This is the trip that started it all. In early December, my wife and I took a trip to Chicago. We had a blast, but unfortunately, the trip ended up costing a bit more than I expected. Ultimately, this lead to the birth of Itinee. In this post, I'll walk you through our itinerary so you know exactly how to tackle Chicago in just three days. Want to cut to the chase and just see how much it cost? Use the itinerary link above for the full breakdown.


So, we're from Louisiana, which, in case you're unfamiliar with US Geography, is quite a ways from Chicago. Certainly far enough that reasonable people would fly. We drove. It was 15 hours and it was a lot of fun, but it was also... a lot. This was my first time driving in a city where there were underground roads and normal roads with the same name, which was quite confusing, both for me and for Google Maps. We ended up checking into our Hotel, the Hyatt Regency at about midnight, and this is where we encountered our first unanticipated expense— parking! I'm so used to free, public parking lots that this really took me my surprise. All told we ended up spending $140 just to be able to park our car under the hotel. Since it was more expensive to come and go than to just leave the car there, we ended up Ubering or walking for all of our stops throughout the city.

Day 1: Winter Wonderland

Our first stop of the day was at the Museum of Science and Industry, which has a huge variety of exhibits. At this museum, you pay for entry, and then can add on additional "experiences" for some of the more interactive exhibits. We only added one "experience," which was to tour the U505 Submarine, a German submarine that the U.S. Navy commandeered during World War II. This tour was super interesting, but probably not a good fit if you're claustrophobic. The tour guide in particular was really engaging, and had great answers to the questions people asked during the tour.

Other exhibits we enjoyed here included:

  • Christmas Around the World (seasonal): This exhibit features all kinds of Christmas trees decorated in accordance with various cultures
  • Extreme Ice: This exhibit featured a video about the melting glaciers, and some gorgeous photography
  • Science Storms: Various interactive exhibits and demonstrations revolving around weather and geography
  • The Great Train Story: A huge, intricately detailed model train, traveling from Chicago to Seattle
  • Colleen Moore's Fairy Castle: An extremely elaborate "doll house" with fully decorated rooms and audio narration
  • Apollo 11: This was a film about Apollo 11 shown in the museum's "Giant Dome Theater"

MSI also features a food court which, while not particularly impressive, was a convenient lunch that allowed us to spend a good chunk of our day at the museum.

U505 Submarine at MSI

After MSI, we headed to Millenium park which is the home of the famous Cloud Gate (AKA "The Bean") sculpture. This is also where the iconic ice skating rink is, which we'll come back to. Following our photo-op with The Bean, we headed to a nearby German Christmas festival called Christkindlmarket. Going in I didn't have super high expectations, but this was actually very cool, and we ended up coming back a few times throughout our trip. There's a ton of little booths and shops featuring food, live music, crafts, and by far the best hot chocolate I've had in my life. Definitely a must-do if you happen to be in Chicago during Christmas.

We then headed to Giordano's, for a taste of Chicago's notorious deep dish pizza. Reactions were mixed. Personally, I loved it; my wife on the other hand was not impressed. We are both pretty big eaters, but we got the small size here and it was still too much. The restaurant definitely felt a little commercial, so there might be some local places with more "authentic" deep dish pizza, but I still don't really have anything negative to say about the food.

Giordano's Deep Dish Pizza

Looking to burn off some calories, we headed back to Millenium Park after dinner for some ice-skating. I did this for my wife, but let me just say I am terrible at ice skating. I did one, maybe two, laps and then sat on the sidelines while she had fun. This is definitely a magical place to be at Christmas time, though. With the Christmas music and giant tree in the background, it's hard NOT to be in the holiday spirit.

This ended Day 1 for us, and we headed back to the hotel for some much needed rest.

Day 2: Michigan Avenue

To start off Day 2, we grabbed a bite to eat at Wildberry Cafe, which wasn't far from our hotel. I remember the pancakes being really good. Then, we headed across the river to Michigan Avenue to do some window shopping. While we didn't buy anything we ended up stopping into a few stores, including the American Girl Store (for her) and the Lego Store (for me). We also stumbled upon a Starbucks Reserve Roastery of which there are apparently only six in the world, and three in the US. This massive coffee shop has five stories, and includes a restaurant and a bar in addition to the normal Starbucks offerings. It was huge, but it had just recently opened so it was fairly packed. We checked out each of the floors but didn't end up hanging around long.

After getting our fill of Michigan Ave, we headed to Navy Pier, which was quite a walk. When we got there, we were a bit disappointed. There were a few very touristy shops, but nothing really spectacular. I'm not sure if we just didn't walk far enough or what, but we ended up just turning around soon after we got there. We hadn't really had lunch yet, so we decided to take this opportunity to get a Chicago hot dog. We headed to U.B. Dogs, and it was SO good. Initially, I was going to pass because it was getting close to dinner, but as soon as I saw my wife's hot dog I knew I had to try one. On our walk there, we walked a big chunk of the riverwalk, which was very nice, but seems like it's probably more active during the warmer months.

Chicago Dog from U.B. Dogs

That night, we had dinner at Volare, which was extremely good. We ended up sitting in their covered patio, which was surprisingly comfortable despite the very chilly weather. I don't remember exactly what I got, but I do remember it being delicious, and the service was impeccable.

Day 3: Sea Lions & Circus

Our last day was pretty laid back. We started at the Shedd Aquarium, which I really enjoyed. In addition to the fish tanks, one of which features a fairly massive turtle, there's a free dolphin show that lets you see belugas, dolphins, and sea lions up close. This was definitely worth the stop, and probably only took about an hour or so of our day. Also, just outside the aquarium, there are some great photo spots that give you a clear view of the Chicago skyline.

After the aquarium, we grabbed brunch at Yolk. This is a chain, but it was still delicious, and the service and waitstaff were awesome. Rather than Ubering back to our hotel, we decided to stroll through Grant Park and then Millenium Park to take in the scenery one last time. We got lucky that the weather was absolutely gorgeous for our whole trip--we loved being able to walk everywhere!

Grant Park

That night, we saw an absolutely incredible show that I don't think I'll ever forget. We originally were going to see a Broadway performance, but when we looked online, we stumbled upon a show called "Love Chaos & Dinner" by Teatro ZinZanni. This is a cabaret-style show featuring a four-course meal, and breathtaking, hilarious performances. It's got singing, it's got dancing, it's got standup comedy, it's got acrobatics, magic, and even yodeling. It's like a much more personal Cirque Do Soleil WITH FOOD. Not only that, but Chicago is one of only three places in the country where you can see this amazing performance. This is definitely a can't miss on your trip to Chicago. Our tickets were in the "outer ring seats" which gave us a great view, but it is a really small theater, so any seat will be great.

We packed our bags that night and left very early the next morning. All in all this was a great trip, and totally doable in just three days. You could definitely fit more in if you wanted to, but we enjoyed have some leisure time and not always being in a time crunch.

If you want to see the full cost break down of our trip, click the link below for the full itinerary. A large chunk of the cost was our four-night stay in the hotel. If you were flying instead of driving, you might be able to to arrange your schedule to only need two or three nights.

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