Best Time to Visit Chicago | Local Tips on When to Go (2023)

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The perfect time to visit Chicago is between either April and June or September and early November. You might prefer to visit the Windy City during other times of the year, but these are the times that appeal to most based on optimal weather, crowds, and things to do.

In my five years living here, I’ve seen firsthand that there’s never any shortage of things to do or places to see, but there are some nuances to when to visit. You’ll have a very different Chicago visit in January vs July, but of course, it all comes down to what you want to experience. 

In this article, we’ll cover when to visit Chicago for weather, festivals, food, budget, families, and more. And while you’re here, bookmark my guide to the best places to stay in Chicago to help choose a neighborhood!

Ready to decide when to visit Chicago? Let’s dive in!

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When Is the Best Time to Visit Chicago?

In terms of weather, the most popular times to visit and explore Chicago are during the spring (April to June) and autumn (September to November) seasons. The peak season for tourists is during the summer, but some may want to brave the harsh winter weather for special winter events.

Of course, the best time to visit this city for you will depend on what you want to do here, and which considerations are important to you. So let’s break it down!

🛎️ Need a Hotel? The Pendry Chicago is a favorite in the Loop, or browse a variety of Chicago hotel options for more inspo!

When to Visit Chicago for Good Weather

If experiencing the best weather is top of mind for you, then visiting Chicago when average temperatures are warm but not stifling is key. Generally, this happens from April to May, and then again from September to October (known as the “shoulder seasons”).

Keep in mind that spring weather in Chicago includes a lot of rain, so be prepared with an umbrella if you come during this time.

During these times of the year, you can expect reasonably pleasant weather in the Windy City. You won’t have to deal with the notoriously bitter cold temperatures during Chicago’s winter, nor the intense heat and humidity of the summer months. 

When to Visit Chicago for Cheap Prices

The winter months (especially January and February, after the holiday season has died down) are optimal for visiting Chicago on a budget. You’re more likely to get cheap prices for hotels, food, activities, and flights. Typically, hotel room occupancy is around 50% during this time, meaning you’ll benefit from discounted prices at even the finest hotels.

You’ll also get to enjoy savings associated with indoor attractions during Theater Week in February.

However, if you don’t want to deal with the worst weather the city has to offer, you’ll also benefit from significantly lower prices in the spring and fall without having to deal with frigid temperatures. The summer months are when lodgings and activities are going to be the most expensive.

When to Visit Chicago for Families and Kids

The most popular time to visit Chicago with kids is from June to September. There are many family-friendly activities during this summer season.

However, sites can be extremely crowded and expensive in the summer, so I recommend planning for August if you are coming with your kids. Of all of the summer months, this is the most affordable, and the weather is going to be less hot and humid than in July.

April would be a good time as well if you can navigate your kids’ school schedules appropriately. The weather won’t be so hot, and you’ll still have your pick of family events to enjoy. The Lincoln Park Zoo offers free admission at all times of the year as well!

When to Visit Chicago to Avoid Crowds

If you really want to avoid crowds and have a quieter vacation, then winter is your best time to visit Chicago. You’ll never see hotel occupancies as low as they are in January and February.

Even though winters are notoriously cold in Chicago, this is a great time to come if you want to experience all of the indoor attractions this great city has to offer without paying sky-high prices. You can easily get theater tickets, and the restaurants and museums are going to be a lot less crowded than they are in other seasons.

Also, no matter what time of the year it is, if you want to deal with fewer crowds, it’s best to check out the sites on weekdays rather than weekends.

👉 Looking for more great things to do in Chicago? Check out our epic list of the best Chicago activities and attractions!

When to Visit Chicago for Food

Like any big city, Chicago is a great place for foodies. Sample deep dish pizzas at the Chicago Pizza Party in February, or go to the Chicago Hot Dog Fest in August! For more, see our guide to all the famous Chicago foods you have to try.

If you’re visiting between mid-March and early April, then your visit may coincide with Chicago Restaurant Week, a two-week event where you can enjoy fixed prices for multi-course meals from some of the finest places to eat in Chicago.

The two biggest food festivals in Chicago take place during the summer. There is Taste of Chicago in July, which lasts for five days and takes place in the Chicago Loop. In addition to this, the Chicago Gourmet festival takes place in Millennium Park in September; this is an upscale fine dining festival.

When to Visit Chicago for Enjoying the Outdoors

I recommend visiting Chicago around September to most; this is when the weather is likely to be relatively warm and dry. Also, the changing colors of the fall foliage can make for stunning scenery while wandering the many neighborhoods in Chicago.

However, it depends on your favorite season. One reason why Chicago is so popular in the summer is the 26 miles of Chicago beaches along Lake Michigan. Between late May and early September, the water is great for swimming. You can also go for a scenic walk or bike ride on the Lakefront Trail.

