Chicago Babymoon

It’s been awhile since I’ve been on a plane with my husband Corey, about 1.5 years to be exact. Our last trip together was visiting Europe for the Christmas markets in December 2019. One of the last few months of “normalcy” before the pandemic. With a little one on the way we wanted one last trip in before we become a family of 3. Before we settled on the Chicago babymoon, it took some narrowing down. We wanted to avoid any international destinations due to logistics, avoid tropical locations due to Zika, avoid desert terrain like Arizona and Nevada, and avoid certain states with a higher COVID-19 rate such as Florida, Texas, and Louisiana.

We wanted to visit somewhere outside of the east coast and west coast, which pretty much left us with the Midwest. After a little back and forth, we decided on a Chicago babymoon! We both appreciate good food, the weather shouldn’t be too muggy/unbearable, and the flight + hotel costs were reasonable. We invited my nephew Noah to join us since he has a sense of wanderlust as well.

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Some Chicago Fun Facts

According to ChooseChicago.com, Chicago is home to:

• 26 miles of lakefront with 25 beaches (not that the water looked inviting to swim!)
• More than 8,800 acres of green space and 600 parks
• Over 200 miles of bike lanes
• More than 500 public works of art displayed in over 150 municipal facilities around the city
• Approximately 60 museums, nearly 200 art galleries, and 20 neighborhood art centers
• More than 250 theatres, 225 music venues, and 200 dance companies
• More than 7,300 restaurants and 167 breweries
• 369 landmarks and 59 historic districts
• Lincoln Park Zoo, one of the oldest zoos in the country, and one of the few remaining free zoos in the country
• Willis Tower (formerly Sears Tower), the second-tallest building in the Western Hemisphere.
• Wrigley Field, the second oldest ball park in Major League Baseball

All this to say, Chicago is a city that offers plenty to do for all ages. With just 4 days, we didn’t even scratch the surface. The city itself gets compared to NYC often (the cleaner version if you will). To me, it more closely resembled Washington D.C. The city was clean and spacious. It didn’t have that NYC feel to it, in my opinion. Since it’s currently baseball season, we were in a sea of red Chicago cubs gear. You can feel the pride in that city, they sure love their Cubs! Now, let’s get into our exact 4 day itinerary for my Chicago babymoon.

Day 1 – Friday

We flew American Airlines from Richmond (RIC) to Chicago (ORD). What was supposed to be a non-stop journey ended up having a layover. As a travel agent, I’m used to receiving the schedule change notifications. The pandemic has certainly put a strain on airline resources causing many flights to be cancelled and many routes to be consolidated. With that said, we arrived into Chicago early morning, around 9:00 AM. The ORD airport is pretty big, with lots of bathrooms and restaurants. It was a very clean and organized airport, something I can appreciate. While it was too early to check into the hotel, we decided to head to the world’s largest Starbucks for a pick me up. If you’re staying in the Magnificent Mile, you’ll easily be able to reach this on foot.

World’s Largest Starbucks

Currently, the world’s largest Starbucks is located in Chicago. It’s called the Starbucks Reserve Roastery. If you’re curious what separates that from a typical Starbucks, a roastery offers a selection of the rarest, most extraordinary coffees Starbucks has to offer. It opened on November 15, 2019 and located on 646 N. Michigan Ave. The current hours of operation are daily from 8:00 AM – 7:00 PM. Even if there’s a line wrapped around outside, the line goes by QUICK! There are a total of 4 floors which houses a lot of people. So there are always people leaving and coming in. There’s a friendly security guard at the front entrance for crowd control.

Willis Tower – Skydeck/The Ledge

Around noon, we received a text from our hotel (DoubleTree by Hilton Magnificent Mile) confirming our room was ready. After checking in and getting to relax in the room for a bit it was time to head to Willis Tower. When looking at our bank statement, the majority of charges for this trip was Uber rides. If I weren’t pregnant, I might have been more inclined to walk the few miles it took. But for this trip, I was fortunate for Uber. If you want to visit the famous Skydeck and take your photos on one of the famous “Ledges” I recommend pre-booking your tickets. You can purchase your Skydeck tickets here. At 1,353 feet in the air, the Ledge’s glass box extends out 4.3 feet from the Skydeck. Each group of 3+ passengers had 1.5 minutes to get as many photos as we could.

While masks are currently required at Skydeck Chicago, you are able to take off your masks for photos. The Skydeck offers views spanning up to 4 states. The elevator ride up 103 floors went by so quick too. The elevators operate as fast as 1,600 feet per minute! While you go up, a video shows you the equivalent of your height – such as the Eiffel Tower, etc. There are a few different fast food restaurants within the Willis Tower if you’re hungry. There’s also a gift shop.

