Chicago, IL Calendar of Events

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Fill up your vacation time with fun events by planning your vacation with Chicago, IL Calendar of Events which allows you to search for various events including festivals, parades, trade shows, conventions, and more. Make your vacation time quality time by planning ahead with Chicago, IL Calendar of Events.
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Chicago Event Calendar

April 2018 Chicago Events

May 2018 Chicago Events

July 2018 Chicago Events

September 2018 Chicago Events

  • Monday, September 3
    Labor Day Weekend in Chicago, IL
    Relax from work and take the whole family out for a weekend of fun, activities, music, and more during Labor Day Weekend in Chicago, IL.


  • Saturday, September 1 - Sunday, September 30
    Behind-the-Scenes Chicago Pizza Tour
    Get an exclusive view inside four famous Chicago pizzerias on this 3.5-hour tour and enjoy delicious slices at each!


  • Saturday, September 1 - Sunday, September 30
    Chicago Sunset Dinner Cruise with Buffet
    Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan.


  • Saturday, September 1 - Sunday, September 30
    Chicago Movie Tour
    Movie buff or not, you'll see the best of Chicago on this movie tour of the city!


  • Saturday, September 1 - Sunday, September 30
    Chicago Architecture River Cruise
    Experience one of the world's most beautiful cities on a 1-hour cruise on the historic Chicago River.


  • Saturday, September 1 - Sunday, September 30
    Chicago Small-Group Sightseeing Tour with Optional Boat Cruise
    Don't miss Chicago's famous sights and fabulous views on this small-group sightseeing tour of the city.


  • Wednesday, September 5 - Wednesday, September 26
    Chicago Walking Tour: Tiffany Art Glass Landmarks
    This tour explores the art glass designed, crafted or installed by the Tiffany Glass and Decorating Company, Louis Comfort Tiffany and his contemporaries, in four late 19th Century Chicago landmarks: The Art Institute The Marquette Building The Chicago Cultural Center Macy's on State Street (historic Marshall Field's store) Discover mosaics, lighting fixtures, vaults and domes, as well as the buildings in which they are housed, recent restoration efforts, and the history behind this dramatic art form.


  • Saturday, September 1 - Sunday, September 30
    Chicago Walking Tour: Modern Architecture
    Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles that incorporate new, environmentally-sustainable technology.


  • Saturday, September 1 - Sunday, September 30
    Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs
    Taste the flavors of Chicago, both edible and cultural, on a bike tour through the city.


  • Saturday, September 1 - Sunday, September 30
    Chicago Walking Tour: Art Deco Architecture
    Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour.


  • Saturday, September 1 - Sunday, September 30
    Chicago Walking Tour: Historic Loop Skyscrapers
    Perhaps Chicago's most identifiable claim to fame resides in its architecture.


  • Saturday, September 1 - Sunday, September 30
    Chicago Lakefront Neighborhoods Bicycle Tour
    Accept no imitations!


  • Saturday, September 1 - Sunday, September 30
    Chicago Crime and Gangsters Tour
    Some of the world's most notorious criminals, mobsters and gangsters bamboozled their way through Chicago.


  • Saturday, September 1 - Sunday, September 30
    Chicago Prohibition Tour
    Meet your guide at the Green Door Tavern to start the 3.5-hour journey to four historic Chicago speakeasies used during Prohibition that still operate today.


  • Saturday, September 1 - Sunday, September 30
    Chicago Segway Tour
    The tour begins with a 30 minute training session.


  • Saturday, September 1 - Sunday, September 30
    Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour
    Meet your guide at the southeast entrance of the Chase Tower to start your exploration of the Loop's interior architecture.


  • Saturday, September 1 - Sunday, September 30
    Chicago Architectural River Cruise
    This 90 minute Architectural cruise sails on the Chicago River.


  • Saturday, September 1 - Sunday, September 30
    Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs
    Follow your knowledgeable guide through downtown Chicago and visit a number of stunning indoor spaces including the historic Palmer House Hotel, the Walnut Room and Macy's.


  • Saturday, September 1 - Sunday, September 30
    Chicago Odyssey Dinner Cruise
    For an experience that begins well before the cruise departs, arrive early dressed in your most festive attire.


  • Saturday, September 1 - Sunday, September 30
    Chicago Helicopter Tour Nighttime Experience
    The experience begins with an interactive customer experience terminal and virtual flight simulator.


  • Saturday, September 1 - Saturday, September 29
    Bacon and Brewing Beer Tour in Lakeview and Lincoln Park
    This walking tour begins at a favorite local bar where you will meet your tour guide and enjoy your first tasting of the day.


