When searching for a travel destination, what excites you most? Might it be vibrant art, cultural attractions, and festivals? Then Chicago should be your next holiday getaway. 

Commonly referred to as The Hollywood of the Midwest, or The Windy City, Chicago is teeming with life. It is popular with tourists owing to the diverse social and educational experiences on offer, making it an ideal spot for solo travelers, couples, and families alike. 

And whatever time of year you choose to travel, you can be sure that Chicago will be jam-packed with sights to see and plenty of things to do. So, pack your bags and get ready for a magnificent adventure in Chicago.

Why visit Chicago?

The third most populous area in the United States, Chicago is busy, bright, and bustling at any time of year. 

Chicago is a cultural epicenter, renowned for its art, cuisine, and entertainment. In fact, Chicago boasts more than 40 world-class museums, over 200 theaters, more than 200 independent art galleries, and over 7000 restaurants! With excellent transport links, plus year-round events and activities, you’ll never be short of something to see or do in the city.

When is high season in Chicago?

Because Chicago is such a popular city offering a plethora of local festivities year-round, there’s never really a ‘quiet’ time to visit. 

That said, there are a few peak times for holiday-makers:

  • Mid to late March for St. Patrick’s Day and Spring Break;
  • The summer, owing to good weather, and the period between Memorial Day and Labor Day;
  • The holiday/ Christmas season, from mid-November to early January. 

But, don’t let high season put you off – the city is huge, so you can always find a quieter spot away from the crowds, and plan visits to hotspots at just the right time to avoid the crowds.

These peaks are the most expensive times to visit, however, with air fare and hotel prices increasing.

When is low season in Chicago?

If you want to avoid the crowds as much as possible, we advise a visit in late winter (February), mid-to-late spring (April to May), or early fall (September to October).

In February the weather is a little chilly, but prices for travel and accommodation are at their lowest. 

In both spring and the fall, the weather is mild and can be great times of year for outdoor activities.

When’s the best time to visit Chicago? 

Well, unless you’re picky about the weather, any time of year is a great time to visit Chicago! 

That’s because there’s lots to do and see, both indoors and outdoors, so you can pick and choose the best option for your holiday:

Spring – best time to visit Chicago for food and drink festivals

Springtime is probably best for the adults – whether you’re a group, couple, or solo traveller. That’s because there are also many boozy-filled shenanigans and some amazing cuisine best suited to veteran tastebuds. Some of the biggest events are:

  • St. Patrick’s Dayexpect LOTS of bar crawls across the city, filled with endless pints of Guinness. Bear in mind that the parades often take place the weekend before, so be sure to book early if you want to catch one. 
  • Chicago Restaurant Week – Usually held towards the end of March/beginning of April, diners across the city offer prix fixe menus (several courses at a fixed price) – typically, $25 for brunch or lunch, and $39 for dinner. This year, restaurants will offer a mixture of indoor and outdoor seating. 
  • Taste of Chicagothis is the world’s largest food festival, held for five days in July in Chicago. This festival offers you the best opportunity to try some of the local delicacies, including deep-dish pizza and Chicago-style hotdogs.

Some smaller festivals include:

  • WhiskyFest Chicagofor more of an upmarket feel, try out the best Scotch Whiskey in Chicago. Held at Hyatt Regency Chicago, it’s a pretty glamorous event, usually held in March.
  • Baconfestthe clue is in the name: this festival is dedicated to all things bacon! So, if you are a bacon lover, this festival is for you! The event takes in April in downtown Chicago. 
  • Lincoln Square Wine Strollfor a more laidback feel, the Wine Stroll is the perfect way to explore some of the neighborhoods and local shops – specifically, wine shops! In Lincoln Square and Ravenswood neighborhoods, retailers and restaurants become hotspots for wine tasting and appetizers. This event is usually held in April. 

Summer and Fall – best time to visit Chicago with family

Chicago Downtown


Summer is one of the best times to visit Chicago with family, are there are just so many things to see and do which everyone can enjoy together:


Searching for a sunny beach holiday? Believe it or not, Chicago is home to some of the best beaches, giving you the chance to enjoy a perfect city break, with the added bonus of sun, sea, and sand.

The gold coast is one of the most popular beaches in Chicago – but be mindful that in the summer, it’s likely to be busy.


There are green spaces galore in this huge city, and Chicago boasts some of the best parks in the US. Lincoln Park has an added bonus – The Lincoln Park Zoo. Kinds will love the opportunity to see some exotic animals. 

