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Chicago, IL

December 2022 | Our itinerary

Our itinerary

Day 1: Friday

Friday morning we got up, finished packing the essentials, then loaded the car to head to Love Field. We typically fly American Airlines but in October Southwest was having a huge sale so we ended up getting tickets to Chicago for super cheap. Normally we will take an Uber to the airport but this time we decided to use the Parking Spot instead. If you sign up for their membership (which is free) you get an additional $10 off your first time too! Once we made it to the Parking Spot, we dropped off our car and hopped on the shuttle to the airport. All in all a great first time experience thus far!

The flight from DFW to O’Hare is about 2 hours long so we got into Chicago around 1pm. We then quickly grabbed an Uber to head to the Downtown area and check into our hotel for the weekend. It was only about a 30 minute drive from the airport to the Club Quarters Loop Hotel with very little traffic. And luckily upon arrival, our room was already ready, so we were able to drop our bags off before going to grab a bite to eat. At this point it was about 2pm so we were starved. Fortunately across the street was the Revival Food Hall which is similar to an upscale food court/food truck with tons of different dining options and places to sit. We both decided to eat at Bianca’s Burger. I got the bacon blue burger while Alec had the BBQ burger + we got a side of parmesan fries to share. While enjoying our tasty burgers we also enjoyed some drinks from the Revival Cafe-Bar while watching the end of a World Cup game.

Once we were done eating, we decided to grab a quick cat nap before walking over to the Art Institute. Unfortunately our nap ran a little longer than intended which very much cut into our time at the museum since it closed at 5pm but we decided to still go and make the most of it anyway. The walk from our hotel to the museum was only about 10 minutes so we booked it there giving us exactly one hour to explore before closing. Once we arrived, the check in process was super easy! All we had to do was scan our City Pass QR code and we were off. They also offer a complimentary coat check during the winter months which was super helpful so we didn’t have to lug around our winter coats and accessories throughout the museum. Of course we had to find the infamous painting from Ferris Buller’s Day Off, A Sunday Afternoon on the Island of La Grande Jatte, while also admiring hundreds of other paintings, sculptures, and artifacts from all over the world. Just like clock work, right at 5pm they kicked everyone out and closed for the day.

Afterwards, we decided to wander down to Millennium Park to see The Bean and Maggie Daley Park. To our surprise the whole area was very well protected with a secure entrance to the park and lots of officers around to monitor the area. If you know me at all, you know I am not very skilled in other athletic sports/hobbies, other than gymnastics, so ice skating is off the table for us lol. We have done it a couple of times but let’s just say, for the sake of our marriage, it’s much better if we don’t! So instead, we just watched people ice skate in the glow of the city skyline with twinkling Christmas lights all around. It was such a romantic night, it felt like a scene right out of the movies! As we stood around the rink admiring all of the skaters, we heard some Christmas caroling coming from above that we just had to go check out. After walking by the beautiful Rockefeller-like Christmas tree at the end of the rink, we made our way to The Bean where we also found the Christmas caroling. On every Friday in the month of December from 6-7pm, there is a holiday sing-along where different groups perform for free. Once we took our iconic picture with the city skyscrapers' reflection glowing on The Bean, we stopped by to listen to a couple songs + sing-along with the performers + crowd. After taking in the night skyline one last time, we decided to walk over to Block Thirty Seven (the shopping street) to just do some looking. This is definitely a more crowded street with different people from all walks of life but overall we still felt very safe + enjoyed seeing the iconic Chicago neon sign before moving onto our next adventure for the evening.

As we kept wandering the streets of Chicago, we stumbled across the Christkindl Market and had to pop in! This is a German inspired holiday market that appears in 3 locations in Chicago throughout the month of December. Inside the market are tons of local shops with unique and traditional Christmas decor, toys, and souvenirs. After making one lap around enjoying window shopping at each of the booths, we stopped by the drink station to get some classic Gluhwein, which is just spiced mule wine. Tbh it tasted a lot like warm, spiced apple juice + came in the annual souvenir mug too! The whole market is cash only so if you plan to visit be sure to come prepared! Also parking seemed very limited so we highly recommend walking if you can.

After we finished exploring the market, we decided to grab dinner at Petterino’s. Since we were eating a later dinner we were able to sit right away and started our meal off with a Pinot Grigio for me and an Espresso Martini for Alec. While enjoying our drinks we soaked in all of the festive Christmas decor and eagerly discussed the rest of the plans for our weekend getaway to this very windy city. To eat we ended up splitting a caesar salad and ravioli with burrata cheese & bolognese sauce. All in all it was a very tasty, Italian meal and the perfect end to our first day in Chicago! After paying our tab, we decided to walk back to our hotel to get some rest before our next big day in the city!