  • Saturday, September 1 - Sunday, September 30
    Chicago Lakefront and Museum Campus Segway Tour
    There is nothing like seeing the city on a Chicago Segway tour.


  • Saturday, September 1 - Sunday, September 30
    Chicago Helicopter Tour Daytime Experience
    Located minutes from Chicago area hotels, the heliport and interactive customer experience terminal are ready to offer an exhilarating journey.


  • Saturday, September 1 - Sunday, September 30
    Historic Chicago Walking Bar Tour
    Meet your guide inside the Tribune Tower to begin your pub, architecture and entertainment history tour.


  • Saturday, September 1 - Sunday, September 30
    Food Tour in Chicago's Wicker Park
    This tour is perfect for Chicago natives and visitors interested in exploring a variety of foods, plethora of drinks, and a smidgeon of history, all within 4 blocks of a Chicago neighborhood.


  • Sunday, September 2 - Sunday, September 30
    Chicago Odyssey Brunch Cruise
    Step Aboard.


  • Saturday, September 1 - Saturday, September 29
    3-Hour Walking and Food Tour: Chicago World's Fair of 1893
    This very special walking tour digs into how and why the 1893 World's Fair captures imaginations more than any other event in Chicago history.


  • Saturday, September 1 - Sunday, September 30
    Duneland Wine Country with Gourmet Lunch
    Meet at the InterContinental Chicago Magnificent Mile or receive pickup from your accommodation in the Chicago Loop.


  • Saturday, September 1 - Sunday, September 30
    Private Chicago Craft Beer and Pizza Tour
    Chicago is home to many world-class craft breweries and you'll visit three of them on this private 4-hour evening tour, starting with hotel pickup.


  • Saturday, September 1 - Sunday, September 30
    Underground Donut Tour - Chicago's First Donut Tour
    We've always had a passion for donuts, but only recently did we realize just how many others do too.


  • Saturday, September 1 - Saturday, September 29
    Tickets for Kiss Kiss Cabaret at Uptown Underground
    By the time you pass the dapper doorman and reach the bottom of the grand staircase, you'll have jumped back in time to an era long past.


  • Thursday, September 6 - Friday, September 28
    Old Polonia and Wicker Park History and Food Tour
    Learn about Chicago's lively history by visiting two of its most fascinating neighborhoods — Noble Square and Wicker Park — on this friendly, 2.5-hour food and walking tour.


  • Sunday, September 2 - Sunday, September 30
    Private Sunset Sails
    The Experience Come Sailing is Chicago's Premier Private Sailing Charter offering daily sailing charters, sunset sails, fireworks cruises, and customized sailing experiences.


  • Saturday, September 1 - Sunday, September 30
    Transfer to Chicago Premium Outlets
    Chicago Premium Outlets is located 36 miles (58km) from downtown Chicago.


  • Monday, September 3 - Thursday, September 27
    Auditorium Theatre Historic Tour
    A National Historic Landmark, the Auditorium Theatre is known internationally for its perfect acoustics, innovative architecture, and stunning design.


  • Saturday, September 1 - Sunday, September 30
    Private Guided Suv Tour for Up to 4 Guests
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury SUV with comfortable seating for 1-4 guests plus the guide and driver.


  • Saturday, September 1 - Sunday, September 30
    Private Guided Tour of Chicago by Deluxe Mini-Coach for Up to 12 Guests
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury mini-coach with comfortable seating for up to 12 guests plus the guide and driver.


  • Saturday, September 1 - Sunday, September 30
    Private Guided Tour by Suv for Up to 4 Guests - International Languages
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury SUV with comfortable seating for 1-4 guests plus the guide and driver.


  • Saturday, September 1 - Sunday, September 30
    Private Guided Tour of Chicago - Deluxe Coach for 12 - International Languages
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury mini-coach with comfortable seating for up to 12 guests plus the guide and driver.


  • Saturday, September 1 - Sunday, September 30
    Outbreak Escape Room in Schaumburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Saturday, September 1 - Sunday, September 30
    Bank Heist Escape Room in Schaumburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Saturday, September 1 - Sunday, September 30
    Sorcerer's Secret Escape Room in Schaumburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Saturday, September 1 - Sunday, September 30
    Lost in Time Escape Room in Schaunburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Saturday, September 1 - Saturday, September 29
    Spirit of Chicago Lunch Cruise with Buffet
    For groups of all sizes, a Spirit Cruise is the venue that delivers a memorable experience where guests will have fun from start to finish.


