Chicago Travel Guide


I’m still getting accustomed to living in Florida. I moved down here from Chicago two years ago, and I occasionally still expect to open my front door and step foot into freezing cold temperatures instead of 80 degrees and sunshine. While I definitely don’t miss the negative 30 degree wind chill, I do miss a lot of things about living in the Windy City. Chicago is such a special place. There’s always something fun to do- plenty of restaurants to try, museums to experience, sporting events to attend, all while situated next to beautiful Lake Michigan. I think that’s my favorite thing about Chicago- the proximity to the lake and the abundance of public parks, outdoor space, and beaches that allow you to still connect with nature, breathe in some fresh air, and never feel like you’re trapped in a concrete jungle. I’ve rounded up some of my favorite places to check out if you’re ever in the Windy City, let me know if you’ve ever been to any or if there are any great spots I missed!

Let’s start with food (of course)

Chicago Staples:


Lou Malnati’s: this is everyone in my family’s all-time favorite Chicago pizza. Definitely get the deep dish and a Malnati’s Salad to share with the table.

Gino’s East

Giordano’s: my personal favorite Chicago pizza. I love the softer, doughier crust and flavorful sauce.


Grace Wynn Health Chicago Travel Guide

Chicago Pizza and Oven Grinder

Hot Dogs-

Portillo’s: the cheese fries here are also amazing, and so is the chocolate cake shake (a slice of their famous chocolate cake is mixed into a chocolate milkshake, so decadent and delicious). I love their chopped salad!

Quick Healthy spots:

Protein bar: yummy smoothies and bowls. They now offer cauliflower rice as a base which I love!

Naf Naf: Quick Mediterranean food. Amazing pita bread. I get the salad bowl with chicken shawarma and hummus.

LYFE kitchen

True Food Kitchen


Wildberry: amazing pancakes and omelets.

Yolk: huge portions and reasonable prices.

M Henry

Hampton Social: do it for the ‘gram. Home of the infamous “Rosé All Day” neon sign.

3 Arts Club Cafe: The atmosphere here is so beautiful. It’s located in Restoration Hardware.

Lula Cafe


Athenian Room

Cafe Ba Ba Reeba: fun tapas style eats. Great place to enjoy dinner with friends.

The Purple Pig


Girl & The Goat

Au Cheval: the best burgers in the city. Can get crazy busy so try to go during “off” hours or right when it opens!

Wildfire: I love the salmon, chopped salad, and seasonal berry crisp.

Clever Rabbit: great plant based options.

Smoque BBQ: the brisket is killer and so is the mac and cheese and peach cobbler.

Gibson’s Steakhouse: my favorite place to get steak in the city.

Bub City BBQ: the definition of comfort food.

Twin Anchors: hole in the wall bbq joint. Part of The Dark Knight was filmed here, and the ribs are out of this world good.


Sprinkles Cupcakes- my favorite flavors are strawberry, salted caramel, red velvet, banana, black & white, and the seasonal lemon blueberry (ok, basically all of them).

Beatrix: Get the “oh my caramel pie”.

Favorite Rooftop Bar:

Cindy’s: amazing panoramic view of the lake.

Things to do:

GWH Chicago Travel Guide

Millennium Park: Great place to ice skate in the winter, or go to an outdoor concert in the summer. Make sure to take an obligatory photo with the bean.

Maggie Daly Park: another fun spot to ice skate in the winter.

Lincoln Park Zoo: it’s completely free and a great place to spend the day walking around and learning about the animals.

Shedd Aquarium

Wrigley Field: Catch a baseball game in the summer. You can usually find bleacher tickets for a reasonable price.

Field Museum

The Art Institute

Walk down Michigan Avenue: so many fun places to window shop.

Grant Park: visit the Taste of Chicago in the summer and be sure to check out Buckingham fountain.

French Market: in Ogilve Transportation Center. Great place to walk around and explore the cute shops/restaurants.

Crystal Gardens Conservatory at Navy Pier: I love walking around and seeing all the plants.

Oak Street Beach

If you’re visiting Chicago, I hope you enjoy your time! And if you live in Chicago and are looking for new places to try I hope you found a new spot to check out! Stay warm up there, friends.