Chicago, the nation’s third largest city, is also home to a
multitude of historical sites, world-renowned architecture, acclaimed
shopping, a lively nightlife, scores of gastronomical hot spots and
a list of one-of-a-kind attractions that are unrivaled the world over.
No matter what the season, visitors to the Windy City will enjoy year-round
sporting events, music festivals, boat parades and so much more. To
help you plan your itinerary, consider this list of Things of to Do in and Around Chicago…
 ANNUAL FESTIVITIES
Go Fly a Kite
Held every year during the month of May, this annual event – Kids and Kites Festival – sponsored by the Office of the Mayor of Chicago, invites families to the front lawn of the Museum of Science and Industry (www.msichicago.org) to fly kites and enjoy other festival activities such as storytelling, face painting, and much, much more.
Enjoy a ‘Great’ Escape
Established in 1999, the Annual Great Chicago Places and Spaces Festival celebrates architecture and design throughout the Windy City. Highlights include tours of the Trump International Hotel & Tower, the new Spertus Institute and the Center on Halsted, as well as Chocolate Tours, city jogging tours, boat tours and rooftop garden tours.
Find the Gospel Truth
After more than two decades, the Chicago Gospel Music Festival is one of the many events that is sponsored by the Mayor’s office to celebrate Chicago's diverse musical heritage. Usually taking place near the end of the May, this Gospel Fest is free to the public and highlights music from many genres within gospel music drawing from classical to R&B to traditional.
Shake off the Blues
The Chicago Blues Festival, a mid-year fixture for the last quarter century, has long been considered one of the best events in the country. Showcasing luminaries among the Blues music scene, this event celebrates the heritage of the blues by remembering the legends who created the music.
Taste and See
Celebrated during the heart of the summer, the annual Taste of Chicago has come to represent the second largest tourist attraction in Illinois. Spanning 10 days, this event is admission-free and highlights cuisine from more than 70 restaurants from all over Chicagoland.
Relish the Great Outdoors
The Chicago Outdoor Film Festival is a throwback to a time when films were shown in the park. Now, nearly 10 years old, this annual event lasts more than a month long, starting in July, and features cinematic classics as well as pop culture favorites.
Some Venetian Evening
Taking place at Monroe Harbor, the Annual Venetian Night features illuminated and decorated boats that meander down Lake Michigan and then culminates with an impressive fireworks display.
By Air, Land & Sea
In 2008, the Chicago Air & Water Show hit the 50-year mark and has been heralded as one of the world's premier aviation events.
Viva La Musica
This musical festival – Viva! Chicago Latin Music Festival – is held in late August in Grant Park every year and typically offers a tour-de-force of the musical performances from Latin music superstars from all over the world that cover genres cumbia, reggaeton, salsa, merengue, tango, bachata, banda and Spanish Pop.
Jazz it Up
Ranked as the city’s longest running music festivals, the Chicago Jazz Festival , typically held on Labor Day weekend, showcases the diverse talent of local, national and international musicians, with many different genres of jazz music represented throughout the celebration.
ATTRACTIONS
Pier into a Day of Fun
Ranked as the #1 tourist and leisure destination in the Midwest, Chicago’s Navy Pier attracts more than eight million visitors each year. Complete with its famed 150-foot Ferris wheel, boardwalk, boat tours, shopping, and a multitude of dining options, this destination embodies “fun” at every turn. Special attractions include the Chicago Shakespeare Theater, Chicago Children’s Museum, Smith Museum of Stained Glass Windows, an IMAX Theater, and Skyline Stage. And not to be missed, during the summer, fireworks illuminate the sky each Wednesday and Saturday nights.
Park Yourself Here
Located in downtown Chicago, Millennium Park is an extraordinary showplace for world-class art, music, architecture, and landscape design. Encompassing 24.5 acres, the Park offers a potpourri of sights and sounds and offers a diverse range of activities from ice skating in the winter to fountains to splash in during the summer. Not to be overlooked, Millennium Park is also an architects/art-lovers delight with several highlights including the dazzling Jay Pritzker Pavilion designed by Frank Gehry, the Cloud Gate, the mammoth-sized stainless steel sculpture by British artist, Anish Kapoor; and the Crown Fountain designed by Spanish artist, Jaume Plensa.