  • Saturday, September 1 - Sunday, September 30
    Gateway to the West Loop
    An expert guide helps you to easily navigate the exciting West Loop neighborhood as you discover the diverse history, architecture and culture of the area in this 2.5 hour tour.


  • Saturday, September 1 - Sunday, September 30
    Gangsters and Ghosts Tour in Chicago
    The area most associated with gangster era crime and haunting is known as 'The Loop'. This was the cities vice district during the roaring 20's and 1930's riddled with speakeasy saloons, secret underground tunnels used by bootleggers and the headquarters of famous gangsters such as Al Capone.


November 2018 Chicago Events

  • Sunday, November 11
    Veterans Day in Chicago, IL
    Veterans Day in Chicago IL Isa Day that pays respect to the men and women in Armed Forces who have fought in previous wars and ongoing conflicts.


  • Thursday, November 22
    Chicago Thanksgiving Parade
    The Chicago Thanksgiving Parade runs on State Street from Congress Parkways to Randolph Street through the heart of Chicago, Illinois.


  • Thursday, November 22
    Thanksgiving in Chicago, IL
    Thanksgiving in Chicago IL is today where the community can come together to give thanks and appreciation for all of the blessings in their lives.


  • Thursday, November 1 - Friday, November 30
    Chicago Sunset Dinner Cruise with Buffet
    Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan.


  • Saturday, November 3 - Sunday, November 18
    Chicago Movie Tour
    Movie buff or not, you'll see the best of Chicago on this movie tour of the city!


  • Thursday, November 1 - Friday, November 30
    Chicago Architecture River Cruise
    Experience one of the world's most beautiful cities on a 1-hour cruise on the historic Chicago River.


  • Thursday, November 1 - Friday, November 30
    Chicago Small-Group Sightseeing Tour with Optional Boat Cruise
    Don't miss Chicago's famous sights and fabulous views on this small-group sightseeing tour of the city.


  • Wednesday, November 7 - Wednesday, November 28
    Chicago Walking Tour: Tiffany Art Glass Landmarks
    This tour explores the art glass designed, crafted or installed by the Tiffany Glass and Decorating Company, Louis Comfort Tiffany and his contemporaries, in four late 19th Century Chicago landmarks: The Art Institute The Marquette Building The Chicago Cultural Center Macy's on State Street (historic Marshall Field's store) Discover mosaics, lighting fixtures, vaults and domes, as well as the buildings in which they are housed, recent restoration efforts, and the history behind this dramatic art form.


  • Thursday, November 1 - Friday, November 30
    Chicago Walking Tour: Modern Architecture
    Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles that incorporate new, environmentally-sustainable technology.


  • Friday, November 2 - Friday, November 30
    Tastes of Chicago Bike Tour: Chicago-Style Pizza, Beer, Cupcakes and Hot Dogs
    Taste the flavors of Chicago, both edible and cultural, on a bike tour through the city.


  • Thursday, November 1 - Thursday, November 29
    Chicago Walking Tour: Art Deco Architecture
    Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour.


  • Thursday, November 1 - Friday, November 30
    Chicago Walking Tour: Historic Loop Skyscrapers
    Perhaps Chicago's most identifiable claim to fame resides in its architecture.


  • Thursday, November 1 - Friday, November 30
    Chicago Lakefront Neighborhoods Bicycle Tour
    Accept no imitations!


  • Thursday, November 1 - Friday, November 30
    Chicago Crime and Gangsters Tour
    Some of the world's most notorious criminals, mobsters and gangsters bamboozled their way through Chicago.


  • Friday, November 2 - Friday, November 30
    Chicago Prohibition Tour
    Meet your guide at the Green Door Tavern to start the 3.5-hour journey to four historic Chicago speakeasies used during Prohibition that still operate today.


  • Friday, November 2 - Thursday, November 29
    Chicago Segway Tour
    The tour begins with a 30 minute training session.


  • Thursday, November 1 - Friday, November 30
    Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour
    Meet your guide at the southeast entrance of the Chase Tower to start your exploration of the Loop's interior architecture.


  • Thursday, November 1 - Friday, November 30
    Chicago Architectural River Cruise
    This 90 minute Architectural cruise sails on the Chicago River.


  • Friday, November 2 - Sunday, November 18
    Chicago Food Tour: Chicago-Style Pizza, Beer, Brownies, and Hot Dogs
    Follow your knowledgeable guide through downtown Chicago and visit a number of stunning indoor spaces including the historic Palmer House Hotel, the Walnut Room and Macy's.


  • Friday, November 2 - Sunday, November 25
    Chicago Odyssey Dinner Cruise
    For an experience that begins well before the cruise departs, arrive early dressed in your most festive attire.


