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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

May 2014 Chicago Events

  • Monday, May 26
    Memorial Day in Chicago, IL
    Observe this next year's Memorial Day in the beautiful city of Chicago, IL.


  • Thursday, May 1 - Saturday, May 31
    Chicago Architectural Cruise on the Chicago River
    Part of the charm of Chicago is its location on Lake Michigan, and the Land and River Architectural Cruise will let you see that fabulous skyline from the lake by way of a yacht.


  • Thursday, May 1 - Saturday, May 31
    Chicago Grand Tour
    The Chicago Grand Tour offers Windy City visitors an encompassing view of Chicago that includes Lincoln Park, Washington Park and Grant Park.


  • Thursday, May 1 - Saturday, May 31
    CityPASS - Chicago, IL
    The Chicago CityPASS offers admission to several great Chicago attractions for a great savings and comprehensive time in Chicago.


  • Thursday, May 1 - Saturday, May 31
    Medieval Times Dinner & Tournament - Schaumburg, IL
    Take a voyage back to the days of battling knights, horses, royalty, feasts, and more when you attend Medieval Times Dinner & Tournament in Schaumburg.


  • Thursday, May 1 - Saturday, May 31
    Go Chicago Card - Chicago, IL
    The Go Chicago Card is an all-inclusive visitor pass that offers admission to over 25 attractions, including The Field Museum, Art Institute of Chicago, Shedd Aquarium and much more for one low price.


  • Saturday, May 3 - Saturday, May 31
    Chicago Bike Tour - 3 Hour City Lights At Night
    See what is behind the scenes in the Windy City as Bobby's 'City of Neighborhoods' bike tour takes you off the beaten path into the quiet neighborhoods, city parks, and beaches of Chicago's North side.


  • Thursday, May 1 - Saturday, May 31
    Chicago Lakefront Bicycle Tour - 3 Hour Tour Through Lakefront Historic & Famous Residences
    Take your sightseeing adventures on a fun bicycle ride through Chicago and really get to know the city up close and personal with the Bobby's Lakefront Neighborhoods Tour.


  • Thursday, May 1 - Saturday, May 31
    Chicago Bike Rentals
    If you want to get out and see the fabulous sights of Chicago at your own pace, then Bobby's Daily Bike rental is the route for you.


  • Thursday, May 1 - Saturday, May 31
    Chicago Premium Outlets Shopping Shuttle
    If a day of shopping for name brand items at huge discounts sounds more appealing than learning the history of The Windy City, then the Chicago Premium Outlets Shopping Tour may be just what you've been looking for.


  • Thursday, May 1 - Saturday, May 31
    Chicago Hop On/Hop Off Trolley and Upper Decker Tour
    Enjoy a scenic tour of Chicago's lake front and downtown area aboard trolley buses and upper deckers!


  • Saturday, May 3 - Saturday, May 31
    Six Flags Great America, Chicago
    Six Flags Great America & Hurricane Harbor provides over 60 thrilling attractions including roller coasters, family friendly rides, shows, events, great food, and water rides that are a sure-fire way to beat the heat and have some fun during your Chicago vacation.


  • Thursday, May 1 - Saturday, May 31
    Chicago City Segway Tour
    With the Chicago City Segway Tour, you will turn heads as you pass by pedestrians on your innovative Segway, visiting the city's beautiful parks, waterfront district and other attractions.


  • Thursday, May 1 - Saturday, May 31
    Hop On/Hop Off Chicago Trolley Tour
    Explore all that the Windy City has to offer with this Hop-On Hop-Off Chicago Trolley Tour.


  • Saturday, May 10 - Saturday, May 31
    Chicago Bicycle Tour - 4 Hour Tour Through Historic Hyde Park & Kenwood Mansion
    Explore some of Chicago's most interesting hotspots with the Bicycle Tour - Historic Hyde Park & Kenwood Mansion Tour.


  • Sunday, May 25 - Friday, May 30
    Chicago Bike Tour - 2 Hour Bike Tour For Families
    Created specifically for children who are nine years old and under, Bobby's Tike Hike Kid's Ediction Bicycle Tour held each day in Chicago, Illinois is the perfect recreational outdoor activity for your younger children.


  • Thursday, May 1 - Saturday, May 31
    Chicago North Side Tour
    This is the tour for those looking to experience the vitality and excitement of Chicago!


