Chicago, Illinois

I was fortunate enough to live in Chicago for a few years, and this place will always hold a very special place in my heart. It was the first time I moved out of my native town in San Diego and really embraced learning the ins and outs of a new city. Fun fact – I also got engaged down at the Chicago Riverwalk! (Shout out to Dave). Chicago is overwhelming in the sense that there is SO much to do – even living there for a while I still don’t feel as if I’ve experienced even half of what the city has to offer. But this is just my personal experience of what I did, ate and enjoyed while I was there.

Things To Do

Gosh, where do you even begin. There is so much to do whether you’re downtown or up north in the suburbs, but I’ll just stick to a few for now. I am not a local so I am not claiming to be an expert by any means, these are just a few of my personal favorite things I did and experienced while I was there.

  1. Catch a Cubs game at Wrigley Field

Obvious, but I had to list it. Wrigley Field is incredibly rich with history that any baseball fan would appreciate. Even if you’re not a huge Cubbies fan, Wrigleyville is flooded with restaurants and fun bars to head to before or after the game. We went to Country Club Bar a few times, right across the street from Wrigley Field. Country Club always had a fun atmosphere and is a great place to grab a beer even if you’re not attending a Cubs game.

  1. Shop on Michigan Avenue

You’ll learn that I will try to find the good shopping spots no matter what city I’m in. And Chicago’s Magnificent Mile does not disappoint when in the shopping department! Pretty much every shop, department store or boutique you could ever want is on this street – the options are endless. Besides shopping, there are also top hotels, steakhouses and bars on Michigan Avenue so there’s truly something for everyone.

3. Navy Pier

Navy Pier is located in the heart of Chicago directly on Lake Michigan, making the views no matter where you are on the pier just beautiful. It really doesn’t matter what you’re interested in, Navy Pier has a lot to offer. From rides and games, public art and cultural attractions to restaurants, events and shopping, anyone can find something they’d like here.

4. The Bean

This is probably one of Chicago’s most popular sights and what a lot of people think of when they think of the city. It’s located right in the heart of Millennium Park in the Loop. Hard to miss and there’s always people taking photos around it no matter what time of the year it is.

5. Go to a Bears game at Soldier Field

I spent a lot of time at Soldier Field and went to several Bears games when I lived here. The stadium is located near Downtown Chicago and is always filled with die-hard Bears fans and tailgaters no matter how cold it is outside or how early it is in the morning.

Soldier Field

6. Have a drink at The Signature Lounge at the top of Willis Tower

Talk about having a drink with a view! The Signature Lounge is located on the 96th floor in the Willis Tower right in the heart of Chicago on North Michigan Avenue. While you’re sipping on an Old Fashioned or a glass of wine you can enjoy unmatched 360 degree views of the entire city which is so fun and beautiful. A must-do when in Chicago!

7. Shedd Aquarium

A visit to Shedd Aquarium is a great idea whether you’re having a date day or want to have a fun family outing. Shedd has thousands of animals and multiple exhibits to explore, from Beluga whales and Sandbar sharks to Green Sea turtles and Magellanic penguins.

8. Catch a show at City Winery

This place is awesome. City Winery is not just a fully functioning winery, but also an intimate concert venue. Dave and I were fortunate enough to attend a concert here and it was incredible being so close to the artist while enjoying fantastic wine and unique foods at the same time.


The greater Chicago area has really amazing food, and although you could write novels about the food here and go on forever about all the different restaurants the city has to offer, I’m going to try to narrow it down to my top 10 personal favorites.

  1. The Silo | Lake Bluff

I could write an entire post about Silo. I will start off by saying it’s the best pizza in the country. Yeah, I said it. I know it’s a bold statement but it’s true, ok? Their pizza is SO GOOD. I’ll start off by saying Silo isn’t downtown, and it’s actually not technically in Chicago at all. It’s in Lake Bluff, the cutest town in the world that’s about 40 minutes north of downtown Chicago. If you are visiting Chicago or live there, I highly recommend taking the trip up north one afternoon just to eat here. (It’s an hour train ride from downtown Chicago to Lake Bluff – just do it, ok?)

Silo’s classic cheese pizza

Not only is the restaurant itself adorable (yet spacious!) everything here is just GOOD – from the food to the beer to the atmosphere. Our go-to order was the regular cheese pizza, buffalo chicken thin crust pizza and their house salad. Get the house salad with their blue cheese dressing – it’s homemade and has blue cheese crumbles in it. It is SO GOOD. Now I’m hungry.

