150 Fun Things to Do in Chicago

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Being the largest city in the midwest, the windy city is a a must visit tourist destination. There are countless amounts of fun things to do in Chicago. With a rich cultural music history and well known sports teams, Chicago has plenty of landmarks like The Bean to visit and jazz clubs to be entertained at. Find something epic to do in Chicago today, and even more to do in Illinois tomorrow!

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Hancock Center's Signature Lounge

Sit back and enjoy the view at Hancock Center’s Signature Lounge

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Humboldt Park

Spend an entire day exploring Humboldt Park

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Chicago's Underground Pedway

Avoid the traffic and walk through Chicago’s underground pedway

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Lincoln Park's North Pond

Be one with nature at Lincoln Park’s North Pond

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North Pond Restaurant

Sit by the window while having a sumptuous meal at North Pond Restaurant

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Museum of Contemporary Art

See an exhibit at Museum of Contemporary Art

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Full Moon Fire Jam

Watch a spectacular show at the Full Moon Fire Jam

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Promontory Point

Get a great view of Chicago skyline from Promontory Point

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Chicago Cultural Center

Admire the architecture inside Chicago Cultural Center

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Biograph Theatre

See a play at the historical Biograph Theatre

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Lincoln Park Zoo

Visit Lincoln Park Zoo and see the amazing animals

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Millennium Park

Touch the Cloud Gate at Millennium Park

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Millennium Park

Catch a live event at Millennium Park

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Hotel Palomar

Have Santa deliver your gifts while checked in at Hotel Palomar

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iO

Laugh like there’s no tomorrow at iO

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Lurie Garden

Spot the strangest flower in Lurie Garden

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Lakefront Trail

Get your cardio workout and bike the Lakefront Trail

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Montrose Dog Beach

Play catch with your lovable pet at Montrose Dog Beach

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Wicker Park

Hang out at Wicker Park

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Renegade Craft Fair

Attend the Renegade Craft Fair and find interesting handcrafted items

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Baha'i House of Worship

Find your inner peace at Baha’i House of Worship

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Money Museum tour

Take a tour of the Money Museum and get free (shredded) money

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Garfield Park Conservatory

Be captivated by nature’s beauty at Garfield Park Conservatory

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Hull-House Museum

Know more about history at the Hull-House Museum

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Museum of Contemporary Photography

View the Museum of Contemporary Photography’s diverse collection

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Water Tower

Visit the City Gallery in the historic Water Tower

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Chicago Botanic Garden

See the corpse flower at Chicago Botanic Garden

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Empty Bottle

Dance the night away at the Empty Bottle

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Navy Pier

Ride the ferris wheel at Navy Pier

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International Museum of Surgical Science

View the interesting display at International Museum of Surgical Science

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Art Institute of Chicago

Marvel at the collection of artwork at the Art Institute of Chicago

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Museum of Science and Industry

