Travel Tips

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Best Time to Visit Chicago (Weekend Getaway or Family Vacation)

Plan your perfect Chicago trip! Find the best times for weather, festivals, budget travel, and avoiding crowds in our comprehensive guide. Ideal for weekend getaways or family vacations.

Tobi Miles
July 1, 2022
Best Time to Visit Chicago (Weekend Getaway or Family Vacation)

Chicago is one of those places that everyone comes to love. However, your experience will differ depending on when you visit. So when is the best time to go!?

Chicago is best visited between April and June or late September and early November. These are the times of the year with the best weather, crowds, and activities. However, you are more than welcome to explore the Windy City at any other time. Always pre-register for events to ensure your spot so you don't miss out.

This article will discuss the best times to visit Chicago for the weather, festivals, cuisine, family-friendliness, and other factors. While you're here, be sure to save my list of the top hotels in Chicago so you can pick a neighborhood!

When Should You NOT Go To Chicago?

The winter months of January through March are the worst to travel to Chicago, with February and March being one of the worst. Locals claim that around this period it can be particularly difficult to get through the frigid weather.

The Windy City certainly lives up to its moniker even though it might not be the windiest town in America. If you decide to go, dress in layers and bring a few extra items just in case.

Due to the lack of travel incentives, February and March are frequently uncertain. During certain months, it will be difficult to obtain cheap flights, and you face the danger of not making it to your desired location in time.

If your flight is completely canceled, traveling through stormy skies could be more hassle than they're worth. Additionally, trying to find things to do will be more difficult.

Numerous events, conventions, and the like are held in Chicago, but during this chilly season, those events are a distant dream. Late in the year, beginning in late spring, the popular tourist attractions will open to the public.

This is the time to visit if you want to see Chicago from the perspective of a real local. It's crucial to be ready if you decide to visit Chicago during these times.

There are ways to plan a layover or land somewhere other than O'Hare to obtain cheap airfares (called skip-hopping). But that is the subject of a different piece.

When is the Best Time to Visit Chicago for Budget Purposes?

The best time to travel on a budget to Chicago is during the winter, especially in January and February after the festive season has passed.

Cheaper rates for lodging, dining, activities, and travel are more prevalent. You will benefit from lower rates at even the best hotels because hotel vacancy is typically around 50% at this time.

During Theater Week in February, you may also take advantage of discounts on indoor attractions. You'll also benefit from noticeably lower pricing in the spring and fall without trying to contend with icy conditions.

However, if you don't want to deal with the city's harshest weather. The most expensive times of year for lodging and activities are during the summer.

What Time is the Best Weather in Chicago?

Now that you know more about Chicago's climate, hopefully, you can decide when to visit. Here is a month-by-month guide based on weather, holidays, and events if you want to focus your search even further.


In Chicago, January is typically the coldest month. Most likely, the temperature will be below freezing, and there may even be heavy snow.

Since January has been milder in recent years, it is more common to get lucky and have days when the weather is in the 40s or even 50s.

January is also not a fantastic time to go if you don't enjoy the cold. One of the two months with less visitors and cheaper hotel rates is January.

Things To Do

  • See the Immersive Van Gogh Exhibit
  • Go Sledding
  • Go Outdoor Ice Skating
  • Drive Ice Bumper Cars at Gallagher Way
  • Have Dinner or Drinks in an Igloo


In Chicago, February often ranks second in terms of temperature. There may be lots of snow and a below-freezing temperature.

However, February has been more mild in recent years, so it is not uncommon to get lucky and have days when the thermometer shows it's in the 40s.

February is not the best month to visit if you don't enjoy the cold. One of the two months with less tourists and cheaper hotel rates is this one.

Things to Do

  • Enjoy the Views from 360 CHICAGO Observation Deck
  • Check out the annual car show
  • Enjoy the Chinese New Year Parade in Chinatown
  • Visit the Shedd Aquarium
  • Enjoy Tropical Temperatures Inside the Garfield Park Conservatory


The weather in March can be somewhat erratic. You might have warming weather or you might continue to experience winter weather, including snow.