2. The Lantern | Lake Forest

Another place in North Chicago that’s near and dear to my heart. Another place that’s near and dear to my heart. The Lantern is nestled downtown in the quaint, beautiful little town of Lake Forest, right next to Lake Bluff. Dave and I came here a lot, whether we just didn’t feel like cooking at home on a week night, or on a Sunday afternoon where they had $1.50 Miller Lites (the dream). The Lantern is decked out in Chicago sports memorabilia, from newspaper articles about the iconic 90’s Bulls team to Blackhawks Stanley Cup decorations; you’ll love the Chicago atmosphere The Lantern provides. Also the food is really good, too. My usual order was either their turkey burger with sweet potato fries or their Cobb salad. Aaaand I’m hungry again.

3. Three Dots & A Dash | River North

Talk about a cool spot. Three Dots and a Dash is an awesome underground tiki bar with killer drinks and an awesome all-around fun vibe. They’re known best for their rum cocktails and although you’re paying a lot one drink, they make them STRONG while tasting delicious at the same time. They also come in really cool, large tiki cups that make for a beautiful presentation.

4. Joe’s | Lincoln Park

Fans of country music and southern food will rejoice at Joe’s. Joe’s is famous in the country music world, as legendary performers from Eric Church and Miranda Lambert to Brad Paisley and Dierks Bentley have all had shows here. Even if you’re not going to see a show, Joe’s is a fun bar to grab a drink and a bite to eat as well.

5. Lake Bluff Brewing Co. | Lake Bluff

This is the cutest little brewery I ever did see. Lake Bluff Brewing Co is a small storefront right in the heart of downtown Lake Bluff. They usually have a decent amount of their locally crafted brews on tap and is just a fun spot to hang out and support a local establishment. No food is sold here, but they partner with another local restaurant close by so you can order from them and still eat in the brewery.

Lake Bluff Brewing Co. in downtown Lake Bluff, IL

6. Lou Malnati’s | Various Locations

Lou’s is famously known for their Chicago deep dish pizza. It is sooo good. Their slices are incredibly thick, their crust is flaky and buttery and there is no shortage of Wisconsin cheese on top, either. There’s over 50 locations in the greater Chicago area, from Evanston and Gold Coast to the West Loop and Lincoln Square.

7. Catch 35 | Downtown

What a cool spot! Catch 35 is a high-end seafood restaurant located near the Chicago Riverwalk on W. Wacker Drive. Their food is delicious, with a lot of high quality seafood dishes to choose from and a versatile wine list as well. Fun fact – Dave and I came to Catch 35 for dinner the night we got engaged! A perfect spot for special occasions.

8. Ditka’s Chicago | Oakbrook

I was so sad to hear of Ditka’s Gold Coast location closing! Add it to the ongoing list of “Things COVID-19 has ruined”. Luckily there is another location in Oakbrook. This place not only has a good selection of food, from fresh soups and salads to yummy pasta and seafood dishes. The drinks are good too! Ditka’s is obviously a tribute to “Da Coach”, with historic Chicago memorabilia inside as well.

Moscow mule & Irish coffee at Ditka’s Chicago

9. Tavern on Rush | Gold Coast

I had way to much fun at Tavern one night while one of my best friends was in town for a work trip… and I paid for it the next morning. But it was totally worth it! Tavern on Rush is a fun place, whether you’re looking for a fine dining dinner experience as a date night, or just want to go to have a few drinks with friends.

10. Old Crow Smokehouse | River North

Old Crow is so fun! The River North location has a country vibe with a killer cocktail menu and dozens of TVs so it’s a perfect place to catch a game, a drink and some lunch at that.

Ash & I at Old Crow | 2016

I know there’s so many other things to do and places to explore, but I’m thankful for my few years I got to live in Chicago! I plan on going back many times throughout my life and can’t wait to see what the city has in store for me on my next visit.

Hope you enjoyed reading!


U.S Cities

2 Comments Leave a comment

  1. I love Chicago-especially Lake Bluff! We were there in early December a few years ago, and the little town was all decorated for the holidays. It truly looked like a postcard! I hope one day I can go back to visit!

    Liked by 1 person

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