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The 96 Best Family Entertainers for Hire in Highland, IN

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190 Family Entertainers serving Highland, IN
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Caricatures by Ellen Lustig - Caricaturist / Family Entertainment in Chicago, Illinois Featured vendor banner
Caricatures by Ellen Lustig - Caricaturist / Family Entertainment in Chicago, Illinois

Caricatures by Ellen Lustig

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5.0 (8)
Top Performer badge
  • Map pin icon Chicago, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 17 Verified Bookings

A S. said “Ellen was awesome. Her drawings were cute and our guests enjoyed them. She was very pleasant and prompt.”

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Matt Roberts: Clean Comedy Magic - Magician / Family Entertainment in Chicago, Illinois Featured vendor banner
Matt Roberts: Clean Comedy Magic - Magician / Family Entertainment in Chicago, Illinois

Matt Roberts: Clean Comedy Magic

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5.0 (41)
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  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 57 Verified Bookings

Kerry E. said “We had Matt at a party for our 5th grade children (about 30 kids) and they loved his performance! He was entertaining, engaging, age appropriate and very…”

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Paul Draws You - Caricaturist / Family Entertainment in Chicago, Illinois Featured vendor banner
Paul Draws You - Caricaturist / Family Entertainment in Chicago, Illinois

Paul Draws You

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4.59 (12)
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  • Map pin icon Chicago, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 30 Verified Bookings

Alyse W. said “He was amazing! Showed up early and was very personable with all of our guests. Such an amazing personality and person!”

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Shiva Jamba Entertainment - Face Painter / Family Entertainment in Chicago, Illinois Featured vendor banner
Shiva Jamba Entertainment - Face Painter / Family Entertainment in Chicago, Illinois

Shiva Jamba Entertainment

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4.98 (21)
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  • Map pin icon Chicago, IL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 20 Verified Bookings

Devorah L. K. said “Devorah is an exceptional music teacher who effortlessly connects with children of all ages, creating a delightful and engaging atmosphere for both children…”

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Dennis Christie MD "Master Deceptionist" - Magician / Family Entertainment in Des Plaines, Illinois Featured vendor banner
Dennis Christie MD "Master Deceptionist" - Magician / Family Entertainment in Des Plaines, Illinois

Dennis Christie MD "Master Deceptionist"

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5.0 (36)
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  • Map pin icon Des Plaines, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 40 miles from Highland
  • Check mark icon 88 Verified Bookings

Gary M. said “Everyone enjoyed the magic that was provided by Dennis. His magic show held everyone's attention waiting to see what he would do next. Thank you…”

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Face Painting by Valery - Face Painter / Family Entertainment in Chicago, Illinois Featured vendor banner
Face Painting by Valery - Face Painter / Family Entertainment in Chicago, Illinois

Face Painting by Valery

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5.0 (15)
  • Map pin icon Chicago, IL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 3 Verified Bookings

Jaramee F. said “We hired Valery for a small Corporate Easter party. She was a huge hit! The kids loved the face painting, tattoos and balloons. She was on time, professional,…”

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The Magic of Benjamin Barnes - Magician / Family Entertainment in Chicago, Illinois Featured vendor banner
The Magic of Benjamin Barnes - Magician / Family Entertainment in Chicago, Illinois

The Magic of Benjamin Barnes

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5.0 (9)
  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 14 Verified Bookings

Nina C. said “Benjamin has great interpersonal skills. He can really work a crowd. His magic left us speechless. He does everything with such elegance. What a delight!”

