3 days in Chicago with teens

I traveled to Chicago with my two younger kids last week for a short trip before Thanksgiving. We had a lot of ideas on what to do during our short visit. Here is what we accomplished.

Magnificent Mile Lights Festival

We didn’t plan on this activity, but the Magnificent Mile Lights Festival parade happened to go right in front of our hotel. So, we watched some of the action through the hotel lounge windows and went outside for the finale fireworks.

Chicago’s First Lady Architecture Cruise

My sister and I wanted to go on an architecture river cruise, but my teens weren’t thrilled with the idea. So, they chilled in the hotel while we enjoyed a cruise on Chicago’s First Lady. The launch point was very close to our hotel, the Hyatt Regency Chicago (see my review here).

We went on the first cruise in the morning at 10 a.m. It was a bit chilly in some spots, but I loved hearing about the history of the different buildings.

We saw a spectacular view of the Chicago skyline from our boat:

Ice Skating in Millennium Park

My kids wanted to go ice skating in Millennium Park. There is a free ice rink in front of “the bean” (which is closed for renovations but you can still see it from below) that is open November through March. We had to reserve a time online and pay for skate rental. 

Blue Man Group

One afternoon, we hopped on the L and saw Blue Man Group at the Briar Street Theatre. We had never seen them before. In case you’re not familiar, Blue Man Group is a percussion/comedy show that is hard to describe. It was a fun show. If you sit in the few two rows, be prepared to be sprayed with paint and water.

Macy’s State Street

Macy’s State Street, formerly the Marshall Field’s flagship store, was built in 1902 and is the 3rd largest retail store in the world. The building is now a National Historic Landmark and is listed on the National Register of Historic Places. The store even offers a Holiday Traditions tour on Fridays during November and December. We shopped inside for a bit, and I purchased some local chocolate. We intended to return later, but we never had the chance during our short trip. 

Willis Tower and the Ledge

Of course, we had to go to Willis Tower (formerly known as Sears Tower) and marvel at the views from the top. We purchased tickets to Skydeck Chicago/The Ledge. We enjoyed several interactive displays about Chicago before we checked out the view from the top.

There was even an L train simulation inside!

Once at the top, we looked at the views from multiple spots and then waited in a short line to get into one of five transparent boxes of the Ledge.

Keep in mind, this is 103 stories in the air! Each group gets exactly 2 minutes in the box, and there are timers that go off when your time is up. However, we were allowed to get back in line for another round of photos. My kids were much more comfortable on the Ledge than I was.

Dinner at Greek Islands

I made it a priority to get to Greektown Chicago. A reader recommended Greek Islands restaurant, so that’s where we went. The food was great!

We especially loved our Saganaki (flaming cheese) appetizer.

I’d love to return during the day to see more of Greektown.

Christkindlmarket

Our last activity in Chicago was walking around the Christkindlmarket, the German Christmas market. I’ve been to Christmas markets in the U.S. before, but this was the biggest one I’ve been to. It was filled with food and Christmas trinkets galore!

My daughter and I loved this market! My son, not so much. But, he was mostly a good sport about it.

What we didn’t do

We had several other activities on our wish list for this trip, including Navy Pier, Magnificent Mile shopping, Shedd Aquarium, Adler Planetarium, Lincoln Park Zoo Lights, a few museums…but, it’s good to have some things to save for next time.  Chicago is easy to revisit with the help of miles and points.

Author: Nancy

Nancy lives near Dallas, Texas, with her husband and three kids. Her favorite vacations include the beach, cruising and everything Disney.