Tower over the City
Get a bird’s eye view of Chicago’s scenic beauty from a location unlike any other. Head 103 floors above ground to the Sears Tower Skydeck. Once the world’s tallest building, the Sears Tower now ranks as the third tallest but still towers at 1,454 feet high, and is still the tallest building in the Western Hemisphere. On a clear day, you can see Chicago area landmarks, as well as Indiana, Michigan and Wisconsin.
Observe the Sights
Get another panoramic view of the City from the Hancock Observatory. To reach the observatory on the 94th floor, visitors will enjoy a 39-second ride on the fastest elevator in North America 1,000 feet above the Magnificent Mile. Housed in Chicago’s third-tallest building, the Observatory not only features a spectacular view but also Soundscope 3-D “talking” telescopes that “speak” four languages, and the city’s only open-air Skywalk -- a patio-like enclosure with industrial-strength screens.
It’s All Happening at the Zoo
Home to more than 1,000 mammals, reptiles and birds, the Lincoln Park Zoo – offering free admission – is situated in scenic space along Chicago's lakefront and is a “must see” for all Chicago visitors.
Live Your Nine Lives
Chicago sports a host of 9-hole, community courses that are challenging and enjoyable for everyone from the novice to the pro. Enjoy the Sidney Maravitz Course; and South Shore Golf Course as well as the Diversy Driving Range.
Observe the Beauty Botanical
Considered by many to be the nation’s most stunning botanical gardens, the Garfield Park Conservatory is often referred to as “landscape art under glass.” While simply lovely to “observe,” the Conservatory stands as a living, historical depiction of how nature, urban design, and horticulture helped to shape one of Chicago’s most interesting neighborhoods.
No Lie, This is Also One Beautiful Garden
Another of Chicago’s complimentary attractions, the Lincoln Park Conservatory, is located in the heart of Lincoln Park, adjacent to the Lincoln Park Zoo and is also a beautiful display of flora and fauna.
Seek Out the Cultural Side of Life
To cover your bases, visit the Chicago Cultural Center, the official visitor center of the Windy City and make sure that you don’t miss a thing during your stay. Not only does the Center provide information on everything the city has to offer, but it also showcases a plethora of admission-free exhibits.
Greet and Be Greeted
If a guided tour is something that appeals to you, make a reservation for a docent to provide you with a friendly tour around. The Chicago Greeter Service provides volunteer guides that speak 13 different languages and match greeters with visitors based on their interest and language needs. Best of all, this service is entirely FREE!
Lakefront and Personal
If a leisurely stroll is your favorite tourist attraction, don’t overlook Chicago’s Lakefront Walkways and Parks. With more than 29 miles of walking, jogging and cycling paths along with 13 miles of beaches, the views and the exercise combine for a perfect day.
MUSEUMS, NATURE & CULTURE
Take the Field
Home to more than 20 million biological and anthropological specimens, The Field Museum , most notably lays claim to housing Sue, the largest, most complete, and best preserved T-Rex fossil ever discovered. A sight to behold, the skeleton on display is the real thing – not a plastic model or cast, not a patchwork or a composite of bones from other specimens.
Reach for the Stars
The Adler Planetarium and Astronomy Museum was the first planetarium built in the Western Hemisphere, and is the only museum in the world with two full-size planetarium theaters.
Swim with the Fishes
Or at least look at them at the acclaimed Shedd Aquarium. Home to more than 22,000 aquatic species, the Aquarium has been a Chicago icon and a leader in its field for more than 75 years.
Get Blinded by Science
The Museum of Science and Industry - the largest science museum in the Western Hemisphere - offers over 800 captivating interactive exhibits including the U-505 submarine, a
working coal mine, a Boeing 727 airplane, and much, much more.
