Estimated reading time: 16 minutes, 53 seconds. Contains 3379 words

Planning a trip to Chicago in the middle of winter might sound crazy. You’d be right. Only days before our departure to the Windy City we were hammered by Winter Storm Landon. Bundled in our thickest winter gear there was not much room to cross our gloved fingers but we did! Thankfully, the storm dissipated just in time for us to board our flight early the next morning.

Although the biting cold temperatures might keep some travelers out of the city during this time of year it was surprisingly not our first Chicago Winter Rodeo. We were excited to share the city with friends and family this time around and with fewer crowds, it made for an enjoyable weekend in the typically bustling city.

Day 1 -

When our plane touched down we headed towards the lower levels of the airport and to the CTA (Chicago Transit Authority) station which takes you from the airport to the heart of downtown Chicago in about 45 Minutes (excluding potential delays). Before exiting, make sure you grab a Ventra Card for easy access to public transit. The machines look like an ATM and you can choose to print the card or even get a pass on your phone (Using Google or Apple Pay) if you don’t want to keep track of the card. The Ventra Card/App has 1, 3, and 7-day unlimited ride options. If you’re traveling with a family though, it may be worth it to use the reloadable transit value option, which allows you to pay for other travelers in your party. We used Google Maps to keep track of arrival/departure times and mapping our routes.

Our ride arrived at the Grand Station and we walked a few blocks to our hotel for the weekend. The Embassy Suites Downtown (Ohio & State) was the perfect location for us. Plenty of shops and restaurants within walking distance, a piano bar around the corner, and a brewery down the street. Grand Station will take you to Michigan Avenue and the Museum Campus (Aquarium, Field Museum, & Adler Planetarium).

Embassy Suites are a great option for families or friends traveling together thanks to their multi-room suites, hot buffet breakfast, and complimentary evening reception (2 drink tickets for guests over 21 plus small bites). This one also has an indoor pool. In the winter months, you can snag a heated “igloo” (greenhouse) on the patio of their restaurant Osteria Via Stato.



We paid the extra $20 for early check-in since our room was available (It was 9AM when we arrived, whew!) and dropped off our bags, swapped from travel shoes to walking shoes, and headed out for the day.

Like many social-media-loving-millenials, I have a slight TikTok obsession and had been watching so many videos on the incredible dining in Chicago (2017 Dining Capital of the World). Thanks to TikTok, I was able to discover and make reservations at the NEW Cabra Cevecheria. This gorgeous restaurant is on the rooftop of The Hoxton hotel and in the winter, it’s enclosed and heated! It was just our luck that our first day in Chicago happened to be National Pisco Sour Day (The National Drink of Peru). Cabra features Peruvian-inspired small, shared dishes and delectable cocktails. We arrived in time for brunch and sampled a variety of flavors like Aji de Galina Empanadas, Classic Ceviche, Beet Tiradito, and Quinoa French Toast. We celebrated our arrival with Pisco Sours, Cusqueña (Peruvian Beer), and our favorite - the Warming Up in Oaxaca (a Mezcal cocktail). If you’d like to see videos, check out my TikTok @spiritoftravelpodcast. A podcast episode will be coming soon too and will be available for streaming on your favorite channels (Spirit of Travel).



After brunch, we made our own “Pub Crawl” starting with Cruz Blanca - a Mexican-inspired Brewpub and Taqueria. One important “Faux - Pas” to avoid in Chicago right now is forgetting your Vaccination Card! Every indoor establishment (and transportation) still requires masks and Proof of Full Vaccination. Lucky for me, I had NOT left mine at home, but instead left it at the table in Carbra. Bonus points, I’m married to a former Cross Country Runner who immediately ran out the door and hunted down my coveted golden ticket. We ordered beer flights, margaritas, and Queso Fundido to nibble on. My personal favorite? The 3 Kings Christmas Double Punch Ale. This brew is inspired by a traditional holiday drink of Mexico called “Ponche” and it provided the warmth we needed in 19 degrees Fahrenheit!