  • Thursday, November 1 - Friday, November 30
    Chicago Helicopter Tour Nighttime Experience
    The experience begins with an interactive customer experience terminal and virtual flight simulator.


  • Saturday, November 3 - Saturday, November 17
    Bacon and Brewing Beer Tour in Lakeview and Lincoln Park
    This walking tour begins at a favorite local bar where you will meet your tour guide and enjoy your first tasting of the day.


  • Thursday, November 1 - Friday, November 30
    Chicago Lakefront and Museum Campus Segway Tour
    There is nothing like seeing the city on a Chicago Segway tour.


  • Thursday, November 1 - Friday, November 30
    Chicago Helicopter Tour Daytime Experience
    Located minutes from Chicago area hotels, the heliport and interactive customer experience terminal are ready to offer an exhilarating journey.


  • Thursday, November 1 - Friday, November 30
    Historic Chicago Walking Bar Tour
    Meet your guide inside the Tribune Tower to begin your pub, architecture and entertainment history tour.


  • Saturday, November 3 - Sunday, November 25
    Food Tour in Chicago's Wicker Park
    This tour is perfect for Chicago natives and visitors interested in exploring a variety of foods, plethora of drinks, and a smidgeon of history, all within 4 blocks of a Chicago neighborhood.


  • Sunday, November 4 - Sunday, November 25
    Chicago Odyssey Brunch Cruise
    Step Aboard.


  • Friday, November 2 - Friday, November 30
    3-Hour Walking and Food Tour: Chicago World's Fair of 1893
    This very special walking tour digs into how and why the 1893 World's Fair captures imaginations more than any other event in Chicago history.


  • Thursday, November 1 - Thursday, November 29
    Duneland Wine Country with Gourmet Lunch
    Meet at the InterContinental Chicago Magnificent Mile or receive pickup from your accommodation in the Chicago Loop.


  • Friday, November 2 - Friday, November 30
    Private Chicago Craft Beer and Pizza Tour
    Chicago is home to many world-class craft breweries and you'll visit three of them on this private 4-hour evening tour, starting with hotel pickup.


  • Friday, November 2 - Friday, November 30
    Underground Donut Tour - Chicago's First Donut Tour
    We've always had a passion for donuts, but only recently did we realize just how many others do too.


  • Friday, November 2 - Friday, November 30
    Tickets for Kiss Kiss Cabaret at Uptown Underground
    By the time you pass the dapper doorman and reach the bottom of the grand staircase, you'll have jumped back in time to an era long past.


  • Tuesday, November 20 - Friday, November 30
    Chicago Holiday Stroll and Food Tour
    Meet your guide in downtown Chicago to start your holiday walking tour.


  • Saturday, November 24 - Friday, November 30
    Chicago Holiday Lights Tour by Segway
    Bundle up in your warm clothes and make your way to a conveniently located point near Millennium Park in downtown Chicago to meet your guide for your Segway tour.


  • Thursday, November 1 - Friday, November 30
    Transfer to Chicago Premium Outlets
    Chicago Premium Outlets is located 36 miles (58km) from downtown Chicago.


  • Tuesday, November 6 - Tuesday, November 27
    Auditorium Theatre Historic Tour
    A National Historic Landmark, the Auditorium Theatre is known internationally for its perfect acoustics, innovative architecture, and stunning design.


  • Thursday, November 1 - Friday, November 30
    Private Guided Suv Tour for Up to 4 Guests
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury SUV with comfortable seating for 1-4 guests plus the guide and driver.


  • Thursday, November 1 - Friday, November 30
    Private Guided Tour of Chicago by Deluxe Mini-Coach for Up to 12 Guests
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury mini-coach with comfortable seating for up to 12 guests plus the guide and driver.


  • Thursday, November 1 - Friday, November 30
    Private Guided Tour by Suv for Up to 4 Guests - International Languages
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury SUV with comfortable seating for 1-4 guests plus the guide and driver.


  • Thursday, November 1 - Friday, November 30
    Private Guided Tour of Chicago - Deluxe Coach for 12 - International Languages
    Your expert local guide and professional chauffeur arrive at your hotel in a luxury mini-coach with comfortable seating for up to 12 guests plus the guide and driver.


  • Saturday, November 3 - Saturday, November 17
    Spirit of Chicago Lunch Cruise with Buffet
    For groups of all sizes, a Spirit Cruise is the venue that delivers a memorable experience where guests will have fun from start to finish.