  • Thursday, May 1 - Saturday, May 31
    Historic Chicago South Shore Tour
    Here is a tour full of interest, history, and beauty!


  • Thursday, May 1 - Friday, May 30
    Chicago Culinary Bike Tour - 4 Hour Tour Through Wrigleyville, Gold Coast, Old Town, Lakeview, & Lincoln Park
    The Chicago Culinary Bike Tour allows visitors to see some of the area's attractions on their way to sample some of Chicago’s best flavors.


September 2014 Chicago Events

  • Monday, September 1
    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.


  • Monday, September 1 - Tuesday, September 30
    Chicago Architectural Cruise on the Chicago River
    Part of the charm of Chicago is its location on Lake Michigan, and the Land and River Architectural Cruise will let you see that fabulous skyline from the lake by way of a yacht.


  • Monday, September 1 - Tuesday, September 30
    Chicago Grand Tour
    The Chicago Grand Tour offers Windy City visitors an encompassing view of Chicago that includes Lincoln Park, Washington Park and Grant Park.


  • Monday, September 1 - Tuesday, September 30
    CityPASS - Chicago, IL
    The Chicago CityPASS offers admission to several great Chicago attractions for a great savings and comprehensive time in Chicago.


  • Monday, September 1 - Sunday, September 28
    Medieval Times Dinner & Tournament - Schaumburg, IL
    Take a voyage back to the days of battling knights, horses, royalty, feasts, and more when you attend Medieval Times Dinner & Tournament in Schaumburg.


  • Monday, September 1 - Tuesday, September 30
    Go Chicago Card - Chicago, IL
    The Go Chicago Card is an all-inclusive visitor pass that offers admission to over 25 attractions, including The Field Museum, Art Institute of Chicago, Shedd Aquarium and much more for one low price.


  • Monday, September 1 - Tuesday, September 30
    Chicago Bike Tour - 3 Hour City Lights At Night
    See what is behind the scenes in the Windy City as Bobby's 'City of Neighborhoods' bike tour takes you off the beaten path into the quiet neighborhoods, city parks, and beaches of Chicago's North side.


  • Monday, September 1 - Tuesday, September 30
    Chicago Lakefront Bicycle Tour - 3 Hour Tour Through Lakefront Historic & Famous Residences
    Take your sightseeing adventures on a fun bicycle ride through Chicago and really get to know the city up close and personal with the Bobby's Lakefront Neighborhoods Tour.


  • Monday, September 1 - Tuesday, September 30
    Chicago Bike Rentals
    If you want to get out and see the fabulous sights of Chicago at your own pace, then Bobby's Daily Bike rental is the route for you.


  • Monday, September 1 - Tuesday, September 30
    Chicago Premium Outlets Shopping Shuttle
    If a day of shopping for name brand items at huge discounts sounds more appealing than learning the history of The Windy City, then the Chicago Premium Outlets Shopping Tour may be just what you've been looking for.


  • Wednesday, September 3 - Sunday, September 28
    Chicago Hop On/Hop Off Trolley and Upper Decker Tour
    Enjoy a scenic tour of Chicago's lake front and downtown area aboard trolley buses and upper deckers!


  • Monday, September 1 - Sunday, September 28
    Six Flags Great America, Chicago
    Six Flags Great America & Hurricane Harbor provides over 60 thrilling attractions including roller coasters, family friendly rides, shows, events, great food, and water rides that are a sure-fire way to beat the heat and have some fun during your Chicago vacation.


  • Monday, September 1 - Tuesday, September 30
    Chicago City Segway Tour
    With the Chicago City Segway Tour, you will turn heads as you pass by pedestrians on your innovative Segway, visiting the city's beautiful parks, waterfront district and other attractions.


  • Monday, September 1 - Tuesday, September 30
    Hop On/Hop Off Chicago Trolley Tour
    Explore all that the Windy City has to offer with this Hop-On Hop-Off Chicago Trolley Tour.


  • Saturday, September 6 - Sunday, September 28
    Chicago Bicycle Tour - 4 Hour Tour Through Historic Hyde Park & Kenwood Mansion
    Explore some of Chicago's most interesting hotspots with the Bicycle Tour - Historic Hyde Park & Kenwood Mansion Tour.


  • Monday, September 1 - Wednesday, September 3
    Chicago Bike Tour - 2 Hour Bike Tour For Families
    Created specifically for children who are nine years old and under, Bobby's Tike Hike Kid's Ediction Bicycle Tour held each day in Chicago, Illinois is the perfect recreational outdoor activity for your younger children.


