JetBlue Vacations: Two Perfect Days in Chicago That the Whole Family Will Love

Meet a penguin! Eat some gumbo! Visit Oz!

Photo courtesy of Voyage en Roue Libre/Facebook

You might know all about snapping selfies at the “Bean,” but do you know where to get the most adorable candy in Chicago? Read on to find out!


9:30 a.m.: Rise and shine with carrot cake pancakes and chocolate French toast at Bongo Room in the South Loop.

11 a.m.: Stroll through Grant Park, two blocks to the east, and make your way along the shimmering Lake Shore to Museum Campus. The Shedd Aquarium is particularly popular for kids, what with its dolphin shows, beluga whales, sea otters, and seals.  

Photo by Brenna Hernandez/Courtesy of Shedd Aquarium

1:30 p.m.: Head back across Grant Park into the Loop, the skyscraper-filled heart of downtown Chicago. Make your way to the seventh floor of a historic jeweler’s building to find the festively decorated Heaven on Seven, where you can feast on New Orleans–style dishes like gumbo, po’boys, and jambalaya.

2:30 p.m.: Marvel at the architectural wonders of Millennium Park, a stone’s throw from Heaven on Seven. Snap some selfies in the “Bean” before walking across the bridge to Maggie Daley Park, home to whimsical playgrounds and seasonal activities like miniature golf and ice-skating.

Photo courtesy of Voyage en Roue Libre/Facebook

4 p.m.: Meander up Michigan Avenue to the Chicago River, then take the stairs down to one of the city’s newest outdoor attractions: Riverwalk. Explore the various artsy segments of the riverside park and gawk at the floating gardens.

5 p.m.: Hop aboard a water taxi and enjoy a leisurely, scenic ride down the river to Chinatown. Pass through Ping Tom Memorial Park and find your way to the cozy Qing Xiang Yuan Dumplings. Here, the whole family can share platters of delicious steamed, boiled, or fried dumplings with such fillings as chicken, pork, shrimp, and vegetables.

7 p.m.: After dinner, explore Chinatown Square and its myriad colorful shops. Candy stores are a fun way to round out the day, especially considering the overwhelming abundance of adorable gummies at spots like Aji Ichiban Snack USA.  

Photo courtesy of Aji Ichiban


10 a.m.: Start the day with a comfort food spread at Kanela Breakfast Club in Chicago’s cutest neighborhood: Old Town. Mac and cheese and waffles share menu space with Greek-inspired treats like loukoumades (Greek doughnuts).

Photo courtesy of Kanela Breakfast Club/Facebook

11:30 a.m.: Peruse the quirky trinkets, toys, and gifts at nearby Judy Maxwell Home. The quaint “urban general store” is filled with kid-friendly oddities, like clothes decorated with Chicago hot dogs.

12:30 p.m.: Walk up Wells Street and cut across Clark into Lincoln Park. An ideal place for outdoor exploration, you can check out the nature boardwalk before heading into the free Lincoln Park Zoo to meet penguins, giraffes, rhinos, flamingos, and plenty more.

Photo courtesy of Lincoln Park Zoo/Facebook

1:30 p.m.: Now that you’ve snagged some hot dog swag, why not head to one of the city’s most iconic hot dog stands for lunch? A quick walk from the zoo, the Wiener’s Circle is a local staple, serving up Chicago-style dogs in a casual atmosphere with picnic table seating.

2:30 p.m.: Burn off some energy at another beloved neighborhood spot: Oz Park. Named for The Wizard of Oz, it contains numerous statues of such famed characters as Dorothy, the Scarecrow, and the Tin Man. Plus, it boasts one of the best playgrounds in town.

6 p.m.: For dinner, visit a homey Lincoln Park institution known for its burgers and salad bar. R.J. Grunts is a timeworn favorite among families, offering something for everyone.

Photo courtesy of RJ Grunts via Yelp

7:30 p.m.: Head south to the glistening New City development, home to a variety of shops, restaurants, and family-friendly entertainment options. The Arclight is one of the best movie theaters in town, or enjoy a round of bowling at Kings. You’ll be home for bed with time to spare! Sorry (not sorry), couldn’t help ourselves.

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