In case you don’t know, I was born and raised in the western suburbs of Chicago. Aside from college, I’d spent my whole life there until we moved to Northern VA in 2017. I spent most of that time in the suburbs, but also lived in the city from 2013 until getting married and moving in 2017.
I loved living in Chicago. I’m so, so glad that I took that step to try it out and had 4 great years in the city. From the endless options of places to eat and things to do, to being exposed to different types of people and ways of life, to the energy that reverberates in a city like that, it’s a wonderful place! I love how much walking I did and how accomplished I felt once I mastered the public transportation system and having our “spots” that we’d go to regularly. There’s just something about that city that stirs something inside of me. It will always be home and where I come from and I’m so proud of that!
With all of that in mind, I’ve had a few requests to share my must do/see/eat list with you! While it’s not a comprehensive list and is specific to things that I like to do/see/eat, I always think it’s helpful to share a little insight. There are a ton of resources out there for you to get things like, “the top 10 things to do in Chicago”, etc., but you can’t always hear from a real person who is sharing the things that they loved, you know? So, I’m doing that for you! One thing worth noting, I haven’t lived in the city since 2017, so there are probably more great restaurants and things that I don’t even know about it! Definitely do your own research before visiting and talk to other people, if you can. It’s always helpful to read up on what the majority of people would say to do or see or where to eat!
You must, MUST get Chicago-style pizza when in the city or surrounding suburbs. I’ll be mad at you if you’re in the 312 area code and don’t get it somewhere. You haven’t lived your life until you’ve tried the glory that is deep-dish pizza, just trust me. Mike and I agree that Lou Malnati’s is the best deep-dish pizza you can get your hands on, bar none. We regularly have it shipped to our home in VA, so that we can indulge in the deliciousness still. My mouth is watering just writing about it. We always get just the cheese deep-dish and split their house salad. It’s such a good combo!
Another great pizza place, and my second choice, is Giordano’s. It’s more of a bready pizza and has more cheese (which is so good). My sister prefers Giordano’s to Lou’s, but you really can’t go wrong with either…it’s just a matter of taste preference. You can also get this shipped to your home!
If you ask me, I’d say to not even waste your time on any of the other deep-dish pizza joints. If you’re there for an extended amount of time or don’t want deep-dish (for whatever crazy reason), Jimmy’s Pizza Cafe on Lincoln has great NY-style pizza. My roommate and I used to order a large pizza and do some serious damage on it – it’s so easy to eat!
Other places I’d tell a first-timer to go to:
Portillo’s – another Chicago MUST. Truly. Their Chicago-style hot dogs, Italian beef (I don’t order it, but they’re known for it, so you know it’s good), cheese fries, root beer, and chocolate cake shake would be my recommendations. However, you really can’t go wrong with any of it.
Ann Sather – the best breakfast you’ll have. I miss it on a weekly basis. They have standard breakfast options, but the best part is that you get a side of 2 delicious cinnamon rolls as one of your two sides with your entree. It’s so much food, but it’s so good.
Las Fuentes – my favorite Mexican place in the city. My roommate introduced me to it years ago and it became a staple in our restaurant rotation. I always get the chicken flautas, which are delicious! Their margaritas are some of the best I’ve had and they’ll put you under the table, haha! If you’re there when the weather is nice, sit out on the patio for the best atmosphere.
Margie’s – an old-school ice cream parlor vibe with great treats and flavors. There was one a couple blocks from my last apartment, so Mike and I would regularly walk over for a banana split to share.
Nuts on Clark – A classic Chicago staple. I prefer this big time to Garrett’s popcorn – I just think it tastes better! The cheese and caramel mix, also known as the Chicago Mix, is what you have to order, if you pop in.
Fork – One of our favorite date night spots in Lincoln Square. I always had a delicious meal and liked that it felt a little fancier than our other regular spots.
3 Arts Cafe (inside Restoration Hardware) – such a cool spot with great food options! One of my favorite places to meet up with a girlfriend for lunch or dinner.
There’s no shortage of options and types of cuisines, so you can also search for something specific that you have a taste for. There are a lot of great options in the West Loop area, too! You can find all different coffee shops and donut spots, too. What can I say? We know how to eat good in Chicago.
Grab a drink at the Signature Lounge – we did this a few times during our time in the city! On a clear day/night, you get an amazing view of the city and surrounding area. It’s definitely a popular tourist thing to do, so may be really crowded, depending on when you go.
Grab a drink at Cindy’s Rooftop – we recently stayed at the Chicago Athletic Association Hotel, which holds Cindy’s Rooftop Bar, so we popped out onto the terrace to take in the view. It’s stunning! It was cold and wintry when we were there, but still worth taking in the sights and spending some time up there.
Walk along the lakefront path – if you’re there when the weather is nice, take a stroll along the lakefront path. It’s a cool way to see the lake, as well as the juxtaposition of a big city right on the edge of the water.
Visit the museums – we have great museums that are worth your time! My personal favorites are the Museum of Science & Industry and the Shedd Aquarium, but you’ve got options to choose from.
Walk through Lincoln Park Zoo – when the weather would turn nice, we would regularly walk along the lakefront, down to the zoo, and then ride the el back to my apartment. It’s free to the public, so you can just pass through or spend some time inside!
Go to a Cubs game – If you can swing it and your timing works out right, get tickets to a Cubs game. Even if you’re not that into baseball or sports, Wrigley is an institution and something cool to experience! Plus, they’ve just revamped the entire surrounding area, so there’s plenty to do nearby.
Take an Architecture Boat Tour – We did one of these in my third year of living in the city and loved it! It’s a great way to see the city from a different perspective, cruise along the Chicago River, and learn about some of the history and buildings.
See a show – There are plenty of theaters and options to choose from! Second City is also a popular place for people to take in some entertainment.
Shopping – There’s no shortage of shopping destinations in the city, if you’re looking to do some of that. My favorite places were along Michigan Ave, the Southport Corridor, and North & Clybourn.
A Couple of Tips
I highly recommend utilizing the public transportation system around the city. It’s a great way to get around, save some money on Uber’s, and really get that feeling like you’re in the city. You can use Google Maps to map your route using public transit, so you don’t have to do much work to figure out your route. I utilized both the buses and the el system daily while living there.
If traveling in the winter or colder months, pack layers. It gets cold. Like, really cold. We were just there at the end of November and, while the temperature read in the high 30’s, when you add any dampness in the air and the wind, it felt like it was in the teens. Bring shoes that you can walk in and a coat that will resist the wind.
If you know which direction the lake is, you’re not lost. Just remember, Lake Michigan is to the east of the city. If you know where it is in relation to you are, you can figure out which way you need to do.
It’s a friendly city, for the most part. There will certainly be some folks that are on a mission and just want to get to where they’re going, but most people will be willing to answer your question or give you directions. Just ask!