2 Perfect Days in Chicago

Two Perfect Days in Chicago That the Whole Family Will Love
Planned by the culture experts at What Should We Do?!

DAY 1

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 with kids, what with the dolphin shows, beluga whales, sea otters, and seals.  

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.

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: the 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 fillings like 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 gummy candies at spots like Aji Ichiban Snack USA.  

DAY 2

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).

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.

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 park: Oz Park. Named, naturally, for The Wizard of Oz, the park contains numerous statues of famed characters like Dorothy, the Scarecrow, and the Tin Man. Plus, it’s got 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.

7:30 p.m.: Head south to the glistening NewCity 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.