Chicago; a City By the Lake

We visited Chicago at the end of September this year with several friends. There were 16 of us total which was great because we did things as a group and were also able to split up into groups based on what each person wanted to do. Here are the places we went to that we’ll be sure to revisit as we recommend them to anyone planning a trip to Chicago!

LODGING IN CHICAGO

We stayed in an amazing Airbnb in the Ukrainian Village which was so perfectly located and we highly recommend it. It was safe, clean, and within walking distance to several bars and pubs. Here is a link to the exact apartment we stayed in and we rented both the first and third floors and absolutely loved the place. We plan to return to Chicago soon and are hoping to book the same Airbnb.

EXPLORING CHICAGO

We arrived to Chicago around 11:00 AM on a Friday morning. Because we had time to kill before our airbnb check-in, we decided to explore the Magnificent Mile, the downtown area popular for shopping. It had so many beautiful stores, hotels, and lots of food options. We passed by Downtown Dogs which was PACKED (and rightfully so — their dogs are amazing), so we ended up next door at Pippin’s Tavern which we were excited to learn offers food… FROM DOWNTOWN DOGS! The Chicago dog is amazing and is a must try! The drinks at Pippin’s Tavern were also great and reasonably priced.

On Saturday, we did a lot more exploring. We started out on a 10:30 AM river boat tour which is another must when visiting Chicago. We opted for the architecture tour and it did not disappoint! We booked through Chicago’s First Lady and highly recommend them. The tour lasted about 90 minutes and the boat sells drinks, cocktails, and snacks which made it even more enjoyable. The scenery was breathtaking.

We enjoyed amazing views from the 360 Observation Deck at the John Hancock Building. We also paid a little extra to do the Tilt Experience which was terrifying and so much fun at the same time. It’s a view we’ll never forget!

We were excited to try deep dish pizza while in Chicago. We tried both Lou Malnati’s and Giordano’s, which we agreed were very similar in taste. To be totally honest, we weren’t impressed with the deep dish concept and were more excited to find another Chicago Dog while we were there. In fact, the hotdog stand outside of The Bean’s entrance is great! The Bean was packed, obviously, but it was worth a visit. After the Bean, we strolled along the street it sits off of (Michigan Avenue) which was a lot of fun. We popped into (pun intended) Garrett Popcorn Shop for some Chicago style popcorn (the cheddar mixed with the caramel popcorn) which was 10/10. There are tons of places to buy Bears and Cubs gear on that strip as well as plenty of dining options.

CHICAGO OVERALL RATING

I guess we’re lucky because we end up visiting some of the best places in the world. Of all the cities we’ve been to, Chicago is one of our top ten and we are already planning a time to go back next year! We highly recommend it. Consider it a much smaller, less busy New York City.

Feel free to leave any questions you might have about Chicago in the comments below!