Chicago, Illinois

Published: October, 2023

We have gone to Chicago ever year for the past 4 years. It all started as a date trip when I suddely received a call from Hilton Honors for a promotional get away for four nights at the Palmer Hotel for that November 2019. Of course at $350 I jumped on the chance to go to Chicago for my first time and have my husband show me around. 


Usually my husband goes to Chicago during the marathon, but 2019 was a break year for him. The more recent last three years were for the Chicago marathon where my husband has continued to push the limits of human abilities for himself. Mean while I have taken advantage of getting a little closer to the city, and have ran the 5k myself a few times.  Every year we go we just so happen to find something new in the city. In fact, we've sort of made it our mission to seek out new and interesting attractions so that you don't have oto waste your time skipping through hundreds of websites that outline the same top 15 attractions in Chicago (like, okay, we get it, the Bean is a must!) That being said we did highlight a few in this article, but mostly tried to focus on the off the beating path activities to help you really enjoy the city beyond surface level tourism.

Here are some of my findings that I want to share with you as you fin yourself traveling to this great city! 

Chicago vs. New York

After having been to both cities numberous times througout the last 15 years, I have come to the conclusion that I think I like Chicago better! (Please forgive me my New York Grandma!) There are a few reasons for this well-informed opinion: I found the streets of Chicago to be cleaner and more 'beautiful' (they spend ungodly amounts of money keeping the flower boxes well stocked throughout the city) and the people to be just ever so friendlier within the city. Now I know what you're thinking - New Yorkers are inherend @#$holes. But actually I think it's more about how you approach the conversation that can turn it positive or negative. That being said, I found folks in Chicago were helpful without being prompted to help. The residents really stepped up to the plate and assisted when we clearly got turned around in the city. And I can appreciate that level of attention to detail in the city. 

Budget Expectations

It’s probably no secret that Chicago is not cheap. And while I feel blessed by the universe to be able to experience and explore this city year after year, a little pre-planning budget can go a lot way for self expectations. This is where the itinerary helps because you can plan your spend day by day. If you want a $26 cocktail, you know you won’t be surprised at the bill if you build that rooftop bar into your experience (more on this in a bit.) be aware of 15-20% built in gratuities, although I didn’t experience this as heavily here as I did in Miami. Aim for your budgeted spend- check out menus and pre-plan your selections ahead of time so that you know walking into it what you’ll walk out with. 


Every year after Chicago we do an analysis of where our money went over the course of time during our stay. While some years we stayed up to 10 days(which was nice to feel unrushed, but almost a little too long after becoming familiar with the city ), this year we opted for a little more luxury and upgraded the hotel for the same price but for 5 days. Be aware of your end goals here and how you can stretch your cash.


Preparations & Recommendations

Plan your visit! I can't stress this enough.  If you’re traveling with friends or meeting friends, plan activities together to make the best use of your time and better memories while you're there! Last year we put our friends on our itinerary document and helped set expectations on when we had free time apart, and when we were to meet up at certain places. It felt like we had neighbors in the city and made the trip that much more enjoyable!  This also helps with with booking reservations in those special bucket list places, especially if it’s your friend's first time in the city.  This also helps you plan your budget and allow for other's budgets to be taken into consideration.  Being forth coming about activities and spending expectations makes you look like an expert! So don't be afraid to coordinate with friends, they will thank you for it afterward. 


In the itinerary we shared with everyone, we outlined each date, time of the event, the Location on where we were to be, as well as whether or not it was booked (for prep-planning understanding). This made it super simple for everyone to chime in, and stay on the same page, literally! 

What to Wear?

It’s no secret that Chicago boasts some of the most sleek city fashion in the US yet. And while magnificent mile might make you believe you want to wear that pair of heels my best advice really is to Bring some Walking Shoes for your visit. This is a walking city. While we all love the high fashion of uncomfortable shoes and impractical dress wear, unless you plan on ubering verywhere ($$$), definitely plan on bringing some walking shoes. You will be surprised at how much you do walk even from train to train. And while you don’t need to wear full on running shoes (although your feel will highly thank you) it’s definitely good to be aware of the fit and comfort of the shoes you chose because you could be standing or walking in them for hours.


Packing for the weather & expectations. 

