City guide: Chicago

Your one-stop city guide, packed with information on family-friendly hotels, restaurants, and local and unique attractions.

Jeff Gunn (jeffgunn)
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Oh, Chicago! With its scenic skyline and riverfront, the Windy City is must-see destination for grandparents and their families. From visiting local museums and the popular Skydeck Chicago to enjoying a Super Dawg meal with a 1950s drive-in, your grandkids will enjoy the old-school meets new-school attractions in this amazing city.


The James Chicago
55 East Ontario, Chicago, IL
(312) 337-1000
Price: Rooms starting at $180/night

The James Chicago has a prime location in the city and is one of the most stylish and modern hotels in the area. However, what sets the James apart from the rest is their kid-oriented service. The James has teamed up with artist Paul Frank to offer kids a Julius the Monkey welcome. They’ll receive a selection of books and games, as well as their very own Paul Frank pajamas and coloring pages. 

Key Lime Cove Waterpark Resort
1700 Nations Drive, Gurnee, IL
(866) 797-2563
Price: Rooms starting at $170/night

This indoor waterpark is a little removed from Chicago, but with all the dining and entertainment options and games there’s very little reason to want to go anywhere else. Key Lime Cove Waterpark Resort is a Florida Keys-inspired hotel with over 400 rooms and suites, tons of water slides, and live entertainment for your families to enjoy.

Chicago South Loop Hotel
11 West 26th Street, Chicago, IL
(312) 225-7000
Price: Rooms starting at $170/night

The Chicago South Loop Hotel is a different experience from the rest. Located in the historic Bronzeville District, famous for being the center of African-American culture, it offers families a unique side of Chicago. You and your grandchildren could take advantage of the educational packages available, such as the Museum of Science and Industry Chicago Package or the Field Museum All Access Package.

The Drake Hotel

140 East Walton Place, Chicago, IL
(312) 787-2200
Price: Rooms starting at $159/night

To capture the luxury and glamour that encapsulated Chicago in the 1920s, you and your grandchildren only need to book a night in the Drake Hotel. This National Landmark is not only a great sight to see, but a great place to stay. Young girls in particular will love the hotel’s American Girl Place package, which comes with a personalized welcome letter, an American Girl doll-sized travel bed, and access to the hotel’s library of American Girl books. 

Silversmith Chicago Hotel

10 South Wabash Avenue, Chicago, IL
(312) 372-7696
Price: Rooms starting at $180/night

Although it occupies the historic Silversmith Building, which has been listed on the National Register of Historic Places, don’t consider the Silversmith Hotel & Suites your typical boutique hotel. With great amenities and facilities, including the in-house Ada’s Famous Deli & Restaurant, the service and space provides you and your grandkids with the comfort you need during your stay. Silversmith also offers a Chicago family vacation package, which includes breakfast for two adults and two children at Ada’s and a tin of Garrett’s Popcorn. 


Chicago-style pizza

Eric Chan – Deep Dish Pizza

Super Dawg Drive-In
6363 North Milwaukee Avenue, Chicago, IL
(773) 763-066
Hours: Sunday-Thursday: 11am-1am, Friday and Saturday: 11am-2am
Price: $
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

You might go for the hot dogs, but you and your grandkids will surely stay for the 1950’s drive-in, food ordering style at Super Dawg. Since 1948, this family-owned business has maintained the culture and delicious food that originally made it a success. It’s been listed as a landmark in the bestseller 1,000 Places to See Before You Die, and has even received great recognition in the Food Network’s Unwrapped and Emeril Live.

605 North Clark Street, Chicago, IL
(312) 787-1501
Monday-Thursday: 11am-9:30pm
Friday: 11am-10:30pm
Saturday: 11am-11pm
Sunday: 11am-9pm

Price: $$
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

If your visit in Chicago starts to get a little too ordinary, you can brighten things up by visiting the Rainforest Café. With a wildlife theme that’s sure to drive your grandkids wild, the Rainforest Café offers a creative menu full of dinosaur-shaped chicken, sparkling volcano dessert, and a showcase of some of the jungle friends, Tuki, Nile, and Iggy.

The Choo-Choo-Hamburgers on Wheels
600 Lee Street, Des Plaines, IL
(847) 391-9815
Hours: Saturday-Wednesday: 10:30am-3pm, Thursday-Friday: 10:30am-8pm
Price: $
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

With their hamburgers on wheels and tracks service, the Choo-Choo Restaurant gives fast food a new name. This Chicago favorite serves up patrons their favorite dishes from a toy train set. Your grandkids can choose from hot dogs, hamburger, cheese burger or a grilled cheese from the customized Kids’ Menu.

Eli’s Cheesecake
6701 West Forest Preserve Drive, Chicago, IL
(773) 736-3417
Monday-Friday: 8am-6pm
Saturday: 9am-5pm
Sunday: 11am-5pm
Price: $
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

Who can deny a good slice of cheesecake? This is especially true if it’s an Eli Cheesecake original. What originally started as a marquee dessert at Eli’s The Place for Steak spiraled into a franchise of its own as Eli’s Cheesecake. Since its debut in 1980, this rich and creamy dessert has been a hit with local restaurants and retail outlets.

1001 West Washington Boulevard, Chicago, IL
(312) 850-2663
Monday: 7am-3pm
Tuesday-Thursday: 7am-9pm,
Friday: 7am-10pm
Saturday: Brunch: 8am-3pm, Dinner: 5-10pm
Sunday: Brunch: 8am-3pm

Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

At Wishbone, there’s a sense of folklore and fun that derives not only from the delicious menu, but the artwork as well. This unique restaurant features the oil portraits of Chicago favorite, Lia Nickson, who was the restaurateurs’ mom.


