A Winter Weekend in the Windy City: the Best of Chicago

A Revist to Chicago

Ratings Best Travel Date Cost Length


Not Winter $400 2-3 days

TLDR tips:

  • Book parking ahead and use ride-share throughout your trip
  • Take a boat ride along the Chicago River which crosses the city and head out to the Michigan Lake
  • You can skip the Skydeck if you book a city view hotel that is high enough
  • Could buy a City Pass if you plan to visit Shedd and Skydeck


  • Swissotel Chicago: $40 per person per night
  • Lincoln Park Zoo: Free
  • Parking: $50 for 3 days
  • Skydeck Chicago: $35
  • Shedd Aquarium: $39
    • Parking: $15
  • Food:
    • $25 per person per meal
  • Transportation: $30 per person
  • Total: $400

Day 1

Drive to Chicago

The trip from West Lafayette to Chicago is usually about three hours. It started off really smooth and peaceful, with open roads and nice views. But closer to Chicago, a one-hour trip turned into a two-hour traffic jam, which is pretty expected when you’re heading into the third-biggest city in the United States.


Knowing how tricky (and expensive) it can be to park in downtown Chicago, We booked a parking spot ahead of time. Any online parking app would do, and a three-night parking is only around $50, in comparison if you would’ve paid onsite which would land about $30-$40 per night. It was almost surprisingly cheap. The garage is located beneath the ground level a little bit hard to find, but was right in the middle of everything and near our hotel, which made it a great starting point for exploring the city.

In the remaining trip in Chicago, we decided to use ride-sharing for getting around. It was way easier than driving in the heavy traffic and looking for parking spots. Plus, it let us see a lot more of Chicago without any stress.

Lincoln Park Zoo

Visiting Lincoln Park Zoo was a quiet experience. It was a really cold day, and that seemed to affect both the animals and the visitors. There weren’t many people or animals out, which made the zoo feel a lot calmer than usual. It’s definitely colder than I remembered last year, but thankfully all the indoor animals are still out and gives you a warm break.

A weird little animal that I don't know it's name

Did I mention that the zoo, botanical garden and the park is free admission? Supported by donation only, the zoo is a value visit for anyone.

Botanic garden, the only greens right now

SaiMai Thai Restaurant

Also, before heading the zoo, we warmed up at SaiMai Thai Restaurant for storing energy. I remembered it from 2018, and it was just as good as I recalled. The food was really tasty and comforting, perfect for the cold weather. And the prices were great.

Navy Pier was a new location for me, surprisingly clean with the sky also being clear. It felt like having a little piece of the city all to myself as you get a great view from the pier against the downtown sky scrapper. Unfortunately, the Ferris wheel was closed in the season, but it looked amazing standing still against the sky. There was the Navy Pier water front marketplace that added a bit of life to the place if you are interested in shopping, it’s pretty big too. Also parking spot is available.

View of downtown Chicago

The ferris wheel sitting on the Pier, sadly it's closed

Hotel check-in

Checking into the Swissotel Chicago was great, it is a very modern and newly built hotel. The price was really good, especially for the quality and location. My room on the 40-ish floor had an amazing view of the city skyline. The room was stylish and comfortable, making the hotel a great, affordable choice in Chicago. (I don’t know the price today, but back at 2019, it cost us only $80 a night).

Good view from Swissotel Chicago

Brief Walk on Magnificent Miles

Walking down the Magnificent Mile meant diving into the heart of Chicago. There’s lots of impressive shops, but we don’t have enough time today.

Dinner at The Hampton Social - StreeterVille

Dinner at The Hampton Social in Streeterville was okay. The place had a trendy, bar vibe. The lobster roll was great and the steak too. It was fresh, tasty, and just perfect. It was one of the places where we didn’t need to wait or needed a reservation.

Day 2

Cloud Gate

We started our second day after having our breakfast at Dunkin’ Donuts, right next to our hotel with a couple of sweets and a cut of hot chocolate. The Cloud Gate, known as “The Bean,” sitting right in Millennium Park, I’ve visited before but not my partner, but this time it was at day time. It reflects the city and sky in cool, wavy patterns.

We walked around and under it for about half an hour, watching our reflections stretch and shrink.

Lunch Chinatown

After the park, we headed to Chinatown for lunch through the convenient although not very clean metro line. I always appreciate the strong flavor and the unique smell of Chinese food. We ended up at a small restaurant with incredible roasted lamb legs. (Unfortunately, I forgot to take pictures)

Skydeck Chicago from the Clouds

Then, it was off to the Skydeck in the Willis Tower, which I’ve gone before last year. The ride up to the 103rd floor still felt nice, the wait was not bad either. The view from up there was exactly how I remembered it, I could see everything from Lake Michigan to the city’s endless streets.

We both got a chance on stepping out onto the glass ledge/box, way up high for photo taking, it was both exciting and only a bit scary. It was a great way to see the night light of Chicago.

Glass Box on Skydeck

Shopping at Magnificent Mile

We wrapped up the day with shopping (mostly browsing though) the Magnificent Mile. It’s packed with all kinds of stores, from luxuries brands to cool local shops, and it’s also within walking distance from our hotel, crossing Chicago River and DuSable Bridge right next to the Trump Tower (must be nice to have a boat ride in the summer).

Night view at DuSable Bridge

We had our dinner at Niu Japanese Fusion Lounge, an awesome place, probably the best meal we had in Chicago. I strongly recommend the Spicy Lady and the Lobster Fried Rice (with lobster roe).

Day 3

Museum Campus

Visiting the Museum Campus in Chicago turned out different than I thought. It was closed, but that didn’t ruin the fun. We spent about 30 minutes walking around, taking pictures of the amazing buildings. Even just from the outside, the campus was really impressive. The architecture was awesome for photos and gave us a taste of Chicago’s rich culture and history.

Shedd Aquarium

Then, we went to the Shedd Aquarium, a place I hadn’t been to since I was a kid. I remembered being part of a dolphin show, I was chosen as a child volunteer where I get to touch the dolphin while it’s jumping, I was 7 or 8 years old that time. The aquarium seemed to have changed a lot, or maybe my memories weren’t as clear as I thought.

Re-watching the dolphin show was amazing. The dolphins were so smart and graceful. But, they didn’t have kids join in the show like they did when I was there.

Our day in Chicago ended after the aquarium. It was three days of fun and familiarity, I like getting to know new places and old places all over again.

Dolphin Show at Shedd Aquarium

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