Hello Darling!
A few weeks ago, Hunter and I had the super fun opportunity to spend a weekend in Chicago. It truly was such a blast! Our Brother In Law was going to be running the Chicago Marathon which gave us the perfect excuse to go see him run, and visit this new city. We had heard such amazing things about Chi-Town and the city lived up to every expectation. So today I am excited to share our fall weekend in Chicago itinerary.
Our Fall Weekend In Chicago Itinerary
Saturday
Our weekend started bright and early on Saturday morning with the first fight out to Chicago from Houston. We wanted to make sure to get a full day in the city on Saturday and were able to make it in by 9am.
From the airport we grabbed an Uber and headed into the city to our hotel. With traffic, it only took about 30 min which was not bad at all! We set up an early check in with hotel prior to our arrival and were able to get our keys quickly and promptly as soon as we arrived.
Hotel
We had the pleasure of staying atThe Peninsula Chicago and let me tell you, it as a DREAM! I have had the honor of staying at two other Peninsula locations within the years and just like the others, this hotel did not disappoint. From it’s incredible Michigan Ave location, beautiful rooms, and incredible service/amenities it made our trip even sweeter!
(Booking Note- With it being race weekend all hotels were more expensive than normal. However, we were able to find and incredible deal via Expedia)
Brunch
After checking in to our hotel and settling in, it was lunch time. You can bet this momma was ready to eat. 😉 We headed to Nico Osteria located in the beautiful Thompson Hotel for brunch. It was only about a 10 minute walk from our hotel and we opted to walk there and enjoy the beautiful weather.
(Note- one of the reasons why we booked The Peninsula was because of it’s central location to everything we were going to be doing)
Brunch was delicious! Between a hungry momma and a carbo-loading marathon runner, we definitely indulged ourselves. Our favorite dishes included the avocado toast, brussel sprout bruschetta, and french toast. We also loved their selection of mockcocktails and cocktails. I was able to sip on a yummy Yuzu Fizz mocktial, which my sister enjoyed a Fearless Leader cocktail.
Site seeing and Exploring
With all the yummy food in our bellies, we were ready to do some exploring. We headed to Millennium Park to site see. Our first trip to Chicago would not be complete without visiting the park and seeing the “Bean” or formally known as the Cloud Gate Statue. There were quite a few people there as it is one of the biggest site seeing spots in Chicago. We were still able to grab a few photos with it.
Our next stops included the River Walk as well as doing some window shopping along Michigan Ave. We loved seeing what a gorgeous city Chicago is. Walking around and exploring was truly one of our favorite things we did in the city.
High Tea
After all the walking we were ready for some Afternoon tea. We hopped in an Uber and headed to The Allis. Tea was AMAZING! Between the adorable decor and the delicious tea it was such a fun experience!
(Note- Definitely call ahead for a reservation when booKing for afternoon tea)
Dinner
We then headed back to the hotel and got dressed for dinner. Dinner was at the delicious Formento’s. It truly was SO good! Really all the food we ate in Chicago was spectacular. Also, on race weekend most spots had special menus for those who were racing or just for those who enjoy carbs. 😉 We loved their homemade pasta! Definitely a spot to check out when in Chi-Town.
Sunday
Race Day
Sunday was race day. So we got up early, watched the start of the race on TV, and grabbed a quick bite before heading to mile 13 to catch Seth running. If you ever plan to go watch someone run the Chicago Marathon, they have an awesome app that will allow you to plug in their number to track and watch them run. That way you can meet up at spots to cheer them on.
It was so much fun getting to watch the race and explore the city more. Quite a few roads in the city are completely blocked off this day, so it made it super accessible to walk around. We were even able to run into one our best friends who just so happened to be in Chicago the same weekend.
(Note- if you plan to visit Chicago on race day, it’s important to know that catching an Uber is super hard since so many roads are blocked off. So plan to walk. )
We met Seth near Millennium Park since spectators are not allowed at the finish line. We grabbed some photos, gave him big hugs and headed to get him some much deserved BRUNCH.
For brunch we headed to Hampton Social. We did have to walk there because of the closed roads, but it was not bad at all! Brunch was super delicious! If you go, try the Frosé for me. I was not able to try it this trip, but can’t wait to visit post baby and try it! It truly looked so yummy! After brunch we headed back to the hotel for some much needed naps and down time.
Night On The Town
This night was a night of celebrations! After such an incredible race day for Seth we all wanted to celebrate. Our first stop was to Terrace 16 for drink located in the Trump Tower right along the river. The bar was incredible but the views were even more spectacular! It was a little windy and chilly this night but we made our way out to the terrace to take in the views and snap some photos. For sure a spot to visit in Chi-Town.
After drinks we headed right around the corner for dinner at Siena Tavern. Again, another INCREDIBLE dinner. I opted for past and was not disappointed. I was also very impressed with their wine list even though I could not indulge during this trip.
(Note- another place to definitely make a reservation ahead of time)
After dinner Hunter and I headed back to our hotel to enjoy the views from the Z Bar located on the rooftop. We then headed back to our room, ordered some room service dessert and called it a night. It truly was perfect end to a great day!
Monday
Breakfast
Our last morning started off with breakfast at the beautiful Lobby, one of the hotels on site restaurants. We enjoyed their incredible breakfast buffet and geared up for another day of expiring before our flight later that evening.
Shopping
After fueling up for the day, we headed out to do a little shopping and exploring on Michigan Ave. We were super lucky that this weekend was extremely beautiful outside. Temperatures were in the 40’s and the sun was shining the entire time! It made exploring the city that much better!
Another street we walked to that had SPECTACULAR shopping was Oak Street. From Chanel, Tom Ford, and Tory Burch there was so much beauty! I loved every second.
Deep Dish Pizza
Before we left Chicago we had to grab a bite and try some of the famous deep dish pizza. This was what Hunter had been looking forward to all weekend. After unanimous recommends to go to Lou Malnati’s we decided it was the place to go and it did not disappoint! SO GOOD! If you are looking for a deep dish spot to visit this is it!
(Note- Expect to see long lines, however once you put your name in make sure to head to the counter to order your deep dish early so that it will be ready by the time you sit down.)
This weekend in Chicago was truly the best! If you are looking for a fun weekend getaway, definitely check out Chicago. We can’t wait to visit again soon!
YOU ARE SO LOVED!
XOXO,Tay
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