Time passed by quickly in the afternoon and we had dinner plans but FIRST - we wanted to share an old favorite of ours. Chicago is known for its speakeasies and our visit in 2017 was when we first stumbled upon the oldest gem, The Drifter. Found in the basement of the Green Door Tavern this hidden icon has a revolving drink menu (Listed on Tarot Cards) and a cheeky burlesque show. We had a bit of time to spare before the doors opened so we grabbed a table by a cozy fireplace for a quick sip and bite before. We weren’t going to eat as we already had dinner plans with friends, but the menu listed “Poutine” and it did NOT disappoint. Crispy fries covered in a tangy gravy, cheese curds, and veggies - it was the perfect fireside snack to share.

When we paid our tab upstairs, we made our way to get in line and had a short wait for our turn to walk through the secret door (no password needed). The Drifter is quite small so arrive early or prepare to wait. We were lucky to get a table in less than 10 minutes and our drinks arrived shortly after we sat down. Sadly, our dinner reservations would keep us from seeing the show (starts at 7:00PM) but the atmosphere and memories of our last visit made the trip to this quintessential locale worth it.

If you’re a foodie in Wichita, you know there are some tasty treats missing in our lovely hometown. For us, that missing piece is Dim Sum. This style of food is made up of steamed dumplings and other small dishes served in bamboo steam baskets. Some bring them to your table on a cart, others you order from a menu. We had told our friends the ONE thing we had to have was Dim Sum. So they picked us up at the bar and drove us to Chinatown. We grabbed a table and hot tea at Imperial. Not all restaurants serve Dim Sum all day so be sure to check their website before making the journey. Of course, if you get there and missed out, there are plenty of others to discover. Imperial serves authentic Cantonese Dim Sum and as usual, we ordered more than enough. Somehow, we managed to eat it all though! I’m still dreaming about the Steamed BBQ Pork Buns.



At the end of the day, we nearly had to be rolled out of the restaurant. It was time to make our way back to the hotel and get some rest before Museum Day.

Day 2 -

It is a lot easier to look forward to a busy day when you know breakfast is waiting for you. The Embassy Suites Downtown buffet breakfast had waffles, bacon, sausage, eggs, and made-to-order omelets. Cold items like oats and cereal, fresh fruit, and bagels were also available. A variety of juices, hot teas, coffee, and even hot chocolate were a nice boost before getting started on our adventure.

From Grand Station, it takes about 5 minutes plus 10 minutes walking to get to Museum Campus where you can find some of Chicago’s most iconic attractions and incredible views of the city skyline. We started our morning at the Shedd Aquarium. This family-friendly attraction has been open since 1930 and was once the largest indoor aquarium in the world (Georgia Aquarium took the title in 2005). Visitors can view sharks, Amazon creatures, Beluga Whales, and dolphins. Keep an eye out for educational “Keeper Chats” and entertaining shows in the Oceanarium. For $5, you can add on a 4D show in their theatre where it feels like Octopus tentacles reach out for your feet and bubbles float above your head as if you were under the sea. Don’t worry about spending all day here! The cafe by the oceanarium has a variety of dining options and looks over Lake Michigan and downtown Chicago.

I say “Don’t worry about it” but really, you should plan for it. We truly thought we could fit two museums in one day, especially since we had been to the aquarium before. Alas, we underestimated the amount of time we would enjoy revisiting this one and only had a few hours to spend at our next stop.

The Field Museum is the permanent home of T-Rex Sue. My first encounter with the world’s largest and most complete T-Rex was over 20 years ago. When I was 9, my grandparents took me to Hays, Kansas when she arrived on tour. That was my first trip out of town with them and one of my last (they are still here, we just don’t travel together). On this trip to Chicago, my grandmother joined us and I decided when we booked to keep it a secret that Sue was part of our trip. This adventure was filled with many firsts for us together and I cherish that I am blessed to explore with her still. It was our first time flying together, our first time out of the state together, among many other small but memorable moments for us both.

When we arrived at Field Museum, we made our way to the elevator to go to the top floor, where Sue is hiding in the shadows of Griffin Halls. As we waited for the doors to open, I finally revealed the surprise that was awaiting us. Standing next to this giant dinosaur with my grandmother from child to adult is a memory that will stay with me forever. Never underestimate those small, fleeting moments with your loved ones.