The weekend just before St. Patrick's Day, which is a big thing in Chicago, is when tourism starts to increase in March. Due to the fact that many US schools are out for spring break at this time, there are also more tourists in town.

Things to Do

  • Participate in the St. Patrick's Day Downtown Parade & River Dyeing
  • Check out the Shamrock Shuffle
  • Take an Architecture River Cruise
  • Visit Adler Planetarium
  • Enjoy the Garfield Park Conservatory's Spring Flower Show


Although the weather has likely begun to heat up a little by April, it is still uncertain. Carry a portable umbrella because April is among the rainiest months.

Due to spring break holidays, early April might be congested. Around the middle of April, when wild flowers begin to blossom, the city becomes more picturesque.

Things to Do

  • Visit The International Exposition of Contemporary & Modern Art (Expo Chicago)
  • Enjoy Lincoln Park Conservatory's Spring Flower Show
  • See the Tulips on Michigan Avenue
  • See the Cherry Blossoms in Jackson Park
  • Attend a Candlelight Concert

Related Read: 25 Best Hiking Trails in Illinois


In terms of temperature, May is frequently one of the best months. Before summer vacation and the bustling tourist season begin, it's a terrific time to visit Chicago.

Things to Do

  • Participate in Mayfest
  • Check out the Belmont-Sheffield Music Festival
  • Check out Mole de Mayo
  • Take a Lake Cruise
  • Have Fun at Navy Pier


Credit: Shutterstock

Although summer has arrived, it is not yet very hot. June might occasionally still be chilly. Unfortunately, June has a higher chance of rain than later in the month.

Chicago's busiest season is the summer, when travel demand increases and more festivals and outdoor events take place.

Things to Do

  • Kick back at the Chicago Blues Festival
  • Visit the Wells Street Art Festival
  • Participate in Chicago Pride Fest
  • Check out United States Sail Grand Prix
  • Visit the Gold Coast Art Fair


The weather may be quite hot and humid in July, which is often the warmest time in Chicago.

With numerous events and festivals taking place, including celebration for the Fourth of July, July is a busy month for tourists in Chicago.

Things to Do

  • Get a Taste of Chicago
  • See the Millenium Art Festival
  • Join the Lollapalooza Festival
  • Check out Prince: The Immersive Experience
  • Watch a spectacular Fireworks show


In August, the weather is the most humid in Chicago. If you are sensitive to humidity or heat, it's a better idea not to visit Chicago during this time.

However, if you're able to withstand the heat, August also has the most festivals and events. There are air and water shows, as well as music festivals.

Things to Do

  • See the Chicago Air and Water Show
  • Get your dose of funny at C2E2: Chicago Comic & Entertainment Expo
  • Watch Digital Art at Art on theMart
  • See The Bean at Millennium Park
  • Splash in Crown Fountain


The best weather, in my opinion, occurs in September. This is also the driest month, thus there is less chance of rain because the temperature is still typically warm. Early to mid-September (but after Labor Day weekend) is a fantastic time to visit if you like summer activities with fewer crowds.

Typically, late September is still warm throughout the day but begins to cool off at night. If your resort has an outdoor swimming pool, it will likely be less crowded in September than it is in the summer because the weather is normally mild enough to swim outside.

Things to Do

  • Enjoy the ARC Music Festival
  • Experience the Hyde Park Jazz Festival
  • Check out Riot Fest
  • Look for Street Art
  • Walk or Bike the Lakefront Trail

Related Read: 15 BEST Boozy Bottomless Brunch in Chicago


In terms of weather, October is a wonderful month to travel to Chicago. It is now much more pleasant to wander around it and explore Chicago because the temperature has begun to decrease.

If you favor warm weather, early October still might feel like summer. The second week of October is when you may see the most fall foliage. Mid- to late-October sees the first signs of fall-like weather. There are lots of Halloween-themed events happening all month long if you like that holiday.

Things to Do

  • Run the Bank of America Chicago Marathon
  • Experience the Arts in the Dark Halloween Parade
  • Participate in the Haunted Halsted Halloween Parade & Costume Contest
  • Join the Open House Chicago
  • Visit Local Farmers Markets


November is a fantastic time to travel if you like mild or moderate temps. Although it rarely snows in November, the environment can be a little unpredictable. Early November sees fewer visitors at attractions.

