Without the Kids? How did we get this once in a blue moon chance to travel without kids? We combined expiring frequent flier miles, a willing mother-in-law babysitter, a strong desire for deep dish pizza, plus a 15 year yearning to see George Seurat’s A Sunday on La Grande Jatte. Ahhh CHICAGO is my kind of town!

In October? Oh yeah, perfect time to travel. Temperatures average in the mid to lower 60s. Windy city? What wind? It was beautiful the whole time. And talk about the most ‘walkable’ city I’ve ever been too!? (I lived in Brooklyn, and walked to the hospital for my first childbirth!) I know about walking in cities. You could choose from literally hundreds of hotels all around the city and still be within walking distance of ‘The Loop’, Millennium Park, Navy Pier, the Magnificent Mile or all Four!

Without the Guilt? How did we travel sans bambinos AND sans parent guilt? Easy. We are already planning a great family trip back to Chi-Town. Making it easy to choose which grown up, yet still tourist centered places and events we wanted to see and do. Knowing if we had the kids along we couldn’t manage them (plus enjoy them a lot less!)

Top Chicago Grown-Up Tourist-y Things to do in Chicago:
(But KIDS might hate)

• Spend as much time as we want inside the Art Institute of Chicago. Sitting and pondering the painting I’ve waited 15 years of my life to see, with no whining kiddos complaining they are bored or tired or hungry! Seurat, O’Keefe, Van Gogh, Cassatt… it is impressionism Mecca!
• Enjoy riding the Shoreline Architectural Boat Tour. Calm and slow.
• Walk an extra 6 blocks to find the BEST Chicago pizza (according the local-yokel on the street). Worth every single extra step! (Hint: Giordanos on Rush)
• Connect with local Chicago mom blogging pals for a Friday Brunch at FoodLife in Water Tower Place. (HI @ChefDruck @MJTam & @ConnectingWomen!)
• Watch ‘Cat on a Hot Tin Roof’ at the Raven Theater. Not only was this NOT an appropriate play for kids, but it was a 30 min train ride and a 15 minute walk one way to the theater from our hotel. (PS. Use HotTix.com for cheap tickets. Cha-ching!)
• Find the Newberry Library from my most favorite novel: “The Time Traveler’s Wife”.
• Ride the whole “L-loop” just for fun. (Okay, kids would totally love this!)
• Walk along the Chicago River Walk. Stopping and reading the plaques and stopping for no reason at all!
• NOTHING. Seriously, sometimes when traveling - grown ups just want to head back to the hotel and take a nap!

Top 10 Things to do with Kids in Chicago:

• Any boat tour! (Yes, even the Architectural one), they will love being on the boat. And at one hour, it was the perfect tour length for kids.
• Deep dish pizza, for sure! But no extra walking. Taxis are your friend. (And of course testing out 2 or 3 hotdog joints, then voting on the best Chicago Dog).
• Visit Willis (Sears) Tower and walk out on that scary sky deck glass floor thing!
• Navy Pier. Any of the rides: 5 Story Ferris wheel, miniature golf, carousel more…
• Chicago Children’s Museum (also at Navy Pier).
• Fireworks at the Navy Pier, Free! Saturday nights.
• American Girl Doll Store (my daughter will salivate at the thought).
• Chicago Museum of Science and Industry (my little boy is a total science nut, I hear this is one of THE best science museum’s in the nation!?). Also Shedd Aquarium and the Adler Planetarium for my oldest who wants to be an astronomer.
• Wrigley Field Tour (We’re thinking about planning our trip around the baseball season!).
• Play in the many fountains and parks in Chicago: Buckingham Fountain, The Crown Fountain, The children’s fountain, Fountain of the Tritons. You could make a treasure map to find as many fountains in the city as you can!

For great ideas on how to travel to Oahu with & withOUT the kids, check out Carissa’s insightful post: Travel Without Kids (or Mommy Guilt).

Carissa is a writer for Travelingmom, she received no compensation from any of the sites or companies mentioned.