Weirdly enough I can attest that we’ve experienced every kind of weather in Chicago you can image all in the same annual window year over year.  From 75 degree days one day, to having had run the 5k at 31 degrees that morning, that same trip. Having a good variety of options leading up to your trip will help you plan your over all look. And as the time to travel gets closer, pair down your options to what the weather looks like it will finally decide to be. Weather in the mid west can be wildly unpredictable- just ask our first October day this year in Minneapolis!! (91 degrees!!) 


If you’d like to see what I’m wearing this year as part of a colder year in Chicago, check out my fashion page where I detail all my outfits in a complete black and white theme for this 5 day trip! 

Flight Hacks!


I absolutely love the app Hopper. Learned about this app in 2015 when I was a Lyft driver driving a passenger, and it has saved me so much more money and head ache than any other competitor out there.  Hopper has an easy to understand cost fare calendar which indicates which days tend to be more expensive to book throughout the year, and will show you the fare difference.  If you opt for their VIP service, you get peace of mind cancellations and priority customer service, which we had to use on our last trip to Chicago when my husband suddenly had to fly out of the country to get his passport renewed. 


That being said, this wouldn't be a fair article if I didn't level the playing field a bit. In addition to Hopper, I will frequently cost compare, just in case, against other discount sites, and directly on the airline's website as sometimes the airline can have better deals when you book directly. In this case, I also recommend checking out the perks when looking to book your flight. My husband often upgrades if we are flying back on a long flight after a long trip, and sometimes those perks include complementary adult beverages! 

Accommodations Recommendations

If going during Chicago marathon, try to book as early as possible. We usually book a year in advance when we go to Chicago for the Marathon and because we book so far in advance, I try to use airfare and hotel websites and services that offer discounts and free cancellations up until the point of expected travel. Often times we book without knowing whether my husband will get into the race as we wait for the qualifier times, so these features lend themselves well to this sort of flexible spending. 


That being said, the city is known for jacking up prices on hotels during this weekend and having a lot of unavailability so we use Agoda to book a year in advance if we know we’re coming back. Agoda gives us the flexibility to cancel nearly last minute without fees in case plans change. This app has been the best I’ve found so far for great deals when comparing others like Kayak and direct hotel booking. That being said, we tend to look for hotels in the Hilton Family as well as we have a Hilton card, and after plowing all the charges for the wedding on my card, I ended up a Diamond member with Hilton in their highest membership tier, which provides extra perks in itself like a $50 food and beverage credit,  free priority upgrade in the room, and discounts at the spa. In order to claim these things though it’s important to call ahead- since we didn’t book directly through Hilton you must sort of alert the front desk that you’re a member, and attach your member number to redeem the perks. One last perk about Hilton is if you regularly use your card but aren’t projected to travel much, these points can be exchanged for Amazon points, which, since we bought our house, has been really helpful for filling the gaps of all the little things we needed.


Okay, back to Chicago! 

Hotels we Recommend


After so many stays in the city of Chicago, we have a few recommendations in places to stay depending on your budget and our ratings for those locations based on our experience over the past 4 years. 


Waldorf Astoria Chicago Hotel (9/10)


We booked 1 night here with points through the Hilton site (and then later stayed at another hotel mentioned below with Agoda) and had an absolute blast.  We treated with extra champagne during our massages as a congrats to our wedding anniversary and made to feel like royalty during our entire time.  The rooms have fancy shades, real gas fireplaces, and high end fixtures. The common area spaces were really nice as well, and the staff always made sure we had what we needed. The on-site restaurant had some of the most delicious $75 pancakes I’ve ever eaten- service is next to none. Not to mention the beautiful vibe here where again, you feel as if you were the late Queen herself being treated to the best of the best. 


This hotel hits the top of our list for a few reasons. One of the other major reasons for this being our favorite hotel is that is has one of the nicest onsite spas. While there are a few stand alone spas in the city, we actually booked a return visit back to this spa due to such a positive experience the first time. My husband and I were celebrating our wedding with our last Chicago trip by staying here, and the massage therapists greeted us with Champage after our massage. We also enjoyed the onsite pool, hot tub, and steam room. While they have a sauna as well, it wasn't in operation last time we were there. We will update this article with this years experience if that has since changed. 


