increase. As the temperature increases, hotel rates increase. This is an excellent month if you’re looking for a budget-friendly hotel rate and above-freezing temperatures.


  • Temperature: Average High 56°F (13°C)
  • Rain: 7 Days on average
  • Crowds and Hotel Rates: Moderate
What to Wear

April in Chicago has an average high of 56°F. In this month, the snow is mostly melted, and you can expect an average amount of rain – approximately 7 days. With the temperature warming up, you can wear lighter jackets, pants, boots, or closed-toed shoes.

For chillier nights, you may still want to bring a scarf or hat. Once the sun goes down in Chicago, temperatures can drop quite a bit.


The crowds in Chicago in April are more than what you would see during November through March. With children in school still during this month, you’ll be able to avoid some of the crowds that you would see in the summer.

The warmer weather and with crowds at bay, this is a great time to see Chicago. It’s warm enough to explore outside without getting too hot.


Hotel rates in April are on the rise in Chicago, yet still moderate. With the more bearable temperatures, more people are interested in heading to Chicago. This is still an excellent time to visit Chicago.

Tip: Find more tips for this month in our complete guide to Chicago in April (Weather, Clothing, Things to Do)


  • Temperature: Average High 66°F (19°C)
  • Rain: 7 Days on average
  • Crowds and Hotel Rates: Moderate
What to Wear

May in Chicago boasts an average high of 66°F. This is an excellent temperature for outdoor activities. During hotter days in May, you can get away with wearing shorts, a t-shirt, gym shoes (expect to walk a lot), and a light jacket or sweater.

This is an optimal time to do outdoor activities. You won’t get overheated but will stay at a perfect temperature while walking around and exploring the city.


During May, crowds are starting to form with the warm weather. You’ll still get a slight reprieve from the number of people that usually go out in the summer as school is still in session.

Expect a good amount of people out and about as well as at indoor activities. This is the first month that people can go out and enjoy the weather. May will be more crowded than November through March.


Hotel rates in May are moderate bordering on high. Throughout the year, the cost of hotels and amenities rises and falls with demand. Most people will be visiting Chicago May through October, which explains the higher hotel rates.

You may still be able to find a deal here or there in May, but rates will be higher than in the colder months.

Check out more tips in our Chicago in May guide.


  • Temperature: Average High 77°F (25°C)
  • Rain: 9 Days on average
  • Crowds and Hotel Rates: High
What to Wear

In June, Chicago is a beautiful 77°F for the average high temperature. Make sure to wear/bring shorts, t-shirts or tank tops, sneakers or comfortable sandals, and your best pair of sunglasses.

June is a beautiful time to be outside. Make sure to bring sunscreen as well, so you don’t have to deal with sunburn on your vacation.


You can expect the crowds in June to be very high. This is the first month when schools will be out for summer break, and the kids are excited to be free from schooling.

You will find crowds outdoors, and indoors for events, activities, and restaurants. Prepare yourself for the number of people you’ll find in downtown Chicago during this month.


Hotel rates are high in June as demand is high. This month is the first summery month and with it brings people who want to visit Chicago. The rates are not the highest you will ever see. However, be prepared for higher rates than listed rates for January, February, and even May.


  • Temperature: 82°F (28°C)
  • Rain: 6 Days On Average
  • Crowds and Hotel Rates: High
What to Wear

July in Chicago has an average high of 82°F. At these temperatures, you’ll want to wear shorts and a t-shirt or tank top. Make sure to bring a hat or sunglasses as the sun can get very bright, especially near the lake.

You may even want to wear a very light cotton long-sleeve shirt in a light color. This will help protect your skin from the sun. Make sure it’s a breathable fabric, so you do not get overheated.


Crowds will be high in July because of the enjoyable weather. There will also be more tourists during this season due to the warmer temperatures. To avoid the crowds, head out early in the morning.

Once 11 am hits, the crowds start to come out, and it gets hectic. This will be for both indoor and outdoor activities. If you’re heading to the beach, the earlier, the better. This holds for museums as well.


The rates for hotels and accommodations in Chicago in July are high. Many travelers want to visit Chicago in the summer so hotels can charge more. Book your accommodations as far ahead as possible – this will ensure you are getting the best hotel rates.

This is one of the months with the highest hotel rates all year long. Expect to pay more if you visit during July.


  • Temperature: 81°F (27°C)
  • Rain: 6 Days On Average
  • Crowds and Hotel Rates: Moderate
What to Wear

August is another hot month in Chicago. Generally, August is the second hottest month here during the year. You’ll still want to wear a t-shirt and shorts during this month to avoid getting overheated. The sun can be very hot during the day as there is not always shade available.

If you are walking around downtown, make sure to take an ample amount of water with you and stop in the shops occasionally to get a break from the sun.


The crowds in August are still very high. During this month, expect to continue seeing a lot of people at indoor and outdoor events.

If you plan to get to the beach and want to visit in a more peaceful setting, you’ll want to head out very early in the morning. Even at 6 am, people will already be out and about. However, at this time, there are much smaller amounts of people.

For more details visit our Chicago in August (Weather, Things to Do, Clothing) article.


The rates for hotels are moderate in August. Towards the end of this month, children are starting to go back to school. As such, you’ll see more people traveling at the beginning of the month and less at the end. The rates usually decrease during the end of the month.