  • Monday, September 1 - Tuesday, September 30
    Chicago North Side Tour
    This is the tour for those looking to experience the vitality and excitement of Chicago!


  • Monday, September 1 - Tuesday, September 30
    Historic Chicago South Shore Tour
    Here is a tour full of interest, history, and beauty!


  • Monday, September 1 - Tuesday, September 30
    Chicago Culinary Bike Tour - 4 Hour Tour Through Wrigleyville, Gold Coast, Old Town, Lakeview, & Lincoln Park
    The Chicago Culinary Bike Tour allows visitors to see some of the area's attractions on their way to sample some of Chicago’s best flavors.


November 2014 Chicago Events

  • Tuesday, 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 27
    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.


  • Saturday, November 1 - Sunday, November 30
    Chicago Grand Tour
    The Chicago Grand Tour offers Windy City visitors an encompassing view of Chicago that includes Lincoln Park, Washington Park and Grant Park.


  • Saturday, November 1 - Sunday, November 30
    CityPASS - Chicago, IL
    The Chicago CityPASS offers admission to several great Chicago attractions for a great savings and comprehensive time in Chicago.


  • Saturday, November 1 - Sunday, November 30
    Go Chicago Card - Chicago, IL
    The Go Chicago Card is an all-inclusive visitor pass that offers admission to over 25 attractions, including The Field Museum, Art Institute of Chicago, Shedd Aquarium and much more for one low price.


  • Saturday, November 1 - Monday, November 17
    Chicago Lakefront Bicycle Tour - 3 Hour Tour Through Lakefront Historic & Famous Residences
    Take your sightseeing adventures on a fun bicycle ride through Chicago and really get to know the city up close and personal with the Bobby's Lakefront Neighborhoods Tour.


  • Saturday, November 1 - Sunday, November 30
    Chicago Bike Rentals
    If you want to get out and see the fabulous sights of Chicago at your own pace, then Bobby's Daily Bike rental is the route for you.


  • Saturday, November 1 - Sunday, November 30
    Chicago Premium Outlets Shopping Shuttle
    If a day of shopping for name brand items at huge discounts sounds more appealing than learning the history of The Windy City, then the Chicago Premium Outlets Shopping Tour may be just what you've been looking for.


  • Saturday, November 1 - Sunday, November 30
    Chicago Hop On/Hop Off Trolley and Upper Decker Tour
    Enjoy a scenic tour of Chicago's lake front and downtown area aboard trolley buses and upper deckers!


  • Saturday, November 1
    Six Flags Great America, Chicago
    Six Flags Great America & Hurricane Harbor provides over 60 thrilling attractions including roller coasters, family friendly rides, shows, events, great food, and water rides that are a sure-fire way to beat the heat and have some fun during your Chicago vacation.


  • Saturday, November 1 - Sunday, November 30
    Chicago City Segway Tour
    With the Chicago City Segway Tour, you will turn heads as you pass by pedestrians on your innovative Segway, visiting the city's beautiful parks, waterfront district and other attractions.


  • Saturday, November 1 - Sunday, November 30
    Hop On/Hop Off Chicago Trolley Tour
    Explore all that the Windy City has to offer with this Hop-On Hop-Off Chicago Trolley Tour.


  • Saturday, November 1 - Sunday, November 30
    Chicago North Side Tour
    This is the tour for those looking to experience the vitality and excitement of Chicago!


  • Saturday, November 1 - Sunday, November 30
    Historic Chicago South Shore Tour
    Here is a tour full of interest, history, and beauty!


  • Monday, November 3 - Friday, November 7
    Chicago Culinary Bike Tour - 4 Hour Tour Through Wrigleyville, Gold Coast, Old Town, Lakeview, & Lincoln Park
    The Chicago Culinary Bike Tour allows visitors to see some of the area's attractions on their way to sample some of Chicago’s best flavors.


December 2014 Chicago Events

  • Thursday, December 25
    Christmas in Chicago, IL
    From gorgeous floral and lighting displays to legendary department stores, Chicago, IL has it all during the Christmas season.


  • Wednesday, December 31
    New Year's Eve Fireworks at John Hancock Center, Chicago, IL
    Enjoy New Year's Eve this year in a unique way by attending the New Year's Eve Fireworks at the John Hancock Center, located at 875 N Michigan Ave in Chicago, IL 60611.