If you enjoy the cold, then you might love Chicago winters as well. There are many ice skating rinks open between November and early March. You can go sledding at Soldier Field Sledding Hill or snowshoeing at Northerly Island.

When to Visit Chicago to Enjoy the Architecture

Chicago has one of the most iconic skylines in the world. You can take in the amazing view on a cruise, via an observation deck like 360 CHICAGO, or by just walking around.

However, you want to make sure that you have a clear view of all the breathtaking buildings and the picturesque Chicago River, and you don’t want cold weather to put a damper on your experience.

If you want to go on a boat cruise with the Chicago Architecture Foundation, then I recommend going between April and mid-November. On foot, March to June and then September and October are the best times. Late August through mid-September will give you the clearest view of the skyline from an observation deck.

When to Visit Chicago for Arts and Culture

Chicago is definitely a hub for arts and culture. Theater Week is in February and features more than 100 performances over the course of 10 days. April is Chicago Dance Month with over 50 performances, as well as other events and classes at low prices.

Meanwhile, Chicago summers are known for many music festivals. Lollapalooza in July may be the most well-known of these, but there is also Do Division in June, Riot Fest in September, and countless music festivals of all sorts in between.

Many world-class museums in Chicago, including the Chicago Children’s Museum and Money Museum, will grant free admission on certain days as well.

When to Visit Chicago by Month

January

With an average high temperature of 32°F (0°C), January is the coldest time in Chicago. However, if your primary concern is avoiding crowds, then this is the best time to visit. You can stay warm in the Garfield Park Conservatory, the Art Institute of Chicago, and the museums of South Loop.

Outdoor winter activity lovers can enjoy food and drinks in an outdoor igloo, drive ice bumper cars at Gallagher Way, and go ice skating!

February

February is typically almost as cold as January. You’ll probably have to deal with snow and temperatures below freezing, but you’ll still enjoy fewer crowds and lower than average prices on lodgings.

You can continue to do all of the fun outdoor and indoor winter activities that are available in January, and you can also go to the Chicago Auto Show in mid-February.

March

In March, temperatures start warming up, although winter sometimes sticks around. Crowds are not usually an issue, although spring break tends to draw in more visitors. I recommend watching a basketball or hockey game at United Center, enjoying exquisite food during Chicago Restaurant Week, or seeing a beautiful flower show at Lincoln Conservatory.

Chicago is particularly known for its celebration of St. Patrick’s Day – there are St. Patrick’s Day parades, block parties, and the infamous dyeing of the Chicago River!

👉 Pro Tip: On St. Patrick’s Day, the Chicago River is traditionally dyed green, and this effect lasts for days, visible between Columbus Drive and State Street. Here’s a fun Chicago fact for you: the dye is actually an orange-red vegetable-based powder!

April

Chicago weather continues to warm up in April, but it can be rainy. Some crowds may be present in early April, due to spring break (spring breakers can either show up in March or April). The city can be absolutely gorgeous starting mid-April when flowers bloom all over the city.

Baseball fans can enjoy the Chicago Cubs opening day at Wrigley Field. There’s also Chicago Restaurant Week in downtown Chicago and the Feed Your Soul Jazz Brunch in West Loop for the foodies.

May

Chicago continues to warm up in May, but the late spring can also be quite rainy. This might be a good time to visit before summer vacation brings in crowds.

There are many fun outdoor events in May. Enjoy a cold beer and great entertainment at Mayfest in Lincoln Park and the Belmont-Sheffield Music Fest in Lakeview. Also, at the end of May, the twice-weekly Navy Pier Fireworks will start, continuing until Labor Day weekend.

June

The month of June can be somewhat rainy, but you’ll see the start of summer. This means longer days, warmer temperatures, and the start of crowds, although the summer rush happens later.

Early summer marks the start of a season of festivals in Chicago. Music lovers can enjoy the Do Division Street Fest and Chicago Blues Festival. Visitors can also join in the large-scale celebration of Pride Month with many parades and festivities at Chicago’s Navy Pier.

July

July in Chicago is known for heat and humidity. Also, because of all the events, such as the Chinatown Summer Fair and Taste of Chicago, the city gets extremely crowded. Many families with kids choose July, well into summer break, for their vacation.

Chicago’s best-known event in July is Lollapalooza, a four-day music festival in Grant Park. Also, Chicago’s National Sports Card Convention, including the ‘Chicago Drop,’ will appeal to many sports card enthusiasts.

August

August is generally less hot and humid than July, but often not by much. It is also often just as busy and crowded as July.

In August, you can experience the Bud Billiken Parade and Picnic to celebrate African-American history and culture or see the Chicago Air and Water Show over the lake for free. Throughout the summer, enjoy the Ravinia Festival’s performances and masterclasses and the Millennium Park Summer Film Series.

