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April 4, 2025
Chicago, IL

Caitlin & Nick

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    Things To Do in Chicago

Things To Do in Chicago

We're so excited to share some of our favorite places in the city with you! Chicago has some of the best restaurants so we tried our best to narrow it down.

Museum Of Contemporary Art Chicago

220 East Chicago Avenue, Chicago, IL 60611

We had one of our earliest and most memorable first dates at the MCA! A great place to visit, especially if the weather is chilly in April.

Wendella Tours & Cruises

400 North Michigan Avenue, Chicago, IL 60611

Experience the city’s legendary architecture from the best seat in the house—the river. This comprehensive tour navigates through the heart of the city on all three branches of the Chicago River. It’s the one thing everyone tells you to do in Chicago, done right. Can be done rain or shine, so please dress accordingly :)

Portillo's & Barnelli's Chicago

100 West Ontario Street, Chicago, IL 60654

$ A Chicago staple! Nick's order: Maxwell polish with mustard and grilled onions & onion rings with cheese sauce Caitlin's order: Cheeseburger (everything, add mustard) & onion rings. Must try the chocolate cake shake if it's your first time!

The Aberdeen Tap

440 North Aberdeen Street, Chicago, IL 60642

$$ *Insert the Cheers theme song* The #1 neighborhood bar in the city (or the world if you ask Caitlin) with a rotating list of draft beer and amazing bar food. Must try the mac and cheese squares. Nick's order: Gumball Head and the duck grinder with a side of BBQ sauce Caitlin's order: A peach high noon or Tito's soda (really depends on the vibe) and a blackened chicken wrap with a side of ranch and buffalo sauce.

Mart Anthony's Italian Restaurant

1200 West Hubbard Street, Chicago, IL 60642

$$ A family-owned, old-school Italian restaurant. We celebrated our first Valentine's Day here and love sitting at the bar or dining on the front patio. Must get the bruschetta and stuffed artichokes. Nick's order: Fettucini Lucia and a Peroni Caitlin's order: Pastina & veal saltimbocca with a fat glass of red wine. The oysters rockefellar are also beyond (if you don't have a shellfish allergy lol)!

Nancy's Pizza Chicago West Loop

1000 West Washington Boulevard, Chicago, IL 60607

$$ Nancy's started in Chicago and is our go-to pizza spot! Our order: Super thin crust or deep dish, depending on the mood, with whatever toppings you prefer.

Au Cheval

800 West Randolph Street, Chicago, IL 60607

$$$ Elevated diner-style food in a cozy yet trendy space. Au Cheval is a very popular destination and does not accept reservations, so plan accordingly. We recommend putting your name on the list and popping next door to Lone Wolf for a cocktail or two. Go hungry and with someone you can share food with :) Our order: Roasted bone marrow & General Jane's honey fried chicken, a single (which has 2 patties) burger or the fried bolonga sandwich to share, and any of the salads on the menu to balance it all out (Caitlin loves the kale ceasar). Don't forget to add a side of fries!

Obélix

700 North Sedgwick Street, Chicago, IL 60654

$$$ Amazing for dinner but even better for brunch! Reservations recommended but they are usually able to take walk-ins at the bar. Our order: The gem salad and as many pastries as your heart desires to start. The Waygu pastrami sandwich split and a glass (or 3) of champagne.

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