302 N Green St 3rd Floor, Chicago, IL 60607

Aba, meaning father in Hebrew, is a Mediterranean restaurant with a California influence. The menu features Chef CJ Jacobson’s modern approach to Mediterranean cooking and the beverage program showcases spirits and rare wines from lesser known Mediterranean regions.

410 N Michigan Ave, Chicago, IL 60611

Lou Malnati's Pizzeria is home to the best deep dish in Chicago. Lou’s has stayed true to the original Chicago deep dish pizza recipe created by Lou Malnati in the 1940s.

800 W Randolph St, Chicago, IL 60607

Au Cheval is a beloved Chicago institution that doesn’t take reservations, so be prepared to wait — it’s worth it. Their menu is a blend of pub fare and diner classics, all executed to perfection. The star of the show is their iconic double stack burger, a mouthwatering masterpiece that will leave you craving more.

201 E Randolph St, Chicago, IL 60601

Millennium Park has a "New Music Mondays" series, where the park hosts a variety of musical performances, from jazz to classical, creating a lively atmosphere for visitors to enjoy. While immersing yourself in the sounds of the city, you can also stroll through the serene Lurie Garden, a beautifully landscaped oasis. And, of course, no visit to Millennium Park is complete without marveling at the iconic Cloud Gate sculpture or "The Bean”.

Grant Park, Chicago, IL

Want to make the most of your Chicago trip? Consider arriving a few days early to experience Lollapalooza, one of the biggest music festivals in the world! From August 1st to 4th, 2025, Grant Park will be filled with incredible music, food, and fun. It's a great way to kick off our wedding weekend and experience the vibrant energy of Chicago while listening to some of the best live music in the world.

Fun fact: Maggie & Timmy have been going to the festival together since they started dating — in 2022, 2023, 2024 and soon, 2025!

111 W Kinzie St, Chicago, IL 60654

Untitled combines award-winning cuisine, lush libations, whiskey, and more whiskey, and live entertainment, from blues to burlesque.

Fun fact: Maggie & Timmy had their very first “hometown” date here over espresso martinis!

1028 N Rush St, Chicago, IL 60611

A Chicago classic, where prime steaks and lively ambiance come together for an unforgettable dining experience. Grab any drink at the bar and soak up the city’s vibrant energy.

20 W Division St, Chicago, IL 60610

This legendary Gold Coast pub is a time warp of festive cheer and good times. Expect a boisterous crowd, a dazzling Christmas decor year-round, and a menu that's as hearty as the laughter. Don’t forget to order “Christmas in Your Mouth”.

410 N Michigan Ave, Chicago, IL 60611

If you’re in the mood for a waterfront beer garden, this is the place to be. Tiny Tapp is located on the scenic Chicago Riverwalk, which means you can enjoy a cold drink and sweeping river views at the same time. Plus — beer, wine, and cocktails on tap!

600 E Grand Ave, Chicago, IL 60611

Navy Pier is an iconic Chicago landmark that offers stunning views of the city's skyline. It's the perfect place to spend a day or evening, with a variety of attractions for all ages. Take a ride on the iconic Ferris wheel for breathtaking panoramic views of the city or visit the Offshore Restaurant to indulge in delicious cuisine and stunning lakefront views.

111 S Michigan Ave, Chicago, IL 60603

Just like in "Ferris Bueller's Day Off," the Art Institute of Chicago is a must-see cultural destination. This world-renowned museum houses an impressive collection of art from around the globe, including iconic works by masters like Vincent Van Gogh, Claude Monet and Pablo Picasso.

1060 W Addison St, Chicago, IL 60613

The smell of hot dogs, the crack of the bat, the low hum of a crowd. It's a place where time seems to slow down, where the world outside fades away. Some of the real magic happens off the field — at Sluggers. The batting cages are a rite of passage, a chance to channel your inner Babe Ruth.