How To Spend a Day in Chicago on a Whim ⋆ Little Miss Martha

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Continuing the sharing of fall break ideas, today we check out a day in Chicago.

The best times are sometimes the most unplanned and unexpected. All of these places listed below were visited on a whim and were not planned at the time we left home. But our inability to plan usually turns out OK and I’m sharing our favorite spots to hit on a whim in Chicago which would make an awesome day away (from Indy) over Fall Break.

Here in Indy, we get two weeks for break, as we are on a balanced calendar which means that there’s lots of time to fill which can get expensive. But a day trip to Chicago doesn’t have to be. Wake up some Saturday or Sunday morning, for those working parents, or weekday for those with time off and drive three hours north to the Windy City…

We drove straight to the Bean at Millenium Park.Parking in Chicago can be tricky, but luckily there’s plenty of it!
We did find a good parking garage close to the bean and tried to not go back there until the end of the day.

MAGGIE C DALEY PARK

From the Bean, walk to Maggie Daley park and explore the beautiful art installations, walk over the highway, or roller blade or walk the Ribbon. I really want to go back when the Ribbon is covered with ice!

If you are in the mood to walk, stroll over to Navy Pier where you can explore small shops, food, and museums.
We choose to take a ride on the Centennial Wheel and grab a bite to eat.
*We did start to walk here, but ended up grabbing a cab after a few {f a i l e d} attempts to make it over there by ourselves.

NAVY PIER

After that, take a another cab over to Michigan Avenue…
We were dropped off near the John Hancock Building…

THE MICHIGAN MILE

Then walked South on Michigan Avenue…
We visited the American Girl Store which is huge… and while we didn’t buy anything, you could bring your own doll and schedule to get their hair done while you are there or enjoy lunch here!

*While we were here, we popped on Open Table to check to see if any close restaurants had reservations available. We did want to do something fun along the lines of like a Rainforest Cafe, but ended up finding SAFEHOUSE and it was the perfect {last min} addition to our trip (more coming up on that).

RETAIL THERAPY

And the Disney Store which is so fun to explore with little ones because of all it’s fun displays and animations around the store.

NHL store which as a really cool piece of “hockey art” at the entrance.

But there are so many places to shop along this run, that it’s super easy to fill an entire day with just shopping! Plus, lots to look at like street performers and protests! We actually ended up in the middle of an animal rights protest which added a little interest to the trip and definitely a few thing to talk about on the way home!

*You could also pop over to the Lincoln Park Zoo for a walk through as it’s completely FREE and pretty good! We ended up popping over for a short walk through to fill some time before dinner.

SAFE HOUSE

After that, we headed over to Dinner because we didn’t want to go too late because remember, this was a day trip. And dinner was the perfect way to end the evening…

We headed over to Safe House. This was a really really fun thing to do both as adults and kids. The experience really sold us on checking it out. We used Open Table to get a reservation because remember, this was also a trip we took on a whim.

Safe House is a super fun spot and the food was really enjoyable! When you walk in, you are tested to make sure you aren’t a Double Agent. They make you dance or act something out — 100% something silly.

And when you are finally let in because you are good to go, you see the monitors from upstairs that everyone downstairs has been watching. There is an elevator if stairs are not your thing.

Occasionally you’ll hear a roar of laughter and it’s because people are seeing someone upstairs being “tested” and it’s hysterical. They sometimes even clap when you come down!

With fun things all around, there’s a spy scavenger hunt for the kids to do while you are there. The entire point is to get up and explore all the interesting things around the restaurant. Ella really loved it. The best part is leaving…

BE A SPY

I won’t spoil it, but you need $1 to make a call at a payphone…
And you should definitely check this out.
It was normal priced too which made it even better in our eyes!

Then, the day was over.
We walked back to the car, said goodbye to the city, and headed home.

BEST DAY IN CHICAGO

All in all, we did all these things which (1) filled our day, (2) kept the kids entertained, and (3) stayed under $300 for 4 people for the day. Which honestly, in the city, isn’t bad at all! Remember we did the following:

Walked Millenim Park
Walked Maggie Daley Park
Rode the Navy Pier Ferris Wheel
Walked American Girl
Short walk through the Zoo
Visited Disney Store
Visited NHL Store
Grabbed a Coffee for all
Enjoyed Dinner at Safe House

I’d say that’s a pretty good day. The hardest part was saying no to anything at all the stores. That’s hard with two kids in any store, but especially American Girl and Disney Store.

Other free offerings in the city include:

There’s so much to do in Chicago that you could go back every weekend and never get bored… Well at least I don’t think so because it’s my favorite city to visit. I love sharing the smells of the street, the lake, the busy streets, the shopping, the towering buildings, beautiful museums, and more with my family!

We might have to add a day trip now to our fall break coming up!