This particular hotel is near the shopping district for higher end goods and not to far from Magnificant mile and is also a Hilton hotel. So if you’re a card holder, be sure to  book through the Hilton site and present your membership for a $50 food and beverage credit if you qualify!  (Heads up! You MUST book through the Hilton site to claim your status and perks!) 


Palmer Hotel (6/10)

This is a Historic hotel with an impressive common area and cool bar setting in the main lobby. As we also got a few drink coupons with our stay as part of the promotion, I ordered a Bloody Mary and I have to say the bar tender was certainly skilled. If you like cocktails, I can honestly say that that was the best Bloody Mary I've ever had.  


We booked this hotel in our first trip together through a Hilton Honors Vacation promotion for 4 days and 3 nights, and absolutely had a blast. This was before discovering Agoda to book hotels. And while there is some super cool history around the hotel itself and the role it has played in Chicago's history,  overall, the glitz and glam of the Rooms weren’t as impressive, but were clean and spacious.  Everything was in order for the most part and it was quite queit in the room, so it was an easy nights sleep. If you get asked if you'd like to upgrade, don't go for it. We did upgrade thinking it would be more luxury, but instead our room ended up having  had a weird bar sink/"kitchen" area (with no fridge), which we didn’t use as it was just the two of us. We think would have been different with a group. The extra leg room was nice if you like to throw your clothes around the hotel. 

Drake Hotel (6/10)

We didn’t stay here but our friend did during this last years marathon, and so we were privy to some of the beautiful sites within the hotel itself as we walked around a bit. The entrance to this hotel is really grandeur in it's presence, and accomplishes that regal feeling that many other older hotels in Chicago miss in their first impressions. The Drake, like many other hotels, is a history landmark of the city. However, the amount of care and attention to keep it's pristine status makes it a must if you'd like to stay in the north loop end of the city, and close to Magnificent Mile. 


I had to throw in that the hotel was in the process of holding a special event, and so included this hotel because of the insane flower display (one of three!!)  they had in one of the event spaces just off the main lobby. 


Knickerbocker (4/10)

Congress Hotel(5/10)



theWit Hotel


(Comming Soon! )

Transportation Hacks!

Trying to convince your aunt to drive you to the airport for free? Looking for a way to hunt down a discounted ride? While Lyft and other popular rideshare apps have taken the main stage for on demand rides, we have gotten wise to the pricetag that can come with that. And that is why we recommend looking in your local area for shuttles or taxis that might allow you to book ahead of time on their website. 


For our airport, we booked with SuperShuttle, which allowed us to pre-book a ride back from the airport to home at the end of our stay in advance. We found it to be roughly $30 cheaper than your on demand rideshare app and without the wait time to be picked up! 

Once you arrive to the Windy city, it will be important to know how to get around. While Lyfts and Taxis are available, we actually recommend grabbing the train. Unless you're feeling bougie, this public transportation option is not only cheaper, but you'll be riding one of world oldest train systems having originally been conceptualized and built in 1892.  If you're open to taking the train there are a few things to know transitioning from plane. 


Look for the Ventra vending machines once you debark from the plane and head toward the train. You'll need to pick up a transportation card, and you have the option to chose from a one time use card, or a card you can load and reload. Pay attention here because if you're planning on seeing all the site or will be in the city for a while, a 7 day pass of unlimited rides might be worth the buck.  

Coming from ORD Airport

You'll want to grab the  Blue Line train to get to the loop. The ride is about 1 hour with no delays so be prepared to entertain yourself.  If you ride this train back upon your departure, build in an additional 30 minutes as railway maintenance can sometimes slow down arrival times. (We almost missed our flight back! No body want's that stress). 


Coming from MDW Airport

If you're arriving at Chicago's south side airport, there is also the Orange Line train available to you with a bit of a shorter lead time getting into the city. Sit back, bring a book, and enjoy your time as you glide into the city. 

Other Trains

If you happen to be coming into the city for an event at the convention center, again! Skip the wait and extra expense for rideshare and hop on the CTA L train that is a direct shot and roughly a 15 minute smooth ride to McCormick Place.  


