ULTIMATE TRAVEL GUIDE TO CHICAGO

5 Tips To Do Chicago Right

Travel is something that is extremely important in our lives. I love visiting new places, experiencing new things and the adventure of living locally in a new place. Since having kids Michael and I have strived to take our boys with us to as many places as we can. What continues to stay true with our travel together is we are always looking for ways to experience the local culture, not the tourist culture. Because there is a major difference. Neither of those aspects are bad, Michael and I simply love the feeling and vibe of really connecting with the local areas we are visiting. With these experiences we’ve found we can show our boys so much more of what the place has to offer and the culture it embodies.

We truly believe you can’t buy culture. Culture is gained through travel, trying new food and cuisines, walking the pavement and experiencing the ways others live life. To help with this I’ve put together a short list of things to do prior to taking your next adventure, gaining culture and experiencing the ways other live their lives everyday!

Location

Clearly, the first thing you need to do is decide where you want to travel to. Do you want the vibe of a big city? Are you looking to relax on the beach? Or is it just a weekend getaway where you want to do something different? 

For us, our last trip was back to Chicago, a place we feel fortunate enough to have called home for a decade. The city has so much to offer during the winter time that we want to make sure our boys are building core memories (thank you Disney “Inside Out” of the reference ????) of winter here. We’ve got a full guide on how to do Chicago with kids in the winter here, just in case you missed it! Knowing we want to visit Chicago every winter means we really want our boys to experience the neighborhoods Chicago has to offer, as each neighborhood has it own unique vibe and feel. 

This time we decided on Lincoln Park. An area we actually never lived in, but have lots of fond memories from experiences at all the surrounding restaurants, cafes, night life, shopping, playgrounds and, of course, the zoo! 

Accommodations

When it comes to a place to stay, comfort is key for us. We are looking for a place that will feel like home, even while we travel and experience new things. With two little dudes by our side having ample space is essential. While we both love the amenities hotels have to ofter, they are lacking in the local vibe and space aspect (unless of course we snag a suite or penthouse…which has never happened). Vacation rentals have been our way of life for quite sometime. The whole living local scene truly speaks to our family. We’ve been renting from Sonder for a while now and absolutely love how they’ve combined the luxury of hotel stay with the vibe of a vacation rental all into one!

For our stay in Chicago last weekend we stayed here and absolutely loved everything about it! What first sold me on the place was there were three bedrooms. Knowing that Ziggy is still and napper and Enzo does every once in a while we love the convenience of having a quiet place for them to regroup for the day.

The kitchen space in this place was pretty AMAZING, although I didn’t do much cooking this time around, I did enjoy dreaming about using this space and it was perfect for delivery! Gotta love the city and all the food options…don’t worry I’ll chat more about that next ????. There is laundry in the unit and yes we used it! You know, kids do that to you! Free-wifi, of course, and a cozy living space with not one but two outdoor areas. Yep, these spaces didn’t get much use as it snowed while we were in town but I could totally see how happy they’d make me in late spring, all of summer and early fall! I love that the living space has three sofas, perfect for everyone to gather in during our early morning hours for coffee and late nights with wine & bourbon ☕️???????? with some friends we don’t get too see often enough.

One last thing about our place we stayed in before we move on to food???? Let’s talk about the bathroom. Literally our bathroom had a shower room! I WANT! Maybe this will need to be the next space we renovate. ???? The boys were obsessing over all the shower heads. AND I love how the water stayed inside the shower, for once. 

Where To Eat

One thing I LOVE about Chicago is all the food options. I literally have a list about two miles long of all the places I want to eat at when we get into town and that doesn’t even include the new places opening up every week! So clearly there are lots of options to choose from and you’re bound to find a place that works for everyone in your group. What’s perfect about staying in the city is you can dine in or out at most places and you guys most deliver too! This trip we did both and I love that about our Sonder stay. On Friday night there was no way the boys were going to sit through dinner at a restaurant so we had dinner delivered right to us! The boys opted for some sushi paired with homemade macaroni and cheese, so I guess I did use the kitchen to make that. 

Since we stayed in Lincoln Park I am going to stick to that neighborhood and give you a few options we love. If I’m missing some please let me know, as this girl is always looking to add to my dining experience. I went ahead and broke them down by meals!

Brunch

Toast

Nookies

Yolk

Lunch

Frances’ Deli

Athenian Room

Fiesta Mexicana

Dinner

Cafe Ba-Ba-Reeba!

Sushi Mon

Pequods Pizza

Sweet treats

Sweet Mandy B’s

Stan’s Dounts and coffee

What To Do

I love doing my research before any trip. But honestly my favorite way to find out what to do once we get to a new place is have conversations with locals. The easiest way to do this is through conversations when dining out. I love finding out what people who live in the neighborhood are doing. Coffee shops often have boards with fliers posted all over them with local events too. If you’re traveling with kids, local parks is where it’s at. I love watching my kids play in new places with new friends. Plus we’ve found some of our favorite things to do in new places from talking with other parents.

Embrace Life 

As much as I like to plan things out I know life just doesn’t always work that way, especially when traveling with little ones. My best advice to you is go with the flow. It’s ok if things don’t go just as you planned. Embrace the fact that you are able to travel, live in the moment and enjoy all the little things that come with travel. 

And finally, one last amazing thing about Chicago. It is a city of neighborhoods. While we stayed in Lincoln Park, we ventured out 5 minutes and were in Lakeview for dinner, and 10 minutes for Brunch in Andersonville. Or 15 minutes for some shopping downtown. There are so many pockets of amazing experiences, you just have to turn the corner and look around. 

I’d love to hear more about how you travel. What are your favorite spots? We are always looking to grow our list!

enjoy

much love,

Danielle

xoxo

Thank you to Sonder for sponsoring this post.