This year we decided to spend Christmas in New Orleans with my family, but prior to heading there, made a pitstop in Chicago for a long weekend with some friends of ours who were also heading back to Nola from Europe. I’d been to Chicago a few times before for work, but never with enough time to truly explore the whole city.
We arrived on a Thursday night, and checked into The Gwen, which is a Luxury Collection hotel, and part of the Marriott group. The hotel is super cute, and our room was fantastic. Our view looked right out onto Michigan Ave, and we were able to walk to everything we had planned for the most part.
The number one item on our to-do list was a river cruise architecture tour. It’s been the highest recommended activity from every single person I’ve ever talked to about Chicago, and we knew we had to do it. The only problem we faced, was that in December, Chicago is COLD. We decided to do the 45 minute tour instead of 90, and we wanted to do it first thing when we had the most energy so that we could spend the rest of the day doing warmer things.
The tour was awesome, and I highly recommend it. We booked through Wendella Boat Tours, and our guide was so knowledgable about the history of Chicago and all of the buildings. If you’re going at a time when it’s not too cold, I’d highly recommend opting for the 90 minute tour, as 45 minutes felt a bit rushed for everything we were seeings.
After the boat tour, we took an uber over to Pequod’s Pizzeria. Pequod’s was listed as one of the top deep dish spots in Chicago, and we wanted to try a couple different ones while we were there. This one was our favorite of all of them, and definitely where I’d recommend getting pizza if you only have time for one. It’s a small spot, and we went super early on a Friday right when they opened. We got a table right away, but it definitely filled up while we were eating. They also have a ton of local beers on tap (which I didn’t get to try because I was pregnant, but next time!).
After lunch, we ubered over to the Birthplace of Ernest Hemingway, which is a museum set up in Hemingway’s childhood home. It’s a little crazy, because the museum is just in the middle of a normal neighborhood, and the houses next door and across the street are just normal houses. The tour was super insightful, and we learned a ton about his childhood and family life. Being December, they had the whole house decorated with the Christmas decorations from that era, and afterwards we were able to pick up a little something in the small gift shop at the front of the house.
Keeping with the theme, our next stop was an independent bookstore called The Book Cellar. In every city I visit, I try to see a few independent bookstores, and this one was highly recommended. It was a super cute little shop, but VERY crowded, and unfortunately their cafe was closed because of COVID still. We grabbed a few books, and then walked over to the Starbucks across the street to warm up with some coffee.
That night we had planned to go out to dinner just the two of us before our friends arrived the next day, but I was SO exhausted. I was in month 3 of pregnancy, and the combination of being pregnant, tired, cold, and it getting dark so quickly just didn’t have me ready to expend a bunch of energy. We ended up deciding to order from Labriola, a fantastic Italian spot near the hotel, and eat in bed while catching up on new episodes of Law & Order. The food was delicious, and the highlight was this croissant, bread, garlic knot appetizer that we ordered. We got to eat some fantastic food, and relax. Vacation is about balance!
Day Two
On day two we got up early and made our way to Stan’s Donuts & Coffee in Wicker Park. Pre-pregnancy I was not really into sweets, but I’ve been CRAVING them, and especially donuts this whole 9 months. I polled everyone on social media for the best donuts in Chicago, and Stan’s had the most votes. We split an original glazed, an old fashioned, and an apple fritter, and they were all fantastic. The spot also has really great coffee, and we were able to relax a bit and warm up before getting the day started.
The area around Stan’s has a ton of shopping, so we wandered the stores for a bit, while waiting for the second independent bookstore on my list to open. Myopic Books is a used bookstore, and has all the charm of an old used bookstore, plus THREE FLOORS of books to choose from. We spent a good hour or so in the store wandering the shelves before deciding on a few items and having to head to lunch.
Lunch was at The Purple Pig, a spot with a ton of great sharables and an extensive wine list. It was my first time at a restaurant that had a non-alcoholic wine on the menu, so I was able to enjoy a nice rosé with our meal! Some of the highlights were the soup of the day, and the incredible chickpea hummus with toasted chickpeas and a whole loaf of toasted bread.
After lunch, we walked off our meal by walking the shops on Michigan Ave, or “The Magnificent Mile” both ways. Afterwards we stopped in the Shoppes at North Bridge which was attached to our hotel. We dropped off our bags, and headed out to meet our friends who had finally arrived just in time for dinner!
Second day, second pizza – we headed to Lou Malnati’s for dinner. Lou Malnati’s is definitely one of the most popular deep dish spots, and the wait can be LONG. We put our names on the waitlist, and it was about an hour, so we waited for a bit at our hotel bar and had some cocktails/mocktails. After stuffing ourselves with SO much pizza, we all crashed so that we could head out early in the morning for another full day of Chicago adventures.
Day Three
Day three started with brunch at Venteaux Brasserie. Walking distance from the hotel, Venteaux has an incredible menu of very fancy brunch foods and incredible brunch cocktails and coffee drinks. My absolute favorite from the menu was the duck and waffle dish, which had SO much flavor. Another favorite was the “Eggs 5 Ways” dish which is one of their most popular dishes.
