The Windy City, the hub of the midwest, and likely the most expensive place to visit north of the Mississippi River. Chicago still seems to hold a place as one of my favorites to visit for a couple of reasons. 1. The history and architecture are enough to steal any inquisitive persons heart. Pair that with Lake Michigan and the Chicago River views – what’s not to love. 2. crazy diversity. The richest people and the absolute poorest people fill the streets. They all stop at the same lights, and walk the same streets in this puzzling synergy that you can only find in the city. And compared to the east coast stereotypes, Chicagoans are pretty friendly. And diverse, did I mention that?
I feel like I should preface this article with a bit about how I like to plan out a vacation. I like luxury things, but your girl is cheap. Frugal, if you will. I simply cannot justify buying insanely priced jewelry, or purses. But, I will 100% splurge and indulge now and then on experiences – especially on a vacation. In this post I’ll share how my husband and I spent our anniversary weekend in September, in the Windy City.
GETTING THERE
This visit we decided driving was the best choice. We’ve taken the train, flown, and driven on separate occasions to Chicago, and I have to say driving ourselves is top tier. The traffic and fast pace is a bit much for a lot of people, myself included but having the option to use your own vehicle when you’d like – elite.
If you’re staying at a hotel you’ll likely have 2 options. One; park the car yourself in a lot assigned to the hotel and pay a nightly fee (usually charged by the hotel) to come and go as you please during your stay. Or two, pull directly up to the hotel and let someone valet your car for you. You’ll still pay the nightly fee if you parked yourself(often more for using the service), tip the valets each time, and only have access to your vehicle by someone getting it for you. While convenient to some, for me personally not being able to walk to my car whenever I want it stresses me out lol
For budgeting purposes I would account for $50-$100 daily for overnight parking at a hotel. Which is also our next topic!
LODGING
As a general rule of thumb I would much rather stay at an Air BNB over a hotel EXCEPT in Chicago. I feel there is a lack of conveniently located BNBs in Chicago. A majority of what I found when looking were in the suburbs of the city and required using public transportation, or Uber to get to most attractions.
If you’re comfortable with that it is definitely more affordable to book outside the city, but just make mental note Ubers get expensive and traffic if you choose to downtown will be heavy.
We chose to book hotel for 2 nights, and had hoped to spend no more than $250 a night. Everyone laugh now because LOL there were maybe 3 options that fit that budget. I should add, that bit I talked about at the beginning, about splurging now and then? Yeah, that was kind of sealed for me with the hotel here.
After the discovery of my budget for a hotel being a slight joke, we decided to look at luxury hotels. Please know I’m not being dramatic when I was getting several quotes for 2 nights being a minimum of $800. The hotel we ended up staying at would’ve been $1,200 for two nights, and it was a Marriott. A very nice one but, uh no, that’s too much for me.
In comes the discovery of Hotwire Hot Deals. After scouring TikTok’s for cheap hotel hacks I found this gem. Say what you will about 3rd party bookings, this one was 100000% worth it.
Let me explain as brief as I can.
You Google Hotwire and type in your dates, desired destination, number of people, then click find hotel. It will then show you hotel options, some of them will be highlighted in red and say hot rate. You’ll see a price slated out that would be roughly what it would be to book directly with the hotel, and below that number, in red writing will be the Hot Rate. These are legit and the slashed price truly is ballpark what it would be to book elsewhere. Rest assured, I called to double check to make sure they weren’t just inflating the number to make the deal look better.
The hotels are categorized by title for reference, and star rating. Examples luxurious, classic, unique, romantic. You get the idea. Y’all these prices are all at least $100 less per night!
However – and here’s the kicker. You don’t actually get to see which hotel you book unit after you confirm the booking based off price. Crazy right?!
It lists 4 national, or regional hotel chains that fit all the checks of the options you inout in the previous steps. In my situatuion all 4 were hotels I called and priced prior to finding this deal. All of which were vetoed simply because cost for 2 nights was insane.
