This was road trip #2 of 2021 with my boyfriend. We had such a fun time on our 1st road trip to Nashville last month, that we decided to take another one, but this time head north instead of south. Because of Covid, this was the longest I’ve ever gone without going to Chicago. I lived in Chicagoland for 10 years and was excited to go back!  With some really great planning and an awesome discount hotel website deal, we were able to do this trip inexpensively and successfully. I am excited to share my discount codes and favorite spots with y’all!

My goal of the trip was to eat and drink at some fabulous restaurants, while catching some views of what I think is one of the most beautiful cities.


All of the 4 & 5 star hotels are so incredibly cheap right now.  When we took our trip to Louisville and Nashville last month, I discovered this discount hotel website, Snaptravel, that I have had such a great experience with!  I was shocked at how cheap all of my favorite Chicago hotels were!  I scored a room at the Gray Chicago for just $130!!  Normally it would go for $300-$400.  If you haven’t ever used Snap Travel, check it out!  You will get 10% off with this link using my discount code DR5OZKJ

The website does all of their communication through text messaging and it’s so easy to search for hotels. It is extremely user friendly.

Chicago Foodie Trip May 2021 Recap Video

I love all of the Kimpton hotels in Chicago ( Monaco and Allegro are two of my other favorites), but the Gray was just fabulous!  You have a personal concierge upon check-in, and all of the communication for your needs is done through text messaging. They made reservations for us, adjusted our prior restaurant reservations, dropped off towels, toiletries we forgot, bandaids, etc.  Every time I texted for something, they got back to me within a minute!

 The hotel is located in the business district, right off the highway, so it was quiet during the weekend and very accessible from the highway.  They also have a free happy hour from 5-6 pm every day!  It was quiet and beautiful and we had an excellent experience.  

We arrived in Chicago late morning on Saturday, just in time to check into our hotel, park and head to our brunch reservation at Althea. Because of Covid, you need a reservation everywhere you go to eat and drink in Chicago.  You may luck out with a last minute cancellation or a bar seat, but to have the most enjoyable Chicago experience, make sure to plan out your meals with reservations.  

Althea is a plant based restaurant at the top floor of Saks Fifth Avenue on Michigan Avenue. Althea is one of Matthew Kinney’s restaurants. Matthew Kinney is a celebrity chef and one of the world’s first leading chefs at the forefront of plant based cuisine.  His story is amazing and he has restaurants all over the world including the first every plant-based food hall in Providence, Road Island, which I can’t wait to go to someday!  

The food’s taste and consistency was so spot on, I don’t think any meat eater would be disappointed. Even though it was in Saks Fifth Avenue, it was a casual, laid back atmosphere and I loved everything about it. 

After brunch at Althea, we walked off our meal and enjoyed the Chicago riverwalk scene.  Since we both always love Hampton Social, we decided to pop in one of the Chicago locations to cool down with some drinks. I loved their “Hampton frosé” and of course their classic sparkling rosé.  It’s usually my go to summer drink.  We were a little hungry and decided to order the fries, since we loved them so much in Nashville.  We were extremely disappointed when they arrived to see that they were about a 1/4 of the size of the fries we ordered in Nashville.  We loved Hampton Social, but they definitely need t step their fry game up. 

We came back to the hotel to rest and enjoy the free happy hour with a glass of wine in their beautiful lobby and library area.  We changed and then went out for an evening in the Fulton Market District in the West Loop.  The West Loop is one of Chicago’s fastest growing neighborhoods.  It is still somewhat industrial and gritty, but filled with a slew of new and popular restaurant openings  centered around Randolph Street. It’s otherwise known as  “Restaurant Row.”  

We lucked out and last minute got into Joe’s Imports, which was just recognized as a Michelin Guide Bib Gourmand.  When planning out your trip to Chicago, I highly recommend looking at the Bib Gourmand guide before making your reservations.  This is where you will find Michelin approved quality food for a good value!

After dinner, we walked down restaurant row and popped into another of my favorite spots, Bar Siena, to say hi to my best friend for a minute! 

We then headed back to our hotel for a late night reservation at the rooftop Peruvian restaurant, Boleo.  The views above you when you are sitting down are incredible!  You can look right up to the Willis Tower.  We had such great customer service everywhere we went.  Chicago is known for its food scene and I’ve always been impressed with the excellence of service I receive.  Our server was  slammed and took a long time to come over and take our orders, so he brought out complimentary glasses of champagne when he finally made it to our table.  It was so sweet and appreciated.  We enjoyed cocktails since we decided to skip drinks during our dinner at Joe’s.  However, we decided to order some food to-go for a late night snack in our hotel room. I am notorious for saying I won’t be hungry later and there is no need to order food to-go, but I ALWAYS end up getting hungry, so I am glad that I ordered something!  We got veggie empanadas and yuca fries. It was the perfect late night snack!  

I texted our concierge last minute late Saturday night and requested a late check-out, which they were more than happy to give us for Sunday morning.  We slept in and then went to our final reservation which was at Cabra at the Hoxton Hotel.  Cabra was another Peruvian inspired restaurant, by the famous celebrity Chef Stephanie Izard.  I had been there before and loved the vibe and views, and was excited to go back for brunch.  The Hoxton is definitely a hot spot hotel, right in the heart of the West Loop and restaurant row.  I’ve stayed there before and highly recommend!   


I used Stitch Fix to style me for my recent Chicago trip.  I’ve been using them on and off for years now and I have kept almost every single item in every fix they’ve ever sent.  For $25 off your own customized box of clothes use my discount link! 


I always get asked where I buy my Jordans, and although I have a few places I shop, my favorite website is Stadium Goods.  You can use my discount link and get $10 off a pair of shoes! 

Chicago Foodie Trip May 2021 Recap Video

Chicago is such an easy road trip from Indianapolis and it’s even better because you gain an hour with the time zone switch.  If you want to get away for a quick trip, I highly recommend planning a 24 hour Chicago getaway!  Just remember to book your room through Snap Travel using my discount code DR5OZKJ and book your restaurant reservations through Open Table and Resy.