After brunch we walked over to Millennium Park at Grant Park for the obligatory photo with the bean/Cloud Gate. Seems like no trip is complete without this mandatory photo opp!
After the bean, we ubered over to Chicago’s Chinatown where we planned to spend the majority of the afternoon. We started by taking some photos by the main gate, and reading a little bit about the history of Chicago’s Chinatown, before diving in and beginning our food tour of the area.
Our first stop was Chiu Quon Bakery for what the internet told us were the best baos, or buns, in the area. To be honest, they were OK – they weren’t warm, and definitely seemed like they’d been sitting out for a while. They might be better if you get there right away in the morning.
Our second stop was Qing Xiang Yuan Dumplings, and OMG this place was incredible. Definitely recommend trying to go with a group, since they sell all of their dumplings in orders of 12. We went with two different fillings, and got one steamed and one fried for a bit of variety. They have most of your standard, traditional dumplings, but also had some fun ones with lamb or truffle that we wanted to make sure we got to try.
A trip to Chinatown would not be complete without stopping in the Aji Ichiban candy store. This spot has ALL of the candy and snacks from Asia that we love, and you can buy them in bulk or buy them by the piece/pound. We each loaded up a pretty big bag of snacks for the rest of the trip.
Our last stop was MingHin Cuisine, specifically to get some noodles and honey walnut prawns. This spot is HUGE and has a very extensive menu of both regular menu items and dim sum. After this spot we were truly stuffed, and didn’t feel like we’d ever be able to eat again. We headed back to our hotel to freshen up, and then figure out our plans for watching football that night.
We ended up going to The Radio Room, which was a sports bar right by our hotel. We wanted to watch a few football games, so we posted up at a hightop, and spent our evening there. They have a pretty standard menu of bar food, which we picked at a bit, but honestly were still so full from our Chinatown food tour earlier in the day. When the games were over, we all fell asleep IMMEDIATELY, ready for our last day of adventure!
Day Four
We started out day 4 with a trip to the Willis Tower. To get to the observation deck, there is a small museum you first walk through with fun history and facts about both the city of Chicago and the building itself.
Once at the top, you enter Skydeck Chicago, where you can take photos from the 360 degree view windows, and you can wait in a line to take pictures in the skyboxes, small glass boxes that jut out from the building and give you incredible views, and crazy scary photo ops. They give you two minutes to take as many photos as you’d like with your group, as well as take some professional photos if you’d like. The woman manning our box was fantastic and knew just how to angle the cameras to get the best shots.
After our trip to the skydeck, we were hungry, and hit up what might be the coolest attraction from the whole weekend – Hamburger University. Hamburger University is located in the McDonald’s headquarters in Chicago, and features a Global McDonald’s. This McDonald’s has all of your normal favorites, plus a rotating menu of global menu items from around the world. When we visited, they had the chicken mac (which we’d had once before in India) and a phenomenal burger from France that had an entire mozzarella stick patty on top. Not pictured, but also very fun, was the Matcha McFlurry from Japan. The menu changes regularly, so you can stop in and try out some fun new items!
Afterwards, we walked around the area to some of the nearby shops, while slowly making our way to our next food destination. It was honestly hard to control ourselves and not overeat everywhere we went!
Our next stop was BomboBar, which is known for their incredibly decadent hot chocolates, complete with mini bombos, which are stuffed Italian donuts. The make your own hot chocolate allows you to choose your type of chocolate, type of cone, and toppings, as well as the type of bombo you’d like as the final touch. We split one of these between four of us, they were SO rich and delicious.
We decided to walk the hour walk back towards our hotel because we REALLY needed to walk off some of the food, and we stumbled upon the cutest little bookstore called Open Books on our way. This spot had both new and used books, and this adorable staircase made of book spines. Highly recommend adding this to your independent bookstore list in Chicago!
We also stumbled across the Chicago French Market, which is an adorable little food hall with a ton of French, and non-French spots. I had actually been here once before for lunch on a work trip, and while we were waaay too full to try anything this time, all the spots I’d tried before have been delicious. If anything, it’s a fun atmosphere for a quick walk around!
Before ending our trip, we still had two more food stops to make to hit all the Chicago classics. Our first was Al’s #1 Italian Beef. We arrived with enough space in our bodies to split one sandwich between the four of us – just enough to get a taste. The sandwich was good, although I don’t know if I’d ever go out of my way to get one again. Definitely something to do once to say you’ve accomplished it!
Our last stop was Portillo’s for a Chicago hot dog, and this is a place I’d add to my list again. I’m a big hot dog fan, and this one did not disappoint. Afterwards, we were sufficiently full forever, and headed back to our hotel.
We packed up and had some last drinks at Upstairs at The Gwen before our flight to New Orleans for Christmas with the family. They had some non-alcoholic beer on the menu, which was great for me, and we had a bit of relaxation time before we needed to head off to O’Hare. Overall, this was a jam-packed four days in Chicago, and we had a blast really getting to explore the city. We can’t wait to go back (hopefully NOT in the coldest month of the year) and explore even more – let us know what places we need to hit up next time in the comments!
