Hometown Series: Chicago, Illinois


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!

3.) Mahalo

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!

Author Biography:

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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  1. Chicago is such a great city! I lived there for 6 months and it was the best experience of my life. Plus, the food is incredible. Oh so incredible. I need to go back sometime soon.

    1. I love Chicago so much, it’s so beautiful and I’m so glad I went. I am glad you had the best experience of your life there. My guest blogger did a wonderful job outlining her city. You can definitely tell she is super proud of it.

  2. Thank you so much for showing us “You Chicago”. You are so lucky to have been growing up just 40minutes away. These places are so beautiful and worth visiting. It’s not only touristy spots but so much more, especially the Wrigley Field. I spent a week in Chicago and totally loved it. Love the skyline and the general atmosphare! Would love to visit the German Christmas Market, too!

    1. My guest blogger did a wonderful job, makes me want to go back. Everything about Chicago was amazing. Thank you for your wonderful and incredible feedback.

  3. I love Chicago! You showed off your hometown so well. Makes me want to visit again soon!

    1. Thank you, my guest blogger did a wonderful job. Definitely made me want to go back ASAP! Thank you for your wonderful feedback, I definitely appreciate it.

  4. Great post, Lauren! I have always wanted to visit Chicago, but it has never really worked out. I love the idea of a roof top bar though! Especially in the cold midwest winter! Thanks again!

    1. I hope you get to go to Chicago one day. Midwest winters are definitely very cold. Thank you for the wonderful feedback!

  5. We’ve been to Chicago but experienced most of the “tourist spots” while we were there. I loved some of your ideas for less crowded but must-do restaurants and parks. I definitely want to visit the Christkindle Market one holiday season!

    1. I thought the market sounded neat as well! My guest blogger did a great job, thank you so much for the wonderful feedback! I really appreciate it.

  6. Awesome! I’ve never been to Chicago, but I’ll keep this post in mind when I do go. It’s always great to hear advice from people who live near tourist destinations because I like to avoid the crowds and overpriced food if possible.

    1. Thank you so much for your feedback, I really appreciate it. I definitely second the getting advice from people who live there to avoid the touristy places if you don’t like the crowds. My guest blogger did great outlining her hometown!

  7. Very detailed list! I’ve been to Chicago and done the architecture boat tour, that’s a cool experience, especially on a sunny summer day.


    1. Thank you so much! I really appreciate your feedback and your thoughts. I definitely want to do one of those boat tours the next time I go back. My guest blogger and you have sold me on going on one.

  8. I really want to visit Chicago in the summer time! I have heard so many awesome things! And i really want to see Grant park and the Navy Pier! Thank you so much for sharing!

    1. Chicago is truly beautiful, I hope you get to go sometime! Grant Park and the Navy Pier are so neat! I definitely think my guest blogger did a wonderful job outlining her city! Thank you so much for your great feedback, I really appreciate it.

  9. Its great that you love your city. I’ve never been to Chicago– its on my bucket list– for a future SUMMER visit. lol

    1. I love the passion and love from my guest blogger of her city! I love Chicago as well, it’s an amazing city! I hope you get to go sometime. Fall is pretty and nice as well (that’s when I went). Thank you for your great feedback!

  10. Everything looks amazing! Hope to visit the city soon!

    1. Thank you very much. Chicago is a wonderful city, I just recently went there and fell in love with it. I hope you get to go sometime!

  11. I make sure to save your post. I have a conference in Chicago in July, It will be helpful to find places to visit when I will be there.

    1. That is amazing, I hope you have a wonderful time. Chicago is a beautiful city, definitely tons to explore and see. Thank you for your feedback!

  12. I’d love to check out Chicago. I have a friend who also calls it her hometown and she is constantly trying to get me to visit. Looks like I may have to. 🙂 Thanks for the tips.

    1. Chicago is beautiful! I definitely love it as well as my guest blogger. I hope you do get to go sometime, it’s definitely worth it. You are welcome. Thank you for the great feedback!

  13. Chicago is on my list of cities I want to visit and I was hoping to be in the marathon in 2018 but didnt get a place. One day I will reach the windy city. Loving the post and giving me a few tips on what to do when I eventually get there.

    1. I hope you get to go sometime! It’s truly a wonderful city, I loved every minute I was there. My guest blogger did a wonderful job. Thank you for the wonderful feedback.

  14. This is amazing article . It creates a positive & optimistic attitude…Thanks for sharing

    1. Thank you for the wonderful feedback. I love the love my guest blogger has for her hometown, it truly stands out!

  15. I have not visited Chicago but I have flown through it. I had a layover there and it was one of the most beautiful sights to see from the air. I’m hoping to actually visit on day so that I can see some of the places you’ve mentioned here.

