I am biased when I say Chicago is the best city in the country. My love for the skyline, the smells, and the sights will never change. I have been thankful to grow up 45 minutes away just over the border in Indiana where Chicago was a place where I frequently visited. Baseball games, sightseeing, Navy Pier, Christmas Lights and all the other tourist spots were frequently visited by my family.Many of you who have not visited Chicago have heard of the “Bean”, Navy Pier, The Sears (Willis) Tower, and John Hancock building. You can easily see these sights when you look at pictures of Chicago or look at any tourist website.
I want to show you want “My Chicago” is like. I have put together a few of the spots you MUST check out when you come and visit (especially if you don’t want to be bombarded with tourists and if waiting for deep dish pizza for over an hour isn’t your thing!)
1.) Cindy’s Rooftop
Located right on Michigan Avenue (The Magnificent Mile) is a rooftop restaurant and bar that has THEE best view on the whole street. It is open year round despite being a rooftop bar, because most of the restaurant is mostly inside. There are a few tables, a group table and an outside bar but the balcony is meant to be more of a hangout spot where you can enjoy some of their top shelf cocktails (Howl at the Jun is my FAVORITE!) and enjoy the spectacular view of Millennium Park, the Bean, and Lake Michigan. It is an unobstructed view of the Lake where you can see the sailboats and even a glimpse of some of the skyline and Navy Pier. It is beautiful year round, as the view can be seen through glass windows and even step out onto the balcony to get a glimpse of the amazing views despite being cold outside. It is worth it! Cindy’s is on the expensive side but again, worth it if you want to dine at a place where the view is spectacular. It is also VERY popular, where this usually isn’t a place where you can simply drop by and get a table. I booked brunch reservations TWO months in advance, so if you want to check it out, book way ahead of time! If you want to simply grab a drink, the afternoon during weekdays is the slowest time and you can possibly grab a seat by the bar, or you can hang out on the balcony in the sunshine!
2.) Grant Park
Unless there is something going on (which normally there is in the summer time!) you might mistake Grant Park as a giant open grassy field. This area surrounds Buckingham Fountain and is in the heart of the city. There are tennis courts, some open baseball fields (slow pitch softball played in the summers) and a few open-air stages sit year round. It is in between Lake Shore Drive and Columbus and it is the heart of many of my favorite events. Lollapalooza is hosted here every year in the middle of the summer, many of the most popular races are started and finished here, and so many festivals are hosted here. What is amazing about Grant Park is that while it is in the heart of the city, you are right in the middle of enjoying the entire skyline and you are right next to Lake Michigan. It is one of the best areas to be in the middle of a summer night where you are enjoying the sights of the beautiful skyline.
One of my favorite events I have attended at Grant Park is Lollapalooza. In case you don’t know, this is a world renown music festival that has all sorts of acts from all different genres. At one stage you have Paul McCartney playing and on the other side of the park you have The Weekend performing. I must say, if you don’t like crowds, you might not like the idea of this festival especially during the bigger acts. But unlike some other fests, Lollapalooza is set up so spread out where there are tons of things to do at any given moment. There are 6 stages (even a kid playground and stage!), so many bathrooms, food stands, drink stands where you are barely ever waiting in line (with the exception of maybe bathrooms later on in the day). By the end of the day, your feet are hurting and you are tired especially if it is hot out (concert is usually at the end of July!) but it is WORTH IT! One of my favorite memories is seeing big name acts on a stage where you have the skyline directly behind it at night. All of the lights, the warm summer breeze off the lake, there is NOTHING like it!
A few other things that I love about Grant Park is the host to my favorite running races. The Shamrock Shuffle happens at the end of every March and is my all-time favorite race. It is known as the “official” start to the Chicago running season and it is an 8k (five mile race) and you are greeted with a medal no matter what and a beer included with your race entry! Can’t say no to the beer!
I also participated in a 5k Cancer Run this summer for Northwestern Memorial Hospital. This is where I received my cancer treatments and it is ranked as one of the most prestigious hospitals in the United States. There was a little fest to celebrate cancer survivors right in the middle of Grant Park.
Grant Park also hosted Wanderlust fest this spring. It was the perfect day – 75 degrees in May and it was a “Triathlon of sorts” where you participated in a 5k, followed by an hour of yoga and then an hour of meditation with a bunch of food, free samples and other activities to participate in. Doing yoga in the middle of Grant Park and all those views? YES PLEASE!
One of my favorite restaurants in Chicago. Mahalo is located in the Wicker Park neighborhood. Hawaii has a soft spot in my heart where I have always wanted to go and was able to finally go with my husband on our honeymoon. For our first Valentine’s day as a married couple, we went here for dinner. You walk in and everything is bright and colorful and despite going there possibly in the winter time, you forget it is cold outside. Lights hanging everywhere, and white walls light up this place. It has a laid-back vibe and serves Asian – Hawaiian food. The food we had was awesome, and the drinks are also delicious. This place also is a great spot for the summer as it has a rooftop bar!
4.) RPM Italian
Have you heard of Giuliana and Bill Rancic? They own this place – along with the RPM Italian in Washington DC and RPM Steak that is also in Chicago. This place is almost impossible to get last minute reservations to as well, but again if you plan to go to Chicago this is something to plan out as well. This is an upscale restaurant, but the money is worth it. I have had my sights set on this place for a long time and I was able to do this for my 30th birthday where my husband organized a group dinner where I was able to do a custom menu! They were MORE than accommodating and had bottles of wine waiting for us at the table. We NEVER had to ask for refills, more wine or anything. My experience was amazing and the birthday dessert they brought over was also delicious. I highly recommend this place as it was amazing, and I can’t wait to go back!