We were able to wander through the footsteps of pre-historic creatures, into the special exhibit of China, and the Plants of the World. This wasn’t even half of the top floor (there are 3 floors) and it’s all we had time for with 2 hours before closing. The Field Museum we learned could easily be a full-day activity by itself.

After a busy day exploring the many wonders of the world, it was time to refuel. We don’t really have a sweet tooth to share between us but TikTok once again inspired a visit to a trendy spot not far from the hotel. Known for their “Crazy Shakes” and Pop Up Experiences, we made our way to Jojo’s Shake Bar and their Candy Land tent. This bright and colorful heated venue was filled with giant gummy bears and popsicles, candy flower chandeliers, and igloos with twinkling lights. The igloos are not available for reservations but if you’re lucky (like us) you can snag one on a first-come, first-serve basis. The best part was that we didn’t even ask for it, but that’s where we were seated. I may have done a little happy dance when they took us to our table.

Every few months Jojo’s changes the theme of their pop-up. They’ve done Halloween, Christmas, Wild West, Throwbacks, and more. Each new experience comes with different decor, cute photo booths, themed cocktails, and of course - NEW Crazy Shakes. We stuck with some of their traditional items like the Margarita Tower and Girl Scout Shake (complete with a cookie, smores, and huge toasted marshmallow). All were impressive although, I was disappointed with myself when I saw the “Peeps” Shake as we walked out the doors.

They also had some excellent Mac & Cheese (I would know, I’m an expert Mac Taste Tester) and Charlie said the Chicken Pot Pie was top notch. This will definitely be a stop on our next trip to Chicago (Is that you Summer?).

Day 3 -

Our friends who met up with us for dinner the first night are local to Chicago. Kari, who was born in Chicago, also used to work with me as an agent at Sunflower Travel. We sure do miss her so it was amazing to spend time with her and her lovely mother. We met up again on the third day so they could share bits of Chicago’s history with us and tell us their stories as well. A few years ago her family moved back to Chicago and she had started 606 Tours in Chicago which provided food, culture, and history tours of her home city. I had always remembered this and when we planned our trip to Chicago, I asked Kari if we could take one of her walking tours. Although she no longer offers these tours, she was happy to take us around to some of their favorite spots.

Our exploration began at the Chicago Athletic Association. I strongly recommend a walking architecture tour of this city. Kari recommends booking a tour through the Chicago Architecture Center. Going inside of these historic buildings absolutely took my breath away. This 19th-century landmark and former Men’s Athletic Club is now a hotel, bar (multiple to choose from), restaurant, event venue, and an all-around great place to relax. Its history is woven from the post-Chicago Great Fire Era and was a key architectural piece in the 1893 Chicago World’s Fair. You can see the old-world atmosphere, Carerra marble, stained glass windows, and more throughout its design. Kari recommends Cindy’s for an incredible rooftop view over Millenium Park with refreshing cocktails in the summer (See? We have to go back).

Of course, we had to see “The Bean” - Chicago’s gleaming symbol of movement throughout the city and Millenium Park. Cloud Gate is the actual name of this sculpture, created by Anish Kapoor, and is one of the largest outdoor art installations. If you’ve seen a photo of Chicago, you’ve probably seen Cloud Gate. You can learn more about this unique sculpture by visiting milleniumparkfoundation.org.

Across from Millenium Park is the Chicago Cultural Center and former Chicago Library. Entry into this historic building is free and it is open daily. Year-round you can learn the history of Chicago, the Great Fire, and view special traveling exhibits focused on art and culture. When you enter the South lobby you’ll see the grand staircase filled with mosaic inlays. Take the stairs up to the world’s largest Tiffany Glass Dome, made with 30,000 pieces of glass.

Did you know that Chicago has an underground “Pedway”? The city is filled with so many hidden gems and in the winter you’ll find many to explore beneath the surface. The pedway connects nearly 50 buildings and 40 blocks in the downtown loop and has been used since the 1950s. These tunnels are filled with shops, offices, markets, and even trendy food halls for dining (We liked Revival). The Macy’s on State Street has an enticing entry to this underground adventure filled with a stained glass installation, reminiscent of the Tiffany Glass Mosaic ceiling at the Cultural Center and inside the store. This mosaic dates back to 1907 when the building originally housed the “Marshall Fields” department store and spans over square 6,000 feet.

