If you follow me on Instagram, you’ll know that I’ve been in Chicago the last few days visiting my friend. It was my first time to Illinois and I had an absolute ball! My girlfriend lives in Lake Forest, but we spent most of our time in the city. Since we had so much to do in so little time, I really feel like we made the most of my visit. Keep reading to find out what we did, where we ate, and how we were able to cram so much fun into 3 short days!

Day 1

My flight to Chicago landed at 11:30pm on Thursday night and since the drive from the airport to Lake Forest is about 45 minutes, it was practically Friday by the time I arrived to my friend’s house. As it was late, I quickly got settled in and got some sleep. Friday morning, we woke up early so I was feeling a little sleepy, but was excited for the day my friend had planned.

We caught the Metra North Line at 8:24am and headed to Downtown Chicago. Luckily, we were able to check in to our room at the James Hotel where we would be staying that night. We settled in, got changed and headed to brunch at the Drake Hotel. The Drake is known for it’s gorgeous architecture and afternoon tea so I knew that we’d have a great time. Gavin’s mom (who previously worked for Hilton) was able to use her connections to get us one of the best tables in the Palm Court and also sent a bottle of Veuve (thanks Joyce!). After brunch, my friend took me to explore Michigan Avenue and ice skate in Millenium Park. Ice skating is my absolute favorite way to ring in the holidays and the decorations in the area were absolutely stunning. Millenium Park is right by the Bean, so we were able to see that too!

After adventuring, we went back to the hotel room to get ready for dinner. Our reservation wasn’t until 8:30pm, so we decided to go to the John Hancock Signature Lounge first for an appetizer and a drink. The view from here was amazing, there were even girls taking pictures in the restroom as it has floor to ceiling windows. Dinner was at Momotaro – a lovely restaurant with authentic Japanese cuisine. The food was absolutely fantastic and the sake was delicious. My friend’s boyfriend did all the ordering, and the menu is constantly changing, so I’m not quite sure what we ate – but here are some pictures for you! 🙂

Day 2

After getting a much needed nights sleep, we checked out of the James Hotel. We walked around and shopped and admired the holiday chaos until we worked up an appetite. Lunch was at Restoration Hardware 3 Arts Club Cafe, and while they don’t take reservations (we waited for two hours), we got a great seat and the food was so so good. I ordered the Gem Lettuce salad (pictured below) and some fries and was pleasantly surprised! Most people go for the ambiance, and for a good reason. The restaurant is stunning, and while you’re waiting, I suggest grabbing a glass of champagne, a croissant, and heading to the rooftop to hang out.

Once our bellies were full, we ventured to the Skydeck at the Willis Tower. We decided to walk to get some fresh air and work up an appetite for dinner. What a view! I mean it was breathtaking. Honestly the best way to get the perfect birds eye view of the city and and a photo that looks like you’re floating on air. The only complaint I had, was that we waited for over an hour and it was PACKED. So, if you’re going to visit, I suggest going on a week day and not on Saturday night (or pay extra for the front of the line pass).

It wouldn’t be a trip to Chicago during the holidays unless you visit the ChristKinlMarket so of course we had to go. I absolutely love the holidays and this was the perfect way to get into the spirit! The unique shopping experience paired with German food and drinks, attracts more than 1 million visitors a year and admission is always free! My friend got a hot cocoa and I got a hot apple cider. This was also super crowded so we didn’t stay too long. Instead, we headed to the river and decided to drink our beverages in peace.

We originally had reservations at Cindy’s Rooftop, but since the Willis Tower took so long we missed them (but I’ll be back!!). Cindy’s is a stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with a seasonal menu. Another great place to get a view of the city from above and definitely worth checking out! Instead, we went to a place called Gino’s East which has amazing deep dish pizza. The wait was only 15 minutes and the pizza was so good.

After pizza, we went back to Lake Forest.

Day 3

My flight back home wasn’t until 6pm, so we really had the whole day to do whatever we wanted. This was the perfect opportunity to get breakfast with my girl friend and her family at Egg Harbor (such good breakfast!) and to explore the Lake Forest area. Honestly, if you’ve never been to Lake Forest, I highly suggest taking a trip up there if you’re ever in the city. It’s a gorgeous suburb just North of Chicago along Lake Michigan and the homes are STUNNING. Not to mention you can drive down to the beach and enjoy your morning coffee. Also, if you’re looking to stay in the area, the Deer Path Inn is so quaint and offers an amazing Sunday brunch!

As my trip came to an end and Jess drove me to the airport, I thought to myself, it’s the trips like these, where you get to visit someone’s hometown that may not always be a “destination,” where I have the most fun.

I truly had such an amazing time and I’m so grateful for my friend and her family. It was an incredible trip and I can’t wait to go back!