Check Yourself into this Institution
Offering a world-class collections of art, textiles, photography and painting, The Art Institute of Chicago’s offering rivals that of the Louvre. If you are a lover of art, this is a “must see” stop in the Windy City.
Be A Shutterbug
Photography is in focus at The Museum of Contemporary Photography, the Midwest’s sole museum committed exclusively to this medium, and changing Chicago-focused installations at City Gallery at the Historic Water Tower.
Diversify your Mind
In this city that celebrates its diversity, such institutions as Spertus Institute of Jewish Studies, DuSable Museum of African American History, and The Oriental Institute, hold a special place of honor.
NIGHTLIFE
Shake off the Blues
In “The only Blues Capital of the World,” there is no shortage legendary jazz and blues to visit during your Chicago adventure. Favorite clubs include Blue Chicago, Buddy Guy’s Legends, House of Blues, and Kingston Mines. If Jazz Music is more your style, don’t overlook Andy’s Jazz Club, The Back Room and Green Dolphin Street.
Lounge Around in Style
Imbibe in style at one of these trendy bars and lounges. At Martini Park (http://www.martinipark.com/chicago/), patrons will enjoy a “playground for grown-ups” complete with live entertainment and over 20 specialty martinis. Also consider Fulton Lounge,
Republic and Pops for Champagne.
Dance the Night Away
If dancing is your thing, Chicago offers some of the best dance clubs in the country that boast the hippest deejays and high-end bottle service. Get your groove on at clubs like Crobar Enclave, Excalibur Nightclub, Le Passage, and Sound-Bar.
Spare Some Time to Hit the Lanes
Bowl a strike at any of these local bowling centers, including 10-pin Bowling Lounge, a chic center that combines lucky lanes with a chic lounge atmosphere; Lucky Strike Lanes, epitomizing all the charm of a traditional bowling “alley;” and Diversey River Bowl, a fun center that offers music and strobe lights to add action to the pin game.
Howl at the Moon
Channel your inner “American Idol” and spend the night singing along with your favorite torch songs and show tunes. Popular piano bars such as Howl at the Moon, Jilly’s Piano Bar , and the Red Head Piano Bar.
PERFORMING ARTS
Head Back to Broadway
“They say the neon lights are bright…on Broadway” – and no where are they brighter than in Chicago’s bustling Downtown Theater District. Here you’ll find world premiere productions, mega-hit musicals, plays and dance performances, straight from Broadway, at theaters including the Cadillac Palace Theatre, Ford Center for the Performing Arts/Oriental Theatre, LaSalle Bank Theatre and Auditorium Theatre.
Go from Good to Great
Another treasure in the city’s theater district is the Goodman Theatre, an award-winning destination that has been lauded with a special Tony Award for Outstanding Regional Theater. Productions at The Goodman include both classic and contemporary works that are always entertaining.
Dance the Light Fantastic
The Harris Theater for Performance and Dance prides itself on being a national model of collaboration between the philanthropic community and performing arts organizations, and features world-renowned dance and music institutions, and hosts acclaimed national and international companies.
Take a Magic Carpet Ride
Founded in 1976, the Steppenwolf Theater Company, located in the Lincoln Park neighborhood, features an internationally renowned company of more than 40 ensemble artists whose talents include acting, directing, playwriting, filmmaking, and textual adaptation. Now in its third decade as a professional theater company, no other American theater ensemble has survived as long and thrived as much as the Steppenwolf company of artists.
Go for Second Best
A longtime landmark in Chicago, The Second City is known for launching the careers of such comic greats as John Belushi, Mike Myers, Bill Murray, Gilda Radner, and more, offers nightly comedy shows, as well as a variety of other programs and services. With its two resident stages - The Second City Mainstage, which seats 290 and The Second City e.t.c., which seats 180 – each theatre has a resident troupe that writes and performs an original comedy revue. The shows are smart, funny, and highly original. The Second City Training Center operates a third theatre in the Piper's Alley complex on Wells Street called Donny's Skybox Studio Theatre. Donny's Skybox features an eclectic mix of student productions as well as other alternative shows.