Chicago Children’s Museum (CCM)
700 East Grand Avenue Chicago, IL
(312) 527-1000
Hours: 10am-5pm (daily)
Summer Hours: May 25-September 3
Sunday-Wednesday: 10am-6pm, Thursday-Saturday: 10am-8pm

Price: Children & Adults (ages 64 & under): $12, Seniors (ages 65+): $11
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

The Chicago Children’s Museum has come a long way since it was first established in 1982, in response to the general cutbacks to the city’s public schools. Now, it’s one of the top attractions in Chicago and the second most visited children’s museum in the country. Your grandchildren will enjoy seeing their inventions come to life in the Inventing Lab, as well as experience life in their own size in Kids Town.

Skydeck Chicago
233 South Wacker Drive, Chicago, IL
(312) 875-9447
April-September: 9am-10pm (daily)
October-March: 10am-8pm (daily)

Price: Youth (ages 3-11): $11, Adults (ages 12+): $17.50
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

What better way to view Chicago than from 1,343 feet above the ground? That’s the Skydeck Chicago experience. What’s more is that on a clear Chicago day your grandchildren can see across four states: Illinois, Indiana, Wisconsin, and Michigan. You can also see if you could get them to stand on The Ledge, a glass box that extends 4.3 from the Skydeck on the 103rd floor.

Shedd Aquarium
1200 South Lake Shore Drive, Chicago, IL
(312) 939-2438
Memorial Day-Labor Day: 9am-6pm (daily)
Labor Day-Memorial Day: Monday-Friday: 9am- 5pm, Saturdays, Sundays & Holidays: 9am-6pm

Price: Children (ages 3-11): $6, Adults (ages 12+): $8
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

In Chicago, the opportunity for your grandchildren to explore the ocean is just a short drive away. We’re talking about the Shedd Aquarium on Chicago’s Museum campus. With their amazing Aquatic Show, featuring soaring dolphins and dancing belugas to their 4-D experience with special FX seating (think strange smells, bubbles and wind), kids will dive into all the fun and learning.

Navy Pier
600 East Grand Avenue, Chicago, IL
(888) 463-0214
Summer Hours (June 1-September 3): Sunday-Thursday: 10am-10pm, Friday-Saturday: 10am-12am

Fall Hours: Sunday-Thursday: 10am-8pm, Friday-Saturday: 10am-10pm
Winter Hours: Monday-Thursday: 10am-8pm, Friday-Saturday: 10am-10pm, Sunday: 10am-7pm
Price: Free
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

What’s a day like by Lake Michigan? You and your grandchildren can visit Chicago’s Navy Pier to find out. There are fine restaurants, retail shops, the popular Family Pavilion, and a 15-story tall Ferris wheel to top the experience. Several cruises are available to explore beyond the lakeshore from the pier’s Dock Street.

Buckingham Fountain
Columbus Drive (301 East) and Congress Parkway (500 South), Chicago, IL
(312) 742-7529
Hours: April-October: 8am-11pm (daily)
Price: Free
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

Chicago does everything big, including building the largest water fountain in the world. Dedicated in 1927, Buckingham Fountain is considered the city’s front door as it’s located in Grant Park, the intersection to the main parkways. Families will enjoy regular water shows and evening color-light shows.

Local uniques:

Children’s Theatre
1464 North Milwaukee Avenue, Second Floor, Chicago, IL
(773) 227-0180
Hours: Call ahead for show times
Price: $36 per person
Age Range: Preschooler, Elementary, Tween, Teen

Children’s Theatre is a great stop for the little performer in your family. Since 2006, this great organization has engaged and inspired young theater-goers with their professional theatre programming and productions, such as Harold and the Purple Crayon.

Jane Addams Hull House Museum
The University of Illinois at Chicago, 800 South Halsted Street, Chicago, IL
(312) 413-5353
Monday, Saturday: Closed
Tuesday-Friday: 10am-4pm
Sunday: 12pm-4pm
Price: $5 (suggested donation)
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

Jane Addams was a pioneer in the woman suffrage movement, social reformer, author and of course, founder of the first settlement house in the U.S., Hull House. This beautiful, historical and recently renovated foundation houses a library, salon and several collections of books, including 19th century titles that inspired Addams’ movement.

Robot City Workshop
3226 North Sheffield, Chicago, IL
(773) 281-1008
Hours: 11am-7pm (daily)
Age Range: Preschooler, Elementary, Tween, Teen

From R2D2 to Wall-E, kids have always been fascinated with robots and likely your grandkids aren’t an exception. Robot City kicks into high-gear the imagination and drive to create something that’s out of this world with their fascinating workshops, summer camp, and even after-school program for local Chicago students.

Broadway Armory Park
5917 North Broadway, Chicago, IL
Hours: 7am-9pm (daily)
Price: Free
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

Broadway Armory Park is Chicago Park District’s largest recreational building, with over five gym facilities, newly completed elevated track, and other recreational activities. What’s more, your grandkids can also try to tackle the awesome 35-foot tall climbing wall! Before becoming a haven for active families and community programs, the armory was home to the Illinois National Guard and was used the building for drilling and training.

Chicago Cultural Center
78 East Washington Street, Chicago, IL
(312) 744-6630
Monday-Thursday: 8am-7pm
Friday: 8am-6pm
Saturday: 9am-6pm
Sunday: 10am-6pm

Price: Free
Age Range: Baby, Toddler, Preschooler, Elementary, Tween, Teen

It isn’t the “People’s Palace” for nothing! As the nation’s first free municipal cultural venue, the Chicago Cultural Center is home to hundreds of free international, national, regional artists, musicians and performers each year. This landmark, which was established in 1897, houses the Chicago Office of Tourism and the Department of Cultural Affairs and Special Events.