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Caricatures By McGee - Caricaturist / Family Entertainment in Chicago, Illinois Featured vendor banner
Caricatures By McGee - Caricaturist / Family Entertainment in Chicago, Illinois

Caricatures By McGee

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4.96 (21)
  • Map pin icon Chicago, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 42 Verified Bookings

Alex T. said “Barton drew at my sons 1st birthday party and everyone loved him. He was great with kids and adults and everyone loved their drawings. He even accommodated…”

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Mega Magic- Magician Mike D'Urzo - Magician / Family Entertainment in Chicago, Illinois Featured vendor banner
Mega Magic- Magician Mike D'Urzo - Magician / Family Entertainment in Chicago, Illinois

Mega Magic- Magician Mike D'Urzo

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5.0 (14)
  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 11 Verified Bookings

Surekka B. said “Mike is a pleasure to work with and his show was AMAZING! He ran the show like a pro, with little work involved on our end. We were all in awe of his…”

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John Measner Magic Productions, Inc. - Magician / Family Entertainment in Naperville, Illinois Featured vendor banner
John Measner Magic Productions, Inc. - Magician / Family Entertainment in Naperville, Illinois

John Measner Magic Productions, Inc.

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5.0 (1)
  • Map pin icon Naperville, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 39 miles from Highland
  • Check mark icon 1 Verified Booking

Esther B. said “I only have amazing things to say about John! I just got off the phone with him, he was so friendly and helpful, fun and very very experienced, with over…”

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Chezaday Magic Show - Magician / Family Entertainment in Naperville, Illinois Featured vendor banner
Chezaday Magic Show - Magician / Family Entertainment in Naperville, Illinois

Chezaday Magic Show

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4.96 (119)
  • Map pin icon Naperville, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 39 miles from Highland
  • Check mark icon 1 Verified Booking

Satish T. said “Kids enjoyed the magic show and the Baloon twisting.”

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The Crescent Circus - Magician / Family Entertainment in Chicago, Illinois Featured vendor banner
The Crescent Circus - Magician / Family Entertainment in Chicago, Illinois

The Crescent Circus

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5.0 (16)
  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland

Troy D. said “Any opportunity that you have to watch Crescent Circus perform, do not miss it. The night was full of laughs, acrobatics, slight of hand, juggling and…”

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David Ranalli - Magician / Family Entertainment in Chicago, Illinois Featured vendor banner
David Ranalli - Magician / Family Entertainment in Chicago, Illinois

David Ranalli

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4.91 (11)
  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland

Derek B. said “David was awesome! We hired him to perform for our 2 Easter services at Resonate Church and we couldn't have been happier with the result! He was…”

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Sean Watson Magician - Master Of Illusion - Magician / Family Entertainment in Chicago, Illinois Featured vendor banner
Sean Watson Magician - Master Of Illusion - Magician / Family Entertainment in Chicago, Illinois

Sean Watson Magician - Master Of Illusion

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5.0 (2)
  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 1 Verified Booking

Dani B. said “Everyone at our party had a great time - really great! Thank you to Sean for making it fun, entertaining and special. He went above and beyond to make…”

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Celebration Station Face Painting - Face Painter / Family Entertainment in Chicago, Illinois Featured vendor banner
Celebration Station Face Painting - Face Painter / Family Entertainment in Chicago, Illinois

Celebration Station Face Painting

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5.0 (1)
  • Map pin icon Chicago, IL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 24 miles from Highland

Rebecca S. said “I recently had the pleasure of hiring an exceptionally talented face painter for my child's birthday party, and I cannot express how delighted I…”

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360 Booth Live - Photo Booths / Family Entertainment in Chicago, Illinois Featured vendor banner
360 Booth Live - Photo Booths / Family Entertainment in Chicago, Illinois

360 Booth Live

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5.0 (5)
  • Map pin icon Chicago, IL
  • Vendor category icon Photo Booths / Family Entertainment
  • Travel distance icon 24 miles from Highland

Jessica S. said “I highly recommend 360 booth Live to anyone looking for an amazing 360 Photo booth experience! They made a wedding day! Everyone had so much fun with…”

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Edd Fairman, Wizard of Sorts - Magician / Family Entertainment in Chicago, Illinois
Edd Fairman, Wizard of Sorts - Magician / Family Entertainment in Chicago, Illinois

Edd Fairman, Wizard of Sorts

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5.0 (1)
  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 1 Verified Booking

Bob M. said “We had a nice gathering of friends and family over for our Good Friday Dinner Celebration and Edd’s performance was the cherry on too of a great evening.…”