  • Thursday, November 1 - Friday, November 30
    Gangsters and Ghosts Tour in Chicago
    The area most associated with gangster era crime and haunting is known as 'The Loop'. This was the cities vice district during the roaring 20's and 1930's riddled with speakeasy saloons, secret underground tunnels used by bootleggers and the headquarters of famous gangsters such as Al Capone.


December 2018 Chicago Events

February 2019 Chicago Events

  • Thursday, February 14
    Valentine's Day in Chicago
    Definitely a romantic city, Chicago will be a great host to you and your sweetheart on Valentine's Day.


  • Sunday, February 3 - Thursday, February 28
    Chicago Sunset Dinner Cruise with Buffet
    Celebrate a night out in Chicago with dinner, dancing and sightseeing aboard a three-hour luxury cruise on Lake Michigan.


  • Wednesday, February 6 - Wednesday, February 27
    Chicago Walking Tour: Tiffany Art Glass Landmarks
    This tour explores the art glass designed, crafted or installed by the Tiffany Glass and Decorating Company, Louis Comfort Tiffany and his contemporaries, in four late 19th Century Chicago landmarks: The Art Institute The Marquette Building The Chicago Cultural Center Macy's on State Street (historic Marshall Field's store) Discover mosaics, lighting fixtures, vaults and domes, as well as the buildings in which they are housed, recent restoration efforts, and the history behind this dramatic art form.


  • Friday, February 1 - Thursday, February 28
    Chicago Walking Tour: Modern Architecture
    Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles that incorporate new, environmentally-sustainable technology.


  • Saturday, February 2 - Thursday, February 28
    Chicago Walking Tour: Art Deco Architecture
    Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour.


  • Friday, February 1 - Thursday, February 28
    Chicago Walking Tour: Historic Loop Skyscrapers
    Perhaps Chicago's most identifiable claim to fame resides in its architecture.


  • Saturday, February 2 - Sunday, February 24
    Chicago Helicopter Tour Daytime Experience
    Located minutes from Chicago area hotels, the heliport and interactive customer experience terminal are ready to offer an exhilarating journey.


  • Saturday, February 2 - Sunday, February 24
    Food Tour in Chicago's Wicker Park
    This tour is perfect for Chicago natives and visitors interested in exploring a variety of foods, plethora of drinks, and a smidgeon of history, all within 4 blocks of a Chicago neighborhood.


  • Saturday, February 2 - Saturday, February 23
    3-Hour Walking and Food Tour: Chicago World's Fair of 1893
    This very special walking tour digs into how and why the 1893 World's Fair captures imaginations more than any other event in Chicago history.


  • Wednesday, February 27 - Thursday, February 28
    Outbreak Escape Room in Schaumburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Wednesday, February 27 - Thursday, February 28
    Bank Heist Escape Room in Schaumburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Wednesday, February 27 - Thursday, February 28
    Lost in Time Escape Room in Schaunburg
    Located 1-hour from Chicago in Schaumburg Illinois.


  • Thursday, February 14 - Saturday, February 16
    Valentine's Day Buffet Dinner Cruise
    Make your way to Navy Pier, and step aboard the Spirit for a romantic evening.


  • Thursday, February 14 - Saturday, February 16
    Chicago Odyssey Valentine's Day Dinner Cruise
    Spend an exceptional evening cruising the shoreline of Chicago onboard a luxury yacht, admiring the city's striking architecture as you enjoy a gourmet, 3-course dinner.


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Previous Events
Air and Water Show in Chicago, IL
Chicago Flower & Garden Show in Chicago, IL
Chicago Jazz Festival at Millennium Park in Chicago, IL
Clearbrook Wonderland of Lights at Arlington Park Racecourse
Dance Fest at Six Flags Great America in Chicago, IL
Frankfort Fall Festival in Frankfort near Chicago, IL
Fright Fest at Six Flags Great America in Chicago, IL
Girl and Boy Scout Days at Six Flags Great America in Chicago, IL
Groundhog Days near Chicago, IL
Lincoln Square Winter Brew in Chicago, IL
Main Sweet Dessert Walk near Chicago, IL
Marketing Day at Six Flags Great America in Chicago, IL
Math and Science Days at Six Flags Great America in Chicago, IL
New Year's Eve Fireworks at John Hancock Center, Chicago, IL
Petunia Festival in Dixon near Chicago, IL
Physics Day at Six Flags Great America in Chicago, IL
Summer Sunset Festival in Lake in the Hills near Chicago, IL
Taste of Chicago in Chicago, IL
Visit Santa at 900 North Michigan Shops, Chicago, IL
Winter Wonderfest at Navy Pier in Chicago, IL

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