Day 2: Saturday

Saturday morning we got up pretty early as we wanted to ensure we could get a seat at Elephant and Castle for the big U.S. soccer game! While Alec enjoyed some Geniuses, I had some much needed coffee. For breakfast, I had a toasted bagel and Alec had the French toast. Nothing super special or fancy but exactly what you could expect from a pub for breakfast. Once the game was over, and sadly the U.S. lost, we quickly headed back to our room to bundle up a little bit more to walk to the Willis Tower Skydeck.

After a brisk 10 minute walk over to the Willis Tower, we quickly checked in using our City Pass QR code and started through the museum. When choosing between the Willis Tower and the Hancock Tower there are a few differences but overall the same beautiful skyline view of the city. With the Willis Tower there is a brief museum you get to walk through being taking the elevator ride up that teaches you about the history of Chicago through various fun, interactive elements. From the research we did, it seems like the Hancock Tower doesn’t offer that over; they do have a bar + restaurant at the top of the viewing platform as well as tilt machines that allow you to lay forward overlooking the city from a birds eye view. Originally we had picked the 360 degree Hancock Tower however the Willis Tower was much closer to where we were staying so that’s the one we ended up at. Honestly though we actually really loved it and enjoyed learning about the history of the city at the same time. Once we made it to the elevator ride up to the top, we walked around for a bit just taking in the captivating city skyline. Fortunately we went to the tower on a very clear day so you could see for miles! Another unique offering that Willis Tower has are these 5 glass “ledges” where you can stand in a fully suspended glass box. There is a line you have to wait in to be able to stand on the ledge where they will also professionally take your picture and you can also take your own as well. After we got all the pictures we could in our allotted time frame (60 seconds for 4 or less) we hopped back in line to take the elevator back down to the ground floor.

Once we made it back down to the ground, we decided to make a pit stop for some sunset drinks and apps at Cindy’s Rooftop. This was by far the number one recommended place by y’all to check out so we couldn’t resist. Unfortunately this was not our most well planned trip because we booked it fairly last minute (for us) so when we went to make reservations they were already full. But since Cindy’s was so highly recommended we decided to go test our luck and see if we could get a table as walk-ups. The rooftop is located inside of the Chicago Athletic Association hotel directly across from Millenium Park. Once we walked inside the classic, swanky hotel, we hopped in the walk-ups line located in the lobby of the hotel. After waiting about 15 minutes we made it to the front of the line where we hopped on the elevator to the rooftop. Once upstairs, we officially added our name to the waitlist but could grab drinks from the bar and either stand inside or outside on the heated patio. We did a little of both while waiting about 15 minutes for an open table and boy was it worth it because we got the best seat in the house! Alec sipped on a classic Old Fashioned while I had Deep Purple then we got a charcuterie board to share. Since we sat around 2:30pm the food options were limited due to their midday menu but it was the perfect snack to tie us over until our dinner reservation. By the time we finished our snack and drinks, the sun was already starting to set over the city. After we closed our tab we walked back to our hotel to freshen up a bit before our dinner and drinks reservations.

When we got back to the hotel we decided to relax a bit before getting ready and heading to our next reservations because this is vacation after all isn’t it?! After wandering around the streets of Chicago for a couple minutes trying to find this hidden speakeasy, we finally asked someone where Three Dots and a Dash was and they pointed us in the right direction. Once we arrived, we got seated right away and ordered a pain killer jet pilot. After sipping on our fruity drinks and playing lots of rounds of Uno, we paid our tab and bundled up to make the short walk to our dinner reservation at Sunda Sushi.

Unfortunately we missed our 15 minute grace period for the reservation so they had to seat us at the sushi bar instead of a table which we actually preferred. It was such a neat experience getting to watch the chiefs make the sushi rolls while enjoying our delicious food too. I ordered the Korean Fried Chicken steamed buns while Alec enjoyed a Panda and Red Dragon roll. Once we finished our meal and paid our tab, we decided to walk to the nearest Shake Shack (about 10 minutes away) to grab a late night snack before ubering back to our hotel and calling it a night!

Day 3: Sunday

Sunday morning we decided to sleep and make this a relaxing day overall. With the end of the year near, Alec and I both have been and will be very busy with work so we truly wanted this weekend to be more vacation rather than a trip. Sometimes it can be hard to remind ourselves that when we travel it is meant for relaxing, recovering, and reenergizing so it’s ok to sit down and not be go go go all the time. With that being said, after we enjoyed our long, slow morning we eventually got up to start getting ready for the day.

After our 20 minute walk to breakfast, we finally arrived at Honey Berry Cafe. We couldn’t make a reservation ahead of time but only had to wait about 20 minutes for a table which wasn’t bad at all. Once we were seated, we ordered some coffee to help warm us up + the two eggs any style meal which came with sausage, hash browns, scrambled eggs, and pancakes. We decided to upgrade the pancakes to the Honey Berry special ones (best choice) as well as add a side of bacon since we were splitting this meal. Overall it was the perfect amount of food for the two of us + was so tasty!