Be True Blue
Best known for their theatrical shows, the Blue Man Group, on stage at the Briar Street Theater, offers up a totally unique form of entertainment that combines music, comedy, and multimedia theatrics to generate an evening of entertainment that never disappoints.
Take a Walk Down the Aisle
You are cordially invited to attend Tony and Tina’s Wedding! This much-cherished dinner-theater experience combines delectable Italian food with the theatrics of a traditional Italian wedding reception. Tony n' Tina's Wedding is a complete entertainment package, including a pre-wedding cocktail cash bar, a ceremony full of mishaps, and an evening of dinner, music, and dancing!
Tommy, Get Your Gun
Re-live the roaring 20's with a Chicago dinner-theater favorite, Tommy Gun’s Garage, complete with flappers, gangsters and classic tunes from Cole Porter, George Gershwin and Duke Ellington.
Drury Lane is in Your Ears and in Your Eyes
Be a part of a true theatrical experience at the award-winning Drury Lane Theatre in Oakbrook Terrace. Each season, the theater performs smashing Broadway classics, top-rated musicals, hilarious comedies and unforgettable concert events in this plush theater.
By George, I think they’ve got it!
Located minutes north of Chicago's Loop, the Royal George Theater offers four theaters within one complex ranging in size from the
450-seat main stage – one of Chicago's premier, mid-sized theatres – to 50-seat Gallery Theatre featuring productions by new and developing theatre companies.
Enjoy a Presidential Night at the Theater
The national landmark Auditorium Theatre of Roosevelt University, built in 1889, is a major center for the performing arts and annually hosts a plethora of dance performances by such organizations as the Joffrey Ballet.
Hit a High C
Lyric Opera of Chicago is recognized internationally as one of the great opera companies in the country. Their performances include a standard operatic repertoire as well as a plethora of contemporary works. With a seating capacity of more than 3,500 seats, this opera powerhouse is the second-largest opera auditorium in North America.
Follow the Conductor’s Baton
The Chicago Symphony Orchestra is a musical force in Chicago and around the world. With more than 150 performances each year, the CSO is compiled of 100 talented musicians, two internationally renowned conductors and two award-winning composers-in- residence.
SPAS
‘Anti’-Age with Grace
Taste from the fountain of your at the Christopher Charles Anti-Aging Skincare Spa. Offering treatments that lessen the signs of aging, the Spa will show you how to pamper your skin during your treatment and at home.
See Red
The Red Door Salon by Elizabeth Arden is located in the historic Palmolive Building, and provides an extensive list of services including facials, massage therapy, body treatments, nail care, make-up artistry and a full-service hair salon.
Head to the Peninsula
For the epitome of pampering, head to The Peninsula Spa by ESPA at the Peninsula Hotel. Rated the #1 Urban Spa in North America by Conde Nast Traveler Magazine, the spa offers a collection of treatments that layer European and Asian philosophies for an entirely new, holistic experience.
Choose a Unique Way to Unwind
At the Asha Salon & Spa, devotion to your well-being is its core value. Offering an extensive dossier of services and products, patrons of the spa will enjoy everything from sassy haircuts to enlightening lifestyle workshops.
Spa Where the Celebs Spa
A long-time “hot spot,” Channing’s Day Spa continues to attract celebrities, as well as visitors and locals alike for the last 22 years. Located in a lovely Victorian town house on Oak Street, the Spa offers n eclectic list of treatments and spa packages to please everyone from the first time spa go-er to the spa aficionado.
Ruby’s are a Girl’s Best Friend
Located in Chicago’s historic Wicker Park/Bucktown, the Ruby Room melds fashion with beauty, wellness and art. With three separate shopping environments, the Ruby Room offers an expert beauty bar, salon, spa, yoga lounge, healing sanctuary, crystal bar, apothecary and educational lab.
SPORTS
Batter Up!