5.) Wrigley Field
Alright, this might be a tourist spot, but I am a huge Cubs fan and I couldn’t resist not listing this magical place. The history is amazing, and the feel is awesome to be in such a historic spot. Over the last several years, there has been many changes to the park where they have restored and done construction to make the field bigger, and have more events at the park. The city has also recently introduced “The Park at Wrigley” where there is an adjoining park right next to the field (use to be on sight parking for games) where there are outside bars, a Starbucks, a restaurant/bar with patio seating, jewelry store, brewery, and an exclusive official Chicago Cubs store. The park is only open to those during home day games to enjoy the game but on away games, you can come and watch the games outside on the big screen outside! For me, the Chicago Cubs are my favorite team and every year on my birthday I go to a game. It can be expensive no matter how well they are doing, but now since they have WON THE WORLD SERIES FINALLY in 2016, game prices have increased. Very rarely can you purchase tickets right before the game, but you will have better luck during the week. Every game is nearly sold out, and plan on paying between $30-$60 on a basic ticket. (If you have a family, I suggest staying AWAY from the bleachers!)
Wrigley Field isn’t only the home for baseball games, but also the home to many big concerts in the summer. It is outside, and again you have gorgeous views behind the stadium. I have seen Billy Joel here four times now, four years in a row. He does a baseball stadium tour every year and comes to Wrigley Field each year. There are concerts all summer long at Wrigley Field!
Back to the Park at Wrigley for a second. In the summer time, the park had Farmer’s Markets, run groups, yoga outside, and outdoor summer movies to watch on that big screen I mentioned about! For their first winter this year, they turned the outside park into an outdoor ice skating rink along with an outdoor Christmas Market (I can’t wait to go!) All of the restaurants and stores are open year-round right outside of Wrigley Field too. Every year the Cubs host a 5k race on a Saturday morning at the beginning of Spring where you can run inside the park! It is such a cool feeling to run throughout the streets of Wrigleyville and into the stadium just before the finish line. The race also benefits Cubs charities!
6.) Odyssey Cruises at Navy Pier
So have you been to Navy Pier? If so, did you notice those huge ships outside floating by the dock? These are lunch and dinner cruises! Depending on what night you go, you can watch a “Firework” night at Navy Pier. With the beautiful night sky and the skyline featured with fireworks, it is gorgeous! My husband and I decided to do a dinner cruise this summer for our first wedding anniversary. It was the perfect day and evening. It was at the end of July and it was a warm sunny day. Now I do have a little bit of motion sickness, but this is a huge boat and nothing a little Dramamine can fix! Since it was our anniversary, we were greeted to a table with rose petals and a card that said Happy Anniversary. Everyone who boards the ship is greeted with a glass of champagne (this is kid friendly also by the way!) and you can order as soon as you sit down. Everyone eats at different times, but our salads were brought out right away for us to enjoy. We both had salmon entrees and then were treated to a dessert bar. There are three levels to the ship with a top deck to enjoy the entire skyline. There is a bar and a dance floor on every level with a DJ to host some dancing (slow and fast!). It was an amazing experience because I had never been out on that part of the lake before and to see the skyline from a different angle with a sun setting behind it was something I will not easily forget!
7.) Christkindle Market
A real Chicago Christmas treat – Christkindle Market in the middle of downtown. This is a German Christmas market where there are little wooden houses set up for a month before Christmas that host little shops, German food, beer and wine. It is mostly outside (with the exception of some walk-through trailers and a concession stand house that hosts only fifty people) so if you go and it is cold, dress warm! Most times, there are big crowds and it is not easy to get through. If you plan on eating food, plan on eating either at a table you can stand by or wait for a table inside the concession stand hall. It is tradition every year that my husband and I go to this market with our best friends and purchase an ornament (a tradition we have done every year since we started dating). There is warm mulled wine which is perfect for a warm up on cold days when visiting! They also give out cute little boot mugs; this holds either your mulled wine or your hot chocolate! A cute little souvenir!
Those are a few of my favorite things! There is no shortage of things to do in Chicago on any given day! There are wine fests, beer fests, BACON fests, cheese fests, etc. I mean, you name it, there is a fest for that! There is no shortage of rooftop bars (my favorite) where you can experience all the great views of the city. There are concerts and broadway musicals and unlimited shopping. So many great restaurants all around you and a lot of great neighborhoods to check out! The city is incredible that you can participate in yoga on the Skydeck at the Sears Tower or at the John Hancock 360* deck and then have a fancy dinner down the street at RPM Italian. At night you can enjoy a drink at a beautiful rooftop and do it all again the next day. I love my city and while it might be known for a lot of violence these days, the city is still to be enjoyed and there are millions of people who enjoy it every day. My husband and I are making the move to live permanently in Chicago and there is nowhere I would rather be!
Next time in Chicago, try these out and I can’t wait for you to experience them!
My name is Lauren and I live in Chicago. I am married and have a furbaby named Belle. I have a newly developed travel bug, and I am always up for doing something new; trying new foods or drinks of course is top of my list. Fitness and yoga are also important things in my life and being healthy as become a forefront (while taming my obsession with chicken wings).
I am a blogger myself for Laughalways.net. It is a blog I created in hopes of inspiring and helping people live their best life despite their difficult journeys. I founded Laugh Always when I was fighting my own cancer battle and am developing Laugh Always as a way of life to get through life – you need to laugh through your troubles!
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