Once we paid our bill and drank as much hot coffee as we could, we made the 10 minute walk over to the Shedd Aquarium while getting to walk through Grant Park. This is a beautiful area right on the water with a great view of downtown. As soon as we got inside, we scanned our City Pass QR code and were on our way. This aquarium is by far one of the largest we have ever been to and was super unique. It totally reminded us of the Smithsonian Museum in Washington D.C. with the layout and architecture. After spending almost 2 hours walking through the aquarium, learning about different sea life all over the world, we decided to go grab an app and drink at a local bar before making the long walk back to our hotel.

About halfway between the aquarium and our hotel, we found First Draft which was the perfect spot to warm up a bit and watch some football. Luckily we got there just in time before the rush of people came after the Packers vs. Bears game at Soldier Field (which was super close to the aquarium). While Alec enjoyed a beer on draft, we split the pretzel bites which were to die for! Between the honey mustard and pimento cheese dip, we couldn’t get enough. After hanging out there for a bit, we decided it was time to head back to our hotel. So once we paid, we walked back to Club Quarters and decided to just have a relaxing night in with a takeout pizza from the infamous Giordano’s. We decided to get the meat and more meat deep dish with a side of cheesy garlic bread. And let me tell you, deep dish pizza is no joke! We weren’t sure if one pizza (6 slices) would be enough food but boy were we wrong. After an unforgettable day of running all around time, it was so nice to just unwind and unplug before heading back to Dallas bright and early the next morning.

Day 4: Monday

Monday morning we got up bright an early to finish packing those essentials before hoping in an Uber to head back to the airport. *Pro tip when traveling with your S/O: find out who does what best and make that a part of your travel plan. For example, when Alec and I travel together we both know that when it is time to pack up to head back home, I am in charge of packing the clothes while he is in charge of the toiletry bags and electronics. This just makes our lives so much easier, gives each of us a responsibility (so everything is fair + we are both helping), while also keeping us out of each other’s way during what can be a stressful event.

Overall, we had the best time visiting the Windy City and hope to get to go back again one day! Such a fun trip to round out the year with getting to explore our 27th state together right before my 27th birthday and only a couple months after Alec’s. All in all we feel so lucky to get to spend our lives together seeing new places, eating amazing food, and falling more in love with travel + each other!

A few things we learned during this trip-

  1. It’s called the Windy City for a reason, pack parkas, scarves, and gloves for sure if you visit in the winter months.

  2. They are lots of different parts to visit in the “downtown area” so either be prepared to walk a lot or take lots of Ubers to get around.

  3. Biking and scooting are available but in the winter seem pretty miserable.

A few things we hope to see/do next time we visit-


What to Wear

Winter Inspired Looks


During our weekend getaway to Chicago, we decided to stay at the Club Quarters Loop Hotel. Alec and I first stayed at a Club Quarters hotel when we went to New York City (back in 2018) for my 23rd birthday. We really fell in love with this hotel for it's low prices, convenient locations, and cozy hotel rooms. This is definitely a no-frill, simple hotel stay but has everything you could possibly need during a quick trip.

Other places

Renaissance Chicago


How to get around

When we were originally planning our visit to Downtown Chicago, we went back and forth for a little bit debating if we should rent a car or not. Knowing that it is very much that downtown city vibe, we figured it would be hard to park anywhere + expensive but also knew the airport wasn't necessarily super close by, the major sites to see where kind of spread out, and it was going to be very cold which could make walking places a little more difficult. After doing some research though we made the decision to not rent a car and either walk or Uber anywhere we needed to go.

As mentioned previously, it was very cold which made our walking turn into speed walking for sure but Ubers honestly weren't that expensive so anytime we needed to go a little further than a walk, we just grabbed an Uber instead. Overall the city is super walkable and safe + they have Lime scooters and bikes everywhere which would be great to rent in the warmer months.

Overall we are very grateful we didn't rent a car however not having one did keep us from exploring more of northern downtown Chicago (like where Wrigley Field is and such) but just more of a reason to go back and visit another time!


Where to eat

Beatnik (2 locations)

Hampton Social (2 locations)

Happy Camper (2 locations)


What to do

Maggie Daley Park (Ice Skating depending on time of year)

Walk along the Riverwalk


What to save

If you are planning to travel to Chicago during the winter, you should expect to spend anywhere from $1,000-1,500 (travel & stay included).

Flights: $150/person (bought during Southwest’s Halloween deal) Hotel: $100/night Food, Drinks, & Activities: $250/day


the stegalls

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