September

September is arguably the best time to visit the city, as it is the warmest and driest month. Early fall in Chicago is warm, although nights start to get cooler in late September.

A variety of outdoor activities take place in September. Music lovers can enjoy the Chicago Jazz Festival, North Coast Music Festival, and Riot Fest. There’s also the West Loop Art Fest for art lovers and Chicago Gourmet for the foodies.

October

If you like slightly cool weather, I’d recommend visiting Chicago in October. You can walk around and explore the city, taking in sights of beautiful fall foliage starting in mid-October. The summer crowds have dissipated at this point.

Athletic tourists can enjoy the Bank of America Chicago Marathon. The foodies will love that it’s National Pizza Month, and there are many fun Halloween events, such as the Arts in the Dark Halloween Parade.

👉 Read Next: 17 Best Chicago Day Trips and Excursions

November

If you’re fine with chilly temperatures, then November is a great time to visit Chicago. In early November, you won’t have to deal with crowds, but the holiday season will start bringing in tourists in mid to late November.

Many festive holiday events take place in late November, including the Christmas Tree Lighting Ceremony, Chicago Thanksgiving Parade, and Magnificent Mile Lights Festival. Enjoy a day of holiday shopping on the Magnificent Mile as well!

December

December in Chicago is typically cold and sometimes snowy, but not as cold as January. It’s usually fairly crowded, due to holiday shoppers and tourists spending the holiday season in Chicago.

In December, you can enjoy fun seasonal activities with ZooLights at Lincoln Park Zoo or watch projections of artistic light displays with Art on theMART. The Chicago streets are decked out with dazzling lights, so even enjoying a simple stroll down the street is a fun experience.

Chicago Weather and Climate

The city of Chicago is located in a temperate area and features four very pronounced seasons.

Chicago boasts summers that are generally characterized by hot temperatures and a lot of humidity, while the winters are known for freezing temperatures and tons of snow. Areas closer to the water may experience even colder weather during Chicago’s low season than the rest of the city.

You are more likely to experience pleasant, warm weather while visiting Chicago in the shoulder seasons – spring and autumn. However, keep in mind that the weather can be somewhat unpredictable in the spring, with remnants of the Chicago winter season making it unseasonably cold at times. It can also be quite rainy in the spring, particularly in the month of May.

If you like warmer weather and don’t want to deal with a lot of rain, September and early October are probably the best times to visit. In the early fall, you can enjoy a lot of outdoor activities in Chicago with relatively warm and dry average daytime temperatures.

Generally, the temperature in Chicago will range from 22 °F to 83 °F (-5°C to 28°C) throughout the year, rarely going above 91 °F or below 5 °F (33°C and -15°C)

📚 Related Reading: Check out this guide to the best day trips from Chicago, in case you want to take a short break from the city during your visit!

Tips for Visiting Chicago

Below are some basic tips for choosing when to visit Chicago. For more tips for your visit, see my full list of practical travel tips for Chicago.

Have an Idea of the Weather Before Your Visit

The weather in Chicago can be unpredictable at times, particularly during the spring. It would be a good idea to look at the weather forecast before you come to Chicago, so you can get an idea of what to expect. It may not be completely accurate, but it will help.

Bring Layers of Clothing, Even During Warm Weather

There are many days when the daytime temperatures differ from those in the early morning or later at night. Dressing in layers can be helpful; for example, if it is warm during the day, you can wear short sleeves and bring a light jacket in case it cools down later.

Not sure what to pack for Chicago? Just use our Chicago packing list!

Remember Lake Michigan’s Effect During Freezing Temperatures

To the east of Chicago is the lake, which exacerbates winter weather quite a bit. As you go closer to the lake, winds, and chills can become more intense. If you’re visiting Chicago in the winter, you might want to avoid staying in areas like South Loop and Lakeview.

Familiarize Yourself with Public Transportation

The year-round public transit system in Chicago is very extensive and will take you almost anywhere in the city. The ‘L’ train goes to both airports (O’Hare and Midway). Sometimes, it can transport you faster than a car, especially when there’s a lot of snow on the ground.

🚗 Where to Rent a Car: Even though public transportation is extensive in Chicago, it’s easier to get to many places on the outskirts of the city with a car. See what Discover Cars has to offer during your trip!

Plan Out Your Trip Before You Come

It’s a good idea to plan out your main activities before coming (including seasonal events and festivals). There’s still a chance that you won’t get to all of it, but having some sort of blueprint for your trip will maximize your chances of doing the big things on your list.

FAQs About When to Visit Chicago

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Thanks for reading my guide on the ideal time to visit Chicago! I hope this helped you decide when to plan your trip to the Windy City.

Check out our guide on the best things to do in Chicago to ensure you’re busy no matter when you come!