Booking this was a no brainier for us, and I like a little risk! I selected the ‘luxurious’ hotel category and booked two nights to a a still anonymous hotel for a little under $700. Seconds after payment is processed our hotel was revealed. Chicago Marriott Downtown Magnificent Mile.
This isn’t your mommas Marriott. This place was niiiiiice. And way worth what our nightly rate actually came out to be. A newly renovated 9,000 sq ft fitness center, Starbucks in the lobby complete with food options, a stunning focal point bar, and a farm to table restaurant on site make finding complaints pretty difficult.
The best part for me personally was the fitness center. 9k sq ft packed with Pelaton bikes, cardio equipment that you could simultaneously watch TV on, panoramic city views from mod machines, and curated sections of the space for any type of physical fitness you could want. It’s a small town gym girls dream come true lol I was awake and excited to workout without taking preworkout Saturday morning. Like a kid on Christmas! 
Okay enough about the gym. We had a room with a comfy King size bed, mini fridge, basic hotel toiletries. Our view was the Burberry store and a distant Lake Michigan. Again, no complaints. I will say, I still wouldn’t justify paying full price for this beautiful hotel. Take a chance, save some money and book a Hotwire Hotel. They even have phone support that is actually helpful! (Not an add, but I wish.)
AIRE ANCIENT BATHS
Okay, please refer back to the beginning of this blog and reread the part that says something along the lines of enjoying luxurious things and splurging every now and then. Aire is that. I don’t specifically remember how I discovered this place, but I know my bestie was somehow involved (she likes nice shit too) way back in 2015. Aire is an ancient bath house chain, only found in 8 major cities worldwide. With exclusivity like that, and the additional fact cell phones are not allowed past the lobby, this place is pricey, but worth it in my opinion. Our reservation was for 4 PM and was the most expensive part of our trip, after the hotel coming in at $470. The ambiance is felt immediately upon walking up to the building. Tucked in an alley, the fulll brick building is adorned with weathered signage and accents.
The lobby is dimly lit, filled with oversized pillows, aperfectly aged leather couch, and complimentary hot mint tea, and citrus infused water is available. Immaculate vibes already. There was probably 3 other groups of two going back around the same as us. After a few minutes there was a worker that briefed us with the next steps, we were sent to gender separated locker rooms, given a locker for our clothes, and instructed to change into our bathing suits and these water shoe type things that were provided. Inside the locker was also a robe and a towel. The locker room was very middles school esq. in the sense that everyone changed right out in the open in front of the lockeroom attendants, God, and everyone. I’ve had two kids so I’m not really phased by that kind of stuff – Markus on the other hand let me know he had already seen more than he would’ve liked in the locker room lol
Once I used the single bathroom in the locker room, a staff member led me out a door, and downstairs where I was reunited with Markus.
Upon entering here, immaculate vibes once again. We were given a tour and briefed about the use of all the different baths, and steam rooms. There is no particular order of operations in regards to what bath to start with, but I’ll start with what we did first, I believe there are 6 areas total.
The first bath (more sized a pool than a bath) was a warm salt water one. The level of salt in the bath makes your body becomes extra buoyant, and your encouraged to do so with your ears and head in the water. Peaceful, meditative music is played to hear underwater. Immediate stress reliever. Next to that bath was and indoor/outdoor one, unique to the Chicago location. This one is basically a normal XL hot tub inside, and out, but outside there is a waterfall that you’re encouraged to sit under and let it massage your shoulders and neck.
I should a note quick, our reservation was for the baths and a 45 min massage. You get to to the baths for as long as you’d like until a staff member come and gets you, after the massage you can go back in and do more if you choose. There are no clocks in the place so I really had no concept of how long we were in there until after I got back to my phone. A nice touch actually when the goal os to relax. And we were both SO relaxed literally 5 mins into bath #1.
Tucked next to the indoor outdoor bath is an exfoliation station. A giant mound of Dead Sea salt, some cups to scoop so you don’t have to be a total savage, and s few shower heads to rinse off after. I really liked this simple feature. Across from the exfoliation station is one of several water and tea stations. Fresh bottles juice is also available for purchase, an is the only other thing available to eat or drink in the place. Eat before you come especially if you plan to hit my favotite part, the eucalyptus steam room!