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Kazar The Timewave Wizard - Magician / Family Entertainment in Harwood Heights, Illinois
Kazar The Timewave Wizard - Magician / Family Entertainment in Harwood Heights, Illinois

Kazar The Timewave Wizard

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4.17 (2)
  • Map pin icon Harwood Heights, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 34 miles from Highland
  • Check mark icon 5 Verified Bookings

Amanda S. said “Kazar and his staff was very professional and polite, arriving with plenty of time to set up his equipment. He delivered a really entertaining show, with…”

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FaceArt by Amy Lee - Face Painter / Family Entertainment in Palos Heights, Illinois
FaceArt by Amy Lee - Face Painter / Family Entertainment in Palos Heights, Illinois

FaceArt by Amy Lee

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5.0 (18)
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  • Map pin icon Palos Heights, IL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 19 miles from Highland
  • Check mark icon 26 Verified Bookings

Victoria B. said “Amy went above and beyond at our daughters christening. She was very open to communication and accommodating when we pushed the start time back by 45…”

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King Caricatures - Caricaturist / Family Entertainment in Chicago, Illinois
King Caricatures - Caricaturist / Family Entertainment in Chicago, Illinois

King Caricatures

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5.0 (13)
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  • Map pin icon Chicago, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 18 Verified Bookings

Angela L. said “King Caricatures was amazing to work with. He even went above and beyond what he needed to do. He customized the paper for our event by printing it with…”

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Magic in Chicago - Magician / Family Entertainment in Chicago, Illinois
Magic in Chicago - Magician / Family Entertainment in Chicago, Illinois

Magic in Chicago

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5.0 (2)
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  • Map pin icon Chicago, IL
  • Vendor category icon Magician / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 10 Verified Bookings

Demma S. said “Our event was a massive success and it is all thanks to Mike's amazing performance! Not only does he do a brilliant variety of tricks, but he is…”

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Hurtado Arts - Caricaturist / Family Entertainment in Chicago, Illinois
Hurtado Arts - Caricaturist / Family Entertainment in Chicago, Illinois

Hurtado Arts

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4.94 (27)
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  • Map pin icon Chicago, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 24 miles from Highland
  • Check mark icon 50 Verified Bookings

Candi R. said “Our post prom event had a line at the caricature station the entire evening! The students were so appreciative of their drawings. The work was fabulous!”

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Cute Curiosities Face Painting - Face Painter / Family Entertainment in Forest Park, Illinois
Cute Curiosities Face Painting - Face Painter / Family Entertainment in Forest Park, Illinois

Cute Curiosities Face Painting

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5.0 (13)
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  • Map pin icon Forest Park, IL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 29 miles from Highland
  • Check mark icon 27 Verified Bookings

Morgan B. said “Our facepainter was very prompt, speedy painter, and very talented! The kids absolutely loved her.”

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C & I Caricatures - Caricaturist / Family Entertainment in Wilmington, Illinois
C & I Caricatures - Caricaturist / Family Entertainment in Wilmington, Illinois

C & I Caricatures

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4.77 (4)
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  • Map pin icon Wilmington, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 40 miles from Highland
  • Check mark icon 12 Verified Bookings

Nina C. said “We could not be more please with C & I caricatures. They were so professional, arrived on time and were amazing artists. Their drawings were absolutely…”

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Skin Colour Events - Face Painter / Family Entertainment in Dyer, Indiana
Skin Colour Events - Face Painter / Family Entertainment in Dyer, Indiana

Skin Colour Events

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5.0 (2)
  • Map pin icon Dyer, IN
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 5 miles from Highland
  • Check mark icon 4 Verified Bookings

Jennifer M. M. said “Great to work with and made the attendees happy! :)”

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Your Mobile DJ & Photo Booth - Photo Booths / Family Entertainment in Crown Point, Indiana
Your Mobile DJ & Photo Booth - Photo Booths / Family Entertainment in Crown Point, Indiana

Your Mobile DJ & Photo Booth

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5.0 (5)
  • Map pin icon Crown Point, IN
  • Vendor category icon Photo Booths / Family Entertainment
  • Travel distance icon 10 miles from Highland
  • Check mark icon 10 Verified Bookings

Tamra H. said “They did a fantastic job, very personal and helpful, all of our employees had a great time.”

