Things To Do
Chicago Air & Water Show
Starting in the summer of 1959, the Chicago Air and Water Show has grown to be the largest and oldest free admission air and water exhibition in the country. The best place to watch the show is near the lakefront on one of Chicago’s many public beaches. The show runs for two days - August 20 & 21 - from 10 am to 2 pm.
The Art Institute of Chicago
Matt grew up going to the Art Institute with his mom and also took Hayley here on one of their first dates. Tour the museum and then stroll through Grant Park afterward to see the famous Chicago bean sculpture (Cloud Gate)!
Cloud Gate
A trip to Chicago wouldn't be complete without a selfie here at Cloud Gate - aka "The Bean".
Willis Tower Skydeck
Tour the Sears Tower (no true Chicagoan refers to it as the Willis Tower!), one of the tallest buildings in the world. Not for those afraid of heights!
Chicago Riverwalk
Stroll along Chicago's riverwalk and stop at one of the many restaurants for a drink or quick meal.
Chicago River Architecture Tour
Consistently rated as one of the best tours in Chicago, learn more about Chicago's famous architecture aboard the First Lady river boat.
Cindy's
One of the most beautiful rooftop bars in the city. Located near the Art Institute and the Bean (Cloud Gate), come here for amazing views of the city!
Lou Malnati's Pizzeria
No trip to Chicago would be complete without sampling some famous deep-dish pizza.
Estereo
One of Hayley and Matt's favorite bars. Come here for great vibes and awesome tequila drinks!
Ramen Takeya
One of Hayley and Matt's favorite spots for authentic ramen in the city. They do not take reservations, so arriving early is encouraged.
Izakaya at MOMOTARO
Come here for authentic Japanese food served in a Tokyo-influenced izakaya. Matt took Hayley here on one of their first dates. Reservations strongly encouraged.
Lazy Bird
The jazz club that Hayley and Matt went to the night they got engaged. Located in the basement of the Hoxton hotel, it has free live music, cool speakeasy vibes, and an amazing cocktail menu!
Boka
The restaurant Hayley and Matt went to the night of their proposal. Their food is upscale and creative but unpretentious. Reservations strongly encouraged.
Au Cheval
Come here for the best burgers in Chicago. They don’t take reservations, so arriving early is encouraged.
J.P. Graziano Grocery
Come here for great, no fuss, old school Italian deli sandwiches.
Monteverde Restaurant & Pastificio
Some of the best Italian food in the city, including incredible fresh, handmade pasta. Reservations strongly encouraged.
Aba
Come here for a fun vibe, beautiful rooftop, and great Mediterranean food. Reservations strongly encouraged.
Little Goat Diner
Come here for great brunch food and a fun atmosphere. Reservations strongly encouraged.
Beatrix
Come here for great, healthy breakfast and lunch food. They also have a location in River North (519 N. Clark St.), for those staying closer to that area.
Sawada Coffee
One of Hayley and Matt's favorite local coffee shops.