The eucalyptus steam is just like it sounds. An enclosed glass room, with doors on each end, steamed up so thick you can’t see 2 feet in front of you. It’s a bit intense at first but eventually allows you to breathe deeper than you have in a long time, trust me. Inside the steam room there is also one of many cold plunge pools. If I recall it is about 55 degrees ferenheight, compared the steamy 100+ degree air, that’s COLD, but amazing for your body circulatory system. We did the dip in here probably 4-5 different times during our experience, and 1-2 times in another cold pool in another area. There was also a Russian steam room, far less steam, and scented with cinnamon rather than eucalyptus. Personally wasn’t a huge fan. A hot tub with a 1,000 jets! Lots of water to the face, (RIP to my lashes). A silent bath, an area where talking was encouraged to be at zero. And a caldron bath, the hottest of them all, and problably where we spent the most time sitting. And another highlight, the heated marble lounging area. Just off the silent pool, is a long stretch of marble that is heated. When you need a break from water or steam, this is top tier.
When it was time for our massage, we were led to a room with 2 beds, and 2 massage therapist. 45 min full body, Ive had better, and worse. It was relaxing, don’t get me wrong, but price wise, you’re definitely paying for the experience outside of the massage itself. When the massage ended we did a bit longer in the steam room, and cauldron tub before heading back to the locker rooms to change. They have lotion, hair products, blow dyer etc, so you can freshen up before meeting back in the lobby. I grabbed a strawberry basil lemon juice before we left.
Overall, I think this was a once in a lifetime experience for us. We may be back for the baths, but we will likely keep costs down and skip the massage the next time around.
NAVY PIER
For breakfast on this weekend trip we opted to keep it simple both days and got Starbucks breakfast, typically one of our favorite quick bites. We got duped. Lol Whatever the bagel sandwich from the hotel Starbucks was was booty. An absolute knock off. Closely resembled a microwave gas station sandwich. But momma ain’t raise a quitter, so I drowned it hot sauce and powered through. The second day for breakfast we just opted for Starbucks pasties and scones which did not disappoint.
If I’m being completely honest with you, we totally drank our lunch on Saturday. We headed to Navy Pier to explore and spend our day with no real agenda. A refreshing change of pace from our meticulously planned out, busy ass, daily lives. We arrived here about 10:30 AM after a straightshot, 15 min walk from the hotel. We were surprised to see that 99% of the stores, restaurants, and entertainment options didn’t open until 11. One big thing I was disappointed by here was the closure of Crystal Gardens; a beautiful 1 acre enclosed garden, full of tropical plants and water fountains, and free to the public. A quick Google search led to the discovery that it will not be opening back up as that, rather, renovated to have ‘virtual scenery’. Illuminarium (the proper term) uses projected images, sound, scent, and vibrations to give paying visitors the sense they’re in a different place. Very 2022 of them.
We bought some souvenirs for our kids before heading outside to explore the pier. Outside you’ll find the iconic Ferris wheel (+a few other rides), a tasty churro stand (with the cheapest bottled water in the city), several outdoor drinking spaces, and sprawling views of the Chicago trifecta. The city, the river, and Lake Michigan. Not a bad place to spend a sunny Saturday afternoon in September.
First things first at 11 AM sharp I was the first person in line for a fresh & hot vanilla filled churro. Homeboy was still prepping dough balls for the day and was visibly annoyed, but it was a 12/10, would reccomend.
While I smashed a churro, Markus bought tickets ($40) for us to ride the Ferris wheel. It was pretty simple, and done by scanning a QR code prior to getting in line, purchasing your tickets from your phone, and simple showing the recived ticket upon entering your uhhh, cartt? I’m not sure what to call an enclosed ferris wheel seat? The line filled up quick for this! Thankfully we were early and had our tickets before we got in line.
Once your on, it takes you full circle 4 times! If you’re not into heights, I do not recommend. The cart (we’re calling it a cart?) you’re sitting in swings a bit which kinda sketched me out being so high up, but was so minor compared to the view. I swear the water looks bluer from up here.