Be an explorer at the Museum of Science and Industry

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Wrigley Field

Catch the Chicago Cubs play ball at Wrigley Field

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Michigan Avenue

Find a great bargain at Michigan Avenue

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Mag Mile

Put on your walking shoes and stroll along Mag Mile

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Field Museum

Meet a scientist at the Field Museum

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360 Chicago

Tilt over the edge at 360 Chicago

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Skydeck Chicago

Stand on the Ledge at Skydeck Chicago

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Chicago Symphony Orchestra

Watch a world class performance from the Chicago Symphony Orchestra

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Driehaus Museum

Step back into the past at Driehaus Museum

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Holy Name Cathedral

Visit the Holy Name Cathedral

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Maggie Daley Park

See the Enchanted Forest at Maggie Daley Park

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Pritzker Pavilion

Watch a live concert at Pritzker Pavilion

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Chicago Shakespear Theater

Get front row seats to see Chicago Shakespeare Theater on Navy Pier

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Lyric Opera of Chicago

See a lavish performance at the Lyric Opera of Chicago

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Blue Man Group

Have a fun-filled night watching the Blue Man Group

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Auditorium Theatre

Be dazzled by amazing performances at the Auditorium Theatre

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Neo-Futurists Theater

See “Too Much Light” at the Neo-Futurists Theater

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The Annoyance

Catch an original play at the Annoyance

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Chicago Theatre

Watch your favorite artist perform at Chicago Theatre

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Buckingham Fountain

Make a wish at the Buckingham Fountain

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Oriental Institute Museum

Travel back to the ancient world at Oriental Institute Museum

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Crown Fountain

Find out whose face will appear next at Crown Fountain

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Chicago Riverwalk

Take a romantic stroll on Chicago Riverwalk

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Goodman Theatre

Have a good time at Goodman Theatre

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Shedd Aquarium

Explore the wonders of the sea at Shedd Aquarium

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Lincoln Park

Spend the afternoon relaxing at Lincoln Park

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Chicago Segway Tour

Pick a color and take the Chicago Segway Tour

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Oriental Theatre

See a great musical at the Oriental Theatre

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Bulls at United Center

Show your love for the Bulls at United Center

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The Loop

Find the best places to dine and shop at the Loop

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Chicago River

Hop on a boat and take a fun tour of Chicago River

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Robie's House

Take a tour of Robie House and admire its architecture

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Lincoln Park Conservatory

Look at the pretty flowers in bloom at Lincoln Park Conservatory

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University of Chicago's Harper Quad

Walk around University of Chicago’s Harper Quad

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Tribune Tower

View the rocks from all over the world at the Tribune Tower

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Agora at Grant Park

Take a closer look at the Agora at Grant Park

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Michigan Avenue Bridge

See the water taxis while chilling at Michigan Avenue Bridge

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Kingston Mines

Put on a cool hat and listen to blues music at Kingston Mines

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B.L.U.E.S.

Grab a drink with friends and enjoy a night of music at B.L.U.E.S.

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Buddy guy's Legends

Watch Buddy Guy himself perform on stage at Buddy Guy’s Legends

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House of Blues Chicago

Try Elwood’s Business Lunch at House of Blues Chicago

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Rosa’s Lounge

Hang out with friends at Rosa’s Lounge

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Chicago HIstory Museum

Buy a souvenir from Chicago History Museum’s gift shop

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Chicago Children’s Museum

Let’s play at Chicago Children’s Museum

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Memorial Chapel

Visit the Rockefeller Memorial Chapel

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Cadillac Palace Theatre

Watch a Broadway show at Cadillac Palace Theatre

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Graceland Cemetery

Get a glimpse of Inez Clarke at Graceland Cemetery

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Garrett’s Popcorn

Taste Chicago Mix at Garrett’s Popcorn

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Jazz Showcase

See a cool show at Jazz Showcase

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Fannie May

Get your sweet treats at Fannie May

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Binny's Beverage Depot

Find the wide selection of wines and spirits at Binny’s Beverage Depot

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Nuts on Clark

Snack on Chicago’s own Nuts on Clark

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Reckless Records

Add one more to your vinyl collection from Reckless Records

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Myopic Books

Go book hunting at Myopic Books

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Powell’S Bookstore

Locate hard to find books at Powell’s Bookstore

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Salvage One

Discover rare finds at Salvage One

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Vosges Haut-Chocolat

Sink your teeth in one of the yummy goodness from Vosges Haut-Chocolat

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Chicago Blackhawks

Watch the Chicago Blackhawks play Hockey

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The Rookery

Enter another era at the Rookery

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Daley Plaza

Spot the “Picasso” in Daley Plaza

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US Cellular Field

Find the best seat to see the White Sox at US Cellular Field

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Caldwell Lily Pool

Escape the city and relax at Alfred Caldwell Lily Pool

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Wringley Building

Take a pic of the iconic Wrigley Building in the morning and another at night

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Mercury Theater

Find out what’s playing next at Mercury Theater

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Adler Planetarium

Explore the Solar System and beyond at Adler Planetarium

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Harold Washington Library Center

Look at old and new books at Harold Washington Library Center

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Mccormick Bridgehouse

See the bridge lift at McCormick Bridgehouse

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Peggy Notebaert Nature Museum