Wrigley Field, the second-oldest ballpark in the majors, is not only a true ballplayer’s ballpark it is also home to the Chicago Cubs. Nestled in the neighborhood of Wrigleyville, the “Cubbies” suit up every season in hopes of bringing a World Series Championship back to Chicago, a feat that hasn’t happened since 1908. Go Cubs!!
Go Up on the Roof
Comparable only to Boston’s “Green Monster” Cubs fans get a rare vantage point to watch a game from Wrigleyville Rooftops. Considered to be one of the most unique baseball experiences in the country, patrons can take their pick from three rooftop locations. Once there, fan will enjoy an extensive list of amenities including premiere bleacher style seating, professional catered food and beverage service, and amazingly close views of the game’s action.
Let Chicago Sox You Up
Crosstown rivals, the Chicago White Sox, call U.S. Cellular Field home (also known as “The Cell”). Located in Chicago’s South Side, the Sox brought a World Series Championship home to the Windy City in 2005 making the “Red Line Rivalry” even more heated.
Grin and Bear It!
The Chicago Bears, eight time NFL Champion, and the proud team of the most Hall of Fame inductees with 26, epitomize the game, and the grit of the gridiron. Calling Soldier Field their home since 1971, the “Da Bears,” can also lay claim to some of the most loyal fans in the NFL.
Run with the Bulls
In what is considered the house the “Michael Jordan” built, the Chicago Bulls, the city’s NBA franchise has long been synonymous with NBA royalty. Sharing their home field with their NHL compatriots, the Bulls currently play in the United Center, located near the West Side of Chicago.
Watch with ‘Hawk’ Eyes
A long-time fixture on the sports scene in Chicago, the Blackhawks, the city’s national league hockey team, are a force to be reckoned with. When founded in 1926, the team was part of the original six NHL teams in the newly created league. In 1994, the Blackhawks moved their home to the United Center after 60 years in Chicago Stadium. In the team’s history, they have garnered three Stanley Cup Championship and 13 division titles.
Catch the Fire
Another “great” Fire has swept through Chicago – this time in the shape of the city’s Major League Soccer team, the Chicago Fire. Founded in 1997, on the 125th anniversary of the Great Chicago Fire of 1871, the team resides in Bridgeview, Illinois in the brand-new Toyota Park. With seating for 20,000, Toyota Park is the Midwest’s leading outdoor live entertainment and sporting facility.
WATER WORKS
Sight See Via the Shoreline
Established in 1939, Shoreline Sightseeing Company boasts a fleet of nine touring vessels and eight water taxis. Offering leisurely Architecture Tours on the Chicago River accompanied by a lively narrative, Shoreline also provides Water Taxi service that provide quick and easy access to several Chicago attractions.
So ‘Dee-lightful’
Providing private cruises for groups ranging from 50 to 400, Anita Dee Yacht Charters takes passengers along Chicago’s spectacular skyline. As an added convenience, the company’s fleet is located on the South side of Navy Pier.
Love it When you Cruise Together
For your next corporate or family event, charter a cruise with Kanan Cruises. Get the best view of the fireworks at Navy Pier as well as the cityscape. Also, enjoy the ship’s onboard Piano Lounge and enjoy the cruise with the perfect accompaniment.
Enjoy the ‘Wendella’ City
Considered by many as the original sightseeing tour providers, Wendella Sightseeing Boats offers an array of specialized boat tours such as Wine Tasting Tours, Chicago at Sunset Tours and a combined Lake and River Tour. The company also operates the Chicago Water Taxi service, the City’s original water transportation system.
Sailing…Takes you Away
Chicago Sailing, located on the North end of Belmont Harbor offers the widest range of programs to serve everyone from the novice to the expert sailor. Providing instructional programs from a fully certified staff, the company offers 24 sailboats between 22’and 53’, the largest fleet of its kind within a thousand miles.
TRANSPORTATION
‘L’ For Love…
And how can you not love this easy and efficient way to traverse the City to all major attractions. The “El”, short for “elevated train lines” is just a part of the entire Chicago Transit Authority’s entire public transportation system that also includes buses and a subway train.
