Exploring Chicago

This summer, my husband and I planned a quick getaway to Chicago, Illinois over a long weekend. Here’s an overview of what we did, what sights we saw, and what we ate! Have you visited the city of Chicago? Let me know your favorite places in the city! I hope to return one day. There’s just so many neighborhoods waiting to be explored!

Day One in Chicago

We flew in via Southwest the evening before and checked into our fantastic Airbnb in Lincoln Park. We stayed in and enjoyed the amazing homemade brownies our host left for us and got a good night’s sleep.

Day One in the city was the 4th of July. We started off with an amazing steamed bagel sandwich from Chicago Bagel Authority, then hopped on the L (so convenient!) and headed to Wrigleyville. We started off the day with some beers at a nearby bar and met up with some locals. My husband attended a Cubs game with a friend, while I did some shopping in the area.

After the game and shopping, we got ready for dinner. We decided that deep dish pizza was going to happen eventually, so it might as well be that night. After deciding on a place that was vetted by local Chicagoans, we went to Lou Malnatti’s Pizza. It did not disappoint. I have been to Chicago before and tasted deep dish, but didn’t really care for it. This pizza, however, was really delicious, and the sauce was perfect. There was not too much cheese, and the crispy crust was delicious.

Day Two in Lincoln Park

Our second full day began with a delicious breakfast at Toast, which was a short walk away from our place. I loved walking through Lincoln Park and admiring the gorgeous homes and quaint gardens that lined the streets. At Toast, we had both great service and to-die-for food.

After that, we walked further to the Lincoln Park Zoo. It’s free, so you just walk in and explore! It was a super hot day, but we still enjoyed seeing the animals and the lush greenery around the zoo. The nature boardwalk around the zoo is a lovely place to walk. It’s amazing to be in a huge city, but have this oasis of green and gardens.

After exploring the area around the zoo and Clark St., we decided on dinner at Broken English Taco Pub, which was near our final destination of the night, The Second City.

Broken English had a cool, colorful vibe and the taste to back it up.

Before the comedy show, we had drinks at 1959 Kitchen & Bar, which is located inside the theatre. The Second City show we attended – The Best of the Second City – was a hilarious experience! I would highly recommend this to any visitor to Chicago. It was a mix of sketch comedy and improv, and we enjoyed every second! I was nervous when they sat us in the very front, but it ended up being a highlight!

Day Three in Downtown Chicago

For the third day, we headed downtown, but not before enjoying another mouth-watering bagel sandwich at Chicago Bagel Authority. We started off with a boat tour on the Chicago River hosted by the Chicago Architecture Foundation. We learned a lot of interesting information about the history of the city, as well as the future of its skyline. I would definitely recommend taking the tour.

After we disembarked, we headed over to Eataly. It’s a dream world of everything Italian. You could really spend a day there. We shared some bruchetta, the most amazing cannolli ever, and a refreshing Italian lemon granita.

We had to make a stop by The Bean, or the Cloud Gate, and followed it up with a little window shopping.

We headed back on the L and shopped the area around Armitage and Halsted streets, which boasts a plethora of trendy shops, such as The Tie Bar, Art Effect, and Warby Parker.

We spent our final night in Chicago close to our home base in Lincoln Park. Once again, I couldn’t resist the greystones and beautiful homes along the streets. We headed to Willow Room for a meal, and it did not disappoint. We started off with cocktails, and shared a few plates. We dined al fresco, and enjoyed the cooler weather that finally graced Chicago after a heat wave.

We flew out the next day with memories of a wonderful little getaway to a big city.

Where have you traveled this summer? I’m always looking to add places to my list!