Rain is sometimes a given this time of year, so a rainy day can be spent at the indoor Garden Park Conservatory which houses a Sensory Garden and Play Garden.

And if you want to see some water, why not enjoy some of the cycling tours along the Lakefront Trail?

Outdoor art 

Outdoor art installations are a speciality in Chicago, with the most popular spots including The Millennium Park for contemporary art, and The Crown Fountain for an interactive experience.

There are also many sculptures dotted across the city, including works by Picasso and Marc Chagall – you can’t miss them!

The Chicago skyline

Chicago’s skyline is among the world’s tallest and densest, giving the city one of its most recognisable features. 

Spring and summer offer some of the clearest days to get the best view – but, be mindful that rain can wash over the city on ay day, so always check the forecast.

To get the best view of the skyline, we recommend heading to the Observation Deck, offering a panoramic 360° viewpoint.

Afterwards, you can walk the nearby Magnificent Mile – Chicago’s upmarket commercial area, boasting some impressive architecture from the world renowned ‘Chicago School’ style.  Don’t forget to look up!

Summer and Fall: The Festival Season in Chicago

Festival season really gears up a notch in the summer too, and most of them are free! Some of the most impressive festivals are Lollapalooza and North Coast Music Festival. 

For those who like to dance, there’s also the Chicago SummerDance Celebration, happening every weekend, all summer at Millennium Park.

Festivals like Oktoberfest and regular Halloween celebrations make fall an exciting time to visit Chicago. 

For the kids, there are some great corn mazes to get lost in, and for the adults some wonderful coffeeshops with outdoor seating, and beer gardens to take advantage of. Why not try the Pilot Project for a niche beer-tasting experience?

Fall is also great for fruit and veg picking, so make sure you visit one of the local orchards or pumpkin patches to pick the best of the bunch!

Winter – the best time for indoor fun 

They might have some mean winter weather in Chicago, but there are plenty of ways to shelter from the cold. 

Museums and galleries

Chicago has many museums open year-round, with exhibitions for every taste. Three of them are located within Museum Campus: Shedd Aquarium, Adler Planetarium, and the Field Museum.

Some other excellent museums include the Museum of Science and Industry, the Peggy Notebaert Nature Museum, and the DuSable Museum of African American Culture. 

The city is also home to some impressive art galleries, such as the Art Institute of Chicago and the Woman Made Gallery. 

Theater and comedy

Theater and comedy shows are notorious in Chicago, with companies such as Broadway In Chicago showcasing some of the hottest productions, at five different historic theaters across the city.

The Drunk Shakespeare is a popular spot for some comedy and a tipple, while the Chicago Magic Lounge offers a great experience for all the family. 

Why not catch a performance before you head out and paint the town red?

Nightlife and music

The nightlife in Chicago is certainly something to brag about. It’s a hot partying spot for celebrities – Kanye, is that you? – offering an eclectic mix of lounges, bars, and clubs. For partying and dancing, you can try Stereo Nightclub and DISCO.

And if dancing isn’t for you, but you want to enjoy some music, then Chicago is famed for its jazz bars, including Winter’s Jazz Club, House of Blues, and Jazz Showcase. These places are also ideal if you want dinner and a show.

The Holiday Season

This is one of the busiest times of year, but if you want to round off your year in style, then do so in Chicago.

There are lots of indoor (and outdoor) Christmas displays to be seen. Many of the museums mentioned above offer festive displays, whilst the Botanic Garden lights up spectacularly with light tunnels.

There are also pop-up Christmas shops galore across the city, and you can watch festive shows such as The Nutcracker at The Auditorium Theatre.

Best time to visit Chicago: the bottom line

As you can see, there’s so much to do and see in Chicago each season. That’s what makes Chicago a great place to visit all year round. However, the best time to visit Chicago is different for every traveler. It will depend on what you want to do and see. If you want to visit Chicago on a budget, the best time to visit the city is in the low season. In February, hotel prices in Chicago are at their lowest. So, you might want to take advantage of that. However, if you prefer warmer temperatures and want to enjoy the numerous outdoor activities that the city has to offer, the best time to visit Chicago would be from late spring to early fall. If you are into sightseeing, the best time to visit Chicago is in May or September, as temperatures outside are still warm, but not overly hot.

We hope that this guide has helped you make a decision on the best time to visit Chicago!

Perhaps, you are already planning your travel? Click here to see the 10 best hotels in Chicago.