Nevertheless, beginning in the middle of November, tourism begins to increase as more people travel to Chicago for Thanksgiving, Christmas shopping, and other seasonal activities.

Things to Do

  • Watch the Christmas Tree Lighting Ceremony
  • Join the Magnificent Mile Lights Festival
  • Watch the Chicago Thanksgiving Day Parade
  • Enjoy the End of Fall Colors
  • Visit an Authentic German-Style Christmas Market


Although there may be snow and cold weather in December, the temperature is typically relatively warm.

There will be traffic and crowds of people going holiday shopping or coming to Chicago for holiday festivities if you are staying downtown.

Things to Do

  • Check out Christkindlmarket
  • Enjoy the Zoo lights at Lincoln park
  • Experience the One of a Kind Show
  • See the City of Chicago Christmas Tree
  • Visit the Christmas Around the World and Holidays of Light Museum

Best Time to Visit Chicago with Family

Chicago family travel is most popular from June to September. This summer offers a variety of activities that are suitable for families.

If you are traveling with children, I advise booking a trip for August as summer may be very pricey and crowded at attractions. This is the least expensive summer month and will have less hot and humid weather than July.

If you can work around your children's school schedules, April would also be a wonderful time. You'll still have your choice of family events to enjoy, and the weather won't be as scorching. Additionally, entry to the Lincoln Park Zoo is always free!

Related Read: 15 Best Waterfalls Near Chicago

Best Time to Visit Chicago to Avoid Crowds

Winter is the greatest time to visit Chicago if you really want to avoid crowds and have a more relaxing holiday. Hotel occupancy rates in January and February are at their lowest level ever.

Despite the fact that Chicago winters are famously frigid, now is a fantastic time to visit if you want to enjoy all of the indoor attractions this wonderful city has to offer without paying exorbitant costs. The restaurants and museums will be much less crowded than they are during other seasons, and it will be simple to find theatrical tickets.

Additionally, it is always preferable to visit the attractions during the weekdays as opposed to the weekends if you want to deal with less crowds, regardless of the time of year.

Best Time to Visit Chicago for Food

Chicago is a terrific spot for foodies, just like any major metropolis. Visit the Chicago Pizza Party in February to sample deep dish pizzas, or the Chicago Hot Dog Fest in August.

Chicago Restaurant Week, a two-week event when you can enjoy set rates for multi-course meals from some of the best restaurants in Chicago, may coincide with your visit if you're there between mid-March and early April.

Summertime in Chicago is when the two largest food festivals are held. In July, the Chicago Loop plays host to the five-day Taste of Chicago festival. A high-end gourmet dining festival called the Chicago Gourmet festival also happens in September in Millennium Park.

Best Time to Visit Chicago for Outdoor Events

The best time to visit Chicago, when the weather is anticipated to be mostly pleasant and dry, is around September. Additionally, while exploring Chicago's diverse neighborhoods, the fall foliage's changing hues can provide breathtaking vistas.

But that depends on the time of year you choose. The 26 miles of Chicago beaches that run around Lake Michigan are one of the factors that make Chicago so popular in the summer. The water is ideal for swimming from late May until early September. On the Lakefront Trail, you may also take a beautiful stroll or ride a bike.

Winters in Chicago can be your favorite season if you prefer the cold. Between November until the beginning of March, there are numerous ice skating rinks open. At the Soldier Field Sledding Hill or on Northerly Island, you can go sledding or snowshoeing.

When to Visit Chicago to Enjoy the Architecture

One of the most recognizable skylines in the world is in Chicago. On a cruise, from an observation deck like 360 CHICAGO, or by simply strolling about, you may enjoy the breathtaking view.

Although you don't want the cold to ruin your experience, you do want to make sure that you do have a better sight of all the magnificent skyscrapers and the lovely Chicago River.

We advise traveling between April and mid-November if you wish to take a boat tour with the Chicago Architecture Foundation. The best months for walking are from March through June, followed by September and October. The best time to observe the skyline from an observation deck is from late August to mid-September.

