Best time to visit Chicago

11 days
  • Sep
  • Oct
  • Nov
  • Dec
  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
Tue Oct 23Nov 02 Fri

Best time of year to visit Chicago

April to May and September to October is the best time to visit Chicago as the weather is mild and tourist numbers are moderate. In late spring, celebrate local beer culture at the Mayfest. Summer in the city is famous for its hotel rates going through the roof and unstable weather when agonizing heat waves from June to August can hinder your sightseeing experience. However, Chicago is lucky to be located next to the lake, that's why festival goers boldly and enthusiastically attend Lollapalooza and other great summer events. September says goodbye to the summer at the Chicago Jazz Festival and during the Chicagohenge at the end of the month. A freezing and windy period between November and March offers you great deals on airfare and accommodation, just pack your warmest layers. St. Patrick's Day turns the Chicago River green in March, probably one of the best sights of the city!


Summer Fireworks at Navy Pier

June–August • event

For the whole summer you have a chance to see the beautiful fireworks twice a week!

4th of July Fireworks & Events

July 04 • event

Enjoy the most important holiday of the summer on the shore of Lake Michigan

Beach Season

July–August • activity

Chicagoans love summers, even though they are extremely hot and humid. Part of this love is surplused by the existance of beaches

Kayaking Season

June–October • activity

Take a kayaking trip on the beautiful Chicago River

The Plant Chicago

all year round • activity

A former meatpacking facility is transformed into a human-made ecosystem

Willis Tower (Skydeck Chicago)

all year round • activity

Step to the glass box ledge and walk in the air 1,353 feet above Chicago

Sailing Season

May–October • activity

Sailing is much time limited in Chicago due to the weather conditions



March 20 • nature

This remarkable urban scene happens twice a year!

Chicago Air and Water Show

August 18–19, 2018 • event

The oldest and largest show of this kind in the United States

St. Paddy's Day

March 16, 2019 • event

St. Patrick's Day in Chicago is definitely a party of a lifetime!

Roscoe Village Burger Fest

July 13–14, 2019 • event

The mouthwatering burger festival

Rubber Ducky Race

August 09, 2018 • event

50,000 yellow rubber ducks are splashed into the Chicago River to fundraise for the Special Olympics Illinois

Windy City Smokeout

July 13–15, 2018 • event

Starting as a local barbecue get-together, the Smokeout has become one of the best festivals in town!

Kids and Kites Festival

May 05, 2018 • event

The spectacular and beautiful celebration of the spring's arrival!

Chinatown Lunar New Year Parade

February 05, 2019 • event

Chinese New Year is celebrated heavily in Chicago


March 02, 2019 • event

Isn't it your lifetime dream to race in a cart of food between the neighbourhood bars?

Chicago Polar Plunge

March 04, 2018 • event

Raising money for a cause is always a good idea, even if it means jumping into the frosty Lake Michigan!


May 17–19, 2019 • event

As an Oktoberfest's counterpart, this festival offers you plenty of foods and drinks as well as beer gardens!

Chicago Blues Festival

June 7–9, 2019 (TBC) • event

The largest free blues festival in the world and one of the greatest music festivals in Chicago

Chicago Jazz Festival

August 24–September 02, 2018 • event

A favorite Labor Day Weekend tradition with great music all over the city

Ribfest Chicago

June 08–10, 2018 • event

One of Chicago's trademarks, the Ribfest attracts crowds annually

MB Bike the Drive

May 2019 (TBA) • event

Once in a year a lakefront road is closed for cars and open for the cyclists!

Chicago Pride Parade & Fest

June 22–23, 2019 | June 30, 2019 • event

A colorful celebration of freedom, diversity and culture

Ginza Holiday Festival

August 10–12, 2018 • event

Lots of Japanese food, culture and entertainment

Dragon Boat Race for Literacy

June 23, 2018 • event

Traditionally ornated Chinese Boats race through Chicago River for Literacy

Chicago Auto Show

February 09–18, 2019 • event

The biggest auto show in North America

Arts in the Dark Halloween Parade

October 20, 2018 • event

The most fun fall event loved by kids and adults

Chicago Marathon

October 07, 2018 • event

Check out the scenic course of one of the largest marathons in the U.S.

Chicago International Film Festival

October 10–21, 2018 • event

The longest-running competitive film festival in the USA

Chicago Museum Week

January 18–26, 2018 • event

Free events, special programs and promotions at Chicago's best museums

Chicago Theatre Week

February 2019 (TBA) • event

A range of extraordinary theatrical offerings returns to Chicago every year in February

Cupid's Undie Run

February 2019 (TBA) • event

Chicago loves running wearing hardly anything. Of course, for the good cause

Taste of Chicago

July 2019 (TBA) • event

Note down the recipe for an unforgettable food & music festival

Chicago Restaurant Week

January 26–February 08, 2018 • event

So many participating restaurants, so little time

BMO Harris Magnificent Mile Lights Festival

November 16–17, 2018 • event

The holiday spirit takes over the Michigan Avenue on that night

Chicago Food Truck Festival

September 22–23, 2018 • event

The city by Lake Michigan is obsessed with food trucks

Chicago Thanksgiving Parade

November 22, 2018 • event

One of the biggest fall events in Chicago

World Music Festival Chicago

September 07–23, 2018 • event

Musicians from over 20 countries give about 50 performances with free admission

Chicago Latino Film Festival

April 05–19, 2018 • event

A great selection of films, documentaries, and shorts from the Spanish-speaking world

Memorial Day Parade

May 25, 2019 • event

Don't miss your chance to see the largest Memorial Day Parade in the country


August 01–04, 2019 • event

One of the oldest and most famous alternative music festivals is a must-visit!

Critical Mass

April 27, 2018 • event

The monthly event to make it clear how many cyclists are there


December–February • activity

Linkoln Park Zoo is not only one of the biggest and oldest zoos in the USA, but it also boasts some perfect winter scenery


July 20–22, 2018 • event

One of the trendiest festivals, Pitchfork sets the music scene

Chicago Craft Beer Week

May 18–25, 2018 • event

The Illinois Craft Brewers Guild organizes the massive 11 days long craft beer event

Tour de Fat

July 30, 2018 • event

The festival of bikes and environmentally conscious people!


April 05–06, 2019 • event

A festival dedicated to bacon? Definitely one of the best ideas in the world!

Journey to the End of the Night

June 01–30, 2017 • activity

The urban game that attracts thousands of people

Santa Speedo Run

December 01, 2018 • event

Be merry, be positive, be helpful, be Santa! Thousands of Christmas fans running in the swimming suits.