    1. Chicago truly is an amazing city, I hope you get to go one day! Thank you for the wonderful feedback, my guest blogger and I really appreciate it.

  16. Chicago is a city I definitely want to visit. I have some relatives there, but haven’t been myself yet. I would have to go in the summer, though. I can’t handle the cold weather!

    1. Chicago definitely is a great city, I hope you get to go there one day! Fall is great for visiting as well, I just went to Chicago this fall and it was amazing. Thank you for the great feedback!

  17. I have only been to Chicago once but want to go back to do some sight seeing. I was on a working trip the one time I went. I will save this post so when I do go back, I’ll know where to go and have a list of things to do.

    1. I hope you get to go back and do some sightseeing. There is definitely plenty to do and see. I love the city and all it has to offer. Thank you for the great feedback. So thankful my guest blogger did such a wonderful job sharing her love for this city!

  18. I had never thought of going to Chicago. Big cities freak me out. Thanks for making it not as scary. Now there are a few things I could look into.

    1. I definitely understand how big cities can freak you out. I get very overwhelmed by them. If you have an idea of what you would like to do and just go those places that definitely helps me out. I hope you do go someday, it’s definitely worth it to go. Thank you for your great feedback and sharing!

  19. Was not aware that many of these places existed. Pinning for later reference.

    1. There are a ton of places to see in Chicago! I recently also did a Chicago city guide you can check out as well. I hope you get to go someday and check them out. Thank you for the great feedback.

  20. I should have known this was your post Lo I loved it and I LOOOOVE Chicago as I am always posting about it. I am totally going to try the dinner cruise and the rooftop bar AND the Hawaiian themed restaurant. They sound amazing!

    1. She sure does love her city and I love her love for it! I love Chicago as well, it’s an amazing city! She did such a wonderful job suggesting places I didn’t even find! Thank you for the great feedback!

  21. It’s good to see a positive account of the city. I’ve had some not so fun associations with it.

    1. Oh I’m sorry about that. Chicago is definitely a beautiful city, I hope you have been associations with it the next time you go back (if you do).

  22. What a great list for anyone who wants to visit Chicago. The way you’ve described it, Chicago sounds like a great place to be at!

    1. Chicago definitely is a wonderful city, I love everything about it minus the traffic. Thank you for your great feedback, my guest blogger definitely loves her city!

  23. Chicago always sounds like a great city to visit just to go on a restaurant crawl.

    1. There are so many wonderful restaurants to eat at there, it’s hard to pick.

  24. I’ve only driven through Chicago once. Even though I only drove though, I instantly fell in love with the beautiful skyline. Next time I go I’d love to check out Cindy’s Rooftop!

    1. The skyline in Chicago is breathtakingly beautiful! I loved every minute of being in Chicago when I went. Thank you so much for your great feedback! I hope you get to go there sometime and explore it.

  25. I visited Chicago once and had a great time! The roof top restaurant looks really nice, I’ll have to give it a try next time I’m there!

    1. I love Chicago as well! The roof top restaurant does look neat! Thank you for the great feedback, my guest blogger did a great job suggesting places that are a little less touristy!

  26. I didn’t know Chicago had a Christmas market! I need to make a trip there next year for the holidays now. I adore mulled wine. Also, that Cindy’s Rooftop looks like an absolute dream!

    1. My guest blogger definitely made me want to go to Chicago for the holidays! It sounds so pretty and cool! I definitely agree about the roof top!

  27. I’ve only been to Chicago once. If I ever make it back I’ll have to check out these spots!

    1. Same here, my guest blogger definitely made me want to go back. Thank you for your comment, I really appreciate it!

  28. Chicago is on my list of US cities to visit! I will have to check out some of these spots when I do 🙂

    1. Chicago is so beautiful! I hope you get to go one day, my guest blogger made me want to go back and I just went in September!

  29. I’ve never we been to Chicago and lived in the USA for 17 years! Thank you for sharing these gems because you created an itinerary for me!

    Aïchatou Bella


    1. I had never been until Labor Day of last year and I’ve lived here all my life and only 8 hours away from it. So I definitely understand, I hope you make it there one day. This city truly is one of a kind. My guest blogger definitely did a wonderful job sharing her lovely city, made me want to go back.

  30. I’ve never been to Chicago, it definitely has several interesting spots! I only know what is shown in movies, lol.

    1. That’s all I knew before I went there haha. It’s definitely a wonderful city, I hope you make it there one day. Thank you for your amazing feedback, I really appreciate it.

  31. beautiful pictures…have never been to Chicago but Cindy’s rooftop looks like a beautiful place to enjoy a lunch with friends!

