48 Hours playing tourist in Chicago!

“I adore Chicago. It is the pulse of America.” — Sarah Bernhardt

To make the most of a long weekend we spontaneously booked a two-night getaway to Chicago and had so much fun introducing the girls to a new city. We took the kids out of school early on a Friday afternoon and after a quick 1.5 hour flight from D.C. (plus a cab ride and one hour time change) we made it to our hotel by 4pm and hit the ground running in Chicago. It didn't take me long to remember why I love this city so much.

We stayed at the Waldorf Astoria in the Gold Coast neighborhood adjacent to the Magnificent Mile and super convenient to all of the touristy things we wanted to do with the kids. We were blown away by how beautiful the city is kept and how gorgeous the weather was while we were there. Fall is a highly under-rated time to visit. We also happened to book our weekend getaway for the same weekend as the Chicago marathon (oops!) but surprisingly it didn't impact crowds or our plans much at all. In fact, I got home feeling inspired by the runners and persuaded to pull my running shoes out of retirement :)

Once we got settled into our hotel room (and were upgraded to a suite), we walked around the neighborhood to get acquainted and then came back and grabbed a snack and drinks at the hotel before freshening up for dinner. Our kids love to eat out and try new restaurants as much as we do, it's such a fun thing about this age. They genuinely enjoy being with us and we bond over the shared experience. With that said, we took a chance on a late dinner reservation at Alla Vita which was convenient to our hotel and very good, but it was a little loud and the kids were pretty tired at that point. Wish we could've snagged an earlier reservation and gotten the full experience but that's what happens when you book a trip a week in advance and are visiting a city with an amazing and in-demand food scene. We hustled back to the hotel after we finished dinner and I've never seen our kids fall asleep so fast! We woke up refreshed the next morning and ready to conquer the day.

Our Day 1 itinerary looked like this:

Complimentary breakfast and coffee at hotel (SO good)
Walk down the Magnificent Mile to the River Walk and pick up our 11am (1.5 hour) Chicago River Tour. Great way to see the city from a different perspective and appreciate all the cool architecture. Our guide described Chicago as an "archictectural mecca". It's easy to see why.
Walk to Millennium Park and explore. See Cloudgate (aka "the Bean") and the other interactive art that the Park is famous for.
Grab lunch at nearby restaurant The Dearborn
Walk to the Art Institute of Chicago. This art museum is incredible. We especially loved the Ancient Egyptian exhibition, the Korean Art exhibition, and the Impressionism wing. Fun fact, this is where one of the famous "Self Portrait" pieces by Vincent Van Gogh is on display.
Walk back to hotel with a stop at the world's largest Starbucks (girls wanted to check it out, and it honestly was really cool).
Downtime at the hotel plus a little shopping with my oldest then freshen up and Uber to dinner at Ema. Highly recommend. The vibe was dreamy and the small-plates and cocktails were SO good. Our girls are 10 and 12 and loved it too. Walk back to the hotel with a stop at Jeni's for dessert (because obviously).
Crash hard!

Our Day 2 itinerary looked like this:

Sleep in (cozy beds!) then complimentary breakfast and coffee at hotel
Check out of hotel, store our bags and walk to Navy Pier. Rides, mini golf, and Centennial ferris wheel. Spent a couple hours here and kids loved!
Walked and explored our way to a mid-afternoon reservation at Giordano's for deep dish pizza because a trip to Chicago would not be complete without it. Needless to say we couldn't think about food after and it's a good thing - our return flight was delayed three hours and we didn't get home until after midnight. Thankfully, we all had Monday off as a holiday so we had the day to recharge, veg out, and get ready for the week!