When to Visit Chicago for Arts and Culture

Undoubtedly, Chicago is a center for the arts and culture. Over the course of 10 days during Theater Week in February, there are more than 100 performances. Chicago Dance Month takes place in April and features over 50 performances in addition to numerous activities and inexpensive workshops.

The summer months of Chicago are recognized for their numerous music festivals. The most well-known of them is probably Lollapalooza in July, but there are also many other music festivals of different kinds in between, like Do Division in June and Riot Fest in September.

On specific days, many renowned museums in Chicago, like the Money Museum and the Chicago Children's Museum, offer free admission.

When is the Windy Season in Chicago?

Let's get one thing straight: The nickname "The Windy City" has nothing to with Chicago's weather. It alludes to Chicago officials in the 1800s who incessantly courted East Coast capitalists for investment in their city; to so many, they were hysterical.

Some people think that Charles A. Dana's editorial in the New York Sun, which cautioned against allowing Chicago and the "nonsensical promises of that windy city" to host the 1893 World's Columbian Exposition, is where the precise moment originated.

However, independent historians have discovered allusions before Dana, despite the fact that his repeated outbursts may have popularized the moniker. (Dana's original quotation has never been found in print.)

With the headline "That Windy City," the oldest, from a Cincinnati newspaper on May 8, 1876, pokes fun at its competitor in the Midwest.

Even though the article was about a recent tornado, it sarcastically observed that the city's buildings "were so heavily burdened down with debts that no windstorm could impact them" and that this contributed to the minor damage.

What Month Has the Best Weather in Chicago?

Fall is typically the ideal season to visit because of the beautiful weather because it is typically more comfortable.

Fall temperature ranges and can be less predictable. Some of the same Chicago outdoor activities (architecture river cruises, outdoor festivals, outdoor dining) are still available in the early autumn (September and early October) but without the crowds.

Late autumn (late October and November) might feel like summer, fall, or even winter because of the unpredictability of the temperatures.

Best time to visit "The Bean" in Chicago

The number of people at the Cloud Gate varies depending on the weekday and the weather. Your greatest chance to avoid crowds is on weekdays and early in the morning, but if you must visit during the summer or on the weekend, try to arrive before 8 am.

Check the Millennium Park website to see if any events or festivals coincide with the day you intend to visit because these also draw larger numbers.

What is the Best Way to Get Around Chicago?

The L train is the greatest method of public transportation for getting around Chicago. The L, or "elevated train," is run by the Chicago Transit Authority and is reasonably priced and simple to operate.

The CTA also runs a vast bus network with routes serving almost all attractions, however it may be challenging for first-timers to use the bus.

There is also the Metra regional train network, which stops in all of downtown Chicago as well as in other towns and suburbs.

From both local airports, you can travel to the city using public transportation. Chicago Midway International Airport (MDW) is situated about 11 miles south of downtown and can be accessed using the L's Orange Line, while O'Hare International Airport (ORD) is situated 18 miles to the northwest and can be reached using the L's Blue Line.

Although pricey due to high starting prices and additional fees, taxis and ride-hailing companies are also available. The cost of parking in garages and on the street is very high, but both airports have car rental companies if you decide you'll need a pair of wheels.

On Foot & By Bike

Credit: Shutterstock

Chicago is too big to go about on your two feet alone. The individual neighborhoods of the Windy City can be readily explored on foot or by bicycle, nevertheless.

The top Chicago walking tours also make it simple to see parts of the city with the assistance of a local.

Chicago is grid-organized, making it incredibly simple to navigate. Additionally, you can rent a set of wheels anytime you need them thanks to the city's Divvy bike-share program (there are hundreds of stations around the city).

Day passes for Divvy are $15; single rides are $3.30. Bring plenty of clothing with you if you're going in the winter to protect yourself from the famously chilly weather, and remember that winter biking may not be possible due to severe snowfall. Another enjoyable option to experience the city without the stress of a car is to go on a Segway tour.

"L" Train

Credit: Shutterstock

The Chicago subway system's eight lines do not all run above ground, despite the fact that most L train stops are lifted as the system's name suggests. The L system, which is distinguished by color , offers wide and prompt service to 145 stations around the city, including the two airports.