    1. Thank you for your great feedback! Chicago is a wonderful city, I definitely love how my guest blogger showed places that were less touristy. I hope you get to go one day.

  32. I’m partial to DC and SLC but this post for sure has me ready to visit! The rooftop!?? YES please give me all the food and a view. I haven’t been to Chicago in years. It’s back on my list.

    1. I hope you get to Chicago one day, it’s an amazing city! My guest blogger did a great job making people want to go, I definitely want to go back after publishing her work!

  33. I have always wanted to visit Chicago as it looks so beautiful. This makes me want to go even more.

    1. I hope you get to go one day, it truly is a beautiful city! My guest blogger definitely made me want to go back. Thank you for your comment!

  34. Lolapalooza sounds like such a great event. Didn’t know it was based in Chicago. The rooftop place sounds really nice.

    1. I’ve always heard great things about Lolapalooza. My guest blogger definitely came up with great things to do and see in Chicago. Thank you for your great feedback!

  35. We live about 6 hours from Chicago and go there often – we love it! I’ve been to most of the places you mentioned and really like them all. The Chicago marathon is still one of my favorites to run in!

    1. That’s so neat you live about 6 hours from it. I’ve been there once and would love to go back. I used to live 8 and never went. I’m going to have to do the Chicago marathon, you both have sold me on it. Thank you so much for your great feedback, I really appreciate it.

  36. This was a great read! I travel to Chicago often, but there were several places I’ve never been to try out on our next trip. Thanks for sharing.

    1. That’s so neat that you go to Chicago often! I’m glad my guest blogger mentioned some places you have never been. It’s always neat to find new places. Thank you for your wonderful feedback, I really appreciate it.

  37. Ah I want to visit Chicago! It looks like a blast!

    1. I hope you do get to visit one day, it really is a neat place to go.

  38. Chicago is one of my favorite cities and it looks like you had a blast visiting!! I hope to make it back there soon too 🙂

    1. My guest blogger actually lives there, as why it is called the hometown series. But she definitely loves it, I know I do as well. I hope you make it back there as well, thank you for your comment.

  39. Chicago has so much to offer. When we were there we had a great time
    come see us at http://shopannies.blogspot.com

    1. It definitely does, thank you for your comment.

  40. Chicago is the best I absolutely love that city. But too cold to live there full-time!

    1. I definitely agree with everything you said. Plus they get the lake/water effect and I could not deal with that. Thank you for your comment, I really appreciate it.

  41. I was just in Chicago for New Year’s! I could have used this post. I was visiting a close friend who recently moved there. I am taking this list next time!

    1. That’s amazing! I hope you had a wonderful time in Chicago for New Years! I am glad you found this list helpful. Thank you for your comment, I really appreciate it.

  42. You have a talent for promoting Chicago girl. I have never been there but will sure love to now 🙂

    1. She definitely does, she truly loves her city and it definitely shows! Thank you so much for your feedback, I really appreciate it. Chicago truly is a wonderful city so I hope you get to go sometime.

  43. Hometowns are special, aren’t they. And sometimes people don’t explore them as much as they should. Chicago looks great from your eyes. I would love to do the river cruise.

    1. They really are, my guest bloggers love for Chicago really shines through. Chicago is a wonderful city, I definitely enjoyed it. The river cruise does look amazing, my guest blogger definitely made me want to go back and do that. Thank you for your wonderful comment, I really appreciate it!

  44. Chicago is my all time second favorite US city. And I love the marathon. It’s one of my favorites.

    1. I am going to have to do the Chicago marathon, so many people recommend it. What is your first favorite US city?

  45. I have heard a lot about Chicago and it seems all that they have said was true. Chicago is really a wonderful and lovely place.

    1. I truly loved Chicago when I went. My guest blogger definitely made me want to go back. Thank you for your comment.

  46. I grew up in the Chicago burbs and as a kid spent many weekends in the city. Great city for sure. I haven’t been back in years, but if I do I am definitely going to check out Cindy’s Rooftop and Mahalo – love a rooftop bar!

    1. That’s awesome that you grew up there. I loved the city when I went for a visit, I would love to go back and try the rooftop bar you both speak of! Thank you for your comment, I really appreciate it!

  47. My husband and I took our girsl to Chicago many times in the past but we grew tired of doing the same thing every time. Its now been probably 10 or more years since I’ve been there. You’ve given me some new things to consider when visiting next time. Thanks! You really know the city well.

    1. I can definitely understand growing tired of doing the same thing over and over again. I am glad my guest blogger gave you a new set of things to consider, she definitely loves her city. Thank you for your wonderful comment, I really appreciate it!

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