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Balloontacular! - Balloon Twister / Family Entertainment in Crown Point, Indiana
Balloontacular! - Balloon Twister / Family Entertainment in Crown Point, Indiana

Balloontacular!

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5.0 (2)
  • Map pin icon Crown Point, IN
  • Vendor category icon Balloon Twister / Family Entertainment
  • Travel distance icon 10 miles from Highland
  • Check mark icon 7 Verified Bookings

Brittani B. said “Everything was amazing from the beginning. Communication was clear and responses were very quickly! Day event came prepared and on time. The kids loved…”

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Ernest Posey Caricatures - Caricaturist / Family Entertainment in Flossmoor, Illinois
Ernest Posey Caricatures - Caricaturist / Family Entertainment in Flossmoor, Illinois

Ernest Posey Caricatures

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5.0 (14)
  • Map pin icon Flossmoor, IL
  • Vendor category icon Caricaturist / Family Entertainment
  • Travel distance icon 12 miles from Highland
  • Check mark icon 23 Verified Bookings

Brittany J. said “All of the guests enjoyed being able to take home a great caricature!”

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TotallyTia Face and Body Art - Face Painter / Family Entertainment in Matteson, Illinois
TotallyTia Face and Body Art - Face Painter / Family Entertainment in Matteson, Illinois

TotallyTia Face and Body Art

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5.0 (2)
  • Map pin icon Matteson, IL
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 14 miles from Highland
  • Check mark icon 1 Verified Booking

Victoria J. said “Tia is an amazing face painter. She is professional and fun. We have worked with her several times over the years and her service remains exceptional.…”

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Paint Time FUN! - Face Painter / Family Entertainment in Portage, Indiana
Paint Time FUN! - Face Painter / Family Entertainment in Portage, Indiana

Paint Time FUN!

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5.0 (6)
  • Map pin icon Portage, IN
  • Vendor category icon Face Painter / Family Entertainment
  • Travel distance icon 14 miles from Highland
  • Check mark icon 1 Verified Booking

Leanne K. said “Felicia was amazing! Her tattoos and face paintings are simply adorable. She was so great to work with and has the sweetest personality. I highly recommend…”

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Family Entertainment in Highland, IN


Finding entertainment that’s full of variety and fun for all ages doesn’t have to be difficult. You just have to know where to start!

First, you’ll want to determine what your event needs. For small celebrations, strolling performers are a popular option for creating a fun atmosphere. For bigger gatherings, carnival games and inflatables are a big hit! Once you’ve determined what type of entertainment to book, search online for professionals in your area. Most entertainers and vendors have online profiles that show their services, and many offer various party packages to fit your budget. Check out performance descriptions and photos, and if possible, read through reviews from their past clients. When you’re ready to contact an entertainer for their rates and availability, make sure to give them as much information about your event as possible. Discuss important details such as performance space, power supply, expected number of guests, and any unique aspect of your event. The more info you give the professional, the easier it is for them to provide a customized quote. Lastly, confirm the agreement and details in writing. With GigSalad, everything you need to find and book family entertainment is in one simple platform. Browse profiles, get free quotes, and book with the added security of our Worry-Free Guarantee! Search for Family Entertainment in Highland, Indiana above.

Please note that these Family Entertainment may also travel to Dyer, Lynwood, St John, Sauk Village, Glenwood, Ford Heights, Burnham, Thornton, Wolf Lake, Whiting, Phoenix, Lake Station, Steger, Crete, Flossmoor, Hazel Crest, Olympia Fields, Markham, Posen, Cedar Lake, Calumet Park, Richton Park, Matteson, Winfield, Ogden Dunes, University Park, Wheeler, Midlothian, Robbins, and Merrionette Park.

Find Family Entertainment in nearby cities

Griffith Munster Hammond Lansing Schererville Calumet City
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