Jojo’s Milkbar

This pregnancy I have been craving so much chocolate! It was only fitting to get reservations at Jojo’s Milkbar for their amazing shakes and food. The only two Jojo’s locations are currently available are Hubbard Street and Water Tower Place kiosk. We ate dinner at Hubbard Street. The Water Tower Place just offered the shakes (not full meals). I ordered the Chocolate Nirvana shake. Chocolate Oreo shake with double chocolate marshmallow and chocolate chip cookie. Amazing! Corey ordered the Rocky IV shake. That consisted of a Banana Reese’s pieces shake with toffee marshmallow, a white chocolate boxing glove, and  peanut butter cookie. We also ordered some burgers and fries. It put us in the perfect sugar coma before heading back to the hotel to relax the rest of the night.

If you’re not up for Jojo’s Milkbar, some other fantastic options to get you introduced to the city are:

• Michael Jordan’s Steakhouse (calling all basketball fans!)
• Portillo’s (for a famous Chicago-style hot dog)
• Giordano’s or Lou Malnati’s for Deep Dish Pizza
• Au Cheval (famous burgers)
• Girl & The Goat
• The Purple Pig
• BLVD – nice dinner in the LOOP

Day 2 – Saturday

Since we had an early rest, we were up early ready for Day 2. We decided to explore The Navy Pier, Millennium Park, and Lincoln Park. This was also our time to try famous deep dish pizza (another craving)! If you’re visiting Chicago for the summer, I highly recommend a cruise around Lake Michigan. You can book a standard sightseeing tour, an architectural informative cruise, or a lunch/dinner cruise. For the lunch/dinner cruises, it looks like there’s two options: Spirit Cruises or Odyssey Cruises (a bit more higher end). We opted for the Skyline Lake Tour with Shoreline.

Navy Pier

Our Uber ride was pretty quick to Navy Pier. We got there around 9:00 AM and our sightseeing cruise departed at 10:30 AM. So that time we walked around getting to experience all that the Navy Pier offers. Navy Pier is where you go in Chicago for events, attractions, culture, dining, shopping, and great skyline views. In the summer time, you can see fireworks on Wednesday and Saturday evenings.

There are a ton of full service restaurants there that fill up quickly: Harry Caray’s Tavern, Jimmy Buffett’s Margaritaville Bar and Grill, Billy Goat Tavern, Giordano’s, and more. On some weekends you can catch concerts and live music. If the weather is too hot, I recommend seeking refuge inside the Navy Pier terminal building. You’ll find restrooms (very important for pregnant women!), various gift shops, a candy shop, and more. You’ll also find famous Garrett’s popcorn being served. If you have a child with you, the Chicago Children’s Museum is located on the Navy Pier as well.

After walking around, it was time for our Skyline Lake Tour with Shoreline. It was a 40-minute boat tour around Lake Michigan. Taking in the skyline views makes for a nice summer day in Chicago. We also learned a little more about the city along the way.

Millennium Park

After linking with my cousin Mohria for the sightseeing cruise, we grabbed a quick lunch at Shake Shack. Then she drove us to Millennium Park. This park offers a lot to locals and travelers alike. There are summer workouts available like Yoga, Lurie Garden, and of course the famous Bean (known as Cloud Gate). This area gets very crowded but it was still a good time. With our new baby onesie purchased in a Navy Pier shop, we were ready for our photo opp!

Pequod’s Deep Dish Pizza

After exploring the city some more, it was time for dinner! I know we wanted a nice deep dish pizza experience. The top 3 restaurants that I kept hearing were:

1. Giordano’s
2. Lou Malnati’s
3. Pequod’s

Ultimately, I ended up deciding on Pequod’s! It’s a much smaller, intimate location. I was very happy with our decision. The location was in Lincoln Park neighborhood, my cousin’s favorite neighborhood. Also in this neighborhood you can find the famous Lincoln Park Zoo, one of the last free zoos left in the U.S. It’s also not too far from Wrigley Field – home to the Chicago Cubs. I ordered the individual pan pizza with sausage and mushrooms. The crust was made with cheese and baked to perfection. It was the perfect pre-magic show dinner. My only complaint was how hot the restaurant was. They had fans blowing but some A/C would’ve been appreciated. I recommend setting up reservations prior to your trip to ensure availability.

Chicago Magic Lounge

At 10:00 PM, we had tickets to the Signature Show at the Chicago Magic Lounge. We were fortunate that the theater just re-opened about a week before our arrival. Pre-purchasing tickets ahead of time is a must. The venue itself is 21+, however guests 16 and older can be accommodated by adults. So my nephew had no issues getting in. They do require proof of vaccination so just a heads up.

The Magic Lounge was full of surprises before the show even began. I don’t want to spoil too much but think speak easy vibes. A hidden door that takes you to your end destination. What makes this lounge so special is that it offers Chicago-style magic. Meaning that the magicians float around the different tables before the headliner gets on stage. It was the perfect time to order some cocktails (for hubby) and mocktails (for me). The cabaret-style seating was very comfortable.

