O’Leary Fire Truck Tours

Where would Chicago be without the legend of Mrs. O’Leary and her destructive cow (who allegedly kicked over a lantern, setting the city ablaze)? Live a little Chicago nostalgia while touring the city in an antique firetruck. You’ll get a kick out of what you learn, and your children will be over the moon as soon as they hop on the truck. Reservations are recommended and tours last a minmum of one hour.

Contact number: (312) 287-6565

Location: 505 North Michigan Avenue, Chicago, IL 60601

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Navy Pier

Rides, fireworks, a Ferris wheel, The Children’s Museum, boats and an IMAX theater are just the begining of the fun to be had at Navy Pier. Jutting out from the most northern end of The Loop, it offers stunning views of Chicago’s skyline. A great event this summer is Cirque Shanghai, a Chinese acrobat troupe sure to amaze your children.

Contact number: (312) 595-7437

Location: 600 East Grand Avenue, Chicago, IL 60611

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Children in Paradise

If Curious George, Eloise, and Spot are you child’s best friends, make sure to take them to Saturday Story Hour at this fashionable downtown bookstore which hosts the self-proclaimed, “largest selection of way-cool children’s books, software, videos, CDs, tapes, cards, and beanie babies in Chicago.” Children in Paradise is a lovely spot to get up close and literarily personal with the children. You’ll both be glad to be away from your TV while you’re there

Contact number: (312) 951-5437

Location: 909 North Rush Street, Chicago, IL 60611

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Chicago Outdoor Film Festival

Share your passion for classic cinema with your children at the Chicago Outdoor Film Festival, held during the summer months at beautiful Grant Park. This Chi-town tradition features iconic films such as The Sound of Music, Butch Cassidy and the Sundance Kid, and Young Frankenstein on a 50-foot by 34-foot screen with state-of-the art sound. You and your kids can spread out a blanket, unpack your picnic, and relax with the starry night above. And should those stars be hidden by clouds, simply don your raincoats and carry umbrellas because films are presented in rainy weather, barring lightning and other severe conditions. Feature films are preceded by presentations of local filmmakers’ short works. Those who arrive on two wheels receive the added benefit of free valet bike parking!

Contact number: (312) 744-3315

Location: 100 South Lake Shore Drive, Chicago, IL 60603

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Chicago Chocolate Tours

Dive into the rich history of chocolate with your child and satisfy your sweet teeth on a guided, walking Chocolate Tour. Company founder Valerie Beck will charm your socks off as she explains the properties of different chocolate varieties before leading you and your child to the city’s and world’s finest chocolatiers, like Leonidas, Godiva, Frango, Hershey’s, and Lindt. Winter tours keep you mostly out of the cold by hitting locations within a quarter mile of each other, while fair weather tours pull you off the beaten path and toward some of Chicago’s lesser-known chocolate shops.

Contact number: (312) 863-8614

Location: 150 North Michigan Avenue, Chicago, IL 60601

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Chicago Architectural Boat Tours

Of the thousand things this city boasts, archictectural diversity is one of the most impressive. We understand walking young children around town to look at a bunch of buildings and explaining their coolness may not be the best way to pique their interest, but getting your clan on a boat to cruise along the Chicago River is guaranteed fun. Young children will love the sheer novelty of boating, and older children will soak up just as much of the local architecture as you.

Contact number: (312) 527-2002

Location: 465 North McClurg Court, Chicago, IL 60611

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Women and Children First

One of the largest feminist bookstores in the country, Women and Children First touts a stockpile of more than 30,000 books, with authors as diverse as Kipling and Taylor. You and your child may immerse yourselves for hours in children’s titles for every reading level. Authors from all over the country make it a point to discuss their work with the bookstore patrons through scheduled forums. On your child’s birthday, bring him or her to Wednesday morning storytime, where store owner and storyteller Linda Bubon will announce the big day, feature your child’s favorite stories, and provide snacks afterward.

Contact number: (773) 769-9299

Location: 5233 North Clark Street, Chicago, IL 60640

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Uncle Fun

A trip to this Belmont Avenue boutique of oddities will surely solidify your title as the most fun mom ever. The aptly named “Uncle Fun,” is widely known to be the finest purveyor of the most delightfully bizarre odds and ends your children have probably never seen. Old favorites like sea monkeys and hand buzzers sit alongside toy robots, rubber pigs and appendages. It’s a perfect spot for the young practical jokester in your family to get lost in the mountain of merchandise and come out with their own heap for a decent price.

Contact number: (773) 477-8223

Location: 1338 West Belmont, Chicago, IL 60657

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Psychobaby

Super hip children will love the quirky selection of clothes, shoes, accessories and toys stocked at this trendy boutique. You’ll find everything from onesies with ironic slogans, mini-Converse Chuck Taylors, backpacks, strollers, playsets, and even kids’ Crocs. The best part is you’re not paying top price for all that style since the store also boasts plenty of bargains.

Contact number: (773) 772-2815

Location: 1630 North Damen Avenue, Chicago, IL 60647

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Mini Me

Not Austin Powers’ sidekick, it’s instead a boutique serving Chicagoland the very best in kiddie haute couture! Mini Me is where uber trendy parents will go to teach their little ones about the virtues of Prada and Burberry and everything chic in between. Definitely not the place to go if you’re shopping on a string, but alot of fun if you want to spoil your little princess. Boys clothing offered up to size four.

Contact number: (312) 988-4011

Location: 900 North Michigan Avenue, Chicago, IL 60611

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