After viewing the various Tiffany domes, we had one more Tiffany surprise to discover at the Palmer Hotel. When entering the historic Palmer Hotel you can view the Bronze Peacock doors designed by Louis Comfort Tiffany. The frame and doors weigh over a ton and are stunning. The hotel recently celebrated 150 years and has been rebuilt twice since its inception in 1871. The opulent design, historical significance, and infamous guests earned its status as Historic Hotel of America.

Speaking of infamous guests - Frank Lloyd Wright spent two decades in Chicago designing homes and contributing to many historical buildings in the city. One of which is The Rookery. His contributions to this building can be viewed on the interior, the elevator doors, and the staircase. There are numerous tours available through the Frank Lloyd Wright Trust and at The Rookery. My husband is quite fond of this style of architecture and we were glad this was included as part of our day. From here we headed back towards the center of the loop where Kari and her mother would drive us to a part of Chicago close to their heart.

Kari’s mother grew up in “Old Polonia” - a historic neighborhood of Chicago that was known for the largest Polish population outside of Europe. This area of West Chicago dates back to the 19th century. They drove us through the charming neighborhoods and historic sites while pointing out their childhood homes and schools. When Kari lived in Wichita she spoke fondly of her heritage and the infamous “Pierogis” (another gem that is missing from the Wichita food scene). When discussing our plans and must-see sites, I told her the only thing that mattered was finding those authentic Pierogis - which we had never tried before.
We found ourselves at Podhalanka, one of the few remaining authentic locales in the Polish Triangle. The setting was cozy and welcoming, as was the Polish man whose name I did not catch. Be sure to visit an ATM beforehand as this gem is cash only. Right away we were brought a pitcher of fresh-squeezed juice which I still don’t what it was made from, but it was tasty. We took the suggestions and ordered soup that was honestly some of the heartiest tomato soup I ever had. Next, we were brought sausages, potato pancakes, and of course - a mixed variety of Pierogis. These savory (or sweet cheese even) polish dumplings warmed us through and through and I can see why Kari raves about them. Here’s hoping Wichita is blessed with these Polish delights soon!

If this seems like a full day, we’re not even finished yet! Ha! The rest of our afternoon was spent closer to our hotel. We found an “Irish Pub” called Kerryman and then stopped by a sports bar to cheer on the USA Team for the Olympics. We ordered some World Famous Wings at Jake Melnick’s corner tap and I took out my UNO cards. I always carry UNO with me whether traveling solo or with others. It’s a great way to keep the conversation flowing and helps to start new conversations with strangers in airports. After a few rounds of craft beers and winning UNO streaks, it was time to tuck in for the night.

Day 4 -

Our time in Chicago was coming to a close and we only had two more places to cross off our list of “Want to Do”. Since our flight wasn’t until the evening, we made plans to visit them for lunch. We wrapped up our last breakfast, packed our bags, and headed out for some last-minute adventures. Starting with the World’s Largest Starbucks. This 4-story Roasterie is just a few blocks from our hotel and has great views over Michigan Avenue. Each floor has a variety of gifts and goods, different treats, and a unique menu. We went to the top floor where we could have crafted Coffee Flights like a Cold Brew or an Irish Con Crema with Whiskey Pairing.

After getting our caffeine overload, it was time to walk it off as we made our way to Eataly. At Eataly, you can shop for Italian treats, gifts, wine, liqueurs, home goods and of course - you can eat! We sat down in the dining hall for a glass of wine with a varied selection of pasta and appetizers. The Lasagna that my husband ordered was incredible and my ravioli was freshly made that day. When our meal was settled, we explored the shops for a bit before it was finally time to collect our belongings and head to the airport.

The long weekend was bustling but the moments were memorable. We developed a new appreciation for this landmark destination and again, look forward to returning. I’m still in awe of the sights and stories we came across and how two trips haven’t been enough.

Chicago, we’ll see you again soon.

Agent/Author - Angie Webb, CTA

awebb@sunflowertravel.com

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