  • Monday, December 1 - Wednesday, December 31
    Chicago Grand Tour
    The Chicago Grand Tour offers Windy City visitors an encompassing view of Chicago that includes Lincoln Park, Washington Park and Grant Park.


  • Monday, December 1 - Wednesday, December 31
    CityPASS - Chicago, IL
    The Chicago CityPASS offers admission to several great Chicago attractions for a great savings and comprehensive time in Chicago.


  • Monday, December 1 - Wednesday, December 31
    Go Chicago Card - Chicago, IL
    The Go Chicago Card is an all-inclusive visitor pass that offers admission to over 25 attractions, including The Field Museum, Art Institute of Chicago, Shedd Aquarium and much more for one low price.


  • Monday, December 1 - Tuesday, December 2
    Chicago Bike Rentals
    If you want to get out and see the fabulous sights of Chicago at your own pace, then Bobby's Daily Bike rental is the route for you.


  • Monday, December 1 - Thursday, December 18
    Chicago Premium Outlets Shopping Shuttle
    If a day of shopping for name brand items at huge discounts sounds more appealing than learning the history of The Windy City, then the Chicago Premium Outlets Shopping Tour may be just what you've been looking for.


  • Monday, December 1 - Wednesday, December 31
    Chicago City Segway Tour
    With the Chicago City Segway Tour, you will turn heads as you pass by pedestrians on your innovative Segway, visiting the city's beautiful parks, waterfront district and other attractions.


  • Monday, December 1 - Wednesday, December 31
    Hop On/Hop Off Chicago Trolley Tour
    Explore all that the Windy City has to offer with this Hop-On Hop-Off Chicago Trolley Tour.


  • Monday, December 1 - Wednesday, December 31
    Chicago North Side Tour
    This is the tour for those looking to experience the vitality and excitement of Chicago!


  • Monday, December 1 - Wednesday, December 31
    Historic Chicago South Shore Tour
    Here is a tour full of interest, history, and beauty!


  • Thursday, December 11 - Friday, December 19
    Chicago Trolley Holiday Lights Tour
    On this holiday lights tour, you will be amazed by the dazzling display of Christmas lights and decorations as you pass famous landmarks such as Lincoln Park and the Magnificent Mile.


January 2015 Chicago Events

  • Thursday, January 1
    New Years Day in Chicago, IL
    Celebrate New Years like you have never before by visiting Chicago, IL on New Years Day.


  • Thursday, January 1 - Saturday, January 31
    Chicago Grand Tour
    The Chicago Grand Tour offers Windy City visitors an encompassing view of Chicago that includes Lincoln Park, Washington Park and Grant Park.


  • Thursday, January 1 - Saturday, January 31
    CityPASS - Chicago, IL
    The Chicago CityPASS offers admission to several great Chicago attractions for a great savings and comprehensive time in Chicago.


  • Thursday, January 1 - Saturday, January 31
    Hop On/Hop Off Chicago Trolley Tour
    Explore all that the Windy City has to offer with this Hop-On Hop-Off Chicago Trolley Tour.


  • Thursday, January 1 - Saturday, January 31
    Chicago North Side Tour
    This is the tour for those looking to experience the vitality and excitement of Chicago!


  • Thursday, January 1 - Saturday, January 31
    Historic Chicago South Shore Tour
    Here is a tour full of interest, history, and beauty!


February 2015 Chicago Events

  • Saturday, 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 1 - Saturday, February 28
    Chicago Grand Tour
    The Chicago Grand Tour offers Windy City visitors an encompassing view of Chicago that includes Lincoln Park, Washington Park and Grant Park.


  • Sunday, February 1 - Saturday, February 28
    CityPASS - Chicago, IL
    The Chicago CityPASS offers admission to several great Chicago attractions for a great savings and comprehensive time in Chicago.


  • Sunday, February 1 - Saturday, February 28
    Hop On/Hop Off Chicago Trolley Tour
    Explore all that the Windy City has to offer with this Hop-On Hop-Off Chicago Trolley Tour.


  • Sunday, February 1 - Saturday, February 28
    Chicago North Side Tour
    This is the tour for those looking to experience the vitality and excitement of Chicago!


  • Sunday, February 1 - Saturday, February 28
    Historic Chicago South Shore Tour
    Here is a tour full of interest, history, and beauty!


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