If you have any contacts in Chicago, you may want to see if you can stay with them. Or, get accommodation in the outskirts of the city and commute each day. This may be a cheaper option. Use the SpotHero app to get excellent parking rates in the city.


  • Temperature: 74°F (23°C)
  • Rain: 5 Days On Average
  • Crowds and Hotel Rates: Moderate
What to Wear

September in Chicago is a great month to wear light, breathable layers that are easy to take off and put on. The weather during this month can be a bit unexpected, so you’ll want to dress for different types of weather.

During the warmer days, head out in a t-shirt or tank top and shorts. During the chillier days, opt for light pants (like cotton) and a more lightweight long sleeve shirt or short-sleeved shirt with a light jacket.

Some days are warmer, and some are chillier. Extra layers will help with the rapid weather changes. Also, make sure to bring a few different types of shoes such as sneakers and flip-flops.

The weather at night during this month is very pleasant. There is usually a light breeze near the lake, so you may want to bring a wrap or light jacket if you’re planning to stay out at night. This is especially true if you tend to run on the colder side.


Crowds during this month are slightly less than June through August. At this point, all children are in school. Most of the people you’ll see out and about fall into the following categories – visitors/tourists and Chicago professionals, most often on a meal break.

If you love doing activities that are usually crowded, such as going to art galleries and hitting the beach, this is a great time for you to visit. You’ll be able to enjoy warm (not too hot) weather and also see some fun places that are less crowded than during other summer months.


September rates for accommodations are very similar to rates for August. They are moderately priced since a good amount of visitors are still heading to Chicago. You may occasionally find some accommodation deals during this period.

This is an excellent month to visit. You’ll get to visit during a warmer month, and hotels will not be overpriced. Plus the crowds will have lessened since the children are in school.

Tip: Find more tips for this month in our complete guide to Chicago in September (Weather, Clothing, Things to Do)



  • Temperature: 62°F (17°C)
  • Rain: 7 Days On Average
  • Crowds and Hotel Rates: High
What to Wear

In October, Chicago temperatures start to drop. You’ll want to bring light to medium jackets, pants, and closed-toed shoes. This is the month when it officially feels like summer is over.

During the day, you might get the occasional warm day in the sixties. However, at night, it will be pretty chilly once the sun goes down. Make sure to bring a few sweatshirts to wear in the evenings or at least slightly thicker jackets or sweaters to throw over your outfit.


Chicagoans love activities that revolve around Halloween and fall time. You’ll see more crowds out towards the beginning and middle of this month. At the end of the month, the crowds will start to lessen as the temperatures continue to decrease.

This is the last month with the weather on the warmer side, so many people will be out enjoying it as much as possible before the temperature goes down in November.


Rates jump up again in October for accommodations. These high rates are caused by many different events to attend and Halloween-themed activities that are available.

If you’re willing to pay more for a hotel, visit Chicago in October. You won’t be disappointed with the number of things to do during this month. Make sure to bring your family with you for a long weekend.


  • Temperature: 50°F (10°C)
  • Rain: 4 Days On Average
  • Crowds and Hotel Rates: Low
What to Wear

The temperatures in Chicago drop quite a bit in November. Make sure to grab a thick jacket, thick pants (think jeans), a long-sleeved shirt, boots, and closed-toed shoes.

November typically brings snow in Chicago, so it’s best to be prepared for every scenario as the weather can change quickly. Throughout the year, the weather in Chicago is pretty unpredictable. Specifically, from October to April. During these months, it’s best to bring a range of clothes from t-shirts, shorts, and lighter jackets to heavy winter outfits.


Crowds are low during this month. Once the cold weather starts hitting Chicago, pedestrian traffic slows down quite a bit in November. You’ll find most people indoors this month.

Indoor activities will still be fairly popular/crowded. If there is a bad snowstorm, most people will stay in their homes as it can get quite slippery in the winter.


Hotel rates are low in November. As the temperature cools in Chicago, people tend to head to warmer destinations. At the end of the month, many city dwellers head to the suburbs to visit with their families.

If you don’t mind the cold, this is an excellent time to visit Chicago. You’ll get great rates and avoid the crowds. You can probably even find a higher-rated hotel in your budget during this month that would normally be quite expensive.


  • Temperature: 37°F (3°C)
  • Rain: 7 Days On Average
  • Crowds and Hotel Rates: Low
What to Wear

December brings very chilly temperatures and typically a good amount of snow. You’ll need to be properly layered clothing-wise to stay warm this month.

Make sure you bring a thick winter coat, long sleeves, long pants, and boots. If you have under layers that you can bring too, like long johns or leggings/tights to wear under your pants, these will help you stay warm. Of course, you’ll need a hat, gloves, and a scarf as well.

Tip: Read our complete Chicago in December guide!


Crowds tend to be pretty low in December. There is an exception to certain popular holiday events that will, of course, bring more crowds. Also, you’ll see quite a few people holiday shopping during this month.

Indoor events are also quite popular during this month. However, you’ll see most people crowding around Santa for pictures than walking around galleries.


Hotel rates and accommodation rates continue to be low in December. The chillier it is in Chicago, the lower the rates tend to be.

You’ll be able to get excellent deals during this month—both with hotels and flights. Of course, if you’re looking to head to Chicago around Christmas, make sure to book far enough in advance.

Many people are flying in and out during the end of the month to visit their families so flights especially can get quite full.

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