Next, we headed to Margaritaville! And even though it was barley noon, it’s always five o’clock there. My favorite way to have margarita? A mango marg on the rocks, sugar rim. And strawberry mango margs just so happened to be the feature that day. We sat inside (against my wishes) so Markus could watch the beginning of the Michigan game (GO BLUE). Fortunately the windows and doors were open wide with a perfect breeze like out of a movie. I’ll try not to geek out about my drink, but it gave a core memory. Michigan won the game as we mildly wasted away. Overall good vibes at this place, and drinks were fairly priced given the taste and ability to give the illusion that you were in fact in the tropics for a minute.
EATs + DRINKs
Okay, I wish this section was more interesting than it’s going to be, but, like I said we drank more than we ate on this trip. Let’s go back.
Dinner Friday night. Our 5 Year Wedding Anniversary, and whole reason for this whole trip in the first place. We wanted a “fancier” place, but we didn’t really want a “must wear a suit” dress code. We wanted food that we didn’t have to ask the waiter to explain, but also no chicky tendies. We wanted something that felt like an experience, not just an expensive meal. Again good ole TikTok came through with this find.
Gibson Italia, fancy for us, and perfect for us. We did make a reservation her about a day before the dinner. Our reservation was for 9:30 PM, and we arrived around 8:45. At check in we let know know those details and they sent us up the elevator to the bar/lounge area, which also had deck access for a seated dinner option. We got drinks here, Markus a beer, and I got one called pinkys up. I won’t say it was great, but I willl say “THATS LIQUOR!” I powered through but definitely didn’t order a second.
When our reservation was ready I requested we be seated outside, and since we didn’t specify in our reservation, it would’ve been an additional half hour wait. Nah. We settled (if you dare say that) for a table inside after requesting a seat with a view (told you I’m extra). They did not disappoint. Our seat had incredible views of the illuminated city, and the river. I ordered one more drink before dinner, a watermelon spritzer thing hoping for a better taste than my previous. 6/10 for her.
The dinner menu featured several aged steaks, and fine cuts of meat. Homemade pasta & sauces, fresh seafood, and hand cut fries. All of our favorites and high quality. Ding ding!! Markus ordered chicken parmigania and fries, and was overall happy with the taste of the chicken. The pasta came as a side and he didn’t eat that lol just the chicken, so I assisted and it was so good and so fresh!
I am not vegan, I like meat. So, I ordered the filet mignon and risotto. I am also not a wild animal, so I ordered my steak well done and it was *chefs kiss* perfect and came with fresh rosemary, and clove of roasted garlic. My dad always says good steak doesn’t need sauce, but I love sauce and ordered horseradish sauce to dip, wise move by me. The risotto was sub par; but thankfully steak, pasta, and overall ambiance made it a great night. The waiter saw that we were celebrating our anniversary and gave us a tiramisu on the house as a gift. Such a sweet gesture. We took our busted breath, full bellied selves back to the hotel extremely content.
One more place that I want to highlight, that I will 100% stop at during every single trip to Chicago is Niu Japanese Fusion Lounge, home of the Worlds Best Coconut Mojitos. I totally deemed the Worlds Best, but I have 5 people to attest. 2 of which don’t even like coconut! Its incredible.
While we didn’t get a meal here on this trip, I have eaten there previously and it did not disappoint. We chose a seat on their intranet front patio where I obviously I ordered 2 coconut mojitos, and Markus opted for a beer. They sold out of Bud Light (the only American light beer on the menu) the night before, so our waitress suggested a Kirin Light, a Japanese version of a light beer. He agreed and was happy with the taste and the fact that it was a 20oz bottle lol
For more simple food options nearby we hit good ole Chick Fill Bae. Some other favorites are Shake Shak, and Portillos – get the cake shake, thank me later. We also hit up an Irish pub called Timothy O’Tooles, because we’re suckers for good late night bar food. Their Rueben was a 10/10 and the extra side of sauce I ordered was a elite.