Walk among the butterflies at the Peggy Notebaert Nature Museum

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Soldier Field

Catch the Chicago Bears at Soldier Field

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Laugh Factory

Bring a date and have some laughs at Laugh Factory

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National Museum of Mexican Art

Visit the National Museum of Mexican Art and see a unique exhibit

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Oak Street Beach

Get your game on and play volleyball at Oak Street Beach

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Mccormick Place

Find out what’s happening at McCormick Place

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North Avenue Beach

See the sunrise at North Avenue Beach

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Sunday Funday Showtunes

Go to Sidetrack for Sunday Funday Showtunes

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Map Room's Beer School

Know more about beers at Map Room’s Beer School

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Violet Hour

Have a romantic nightcap at Violet Hour

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Three Dots and a Dash

Escape to a tropical paradise at Three Dots and a Dash

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Baton Show Lounge

Watch a different kind of entertainment at Baton Show Lounge

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Farmhouse

Hangout at a country themed tavern at Farmhouse

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Scofflaw

Have a toast at Scofflaw

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The Hideout

See a funky performance at the Hideout

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Oz Park

Find the Tin Man, Scarecrow, Cowardly Lion, Dorothy and Toto at Oz Park

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Willie Dixon's Blue Heaven Garden

Attend a free concert at Willie Dixon’s Blues Heaven Garden

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Union Station

Hop on a train at Union Station and explore the city

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Chagall's Four Seasons

Look at Chagall’s Four Seasons, a mosaic masterpiece

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A Walk around Andersonville

Walk around Andersonville and local shops and restaurants

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Milton Lee Olive Park

Get a nice skyline view at Milton Lee Olive Park

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606

Go upward and onward at 606

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Calder’s Flamingo

Take a selfie with Calder’s Flamingo

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Devon Avenue

Explore Devon Avenue

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Pilsen

See the cool graffitti and street art at Pilsen

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Horse-Drawn Carriage

Explore the city on a horse-drawn carriage

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Chicago Food Planet Tour

Sign up at the Chicago Food Planet Food Tour

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Cruise Tour

Take the Chicago Architecture Foundation River Cruise Tour

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Maude's Liquor Bar

Make a dinner reservation at the trendy Maude’s Liquor Bar

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Trenchermen

Have a Sunday brunch at the Trenchermen

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Flora Selection at Grace

Order from the fauna or flora selection at Grace

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Longman and Eagle

Have a mouth-watering meal at Longman and Eagle

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Sable Kitchen and Bar

Whet your appetite at Sable Kitchen and Bar

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Blackbird

Have a taste of Chef Kahan’s signature dishes at Blackbird

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Goosefoot

Admire your plate like a work of art at Goosefoot

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Alinea

Have a magical dining experience at Alinea

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Martyrs’

Eat, drink and be merry at Martyrs’

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Chicago Underground Comedy

Laugh out loud at Chicago Underground Comedy

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Boystown Neighborhood

Explore the colorful Boystown neighborhood

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Brookfield Zoo

Visit the amazing animals at Brookfield Zoo

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Music Box Theatre

See a foreign film at the Music Box Theatre

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Green Mill

Have a blast from the past at Green Mill

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Gray Line Hop on Hop off Trolley Tour

Explore the city and take the Gray Line Hop On Hop Off Trolley Tour

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Drury Lane

Have a romantic night at Drury Lane

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Chicagoland Speedway

Feel the adrenaline rush at Chicagoland Speedway

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Maze Garden

Visit Morton Arboretum and enter the Maze Garden

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Six Flags

Ride all you can at Six Flags

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Hellenic Museum

Know more about Greek history and culture at the Hellenic Museum

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Illinois Railway Museum

Enjoy a train ride at the Illinois Railway Museum

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Lambs Farm

Break away from the city and visit Lambs Farm

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Medieval Times Chicago

Watch the show while dining like a king at Medieval Times Chicago

This epic list of things to do in Chicago may not encompass everything, but we tried to include the most valuable attractions that need to be checked out. However, if you hate that we missed your favorite place in the city, don’t hesitate to reach out and yell at us! Looking to get out of the big city? Check out all of the things to do in Rockford!