The Blue Line, which connects downtown with O'Hare International Airport, and the Red Line, which traverses downtown from north to south, are the two L lines that run continuously.

Based on the line and the day of the week, trains on the other six lines normally begin running about 4 or 5 am and run till some time between 11 pm and 2 am. Standard one-way costs are $2.50 per person, and if you're going to use the L frequently, you should certainly buy a day pass or week pass.

Permits for one day are $10, three day passes are $20, and seven day passes are $28. A prepaid transportation card with L train and bus compatibility, the Ventra Card, is also available for $5. At the machines located in every L station, you can buy or load money onto Ventra Cards.


Travelers may reach many of Chicago's main sites through one of the roughly 130 bus routes that serve the city, plus additional rush hour express routes. There are certain routes that run continuously, though, like the L train, the majority of buses start running about 4 or 5 in the morning and stop between 11 pm and 2 in the morning.

Only during rush hour on weekdays are express services available. An individual ride costs $2.50 per person in cash or $2.25 with a Ventra Card. Bus use is permitted with CTA day passes, which cost between $10 and $28 depending on how many days they cover.

Metra Rail

Credit: Shutterstock

Metra is your most dependable option for travel to the Chicago suburbs. The 11 lines of the system branch out from the Loop, stopping in North, East, and South Chicago before continuing to neighboring towns such University Park, Aurora, Joliet, and Evanston.

The system is segmented into zones, and the quantity of zones you pass through affects your fare: Depending on distance traveled, a one-way trip can cost anything from $4 to $11. Buy a weekend pass for $10, which entitles you to unlimited rides on Saturdays and Sundays, if you intend to use Metra throughout the weekend.

Remember that when accompanied by an adult who has paid the fee, up to three children under the age of seven may ride free during the week and up to three children under the age of eleven may ride free on weekends and on holidays.

Although schedules differ by day and by line, Metra trains run seven days a week from roughly 4 am until after midnight (and occasionally as late as 2 am).


Taxis are an easy, albeit expensive, way to travel about the Loop and to locations outside of downtown. You should have little issue hailing a cab from the street in the Loop and the Near North Side.

Plan to call for a taxi if you find yourselves outside that immediate neighborhood because there aren't as many cabs available. Each mile costs $2.25 and meters start at $3.25.

Additionally, there are additional fees for travel to and from the runways as well as to and from areas outside of the city. Using a ride-hailing service like Uber or Lyft is a more affordable option.

Water Taxi

Credit: Shutterstock

A water taxi is a fantastic way to go through the heart of Chicago. Two businesses, Shoreline Sightseeing and Chicago Water Taxi, ferry tourists through well-known tourist destinations like Chinatown, the Museum Campus, and the Loop along the Chicago River and Lake Michigan.

Only from the end of May to late September or early October are water taxis in operation (or through November, weather permitting). The day, the route, and the firm all affect the fare. Check out the top Chicago boat tours for additional water-based sightseeing excursions.


The grid pattern of the city will be advantageous if you want to drive. However, you should be prepared for highly restricted parking (which is frequently expensive) and congested roads during rush hour.

You may book places and make payments in advance on a number of applications and websites, such as ParkChicago, SpotHero, and ParkWhiz, which can help alleviate some of that frustration.

You'd be better off using public transportation if you're traveling during the winter and lack much expertise driving on snowy roads because snowfall reduces visibility.

Related Read: 12 BEST Water Parks in Illinois

How Much Time Do You Need to See Chicago?

Most people only need about 3 days to be able to get a taste of what Chicago has to offer. If you only have a handful of places you want to go then this is more than enough time.

However, if you're someone who prefers to take their time, or you have a lot of places that you want to visit, you'll need more time. Ideally, to take your time exploring, you will want at least 5 to 7 days.

It helps if you have your reservations booked ahead of time so that you don't have to wait longer than intended to enjoy a restaurant you had your eye on. Call ahead, and book your tickets and reservations before visiting Chicago so that your trip goes smoothly!

Tobi Miles
Article updated:
March 28, 2024
A nomadic wordsmith savoring the world's flavors and penning stories that turn every journey into an epic.
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