Trolley, la, la, la
From Memorial Day to Labor Day, Free Trolleys travel between Navy Pier and State Street along Grand and Illinois every 20 minutes, carrying tourists and locals to all parts of the city.
H2O Taxi
During the warmer months, choose a Water Taxi as your transportation of choice. Running along the Chicago River or the lakeshore, these boats offer an alternate to get around.
Interact with the Streets
If you want to take to the streets yourself, consider easing your parking stress by using the Ciy’s online, fully interactive map that allows you to search for parking options based on your destination.
Cycle about
Recently voted the best bicycling city in the country, the Chicago Department of Transportation’s Bike Program Provides a plethora of information about city biking including maps, parking, and more.
Tunnel Your Way Around
Consider this lesser-known way to get around – Chicago’s underground tunnels and overhead bridges link 40-plus blocks in the heart of the city. A convenient way to travel the Central Business District and connect to public and private buildings and CTA stations, the Pedway is especially nice on rainy or snowy days.
SHOPPING
Bask in the Magnificence of this Mile
The Magnificent Mile (a.k.a Michigan Avenue) is home to Chicago's Historic Water Tower and Pumping Station, the only two buildings to survive the Great Fire of 1871, and one of the most renowned stretches of retail therapy. Offering more than 460 stores within eight city blocks, shoppers will find everything from high-end retail to bargain basement shopping and everything in between. Stores to be found include Macy’s, Bloomingdales, Saks Fifth Avenue, Nordstrom, American Girl Place, and Niketown.
Be Solid as an Oak
Labeled as an international style hub, and home to many of the world’s most exclusive boutiques and salons, Oak Street attracts shoppers from all over the world who seek only the best including from retailers such as Kate Spade, Barney’s New York and Prada.
State Your Case
Located in the heart of or Chicago’s culture and commerce district, the landmark State Street Retail Historic District provides a potpourri of shopping, entertainment, food and fun. Stores to be patronized include Macy’s, Sears, H&M, Nordstrom Rack, Urban Outfitters and Old Navy.
Find a Jewel of a Deal
If diamonds and jewels are on your shopping list, then head one block east of State Street on Wabash Avenue (b/w Wacker Drive and Congress Parkway) and you’ll find Jeweler's Row. Considered to be the Midwest’s largest jewelry district, here’s where you’ll find an extensive collection of find diamonds, gems and more.
It’s Hip to be Square
Recently heralded by Vanity Fair Magazine as “a square mile of sassy boutiques,” the area of Lincoln Park and Armitage Avenue, and Wicker Park-Bucktown offers tree-lined streets peppered with one-of-a-kind
items, trendy clothing, accessories, and furniture. In Lincoln Park, “must see” shops include the Barney's Co-Op, Lori's Shoes, Polo Rugby and Entendre Couture, while in the Wicker Park - Bucktown neighborhood, shops not-to-be-missed include Apartment Number 9, TK Men and Hejfina, all men’s shops. This area has also recently expanded to include Division Street between Ashland and Damen Avenues, with boutiques including Jade, Untitled, Marc by Marc Jacobs, Tangerine, Silver Cloud, Scoop, Clothes Minded and Stitch.
Go North Young Man (and Woman)
Near the north end of the river, discover a collection of 70 world-class art and antique galleries. Shoppers and collectors from around the world visit the River North Gallery District to discover the creations from new and established artists.
Shop & Walk
Customize your shopping excursion and book a tour with Chicago Shop Walk. This company can provide access to private studios (not open to the general public) , personal meetings with the designers, sample sales and discounts at some of the hottest boutiques. All tours include exclusive discounts with some tour options offering specific amenities based on each individual tour.
Let Your Wallet be Your Guide
The Urban Shop Guide provides tours for every occasion – birthdays, bachelorette parties, weekend getaways and showers – that all have a retail therapy spin on it with a flare that only the Urban Shop Guide consultants can provide. Choose from Happy Hour Shopping, Neighborhood All Star tours, Chicago Designer Tours or customize your own tour and have the company make a charitable contribution to your favorite benefactor.
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