24-hour Chicago winter itinerary with kids

On a snowy November weekend, my youngest son and I found ourselves in Chicago. Our trip there was accidental; we had been en route to Savannah, Georgia when we became stranded at O’Hare during the first snowstorm of the season. After 30-plus hours trying to continue our planned itinerary, our flight was cancelled and rebooked two days later. Rather than sit around waiting to depart, we decided to enjoy a Chicago winter itinerary. Here’s what we did with 24 hours in Chicago:


Morning: Head to the Museum Campus

Captain Obvious alert: Chicago in winter is cold! Rather than brave the weather all day long, start your itinerary with an indoors activity. We took Metra to the Museum Campus, which houses both The Field Museum and Shedd Aquarium. Families will want to budget at least three hours for each. Because we wanted to spend some time outdoors enjoying the wintry atmosphere as well, we opted to visit just one indoor attraction—Field Museum—but if you’d rather spend all day indoors (or the weather necessitates it), you could happily spend all day on the Museum Campus, checkout out both attractions.

We chose to visit the Field Museum for its temporary exhibits, including an excellent exhibit on Ancient Egypt and on Mastodons and Mammoths. In order to see these, we upgraded from a standard entrance fee to a full access pass, a difference of approximately $10 per person. With this pass comes admission to the museum’s 3D movie options as well. We started downstairs, checking out these special exhibits first, then moved our way up the museum to end with a 3D movie (check movie times when you enter). Favorite stops among the permanent exhibits included the mammals section and dinosaur section (which has a focus on extinctions during the ages).


We spent all morning enjoying the warmth of the museum, then ate lunch at the museum bistro, which had many healthy options, including a full salad bar and specialty sandwiches and soups. Alternatives include classic Chicago hot dog carts outside and—we were told later—food trucks on the museum ground floor.

Afternoon: Ice skating at Millennium Park

From the Museum Campus, we used the pedestrian underpass to access the nearest Metra bus stop, and took a bus back toward downtown to Millennium Park. We used Google Maps to find the correct bus lines for both the ride to and from the Museum Campus, and had no trouble using the system. If paying cash, our rides were $2.50 for adults and $1 for kids, each way.


At Millennium Park, the McCormick Ice Skating Rink is only about half a block further on foot. On the Sunday before the Thanksgiving holiday, the rink was crowded, but not unmanageable. Plus, the snowy weather added charm to the experience! We waited in line approximately 25 minutes to rent skates (they have a timed system here, so not too many people are crowding the rental area and rink at one time). Once on the ice, we could skate indefinitely. We enjoyed the rink for about 45 minutes, then took a break at the Warming Hut, which serves hot cocoa with a full hot cocoa ‘bar’ (toppings include several kinds of marshmallows, chocolate shavings, candy bar crumbles, and syrups), plus tea and coffee, to which liquors can be added. The hut has a padded floor, so there’s no need to take off skates while warming up.


We continued skating about 30 minutes or so, then unlaced so we could climb the stairs above the rink to check out the famous Chicago ‘bean’ sculpture, which overlooks the skating area. It was fun to see it reflecting the snowy Chicago landscape! We didn’t see much else to do outdoors in the immediate vicinity, but were told that had we been there just a week or so later, the ‘ice skating ribbon’ at adjacent Maggie Daley Park would have been open.

Early evening: City lights

Twilight hit the cityscape at approximately 4:30 pm, and we made our way back to the Metra stop to take a bus to Sears Tower (now called Willis Tower). The SkyDeck allows visitors to enjoy amazing views of the city from the 103rd floor, and even step out onto a glass floor for a thrill. Because we weren’t in the city long enough to warrant buying CityPass (more on this below), we had an hour wait in line for the SkyDeck (including the security line). We loved the views of the city with lights aglow, but agreed the wait was too long. There are two alternatives:


1. Buy CityPass tickets. We always buy CityPass when we visit participating cities, but our visit to Chicago was just too short this time around to make it worthwhile financially. However, if we’d even had one more day, we would have bought the tickets, which are approximately $95 for adults and $69 for kids, and allow entry to 5-7 attractions. With CityPass, families skip the majority of the queue at all attractions, and CityPass holders we saw at Willis Tower enjoyed very little wait time.

2. Head to Hancock Tower instead, and eat a meal at Signature Room on the 95th floor. I’m told the views here are just as amazing, and while you do need to purchase something to eat or drink to enjoy it, the price is less than SkyDeck. Unfortunately, during our visit, a small fire caused the building to close.

Evening: Dining in or out

I polled my favorite Midwest travel writers when I realized we’d be spending a day in Chicago, and they offered several great dining recommendations. Topping the list is Eataly, an upscale but fun Italian dining experience that even includes a Nutella bar. Eataly can be found at 43 E. Ohio. Other top picks are Pizzeria Due at 619 N. Wabash and Flo and Santos at 1310 S. Wabash. Where did we go? Back to our hotel to cozy up with room service! We loved ending our day in Chicago in our robes, looking out our window to watch the Chicago skyline.

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Alternate ideas for a Chicago winter itinerary:

While we couldn’t get to everything we wanted to during this trip, the following additional winter activities are on our radar for next time.

  • Museum of Science and Industry: This year, this museum is hosting an amazing robot exhibit called Robot Revolution, which cutting edge robots around around the world kids can interact with. During the holiday season, it also features Christmas Around the World and Holidays of Light, which depicts holiday traditions from dozens of countries and cultures.
  • Christkindl Market: This annual German Christmas market is held on Daley Plaza, with traditional wooden huts and vendors from Germany.
  • A Christmas Carol: This show is also an annual tradition and almost always a sell-out, so get advanced tickets for the Goodman Theatre.
  • Zoolights: Held every holiday season, Zoolights at Lincoln Park Zoo showcases light displays across the zoo in the after-hours; families can come during daylight to see the animals and stay for the light show.
  • Navy Pier: Though a different experience than during the warmer months, Navy Pier has events and attractions open year round. Pick a day that’s not too chilly to be directly on the water. During our visit, it was simply too windy for us to feel comfortable at Navy Pier!

Where to stay: Westin Chicago River North


We stayed two nights in complete luxurious comfort at Westin Chicago River North, which offered the perfect downtown location for our adventure. Our room on the 9th floor overlooked the Chicago River, and we loved watching the snow fall on the water and bridges. We upgraded to club level, which allowed us to use the club lounge on the 20th floor included in our stay. While an initial investment, I always recommend upgrading to club or concierge level when available. Most offer a complete breakfast service, plus snacks and drinks available all day and an appetizer and small plates spread in the evening to easily feed children and even adults (depending the day’s offering). If you’ll be at the hotel enough to take advantage of at least the breakfast and one additional stop-in during the day or evening, the value is there.

From O’Hare airport, the Westin North River is only one metra train line away (blue line from O’Hare), plus a two block walk. It’s also only two blocks from the metra bus lines. The views are amazing, and the concierge desk is invaluable when planning a last minute itinerary!

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