And if you are human, and like sweets, hit the Girhadelli store and get some chocolate or ice cream! They have make waffle cones on site, and hot fudge out of the chocolate. The smell in here is that of a utopia candy land. There is also a large display in the center of the store that is self serve chocolate. We filled a bag with several mixed and matched flavors, and decided to save the ice cream of next time. The store is located right next to where you check in for the boat tour- dangerously convenient.
ARCHITECTURE BOAT TOUR
And now for the grand finale! If I could emphasize one recommendation it would be this. We booked this through Wadella Tours and Cruises. There are several different companies you can book these types of tours through, some offer dinner, some more informative than other, all different lengths of time, you get the idea. I’m pretty certain we booked this the day of hoping for the sunset cruise at 6PM. It was unsurprisingly sold out, so we opted for the 6:45 ride. This was truly a blessing in disguise. Because of this timing we got the see the tail end of the sunset, and the glowing city when the sun was gone. MAGICAL. Our last visit to Chi town, we did a helicopter tour which was 3X the price of this ($50 bucks a person) and the view from the water was tenfold the view from the air.
Maybe I enjoyed it so much because I personally am obsessed with learning depth behind the place I’m visiting, especially its architecture and history. To learn both simultaneously and from a vantage point only possible from a boat was truly one of the best experiences of any vacation to date.
Our tour guide was an architecture student who was raised in the suburbs of the city , but originally from South Africa. His accent captured my attention and made listening even more fun. There was a guy complaining about sitting under (he literally could’ve sat anywhere) an awning that was obstructing his view, and that was the only downfall of the experience. And I say ‘downfall’ with apprehension because over all it was just that good.
I’m going to gatekeep some of the things learned along the way, in hopes you’ll take it upon yourself to give it a try. However, I’ll share my 2 favorite things learned and some amazing shots I got, some of which were taken using the Dispo App. (An app that uses your phone camera to capture photos that can’t be seen until the next day at 9AM. Its super fun to look back on and see what was actually captured. It also automatically adds a vintage feel to your photos that can’t be edited away)
A personal favorite of the city skyline is the St. Regis Chicago, a luxury property housing 400 high rise condos, and 200 hotel rooms. The buildings exterior resembles waves, is vertically tiered, and is colored in various shade of blue and green to highlight the waters surround it. The architect, Jeanne Gang broke her own record of creating the worlds tallest structure designed by a woman. That’s right, she set the record with a different building in the city, and broke it herself with the St. Regis. If you look closely at the building, you’ll see some of the floor near the top are unfinished and completely exposed. This was intentional, and done to allow wind to pass freely through the building and prevent the rest of the tower from swaying. It is normal for high rise buildings in Chicago to sway 15’-18’ on the windiest days. No bueno.
Another favorite was 150 North Riverside, nicknamed “The Guillotine” for several reasons. This gravity defying building sits on 2 acres of Chicago riverfront, is built above active Amtrak train tracks, and, if you haven’t noticed yet, is significantly more narrow at its base vs the top. For nearly 80 years the property was deemed unbuildable due to the active railroad system, city easement, and Riverwalk safety requirements. These 3 things combined took up 75% of the buildable space, leaving only a 35 foot wide area buildable. Architects from Goettsch Partners, and engineers from Magnusson Klemenic Associates accepted the unsolicited challenge, and created a nearly 1.5 million sq ft, 54 floored illogical building. The project began in 2012, and was completed in 2017 after negotiations on leasing monthly air space from Amtrak, and 2 smaller support buildings were done. Literally anything is possible.
EPILOGUE
Overall, we were thrilled with our quick weekend trip to Chicago. I’ve been several times now, and this one was hands down the best one. Each time I gain more knowledge and experience and I can’t wait until the next visit. (Girls trip???)
I’ll end with one more quick piece of advice. Check online for any events that may be going on the weekned you’re planning to visit. Certain festivals, holidays, and sporting events can cause prices to be higher and traffic heavier than usual. Mentally prepare for at least $200 more each day than your budgeted amount. City taxes, inflation, Uber fees, tips, shopping, they all add up quickly. To make your trip is pleasant, and enjoyed to the fullest keep this in mind.
Until, next time Chi!