By the end of the show, we were all so impressed with each and every act. My recommendation is to upgrade to the table seats to get up close and personal with the magicians. Also, you are given exclusive privileges to the 654 club at the end of the Signature Show. It’s about a 30-minute show close up with another fantastic act. I highly recommend if you’re looking for a little nightlife! My other option was looking into comedy shows but those were all 18+ so my nephew wouldn’t be able to join.

Day 3 – Sunday

After a late night on Saturday, we decided to relax at the hotel for this morning and early afternoon. With grab-n-go breakfast in hand, we were on our way to the rooftop pool to chill for a bit. It was a relaxing experience with some great views of the city. The pool is actually heated so you could likely visit outside of the summer season. The Starbucks on the first floor was very convenient – as was the Hot House Lounge.

I cannot recommend the Doubletree by Hilton Magnificent Mile enough. It was such a pleasant stay and in a great, safe location.

Chinatown Food and Walking Tour

Chicago has either the second or third largest Chinatowns in the U.S. With that said, I knew we should participate in a food and walking tour there. I booked with Viator and the tour company was Bobby’s Bike Hike. As the name would suggest, they offer bike tours, but also walking tours. They also offer various food tours including Chicago Favorites Food tour, Chicago’s signature dishes tour, and of course the Chinatown Food & Culture Walking tour.

So after so much needed relaxation pool time, it was time to take an Uber and head to Chinatown! We met our tour guide around 4PM for the start of the tour. It met at Phoenix Restaurant, which was our first stop. This restaurant gave us dim sum dumplings – delish! We had a combination of pork, shrimp, and vegetable. Our second stop was all about the spice! We sampled spicy Szechuan chicken with rice. That was probably my favorite spot. We found out this restaurant was opened by celebrity chef Tony Hu, lovingly regarded as the unofficial mayor of Chicago’s Chinatown. We sampled culinary delights from 5 distinct Chinese regions and learned interesting facts about China and the history of Chinese immigration.

Our third stop provided us samples of mini lamb sandwiches. These sandwiches had so much Middle Eastern influence, which we learned was from the Silk Trade many years ago. Our fourth stop was at Yummy Yummy Noodles, a top-rated Noodles restaurant (by Chicago Magazine). That was Corey’s favorite dish for sure! The beef just melted in your mouth and the noodles were the perfect texture. The broth had a great flavor and it was absolutely incredible. We ended our tour with a famous Portuguese-Chinese bakery treat. 5 stars all around! Rest of the evening was spent relaxing at the hotel.

Day 4 – Monday

360 Observation Deck

Day 4 of our Chicago babymoon started at the 360 Chicago Observation Deck. Another great option for getting some good views of Chicago. When we went it was very foggy but it was still a neat experience to kill some time before our flight. We purchased the all access pack that includes the Tilt experience, 1 cocktail/soda or gelato, and general admission. We went pretty early (around 10:30 AM) so there wasn’t gelato available. Just a heads up.

The 360 Chicago Observation Deck offers panoramic views of Chicago from 1,000 feet above the famed Magnificent Mile. TILT is Chicago’s highest thrill ride – and Bar 94 the bar located on the 94th floor.

Water Tower Place

After exploring the 360 Observation deck, we headed next door to the Water Tower Place. Water Tower Place is a large shopping mall with 8 different floors. Before shopping there, we grabbed breakfast at Wildberry Pancakes and Cafe. It was delicious! The line was long but went by pretty quickly. After being stuffed with breakfast we headed past the American Girl Store (the first and original) and entered the Water Tower Place.

You’ll see an assortment of popular clothing stores like Forever 21, a LEGO store, Jojo’s Milkbar kiosk serving sweets, jewelry stores and more. While it was a large mall, it felt very empty. The 8 floors only had a few different stores on each level so it wasn’t really that impressive.

ORD Airport

After spending the late morning getting our last minute souvenirs, we headed to the ORD Airport. We pretty much spent the late afternoon and all evening at the ORD Airport. We arrived at least 3 hours prior to departure (arrived around 4PM), thinking we were golden. With a tornado warning in nearby states, thunder/rain, and delays from other airports, we were grounded for the evening and had to stay put. While American Airlines cancelled our flight, they did offer us a 50% discount for a hotel and put us on an afternoon flight out. The airport was a mad house with the screens bleeding red from delays and cancellations.

Day 5 – Tuesday

Unfortunately, our rescheduled flight was also cancelled and we were not notified. So Tuesday morning we booked a United flight back home and have since received a refund from American Airlines for the return flights that were cancelled withour notification. Overall, this was a relaxing babymoon and included some good eating and exploring. It was nice to be back in the sky, albeit with masks on.

Chicago did not disappoint. I’d love to go back in the future and explore some of the museums and maybe visit the Lincoln Park Zoo. Are you dreaming of a babymoon? Let me help you plan it! You can reach me at cassandra@accent-on-travel.net.

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