Citibikes 


Last but not least, if your time is more leasurly in the city and the weather is nice, hop on a Citibike to take a ride around the parts and down to Navy Pier! My husband and I did this one cloudy day and we had an absolute blast. The air was fresh, the ride was super pleasurable, and it gave us a feeling that we were locals in the city. You can find these bikes almost anywhere there is a bikeshare station (and there are a lot) and only require you to have a smartphone in order to unlock them. We actually loved it so much we rented them a few times around the city as we found they were also a little faster than fighting traffic to get to major attractions. If you're not afraid of a little exercise and want to feel like a resident, definitely don't hesitate to take advantage of this great feature of the city!


Best Restaurants to Try


After having been to Chicago so many times, we have plenty of recommendations for places to stop into that will fill your belly and your sould when it comes to delicious food! What restaurants we’ve found and which ones we think are worth the money. But on the note of making sure you have reservations (yes even for breakfast) we recommend OpenTable, an app that

Open table referral links 

Explore the Drop Downs below for 

Breakfast Restaurants


Corner bakery 


Somerset 

This was our last trip restaurant before we headed to the airport and it was also good. At a little bit more of an affordable price point, this again was a restaurant we tried because of the aesthetic and surroundings. The surroundings slightly nod to art deco with a more modern twist. The food was not as unique as other restaurants 

Yolk




Lunch Restaurants


3 Arts Cafe at Restoration Hardware $$$


Giordanno's

If you've never had a deep dish pizza before, Chicago style, Giordannos is the spot to check. While it's a chain within the city, their deep dish pizza's don;t dissapoint and will leave you feeling like you've had an italian thanks giving!  This is a special favorite of ours, and during 2020, we stopped in to Giordanno's  to grab a frozen pizza to share with our family we were driving up to visit. 



Dearborn 

This restaurant was delicious! And like with any higher dollar amount joint, the service is almost always amazing. We loved the VIP treatment we got here, and the food was soo good! The bar is separated by a textured glass, and the subway tile gives this spot a hip vibe that makes you feel like you're sort of transported back into a different time. The coolest feature of this restaurant? When you visit the restroom, check out the wall of wine fridges along the left all the way down the hallways. They have a huge selection of wine to chose from if you're a conteseurre. 

Nobu Chicago 


Nobu is an absolute must when it comes to a fine dining experience. If you're a sushi fan, and like cocktails in an immersive and fanciful dining room - Nobu is it. But Be aware, this restaurant is not light on the budget, but absolutely worth it. My favorite cocktail here is the Lychee Martini. If you've never had Lychee, its a Japanese fruit that is particularly sweet. 


This restaurant boasts amazing service as it does atmosphere, you will feel like you are royalty with how they approach the table. And so if you like to dress up and go out, this restaurant will give you a reason to do so. Did I mention they have a rooftop bar? Exclusive with space?  We are loving the vibe here and highly recommend.

Be sure to use Opentable to book a reservation. They do require a credit card to book the reservation since it's such a high profile place - but they don't charge you unless you no show. Taking a rideshare here? Be aware the ride might drop you off on the hotel side of the restaurant. No worries! The staff will always make you feel like VIP, we got to take the back door into the restaurant and into 


Victory Tap | south loop 

We happened upon this spot during one of our last days last year. Loved the upscale vibe with the bar up front. The service was super friendly a quick and it was busy, like everywhere else in the city, during the marathon weekend. I had the butternut squash and my husband had the lasagna. And while it wasn't an out of this world flavor like some other restaurants we've tried, we can say it was high on the list of deliciousness!


The vibe in s casual and the service is very personable! 


Best Rooftop Bars to Try

Chicago is well known for it's rooftop bar culture, and we are excited to share with you some of the best rooftops to try and Best rooftop bars: most cocktails in the city range in the $15+ range

This rooftop bar also has a great view of the river, and a very eclectic vibe to it! 

London House hotel rooftop & bar

We love this bar for it's upper class. If it’s cold enough, they’ll serve a really good hot toddy. The hotel is of gilded age, but has since been updated, and the rooftop bar loverlooks the vier and you get a great view of the spire of the hotel. 


Best 10/10 shopping & attractions not everyone knows about (&does!)




Field Museum




Let me know your Chicago travel hacks and location recommendations below! There is so much to do and see, and we hope this inspires your visit!